FORM 2
THE PATENT ACT 1970 (39 OF 1970) & The Patent Rules , 2003 Complete Specification (See Section 10 and Rule 13)
Title of the Invention: A Process for Preparing 2(2-chloroethoxy) ethanol
Applicants Name and Address: Viswaat chemicals limited,
Plot No.1, Addl. Ambernath, MIDC, Anand Nagar, Ambernath(E)-421506
The following specification particularly describes the invention and the manner in which it is to be performed

Title: A Process for Preparing 2(2-chloroethoxy) ethanol
Technical Field
The present invention belongs to the chemical industry, in particular to a Pharmaceutical intermediate 2-chloroethoxyethanol.
2-chloroethoxyethanol preparation method thereof
Back Ground of the invention:
Japanese Patent JPS58109441, describes to prepare 2(2-chloroethoxy) ethanol from the reaction mixture of diethylene glycol and hydrogen chloride, in high purity and yield, by using a solvent selected from 1-3C aliphatic chlorinated hydrocarbon, 4-8C aliphatic ether and 6-9C aromatic hydrocarbon, as an extractant. A reaction mixture containing 2-(2'-chloroethoxy)ethanoI and obtained by the reaction of diethylene glycol with hydrogen chloride is extracted with one or more solvents selected from 1-3C aliphatic chlorinated hydrocarbons (especially saturated aliphatic chlorinated hydrocarbons free from H, such as carbon tetrachloride, hexachloroethane, etc.), 4-8C aliphatic ethers and 6-9C aromatic hydrocarbons (especially a mixture of benzene, toluene or ethylbenzene with xylene). The extractant is distilled off, and the remaining product is purified by distillation to obtain 2-(2'chloroethoxy)ethanol useful as a raw material of polyoxyethylene ether having definite distribution of the polymerization degree etc. 2-chloroethoxyethanol, referred 2CEE, is a colorless transparent liquid, having formula.

In the prior art as mentioned, and disclosed prior publication describes the following with specific draw backs as under,
a. Taking Diethylene glycol ether with HC1 direct reaction to give 2-chloroethoxyethanol

b. Production with single etherification of 2- Chloroethanol with ethylene glycol as per below
reaction

The said method still has the issues of bad selectivity, low yield of target product and high cost.

c. Use 1,3-dioxolane compound as base material and reacted with chloroacetaldehyde under the
presence of boron trichloride as catalyst, the synthesis route as below. The base material
required in above synthesis is difficult to obtain and hence commercially not feasible.

d. Use 1,4 dioxane as base materials , the synthesis route is as follows,
The method is still at theoretical stage and hence not suitable for industrial production.

e. Use ethylene oxide as a base material and react with chloroethoxy ester compounds and then
undertake hydrolysis, route as below, Inside X is boron, carbonyls etc. The method is still at
theoretical stage and hence not helpful for commercial production

f. Boric acid is converted in to Metaboric acid and reacted with diethylene glycol followed by
chlorination with thionyl catalyst and finally hydrolysis of the complex to get 2-(2-
chloroethoxy)ethan-l-oI and boric acid. This method claims 68% yield. But this reaction
generates heavy amount of effluent.


The main problem of the above methods is poor selectivity, low yields, difficult to prepare and effluent generation is very high, which are not suitable for commercial production.
For the above mentioned drawbacks in the prior art, the technical problem to be solved by the present invention is to provide a method for the preparation of 2-chloroethoxyethanoI, this method, wherein, to solve the selectivity of the prior art production method, the yield is low, difficult to prepare, is not conducive to industrial production. Objects of the invention:
The present invention address all draw back associated with the prior art, and achieved higher purity, higher yield, no effluent, less pollution causing, accordingly, The primary object of the invention set to prepare a high pure, with higher yield, 2(2-chloroethoxy ethanol
Further of object of the invention is that the method is cheaper and economical thereby produces higher the yield and at higher purity.
Description of the invention:
The present invention relates to an improved method to prepare a 2(2-chloroethoxy) ethanol, with higher purity and yield, with negligible impurity, the said improved process comprising the following steps,
1) taking the reactants 2-chloroethanol and ethylene oxide are weighed in a molar ratio of 2-chloroethanol and ethylene oxide in the first 7 to 9 ; 1, 2- chloroethanol and the first ring ethylene oxide in the presence of a catalyst Lewis acids such as boron trifluoride etherate under reaction conditions to produce 2-chloroethoxyethanol (2CEE) along with 2-chloro-2-ethoxyethoxyethanol (2CEEE) and its higher homologues (2CEE)n under catalyst and reaction conditions as mentioned
2) After the completion of the reaction, reaction mass is subjected to distillation under vacuum to recover excess 2-chloroethanol;
3) After recovery of 2-chloroethanol, mass continued to further distillation under reduced pressure to collect 2-chloroethoxyethanol and solvent,
4) the catalyst for the reaction selected Lewis acids such as boron trifluoride etherate and its derivatives used as a catalyst, Zinc chloride, stannous chloride and Ferric chloride. The amount of catalyst loading is 0.3% to 0.6 mass% of the catalyst is preferably added on 2-chloroethanol.
5) the preferred reaction temperature maintained at 10-100°C, the reaction time is 1.5 hrs to 2 hrs,
6) the degree of vacuum during distillation is 10-15mmHgand temperature of 100 ~ 110 ° C.
The present invention relates to a reaction formula as follows


The present invention is 2-chloroethanol as a raw material, through one step ethoxylation to form 2-chloroethoxyethanol.This method is an effective solution for the kind of impurities formed by direct chlorination. The present invention provides a method for preparing 2-chloroethoxy ethanol using 2-chloroethanol, which is used as a reactant and solvent and also recycled form further use. This method is economical and cost effective. There is a minimum effluent is generated during the process. Hence this process is superior to prior art. The best method of performing the invention is being exampled with following examples,
Scheme
Example 1
In 1000 mL three necked flask was added 2-chloroethanol 644g (8.0mol), BF3.etherate 2.0g, agitator and heater, heated to 40-50 °C(the reaction temperature was maintained between 10-100° C, to control the epoxy ethane access speed, can be used if necessary in a water bath temperature 44g of ethylene oxide was slowly introduced into the flask through the time of 1.5-2h. After the completion of reaction, and stirring was continued for extra 0.5h. Reaction mass was subjected to fractional distillation vacuum between 10-20 mm Hg and temperature below 105 ° C. During distillation, 2-chloroethanol collected about 480g (which can be recycled), followed byproduct, 2-chloroethoxyethanol along with 2-chloro-2-ethoxyethoxyethanol (2CEEE) and its higher homologues (2CEE)n. After completion of the 2-chloroethanol recovered, heating the remaining bottom mass to take middle distillate cut distillate temperature of 100-105 ° C, (vacuum 10-20mm Hg) is obtained as a colorless transparent liquid, the target product, 2-chloroethoxyethanol, 100g of the total.
Example 2
In 1000 mL three necked flask was added 2-chloroethanol 644g (8.0mol), BF3.acetic acid 2.0g, agitator and heater, heated to 40-50 °C(the reaction temperature was maintained between 10-100° C, to control the epoxy ethane access speed, can be used if necessary in a water bath temperature 44g of

ethylene oxide was slowly introduced into the flask through the time of 1.5-2h. After the completion of reaction, and stirring was continued for extra 0.5h. Reaction mass was subjected to fractional distillation vacuum between 10-20 mm Hg and temperature below 105 ° C. During distillation, 2-chloroethanol collected about 480g (which can be recycled), followed byproduct, 2-chloroethoxyethanol along with 2-chloro-2-ethoxyethoxyethanol (2CEEE) and its higher homologues (2CEE)n. After completion of the 2-chloroethanol recovered, heating the remaining bottom mass to take middle distillate cut distillate temperature of 100-105 ° C, (vacuum 10-20mm Hg) is obtained as a colorless transparent liquid, the target product, 2-chloroethoxyethanol, l00g of the total.
Example 3
In 1000 mL three necked flask was added 2-chloroethanol 644g (8.0mol), BF3.Tetrahydrofuran 2.0g, agitator and heater, heated to 40-50 °C(the reaction temperature was maintained between 10-100° C, to control the epoxy ethane access speed, can be used if necessary in a water bath temperature 44g of ethylene oxide was slowly introduced into the flask through the time of 1.5-2h. After the completion of reaction, and stirring was continued for extra 0.5h. Reaction mass was subjected to fractional distillation vacuum between 10-20 mm Hg and temperature below 105 ° C. During distillation, 2-chloroethanol collected about 480g (which can be recycled), followed byproduct, 2-chloroethoxyethanol along with 2-chloro-2-ethoxyethoxyethanol (2CEEE) and its higher homologues (2CEE)n. After completion of the 2-chloroethanol recovery, heating the remaining bottom mass to take middle distillate cut distillate temperature of 100-105 ° C, (vacuum 10-20mm Hg) is obtained as a colorless transparent liquid, the target product, 2-chloroethoxyethanol, lOOg of the total.
The structure of the product confirmed:
IRcm-1: 3388,2869, 1120, 1044.
H1(CDCl3-400 MHz): δ 3.67 (2H, /), δ 3.64 (2H, t), δ 3.56 (2H, t), δ 3.52 (2H, /), δ 3.06 (1H, s)
C13 (CDC13_400 MHz): δ 72.35, 8 71.00, δ 61.40, δ 42.84.
Mass: 125(M+1)
Conclusion: The conversion of A to C was studied in the presence of different catalysts, and a much higher conversion was obtained with BF3 etherate and BF3. acetic acid. All the co-products were removed by fractional distillation of the reaction mixture.
It was observed that the presence of other Lewis acids is effective in the completion of ethoxylation of A. The optimum conditions for maximum yield and purity of C for different catalyst were obtained. The result of this study will be of immense help for further study in this reaction, and it will also help in the scale-up of the process. The study will also be of value to the design engineers for designing a plant for the manufacture.

We Claim,
1. An improved method to prepare a 2(2-chloroethoxy) ethanol, with higher purity and yield,
with negligible impurity, the said improved method comprising the following steps,
1) taking the reactants 2-chloroethanol and ethylene oxide are weighed in a molar ratio
of 2-chloroethanol and ethylene oxide in the first 7 to 9 : 1,2- chloroethanol and the first ring
ethylene oxide in presence of a catalyst boron trifluorideetherate and its derivatives, Zinc
chloride, stannous chloride and Ferric chloridein the range of 0.3% to 0.6 mass% of the
catalyst is preferably added on 2-chloroethanol, under reaction conditions to produce 2-
chloroethoxyethanol (2CEE) along with 2-chIoro-2-ethoxyethoxyethanol (2CEEE) and its
higher homologues (2CEE)
2) After the completion of the reaction, reaction mass is subjected to distillation under
vacuum to recover excess 2-chloroethanol;
3) After recovery of 2-chloroethanol, mass continued to further distillation under reduced pressure to collect 2-chloroethoxyethanol and solvent,
4) the catalyst for the reaction selected Lewis acids such as boron trifluoride diethylether or acetic acid adduct or pyridine or THF adduct and so on. This reaction also works well with Zinc chloride, Stannous chloride and Ferric chloride, the amount of catalyst to the total mass of the system is 0.2- 0.3%.
5) the preferred reaction temperature maintained at 10-l00oC, the reaction time is 1.5 hrs to 2 hrs,
6) the degree of vacuum during distillation is l-15mmHg and temperature of 100 ~ 110 °C.