Technical field
[0001]
　The present invention, xylylene diisocyanate composition, xylylene diisocyanate modified compositions, relates to a two-component resin material and resin.
BACKGROUND
[0002]
　Conventionally, as a raw material for polyurethane resin used in various industrial products, xylylene diisocyanate are known.
[0003]
　Such xylylene diisocyanate is obtained by reacting xylylene diamine with a carbonyl chloride, chlorinated it is known that by-produced during this reaction (e.g., see Patent Document 1.).
[0004]
　Patent Document 1, xylylene diisocyanate to the chloromethyl benzyl isocyanate as by-product chlorides containing 0.1% by weight is disclosed.
CITATION
Patent Document
[0005]
Patent Document 1: International Publication No. 2007 / 010996A1 pamphlet
Summary of the Invention
Problems that the Invention is to Solve
[0006]
　However, polyurethane resin, the purpose and application, are required to have excellent color fastness. However, the polyurethane resin prepared from xylylene diisocyanate described in Patent Document 1, there may not be enough color fastness.
[0007]
　The present invention, xylylene diisocyanate compositions which can be prepared stably with resin excellent in discoloration resistance, provides a xylylene diisocyanate-modified compositions and two-resin material.
Means for Solving the Problems
[0008]
　The present invention [1] comprises a xylylene diisocyanate, a compound represented by the following chemical formula (1), the content of the compound represented by the following formula (1) is at 60ppm or less than 0.6 ppm, xylylene diisocyanate composition It contains.
[0009]
　Chemical Formula (1)
[0010]
[Formula 1]

[0011]
　The present invention [2] may further include a chloromethyl benzyl isocyanate, the content of the chloromethyl benzyl isocyanate is less than 0.2 ppm 3000 ppm, xylylene diisocyanate composition according to the above [1].
[0012]
　The present invention [3], the content ratio of the chloromethyl benzyl isocyanate is less than 0.2 ppm 1600 ppm, contains xylylene diisocyanate composition according to [2].
[0013]
　The present invention [4] is the [1] to the modified composition of xylylene diisocyanate composition described modified in any one of [3], the following functional groups (a) ~ (i) the contains at least one contains a diisocyanate-modified composition.
(A) isocyanurate
groups, (b) an allophanate
group, (c) biuret
groups, (d) a urethane
group, (e) a urea
group, (f) iminooxadiazinedione
groups, (g) uretdione
groups, (h) uretonimine
groups, (I) carbodiimide groups.
[0014]
　The present invention [5], the isocyanate component containing the [1] to [3] or xylylene diisocyanate composition according to one and / or the [4] xylylene diisocyanate modified product composition according to the When the reaction product of an active hydrogen group containing component includes a resin.
[0015]
　The present invention [6] is an optical material includes a resin according to [5].
[0016]
　The present invention [7] is an optical lens includes a resin according to [6].
[0017]
　The present invention [8], the isocyanate component containing the [1] to [3] or xylylene diisocyanate composition according to one and / or the [4] xylylene diisocyanate modified product composition according to the If contains two-component resin material containing an active hydrogen group-containing component.
[0018]
　The present invention [9] is a coating material includes a two-part resin material according to [8].
[0019]
　The present invention [10], a salt formation step for salt formation xylylenediamine hydrochloride was mixed with hydrogen chloride and xylylenediamine, with a xylylenediamine hydrochloride and carbonyl chloride to isocyanate reaction, Kishirirenji It generates a compound represented by the following chemical formula (1) so as to generate an isocyanate, and an isocyanate step of preparing a reaction mass containing the compounds shown in xylylene diisocyanate and the following chemical formula (1), to give the reaction mass includes a purification step of preparing a xylylene diisocyanate composition, a, in the xylylene diisocyanate composition, the content of compound represented by the following chemical formula (1) is at 60ppm or less than 0.6 ppm, xylylene diisocyanate composition It includes a method of making things.
[0020]
　Chemical Formula (1)
[0021]
[Formula 1]

[0022]
　The present invention [11], in the step of preparing the reaction mass, the reaction pressure (gauge pressure), the excess of atmospheric pressure, comprising a method for producing xylylene diisocyanate composition according to the above [10].
[0023]
　The present invention [12], the salt formation step and the isocyanate process is carried out continuously, includes a method of making xylylene diisocyanate composition according to the above [10] or [11].
Effect of the invention
[0024]
　Xylylene diisocyanate composition of the present invention, a xylylene diisocyanate, and a compound represented by the above formula (1), the content of the compound represented by the above formula (1) is at 60ppm or less than 0.6 ppm.
[0025]
　Therefore, xylylene diisocyanate composition of the present invention, and a resin made from a resin material containing it is excellent in discoloration resistance.
BRIEF DESCRIPTION OF THE DRAWINGS
[0026]
[1] Figure 1 is a schematic diagram of an embodiment of a plant for producing xylylene diisocyanate compositions of the present invention.
FIG. 2 is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, the correlation between color difference in xenon irradiation test of the elastomer.
FIG. 3 is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, the correlation between color difference in the UV irradiation test form.
[4] Figure 4A is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, a correlation between the yellow index value of the plastic lens A. Figure 4B is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, a correlation between the yellow index value of the plastic lens B.
FIG. 5 is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, the correlation between color difference in the UV irradiation test of a two-component curable sealant.
FIG. 6 is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, the correlation between color difference in the UV irradiation test of the coating material (A agent 1).
[7] FIG. 7 is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, the correlation between color difference in the UV irradiation test of the coating material (A agent 2).
[8] FIG. 8 is a graph showing the respective content of the DCI and CBI in xylylene diisocyanate composition, the correlation between color difference in the UV irradiation test of laminating adhesive.
FIG. 9 is a respective content of the DCI and CBI in xylylene diisocyanate composition is a graph showing the correlation between color difference in the UV irradiation test one-component curable sealant.
DESCRIPTION OF THE INVENTION
[0027]
　1. Xylylene diisocyanate composition
　xylylene diisocyanate compositions of the present invention, a xylylene diisocyanate containing more than 99 mass% as a main component, is substantially a single compound (i.e., xylylene diisocyanate), as the minor component, the following chemical formula because they contain the compounds shown in (1), it is defined as xylylene diisocyanate composition.
[0028]
　In other words, xylylene diisocyanate composition of the present invention, as essential components, contains a xylylene diisocyanate, and a compound represented by the following chemical formula (1). In the following, a xylylene diisocyanate composition and XDI composition, xylylene diisocyanate and XDI, compounds represented by the following chemical formula (1) and (dichloromethyl isocyanate) and DCI.
[0029]
　Chemical Formula (1)
[0030]
[Formula 1]

[0031]
　XDI is a structural isomer, 1,2-XDI (o-XDI), 1,3-XDI (m-XDI), include 1,4-XDI (p-XDI). Structural isomers of these XDI may be used singly or in combination of two or more.
[0032]
　As XDI, preferably, include 1, 3-XDI and l, 4-XDI, more preferably include 1, 3-XDI.
[0033]
　XDI content of (pure), relative to the total weight of XDI composition, for example, 99.50 wt% or more, preferably 99.70 wt% or more, more preferably, 99.90% by mass or more, e.g. , 99.999 mass% or less, preferably not more than 99.990 mass%. Content of XDI can be measured according to the method described in the examples below.
[0034]
　DCI is a chlorine compound as a byproduct in the production of XDI described later. DCI as structural isomers, o-DCI, m-DCI, includes a p-DCI. Structural isomers of these DCI may be contained one or two or more in XDI composition.
[0035]
　Structural isomers of DCI a by-product in the manufacture of XDI corresponds to structural isomers of XDI produced. Therefore, XDI compositions contain DCI corresponding to structural isomers of XDI described above. That, XDI composition, if containing o-XDI, containing o-DCI, when containing a m-XDI, when containing m-DCI, containing p-XDI, containing p-DCI to.
[0036]
　As DCI, preferably, include m-DCI and p-DCI, more preferably, include m-DCI.
[0037]
　Content of the DCI, relative to the total weight of XDI composition is 60ppm or less than 0.6 ppm. Content of the DCI, in accordance with the method described in Examples to be described later, can be measured by analyzing by gas chromatography. Incidentally, later described in detail the preferred range of the content of DCI according to the use of XDI composition.
[0038]
　Within the content ratio is above the range of DCI, yellowing and / or clouding of the resin produced from XDI composition can be suppressed.
[0039]
　XDI composition may further contain chloromethyl benzyl isocyanate (monochloromethyl methylbenzyl isocyanate) represented by the following chemical formula (2). In the following, the chloromethyl benzyl isocyanate and CBI.
[0040]
　Chemical Formula (2)
[0041]
[Formula 2]

[0042]
　CBI is a chlorine compound as a byproduct in the production of XDI described later. That is, in the production of XDI, with DCI is by-produced in some cases CBI is by-produced. CBI is a structural isomer, o-CBI, m-CBI, includes a p-CBI. Structural isomers of these CBI may be contained one or two or more in XDI composition. Note that structural isomers of CBI a by-product in the manufacture of XDI, like DCI, corresponding to structural isomers of XDI produced.
[0043]
　Content of CBI, based on the total weight of XDI composition, for example, more than 0.2 ppm, preferably, 6 ppm or more, more preferably, 100 ppm or more, e.g., 5000 ppm or less, preferably, 4000 ppm or less, more preferably , 3000 ppm or less, especially preferably, 1600 ppm or less, and particularly preferably 1000ppm or less. Content of CBI can be measured according to the method described in the examples below.
[0044]
　Further, the content of CBI, relative to the content of the DCI, e.g., 2 times or more, preferably, 10 times or more, more preferably, 20 times or more, for example, 800 times or less, preferably 300 times or less, more preferably, the 50 times or less.
[0045]
　So long as the content of the above CBI, can be reliably suppressed yellowing of the resins produced from XDI composition. Especially, if the content of CBI is the upper limit or less, with the yellowing of the resins produced from XDI compositions can be reliably suppressed, it is possible to smoothly proceed the urethanization reaction during production of the resin, the resin it is possible to achieve the improvement of mechanical properties ensured.
[0046]
　XDI composition further dichloromethane imino - methylbenzyl isocyanate, xylylene dichloride (XDC), may contain other by-products such as cyano isocyanate (MCN) represented by the following chemical formula (3).
[0047]
　Chemical formula (3)
[0048]
[Formula 3]

[0049]
　On the other hand, if it is produced by the method of XDI composition XDI composition described below (i.e. liquid phase), cyanobenzyl isocyanate represented by the above chemical formula (3) (MCN) is not substantially contained in the XDI composition .
[0050]
　Specifically, the content ratio of the cyano isocyanate (MCN) shown in the chemical formula (3), based on the total weight of XDI composition, for example, 500 ppm or less, preferably less than 300 ppm, more preferably less than 100ppm , and the example, not less than 0 ppm. Content of MCN can be measured according to the method described in the examples below.
[0051]
　If the content of the MCN is more than the above-described upper limit, coloration of the resin produced from XDI composition (yellowing) can be suppressed more reliably.
[0052]
　The concentration of hydrolyzable chlorine XDI composition (HC), for example, 10 ppm or more, preferably, 20 ppm or more, e.g., 1500 ppm or less, preferably 1000ppm or less. The concentration of the hydrolyzable chlorine (HC concentration) is measured according to Determination of hydrolyzable chlorine, which is described in JIS K-1603-3 (2007).
[0053]
　The concentration of the hydrolyzable chlorine, DCI described above, CBI, and the like other by-products. Therefore, the concentration of hydrolyzable chlorine XDI composition, the content of DCI in XDI composition does not correlate as is clear from the examples described below. As a result, the content of DCI in XDI composition can not be calculated from the concentration of hydrolyzable chlorine XDI composition.
[0054]
　2. Method for producing XDI composition
　Next, a method for manufacturing the XDI composition.
[0055]
　To produce the XDI composition, for example, xylylenediamine as a raw material and isocyanate, after preparation of the reaction mass (before purification composition) containing XDI and DCI, purifying the reaction mass.
[0056]
　In the following, the xylylenediamine and XDA. XDA is a structural isomer, 1,2-XDA (o-XDA), 1,3-XDA (m-XDA), include 1,4-XDA (p-XDA).
[0057]
　(2-1) production step (Step A ~ C) of the reaction mass
　to produce a reaction mass, for example, by mixing the hydrogen chloride and XDA, after salt formation and XDA hydrochloride, hydrochloride and carbonyl chloride reacting (phosgene) and (phosgenation of the amine hydrochloride). That is, the manufacturing process of the reaction mass, isocyanate salt formation step of forming a salt of the XDA hydrochloride is mixed with XDA hydrogen chloride (Step A), is reacted with a carbonyl chloride and XDA hydrochloride, the XDA hydrochloride of and a (phosgenation) isocyanate step (step B). Such salt formation step (step A) and the isocyanate step (step B) is a liquid phase process.
[0058]
　In salt formation step (step A), for example, the XDA and hydrogen chloride are mixed in the presence of an inert solvent, to produce the XDA hydrochloride (salt forming).
[0059]
　As the inert solvent, for example, aromatic hydrocarbons such as benzene, toluene, and xylene, for example, octane, aliphatic hydrocarbons such as decane, for example, alicyclic hydrocarbons such as methylcyclohexane, ethylcyclohexane , for example, chlorotoluene, chlorobenzene, halogenated aromatic hydrocarbons such as dichlorobenzene, dibromobenzene, trichlorobenzene, for example, nitrobenzene, N, N-dimethylformamide, N, N- dimethylacetamide, N, N'-dimethyl nitrogen-containing compounds such as imidazolidinone, for example, dibutyl ether, ethylene glycol dimethyl ether and ethylene glycol diethyl ether, for example, heptanone, diisobutyl ketone, methyl isobutyl ketone, methyl Ketones such as ethyl ketone, for example, ethyl acetate, butyl acetate, amyl acetate, fatty acid esters such as ethoxyethyl acetate, e.g., methyl salicylate, dimethyl phthalate, dibutyl phthalate, aromatic carboxylic acid esters such as methyl benzoate and the like. Inert solvents may be used alone or in combination of two or more kinds.
[0060]
　Among inert solvents, preferably, include halogenated aromatic hydrocarbons, and more preferably include chlorobenzene and dichlorobenzene.
[0061]
　Then, in an inert solvent, both supplying hydrogen chloride gas, and supplies the amine solution XDA is dissolved in an inert solvent. Then, stirring and mixing the hydrogen chloride gas and the amine solution.
[0062]
　Content of XDA in the amine solution is not particularly limited, for example, 3.0 mass% or more, preferably 5.0 mass% or more, e.g., 30 wt% or less, preferably 20 mass% or less.
[0063]
　To the mass of the sum of the XDA and inert solvents, a mass ratio of XDA was supplied (total amine concentration), for example, 3 wt% or more, preferably 5 mass% or more, e.g., 30 wt% or less, preferably, 20 mass% or less, more preferably 15 mass% or less.
[0064]
　Feed rate of hydrogen chloride, relative to XDA1mol, for example, 2-fold mol or more, e.g., 10-fold mol or less, preferably six times mol or less, and more preferably not more than 4-fold mol.
[0065]
　Salt-forming temperature in such a salt formation step, for example, 30 ° C. or higher, preferably, 50 ° C. or higher, more preferably, 60 ° C. or higher, for example, 160 ° C. or less, preferably, 0.99 ° C. or less, more preferably, at 140 ℃ or less.
[0066]
　Salt formation pressure in salt formation step (gauge pressure), for example, atmospheric pressure (0 MPaG) or higher, preferably, more than 0.01MPaG, and more preferably, 0.02MPaG above, for example, 1.0 MPaG or less, preferably, 0 .5MPaG less, more preferably not more than 0.4 MPaG.
[0067]
　Thus, XDA and XDA hydrochloride and a hydrogen chloride generated (hydrochloride formation reaction), a slurry containing the XDA hydrochloride is prepared.
[0068]
　Then, the isocyanate step (step B), by supplying carbonyl chloride to the slurry containing the XDA hydrochloride, is reacted with carbonyl chloride and XDA hydrochloride (isocyanate reaction, phosgenation).
[0069]
　Feed rate of carbonyl chloride, to the XDA hydrochloride 1 mol, for example, 4 times mol or more, preferably 5-fold mol or more, more preferably, 6 times mol or more, e.g., up to 50-fold mol, preferably, 40 fold mol or less, and more preferably not more than 30 times mol.
[0070]
　Feed rate of carbonyl chloride affects the generation of DCI to reaction rate and by-product of the isocyanate reaction. By adjusting the supply proportions of carbonyl chloride in the above range, it is possible to adjust the production amount of DCI. Specifically, increasing the feed rate of the carbonyl chloride, it is possible to achieve an increase in the amount of DCI, decreasing the feed rate of the carbonyl chloride, it can be reduced the amount of DCI.
[0071]
　The reaction time of the isocyanate step, for example, 4hr or more, more 6hr, for example, 25Hr or less, preferably 20 hr or less, and more preferably not more than 15hr.
[0072]
　The reaction time for the isocyanate step by adjusting the range described above, it is possible to adjust the production of CBI and DCI. Specifically, increasing the reaction time of the isocyanate step, while it is possible to reliably reacting carbonyl chloride with XDA hydrochloride, it is possible to achieve an increase in the production of CBI and DCI, the reaction of the isocyanate of step reducing the time, while it is possible to reduce the by-product tar components, it is possible to reduce the production of CBI and DCI.
[0073]
　The reaction temperature in such isocyanate step is, for example, 90 ° C. or higher, preferably, 100 ° C. or higher, more preferably, 110 ° C. or higher, for example, 190 ° C. or less, preferably, 180 ° C. or less, more preferably, 160 ℃ is less than or equal to.
[0074]
　When the temperature in the isocyanate process is lower than the lower limit, it is possible to improve the reaction rate, industrially can be suitably implemented. When the temperature in the isocyanate step is not more than the upper limit, by-products (such as CBI and DCI) can be prevented from being excessively formed, it can be produced XDI composition by simple purification.
[0075]
　The reaction pressure in the isocyanate step (gauge pressure), for example, exceeds the atmospheric pressure (0 MPaG), preferably, more than 0.0005MPaG, more preferably, more than 0.001MPaG, more preferably, 0.003MPaG above, especially preferably, 0.01MPaG (10kPaG) or more, and particularly preferably, 0.02MPaG (20kPaG) or more, and most preferably, 0.03MPaG (30kPaG) above, for example, 0.6 MPaG or less, preferably, 0.4 MPaG or less , more preferably not more than 0.2 MPaG.
[0076]
　However, the reaction pressure in the isocyanate process is below atmospheric pressure (i.e., under vacuum or under atmospheric pressure), the in isocyanate step, it is impossible to sufficiently generate the DCI.
[0077]
　On the other hand, when the reaction pressure in the isocyanate process is lower than the lower limit, in the isocyanate process, it can be generated reliably DCI.
[0078]
　Further, the reaction pressure in the isocyanate process by adjusting the range described above, it is possible to adjust the production of CBI and DCI. Specifically, increasing the reaction pressure in the isocyanate process, the excess carbonyl chloride can be recovered by the cooler, as compared with the case the refrigerator for recovery of the carbonyl chloride is required, to improve the energy efficiency while it can be, it is possible to increase the production of CBI and DCI.
[0079]
　Lowering the reaction pressure in the isocyanate process, the decomposition reaction of the carbamoyl chloride intermediate to the isocyanate can proceed efficiently, while it is possible to reduce the reaction time, reduce the CBI and the DCI generating amount it can be achieved.
[0080]
　Such isocyanate step can be carried out by any batch and continuous type, preferably carried out by continuous. That is, preferably, a slurry produced in a stirred tank (XDA hydrochloride), continuously fed to another reaction vessel and stirred tank from the stirred tank, the reaction with the XDA hydrochloride and carbonyl chloride in the reaction vessel while continuously taking out a reaction mixture (reaction mass) from the reaction vessel.
[0081]
　When carrying out the isocyanate step by batch, in order XDA hydrochloride does not react with an excess of carbonyl chloride for a long time at high temperature, there is a case where DCI is not generated. Further, in the batch of isocyanate step, the concentration is high initial reaction XDA hydrochloride, may be uniformly mixed difficult, the reaction vessel is large in size with a stirrer of a high output is required put away. Further, in the batch of isocyanate step, a large amount of carbonyl chloride to a concentration of relatively XDA hydrochloride is reacted with high slurry and carbonyl chloride in the reaction initial stage is required, recovering apparatus and by-product of the carbonyl chloride chloride processor of the hydrogen gas becomes large.
[0082]
　On the other hand, when carrying out the isocyanate step by continuous, residence time in each reaction vessel is an average value, remains in some long reaction vessel reaction mixture, over time as a result XDA hydrochloride and carbonyl chloride There in order to react to produce a DCI. Further, in the continuous isocyanate step generates the XDI liquid accordance progression isocyanate reaction, because the concentration of XDA hydrochloride in the slurry decreases, it stirred smoothly by a simple stirring device. Furthermore, in the continuous isocyanate step, can be the feed rate and by-product hydrogen chloride gas amount of carbonyl chloride is constant, it is possible to compact the apparatus of the recovery apparatus and hydrogen chloride gas in the carbonyl chloride with, it can stabilize the operation. These, the isocyanate step of continuous, rather than batch isocyanate step, it is preferable from the viewpoint of automatic operation for mass production of XDI.
[0083]
　That is, in a mass-production scale, preferably, the isocyanate step is a continuous reaction.
[0084]
　Also, isocyanate step is preferably from the viewpoint of the volume efficiency in the reaction vessel is carried out as a multistage process. Number of isocyanate step is, for example, less than 5 or more stages 2 stages.
[0085]
　For example, if the number of isocyanate step is a two-stage, the range of the sum of the residence time in the two-stage isocyanate step is the same as the range of the reaction time as described above, the carbonyl chloride in the two-stage isocyanate step range of feed rate is the same as the range of feed rate carbonyl chloride as described above.
[0086]
　Or by, in the carbonyl chloride is reacted with XDA hydrochloride, XDI is produced as a main component. Further, DCI is produced as a by-product, sometimes CBI is produced as further by-products.
[0087]
　Then, if necessary, to the reaction mixture (reaction mixture), the degassing step, carrying out desolvation process and tar cutting step (step C). The degassing step, the reaction solution (reaction mixture), the excess gases, such as hydrogen chloride by-produced carbonyl chloride and is removed by a known degassing tower. The desolvation process, distilling off the inert solvent by a known distillation column from the reaction solution. The tar cutting step, tar ingredients are removed by known tar cutting apparatus from the reaction solution. Incidentally, the reaction mass from which tar ingredients have been removed by the tar cutting step and de-Tarumasu.
[0088]
　Or by (preferably de Tarumasu) reaction mass containing XDI and DCI is produced.
[0089]
　Content of XDI in the reaction mass, for example, 80.0% by weight or more, preferably 90.0 mass% or more, more preferably, 95.0 mass% or more, for example, 99.0 wt% or less, preferably , 98.5 wt% or less, more preferably 98.0 mass% or less.
[0090]
　Content of DCI in the reaction mass, for example, 1 ppm or more, preferably, 2 ppm or more, more preferably, 5 ppm or more, e.g., 80 ppm or less, preferably 70 ppm or less, more preferably 50ppm or less.
[0091]
　If the reaction mass contains CBI, content of CBI in the reaction mass, for example, 0.1 mass% or more, preferably 0.3 mass% or more, more preferably, 0.5 mass% or more, for example, 3.0 wt% or less, preferably 1.5 wt% or less, more preferably 1.0% by mass or less.
[0092]
　If the reaction mass contains an inert solvent, the content of the inert solvent in the reaction mass, for example, 0.1 mass% or more, preferably 0.3 mass% or more, more preferably, 0.5 wt% or more, more preferably, 1.0 mass% or more, for example, 5.0 wt% or less, or preferably more than 3.0 mass%.
[0093]
　(2-2) reaction mass purification step (step D)
　then purifying the reaction mass (before purification composition), to adjust the content of DCI in the above range.
[0094]
　As the purification method of the reaction mass, for example, crystallization, industrial separation method such as distillation and the like, preferably, distillation and the like. To purify the reaction mass by distillation, for example, after distilling off by distillation low boiling substances (low boilers) from the reaction mass, rectifying de low boiling mass in the reaction mass after removing low boiling. In other words, the purification step of the reaction mass includes a de-low-boiling step of distilling off the low boiling substances from the reaction mass, and a rectification step of rectifying the de low boiling mass.
[0095]
　The removal low boiling step, e.g., the reaction mass (preferably, de Tarumasu) was distilled by removing low-boiling column, distilling off low boiling substances.
[0096]
　As leaving low boiling column, for example, it includes plate column and packed column, preferably, a packed column. Number of theoretical plates of the de low boiling column, for example, three or more, preferably 5 or more stages, more preferably, 7 or more stages, for example, 40 stages or less, preferably, 20 steps or less, more preferably 15 stages or less it is.
[0097]
　Bottom temperature of the de low boiling column, for example, 130 ° C. or higher, preferably, 140 ° C. or higher, more preferably, 0.99 ° C. or higher, for example, 200 ° C. or less, preferably, 190 ° C. or less, more preferably, 180 ° C. less.
[0098]
　Top temperature of the de low boiling column, for example, 90 ° C. or higher, preferably, 100 ° C. or higher, more preferably, 110 ° C. or higher, for example, 160 ° C. or less, preferably, 0.99 ° C. or less, more preferably, 140 ° C. less.
[0099]
　Top pressure of the de low boiling column, for example, more than 0.05 kPa, preferably, 0.1 kPa or more, more preferably, 0.2 kPa or more, for example, 3.0 kPa or less, preferably, 2.0 kPa or less, more preferably, it is less than 1.0kPa.
[0100]
　Overhead reflux ratio of de low boiling column, for example, 1 or more, preferably 5 or more, more preferably, 10 or more, for example, 80 or less, preferably 60 or less, more preferably 50 or less.
[0101]
　The residence time of the de low boiling column, for example, 0.1 hour or more, preferably 0.2 hours or more, more preferably, 0.3 hours or more, e.g., 10 hours or less, preferably 5 hours or less, more preferably, at most 3 hours.
[0102]
　From this, followed by distilling off the low boiling substances to obtain a de-low boiling mass is de-Tarumasu after removing low-boiling as liquid exits the can.
[0103]
　Then, in the rectification process, for example, de-low boiling mass was distilled by rectification column, taking out the XDI composition as fraction.
[0104]
　As rectification column, for example, it includes plate column and packed column, preferably, a packed column. Number of theoretical plates of the rectification column, for example, one or more stages, for example, 20 stages or less, preferably, 10 stages or less, and more preferably not more than 5 stages.
[0105]
　Bottom temperature of the rectification column, for example, 120 ° C. or higher, preferably, 130 ° C. or higher, more preferably, 140 ° C. or higher, for example, 190 ° C. or less, preferably, 180 ° C. or less, more preferably, 170 ° C. or less it is.
[0106]
　Top temperature of the rectification column, for example, 90 ° C. or higher, preferably, 110 ° C. or higher, more preferably, 130 ° C. or higher, for example, 180 ° C. or less, preferably, 170 ° C. or less, more preferably, 160 ° C. or less it is.
[0107]
　Top pressure of the rectification column, for example, more than 0.05 kPa, preferably more than 0.1 kPa, more preferably, more than 0.2 kPa, for example, 3.0 kPa or less, preferably, 2.0 kPa or less, more preferably it is equal to or less than 1.0kPa.
[0108]
　Overhead reflux ratio of the rectification column, for example, 0.1 or more, preferably, 0.2 or more, more preferably, 0.3 or more, e.g., 50 or less, preferably 20 or less, more preferably, 10 less.
[0109]
　Fractionator of residence time, for example, 0.2 hours or more, preferably 0.5 hour or more, more preferably, 1.0 hours or more, e.g., 20 hours or less, preferably 10 hours or less.
[0110]
　Above makes it possible to adjust the content of DCI in XDI composition, XDI composition is taken out as a fraction. Incidentally, by adding DCI to XDI composition, the content of DCI in XDI composition can also be adjusted.
[0111]
　3. Plant
　(3-1) plant configuration of
　the manufacturing method of XDI the above composition, for example, is implemented by the plant 1 shown in FIG. As shown in FIG. 1, the plant 1, the isocyanate unit 3 to be described later, is carried out a two-stage continuous isocyanate step is, feed rate of carbonyl chloride as described above, the reaction temperature, and reaction pressure and average residence time There by being appropriately adjusted, the amount of XDI and DCI are adjusted. Then, in the de low boiling unit 7 to be described later, removing low-boiling process is performed, such as overhead reflux ratio described above is by being appropriately adjusted, the content of DCI in XDI composition is adjusted.
[0112]
　As shown in FIG. 1, the plant 1 is an apparatus for manufacturing a XDI composition. Plant 1 comprises a salt forming unit 2, the isocyanate unit 3, a degassing unit 4, a desolvation unit 5, a tar cutting unit 6, the de-low boiling unit 7, and a rectification unit 8.
[0113]
　Salt formation unit 2 can implement the above-mentioned salt formation step (step A), an apparatus for manufacturing a XDA hydrochloride producing XDA hydrochloride from the XDA and hydrogen chloride. Salt formation unit 2 is provided with a stirring tank 21, and hydrogen chloride supply line 24, an amine feed line 22, a solvent supply line 23, an exhaust line 25, and a hydrochloride salt feed line 26.
[0114]
　Stirred tank 21, for example, temperature and pressure is a controllable heat and pressure-resistant container.
[0115]
　Inside the stirring tank 21, stirring blades for stirring and mixing with hydrogen chloride and XDA (not shown) is provided. As the stirring blades, from the viewpoint of dispersion efficiency of the hydrogen chloride gas and XDA hydrochloride, for example, a paddle blade, inclined paddle blade, turbine blade, three swept wing, twin star blade, FULLZONE blade, max blend blade, and their such multistage stirring blades that combine blades and the like.
[0116]
　Further, in the stirring tank 21, coolable cooling device 27 is provided inside the agitation tank 21. As the cooling device 27, for example, the refrigerant can be supplied jackets, cooling coils, and the like external circulation cooler. In FIG 1, the cooling device 27, showing a case where the cooling water (coolant) is a jacket that can supply.
[0117]
　Hydrogen chloride supply line 24 supplies the hydrogen chloride (HCl) gas to a stirred tank 21. The downstream end of the hydrogen chloride supply line 24 is connected to the bottom of the stirred tank 21. Upstream end of the hydrogen chloride supply line 24, although not shown, is connected to a tank for storing hydrogen chloride.
[0118]
　Amine feed line 22 supplies the XDA the stirring tank 21. The downstream end portion of the amine feed line 22 is connected to the top of the stirred tank 21. Upstream end of the amine feed line 22, although not shown, is connected to a tank for storing XDA.
[0119]
　The solvent supply line 23 supplies an inert solvent as described above to the amine feed line 22. The downstream end of the solvent feed line 23 is connected to the middle portion of the amine feed line 22. Upstream end of the solvent supply line 23, although not shown, is connected to a tank for storing an inert solvent.
[0120]
　Exhaust line 25 discharges the excess hydrogen chloride gas from the stirring tank 21 in the salt forming step. Upstream end of the exhaust line 25 is connected to the top of the stirred tank 21. The downstream end of the exhaust line 25, although not shown, is connected to the recovery device of the hydrogen chloride gas.
[0121]
　Hydrochloride feed line 26, a slurry containing the XDA hydrochloride, to feed the stirring tank 21 to an isocyanate of unit 3. Upstream end of the hydrochloride salt feed line 26 is connected to the stirring tank 21. In Figure 1, the upstream end portion of the hydrochloride salt feed line 26 has been connected to the bottom of the stirred tank 21, due to restrictions such as the relationship of the layout, as appropriate, connected to the top or side of the stirred tank 21 it is also possible. The downstream end portion of the hydrochloride salt feed line 26 is connected to the reaction vessel 31A to be described later. In Figure 1, the downstream end portion of the hydrochloride salt feed line 26 are connected to the top of the reaction vessel 31A, it is also possible to feed the liquid in a pipe connected to the side and bottom of the reaction vessel 31A . Although not shown, in the middle portion of the hydrochloride salt feed line 26, a known slurry pump for feeding a slurry, for example, a gear pump, sealless pump, mechanical seal pumps, magnet pumps are provided. It is also possible to feed the slurry by a pressure difference between the stirring tank 21 and the reaction vessel 31A. Further, in the reaction vessel 31A and reaction vessel 31B, or provided with the slurry pump for feeding a slurry, or it may be feeding the slurry by a pressure difference.
[0122]
　Isocyanate unit 3 may be embodied the isocyanate step (step B), a manufacturing apparatus of XDI for manufacturing the XDI by reacting a carbonyl chloride and XDA hydrochloride. Specifically, isocyanate unit 3 may be embodied a two-stage continuous isocyanate step comprises a first isocyanate unit 3A, and a second isocyanate unit 3B, and a carbonyl chloride supplying line 30.
[0123]
　The first isocyanate unit 3A and the second isocyanate unit 3B has the same structure except for the connection portion of the reaction mass liquid sending line to be described later. Therefore, the configuration of the first isocyanate units 3A and described in detail, the description thereof is omitted in the second isocyanate unit 3B.
[0124]
　The first isocyanate unit 3A includes a reaction tank 31A, and exhaust line 33A, a capacitor 35A, a reflux line 34A, and a reaction mass feed line 32A. Incidentally, the reaction vessel by the second isocyanate unit 3B comprises an exhaust line, a capacitor, a reflux line and the reaction mass feed line, the reaction vessel 31B, the exhaust line 33B, a capacitor 35B, reflux line 34B and the reaction mass feed line 32B to.
[0125]
　The reaction vessel 31A, for example, temperature and pressure is a controllable heat and pressure-resistant container. The reaction vessel 31A, the downstream end portion of the hydrochloride salt feed line 26 is connected. In Figure 1, the top of the reaction vessel 31A, but the downstream end portion of the hydrochloride salt feed line 26 is connected, by constraints such as the relationship of the layout, as appropriate, connected to the side and bottom of the reaction vessel 31A it is also possible.
[0126]
　Inside the reaction vessel 31A, the stirring blade for stirring and mixing the slurry with carbonyl chloride (not shown) is provided. As the stirring blades, for example, the above stirring blades and the like.
[0127]
　Further, the reaction vessel 31A, internally heatable heating device 36A of the reaction vessel 31A is provided. As a heating apparatus 36A, for example, heat medium jacket can be supplied, steam coils, and the like external circulation heater. In FIG. 1, the heating device 36A indicates a case where steam (heating medium) is jacket can be supplied.
[0128]
　Exhaust line 33A discharges excess carbonyl chloride, by-produced hydrogen chloride gas and an inert gas component including solvent from the reaction vessel 31A. Upstream end of the exhaust line 33A is connected to the top of the reaction vessel 31A. The downstream end of the exhaust line 33A, although not shown, is connected to the recovery device carbonyl chloride.
[0129]
　Capacitor 35A is provided in the middle portion of the exhaust line 33A. Capacitor 35A is to cool the gas component passes through the exhaust line 33A, to condense and some inert solvent and carbonyl chloride in the gas component. Thus, the exhaust gas containing a carbonyl gas and hydrogen chloride gas chloride, is separated into a reflux liquid comprising an inert solvent and liquefied carbonyl chloride. Although not shown, on the downstream side of the capacitor 35A in the exhaust line 33A, the known control valve is provided for adjusting the internal pressure of the reaction vessel 31A.
[0130]
　Reflux line 34A returns a reflux liquid separated in the condenser 35A to the reaction vessel 31A. Upstream end of the reflux line 34A is connected to a capacitor 35A. The downstream end of the reflux line 34A is connected to the top of the reaction vessel 31A.
[0131]
　The reaction mass feed line 32A of the first isocyanate unit 3A, the reaction mass in the first stage the isocyanate step (primary reaction mass), to feed to the reaction vessel 31B of the second isocyanate unit 3B from the reaction vessel 31A . Upstream end of the reaction mass feed line 32A is connected to the reaction vessel 31A. In Figure 1, the upstream end of the reaction mass feed line 32A is connected to the bottom of the reaction vessel 31A, connected to the side of the reaction vessel 31A, it can be fed by the overflow method. The downstream end of the reaction mass feed line 32A is connected to the reaction vessel 31B. In Figure 1, the downstream end of the reaction mass feed line 32A is connected to the top of the reaction tank 31B, due to restrictions such as the relationship of the layout, as appropriate, connected to the side and bottom of the reaction vessel 31B it is also possible. Although not shown, in the middle portion of the reaction mass feed line 32A, a known liquid feed pump for feeding a reaction mass (primary reaction mass), for example, a gear pump, sealless pump, mechanical seal pumps, Magnetic pump is provided.
[0132]
　The reaction mass feed line 32B of the second isocyanate unit 3B is a reaction mass in the second stage of the isocyanate step (secondary reaction mass), to feed from the reaction vessel 31B to the degassing unit 4. Upstream end of the reaction mass feed line 32B is connected to the reaction vessel 31B. In Figure 1, the upstream end of the reaction mass feed line 32B is connected to the bottom of the reaction vessel 31B, it is also possible to feed connected to the side of the reaction vessel 31A. The downstream end of the reaction mass feed line 32B is connected to a vertical direction substantially central degassing tower 41 to be described later. Although not shown, in the middle portion of the reaction mass feed line 32B, the above liquid feed pump is provided for feeding a reaction mass (secondary reaction mass).
[0133]
　Carbonyl chloride supplying line 30 supplies the carbonyl chloride to each reaction vessel 31A and reaction vessel 31B. The downstream end portion of the carbonyl chloride supplying line 30 is branched and is connected to each reaction vessel 31A and reaction vessel 31B. In Figure 1, the downstream end portion of the carbonyl chloride supplying line 30 are respectively connected to the top of the reaction vessel 31A and reaction vessel 31B, connected to the respective top and bottom of the reaction vessel 31A and reaction vessel 31B and be fed in the liquid in the pipe, it can be connected to each of the bottom of the reaction vessel 31A and reaction vessel 31B. Upstream end of the carbonyl chloride supplying line 30, not shown, is connected to a tank for storing liquefied carbonyl chloride.
[0134]
　Degassing unit 4 may be implemented degassing step described above. Degassing unit 4 is provided with a degassing tower 41, an exhaust line 45, a capacitor 46, a de-gas mass feed line 42, a circulation line 43, and a reboiler 44.
[0135]
　Degassing tower 41 separates the gas, including carbonyl chloride and hydrogen chloride from the reaction mass. Degassing tower 41, known separation column, e.g., a tray tower, packing tower, consisting of structured packing column.
The vertical substantial center of the degassing tower 41, the downstream end of the reaction mass liquid feed line 32B is connected.
[0136]
　Exhaust line 45 is connected to the capacitor 46, after the solvent contained in the gas to be separated in the degassing tower 41 was separated by the capacitor 46 to discharge the gas. Upstream end of the exhaust line 45 of the gas separated in the degassing tower 41 is connected to the top of the degassing tower 41. The downstream end of the exhaust line 45, although not shown, is connected to the recovery device carbonyl chloride.
[0137]
　Capacitor 46 is provided in the middle portion of the exhaust line 45. Capacitor 46 is condensed by cooling the solvent contained in the gas to be separated in the degassing tower 41.
[0138]
　De gas mass feed line 42, the reaction mass after the degassing step (de-gas mass), to feed from the degassing tower 41 to desolvation unit 5. Upstream end of the de-gas mass feed line 42 is connected to the bottom of the degassing tower 41. The downstream end of the de-gas mass feed line 42 is connected to a vertical direction substantially central desolvation tower 51 to be described later.
[0139]
　Circulation line 43, a portion of the de-gas mass which is fed to the de-gas mass feed line 42, is returned to the degassing tower 41. Upstream end of the circulation line 43 is connected to the middle portion of the de-gas mass feed line 42. The downstream end of the circulation line 43 is connected to the bottom of the degassing tower 41. Although not shown, the downstream side or upstream side of the connection portion of the circulation line 43 in the de-gas mass feed line 42, said liquid feed pump for feeding a de-gas mass is provided.
[0140]
　Reboiler 44 is provided in the middle portion of the circulation line 43. Reboiler 44 heats the de-gas mass passing through the circulation line 43. Accordingly, the reboiler 44, adjusts the internal temperature of the degassing tower 41. Reboiler 44, known heat exchangers, for example, can be used thermo siphon reboiler, forced circulation reboiler, and thin-film reboiler.
[0141]
　Desolvation unit 5 can implement the desolvation process described above. Desolvation unit 5 includes a desolvation column 51, the solvent discharge line 55, a capacitor 56, and desolvation mass feed line 52, a circulation line 53, and a reboiler 54.
[0142]
　Desolvation tower 51 removes inert solvent from de gas mass. Desolvation tower 51, known distillation column, for example, a tray tower, packing tower, consists structured packing column, distilling off the inert solvent. The vertical substantial center of desolvation column 51, a downstream end portion of the de-gas mass feed line 42 is connected.
[0143]
　The solvent discharge line 55 is distilled by desolvation column 51, to discharge the inert solvent are agglomerated by the capacitor 56. Upstream end of the solvent discharge line 55 is connected to the top of the desolvation tower 51. The downstream end of the solvent discharge line 55, although not shown, is connected to a tank for storing an inert solvent. Incidentally, the recovered inert solvent is preferably recycled as a reaction solvent for salt formation step and the isocyanate process.
[0144]
　Capacitor 56 is provided in the middle portion of the solvent discharge line 55. Capacitor 56 is condensed by cooling the inert solvent to be evaporated by desolvation column 51.
[0145]
　Desolvation mass feed line 52, the reaction mass after desolvation step (desolvation mass), to feed the desolvation column 51 in tar cutting unit 6. Upstream end of the desolvation mass feed line 52 is connected to the bottom portion of the desolvation tower 51. The downstream end portion of the desolvation mass feed line 52 is connected to a vertical direction substantially central of tar cutting apparatus 61 to be described later.
[0146]
　Circulation line 53, a portion of the desolvation mass is fed to the desolvation mass liquid feed line 52, and returns to the desolvation column 51. Upstream end of the circulation line 53 is connected to the middle portion of the desolvation mass feed line 52. The downstream end of the circulation line 53 is connected to the bottom portion of the desolvation tower 51. Although not shown, the downstream side or upstream side of the connection portion of the circulation line 53 in the desolvation mass feed line 52, said liquid feed pump for feeding a desolvation mass is provided.
[0147]
　Reboiler 54 is provided in the middle portion of the circulation line 53. Reboiler 54 heats the desolvation mass passing through the circulation line 53. Accordingly, the reboiler 54, adjusts the internal temperature of the desolvation tower 51. Reboiler 54 may be used the above-mentioned heat exchanger.
[0148]
　Tar cutting unit 6 can be implemented a tar cutting step described above. Tar cutting unit 6 is provided with a tar cutting apparatus 61, a tar discharge line 62, and a de-Tarumasu feed line 63.
[0149]
　Tar cutting device 61 separates the tar components from the desolvation mass. Tar cutting apparatus 61 is, for example, a known thin film evaporator. Tar cutting apparatus 61 includes a casing 61A, a wiper 61B, and an internal capacitor 61C.
[0150]
　The casing 61A, the suction tube for decompressing the inside of the jacket and casing 61A for heating the casing 61A (not shown) is provided. Wiper 61B is disposed in the casing 61A. Wiper 61B are spaced slightly spacing the inner peripheral surface of the casing 61A. Wiper 61B is rotatable by a motor (not shown). Internal capacitor 61C, for example, consist of a heat exchanger in which the refrigerant is circulated. Internal capacitor 61C is in the casing 61A, it is provided in the bottom wall of the casing 61A.
[0151]
　Tar discharge line 62 discharges the tar components separated by tar cutting apparatus 61. Upstream end of the tar discharge line 62 is connected to the lower portion of the casing 61A. The downstream end portion of the second extraction line 28, although not shown, is connected to a tank for storing the tar components. Incidentally, by a known method from the recovered tar components, to recover the XDI contained in tar component can be charged to one of the units of the plant 1. Thus, it is possible to improve the XDI yield.
[0152]
　De Tarumasu feed line 63, the desolvation mass from which tar ingredients have been separated (de Tarumasu), to feed the tar cutting apparatus 61 in de low boiling unit 7. Upstream end of the de-Tarumasu feed line 63 is connected to the internal capacitor 61C. The downstream end of the de-Tarumasu feed line 63 is connected to a vertical direction substantially central de low boiling column 71 to be described later.
[0153]
　The de Tarumasu feed line 63, a flow meter 63A, and the control valve 63B is provided. Flowmeter 63A is provided in the middle portion of the de-Tarumasu feed line 63. Flowmeter 63A measures the flow rate of de Tarumasu passing de Tarumasu feed line 63. Control valve 63B is provided in the portion between the flow meter 63A and de low-boiling column 71 in de Tarumasu feed line 63. Control valve 63B is capable of opening and closing the de Tarumasu feed line 63. Control valve 63B is based on the measurement result of the flow meter 63A, the flow rate of de-Tarumasu passing de Tarumasu feed line 63, that is, to adjust the supply amount of de Tarumasu for removing low-boiling column 71.
[0154]
　De low boiling unit 7 can implement the removal low boiling step described above. De low boiling unit 7 includes the de-low-boiling column 71, and suction line 72, a capacitor 73, a low-boiling discharge line 74, the overhead reflux line 75, and de-low-boiling mass feed line 76, the bottom circulation a line 77, and a reboiler 78.
[0155]
　De low boiling column 71, to remove the low boiling substances from the de-Tarumasu. De low boiling column 71, for example, a distillation column exemplified in the description of the above removal low boiling step, distilling off low boiling substances. The vertical substantial center of the de low boiling column 71, the downstream end of the de-Tarumasu liquid feed line 63 is connected.
[0156]
　Suction line 72, for example, to connect the pressure reducing device and the de-low-boiling column 71, such as a vacuum pump. Decompressor, the inside of the via suction line 72 leaving the low-boiling column 71 under vacuum, adjusting the internal pressure of the de-low-boiling column 71. Upstream end of the suction line 72 is connected to the top of the de-low-boiling column 71.
The downstream end of the suction line 72 is connected to a vacuum device.
[0157]
　Capacitor 73 is provided in the middle portion of the suction line 72. Capacitor 73 is condensed by cooling the low boiling substances in the gaseous state through the suction line 72.
[0158]
　Low boiling discharge line 74 discharges the low-boiling substances condensed in condenser 73. Upstream end of the low-boiling discharge line 74 is connected to the capacitor 73. The downstream end of the low-boiling discharge line 74, although not shown, is connected to a tank for storing low-boiling substances. Incidentally, by a known method from the recovered low boiling substances, and recovering the XDI in the low-boiling substances, it can be charged to one of the units of the plant 1. Thus, it is possible to improve the XDI yield.
[0159]
　Further, the low boiling discharge line 74 includes a flow meter 74A, and the control valve 74B is provided. Flowmeter 74A, in a low-boiling discharge line 74, provided on the downstream side of the connection portion of the overhead reflux line 75. Flowmeter 74A measures the flow rate of the low-boiling substances discharged through the low-boiling discharge line 74. Control valve 74B is in the low-boiling discharge line 74 is provided downstream of the flow meter 74A. Control valve 74B is capable of opening and closing the low-boiling discharge line 74. Control valve 74B is based on the measurement result of the flow meter 74A, can adjust the supply amount of the low boiling substances discharged from the low-boiling discharge line 74.
[0160]
　Overhead reflux line 75, a portion of the low boiling substances to pass through the low-boiling discharge line 74 and returns it to the de-low boiling column 71. Upstream end of the top reflux line 75 is connected to a portion between the de-low-boiling column 71 and the flow meter 74A of the low-boiling discharge line 74. The downstream end of the overhead reflux line 75 is connected to the top of the de-low-boiling column 71. Further, the overhead reflux line 75, flow meter 75A is provided. Flowmeter 75A measures the flow rate of the low-boiling substances sent back through the top reflux line 75 to the de-low boiling column 71.
[0161]
　De low boiling mass feed line 76, a de-Tarumasu low boiling substances is removed (de-low-boiling mass), to feed the removed low-boiling column 71 to rectification unit 8. Upstream end of the de-low boiling mass feed line 76 is connected to the bottom of the de-low-boiling column 71. The downstream end of the removal low boiling mass feed line 76 is connected to a vertical direction substantially central of the rectification column 81 to be described later.
[0162]
　Bottoms circulation line 77, a portion of the de-low boiling mass is fed to a de-low boiling mass liquid feed line 76 is returned to the de-low boiling column 71. Upstream end of the bottom circulation line 77 is connected to the middle portion of the de-low boiling mass feed line 76. The downstream end portion of the bottom circulation line 77 is connected to the bottom of the de-low-boiling column 71. Although not shown, downstream of the connection portion of the bottom circulation line 77 in the de-low boiling mass feed line 76, it said liquid feed pump for feeding a de-low boiling mass is provided.
[0163]
　Reboiler 78 is provided in the middle portion of the bottom circulation line 77. Reboiler 78 heats de low boiling mass passing through the bottom circulation line 77. Accordingly, the reboiler 78, adjusts the internal temperature of the de low boiling column 71. Reboiler 78 may be used the above-mentioned heat exchanger.
[0164]
　Rectification unit 8 can implement the rectification step described above. Rectification unit 8 includes a fractionator 81, and tar discharge line 86, a bottom circulation line 87, a reboiler 88, and suction line 82, a capacitor 83, and XDI extraction line 84, an overhead reflux line 85 equipped with a.
[0165]
　Fractionator 81 is distilled de Tarumasu, distilling the XDI composition. Fractionator 81 is made of, for example, a distillation column exemplified in the description of the rectification process. The vertical substantial center of the rectification column 81, a downstream end portion of the de-low boiling mass feed line 76 is connected.
[0166]
　Tar discharge line 86, in the rectification column 81, to discharge the tar components remaining after evaporation of XDI compositions from rectification column 81. Upstream end of the tar discharge line 86 is connected to the bottom of the rectification column 81. The downstream end portion of the tar discharge line 86, although not shown, is connected to a tank for storing tar components. Incidentally, tar component of the rectification column 81, it can be charged to the upstream of the unit than the de-low boiling unit 7. Thus, it is possible to improve the XDI yield.
[0167]
　Bottoms circulation line 87, a portion of the tar component passing through the tar discharge line 86, to return to fractionator 81. Upstream end of the bottom circulation line 87 is connected to the middle portion of the tar discharge line 86. The downstream end portion of the bottom circulation line 87 is connected to the bottom of the rectification column 81.
[0168]
　Reboiler 88 is provided in the middle portion of the bottom circulation line 87. Reboiler 88 heats the tar component passing through the bottom circulation line 87. Accordingly, the reboiler 88 adjusts the bottom temperature of the rectification column 81. Reboiler 88 may be used the above-mentioned heat exchanger.
[0169]
　Suction line 82, for example, to connect the pressure reducing device and the fractionator 81, such as a vacuum pump. Decompressor, the inside of the fractionator 81 via the suction line 82 by vacuum, to adjust the internal pressure of the rectification column 81. Upstream end of the rectification column 81 is connected to the top of the rectification column 81. The downstream end of the suction line 82 is connected to a vacuum device.
[0170]
　Capacitor 83 is provided in the middle portion of the suction line 82. Capacitor 83 is condensed by cooling the XDI composition gaseous state passes through the suction line 82.
[0171]
　XDI extraction line 84 is to feed the XDI composition condensed in the condenser 83. Upstream end of the XDI extraction line 84 is connected to the capacitor 83. The downstream end of the XDI extraction line 84 is not shown, is connected to a tank for storing XDI composition.
[0172]
　Further, the XDI extraction line 84, a flow meter 84A, and the control valve 84B is provided. Flowmeter 84A is provided on the downstream side of the connection portion of the overhead reflux line 85 in XDI extraction line 84. Flowmeter 84A measures the flow rate of the XDI composition passing XDI extraction line 84. Control valve 84B is the XDI extraction line 84 is provided downstream of the flow meter 84A. Control valve 84B is capable of opening and closing the XDI extraction line 84. Control valve 84B is based on the measurement result of the flow meter 84A, you can adjust the outflow of XDI composition from XDI extraction line 84.
[0173]
　Overhead reflux line 85, a portion of the XDI composition passing XDI extraction line 84 is returned to the fractionator 81. Upstream end of the top reflux line 85 is connected to a portion between the capacitor 83 and the flow meter 84A of XDI extraction line 84. The downstream end of the overhead reflux line 85 is connected to the top of the rectification column 81. Further, the overhead reflux line 85, flow meter 85A is provided. Flowmeter 85A measures the flow rate of the XDI composition through the top reflux line 85 is returned to the fractionator 81.
[0174]
　Although not particularly shown, stirred tank, the reaction tank, tower, the feed line between the tar cutting apparatus, provided with a control valve and flowmeter optionally suitably adjusted and the supply flow rate of the residence time in each step and controls the, it is also possible to stabilize the operation.
[0175]
　(3-2) Plant operation
　will now be described the operation of the plant 1.
[0176]
　In plant 1, firstly, it is charged in an inert solvent in the stirring tank 21. Then, hydrogen chloride gas, at a feed rate of the continuously fed to the bottom of the stirred tank 21 via the hydrogen chloride supply line 24. Further, XDA is the amine solution in an inert solvent is continuously fed to the top of the stirred tank 21 via the amine feed line 22. Then, the inside of the stirring tank 21 while maintaining the salt formation temperature, and salt formation pressure of the mixed stirring hydrogen chloride gas and the amine solution by stirring blades (salt forming step). Thus, slurry containing the XDA hydrochloride is prepared.
[0177]

The scope of the claims
[Requested item 1]
　And xylylene diisocyanate, and a compound represented by the following chemical formula (1), the content of the compound represented by the following chemical formula (1), characterized in that at 60ppm or less than 0.6 ppm, xylylene diisocyanate composition.
　Formula (1)
Formula 1]

[Requested item 2]
　Further comprising a chloromethyl benzyl isocyanate, the content of the chloromethyl benzyl isocyanate, characterized in that it is less than 0.2 ppm 3000 ppm,
xylylene diisocyanate composition of claim 1.
[Requested item 3]
　The content of the chloromethyl benzyl isocyanate, characterized in that it is less than 0.2 ppm 1600 ppm,
xylylene diisocyanate composition of claim 2.
[Requested item 4]
　A modified composition of xylylene diisocyanate composition described modified in claim 1,
　characterized in that it contains at least one functional group of the following (a) ~ (e), xylylene diisocyanate modified product Composition.
(A) isocyanurate
groups, (b) an allophanate
group, (c) biuret
groups, (d) a urethane
group, (e) a urea
group, (f) iminooxadiazinedione
groups, (g) uretdione
groups, (h) uretonimine groups,
(I) carbodiimide group
[Requested item 5]
　An isocyanate component containing xylylene diisocyanate composition of claim 1, characterized in that it is a reaction product of an active hydrogen group-containing component, a resin.
[Requested item 6]
　Characterized in that an optical material, resin according to claim 5.
[Requested item 7]
　Characterized in that an optical lens, the resin of claim 6.
[Requested item 8]
　An isocyanate component containing diisocyanate modified product composition according to claim 4, characterized in that it is a reaction product of an active hydrogen group-containing component, a resin.
[Requested item 9]
　Characterized in that an optical material, resin according to claim 8.
[Requested item 10]
　Characterized in that an optical lens, a resin of claim 9.
[Requested item 11]
　An isocyanate component containing xylylene diisocyanate composition of claim 1 and A agent,
　characterized by an active hydrogen group-containing component and agent B, a two-component resin material.
[Requested item 12]
　Characterized in that it is a coating material, according to claim 11 two-resin material.
[Requested item 13]
　An isocyanate component containing diisocyanate modified composition according to claim 4 and A agent,
　characterized by an active hydrogen group-containing component and agent B, a two-component resin material.
[Requested item 14]
　Characterized in that it is a coating material, according to claim 13 two-resin material.