FIELD OF THE INVENTION
The present invention pertains to a process for preparing
carboxymethylated alcohols. More particularly, the present invention relates
to a process for preparing carboxymethylated alcohols with surfactant like
properties5 .
BACKGROUND OF THE INVENTION
Fluoropolymers are primarily produced via heterogeneous polymerization
reactions, including suspension, emulsion and microemulsion systems.
10 Generally, each of these reactions requires at least one monomer and a
radical initiator in a suitable reaction medium. In addition, emulsion
polymerizations of fluoro- monomers require a surfactant capable of
emulsifying both the reactants and the reaction products for the duration of
the polymerization reaction. The most suitable surfactants for the synthesis
15 of fluoropolymers are perfluoroalkyl surfactants such as Perfluorooctanoic
acid (PFOA) and other short chain fluorinated surfactants. A high degree of
fluorination in a surfactant avoids atom transfer between a growing polymer
chain and the surfactant during polymerization. A non-fluorinated reactant
would result in lowered molecular weights in the product and likely inhibition
20 of the reaction. Fluoro-surfactants are expensive, specialized materials. In
addition, because of their high stability, they tend to persist in the
environment. Because of their resistance to chemical degradation,
fluoroalkyl surfactants have the potential to accumulate in the environment
and in organisms leading to high toxicity.
25 These surfactants have been banned and search is on for an alternative
approach to carry out fluoromonomer polymerization. In order to address
the environmental and toxicity issues, several different approaches have
been attempted to reduce or eliminate the use of fluorinated surfactants in
the polymerization of fluorinated monomers. One such approach is the use
30 of non-fluorinated surfactants instead of fluorinated surfactants.
3
Carboxymethylated alcohols represent a class of compounds with potential
surfactant like properties.
Numerous processes for the preparation of carboxymethylated alcohols are
disclosed in the prior art5 .
German patents 975,850 and 2,418,444, describe the process of obtaining
alcoholates from alcohol or ether alcohol by reacting with alkali
hydroxidefollowed by carboxy-methylation with sodium chloroacetateThe
major drawback of the aforestated processes is the long reaction period of
10 about 36 hours required to reach a substantial degree of conversion. In both
studies, it was concluded that when long chain alcohols are used, the yield
of the desired product during the subsequent carboxymethylation is greatly
reduced.
U.S. Pat. No. 2,183,853; British Patents 1,027,481 and 1,337,401 reported
15 the use of metallic sodium instead of sodium hydroxides for
carboxymethylation reaction. The use of metallic sodium, however, is
expensive, complicated and time consuming, and does not always lead to
satisfactory results. Carboxymethylation of alcohols, ether alcohols, or alkyl
phenols, thio(alcohols) and thio(ether alcohols) was reported in CA
20 1204771A and U.S. Patent 3,992,443, by reacting with chloroacetic acid and
aqueous base. An additional step for the ethoxylation of the alcohols before
reacting with chloroacetic acid and base was included in the process.
Although, this reaction is solvent free, it was carried out at an elevated
temperature of about 60-120oC, and under a pressure of about 10-100
25 mbar. The chloroacetic acid (80%) and the alkali solution (50%) in aqueous
medium were conveyed by means of metering pumps.
German Patent 2,418,444 teaches that free chloroacetic acid can be
employed in place of sodium chloroacetate, however, no detailed
30 instructions for carrying out the process are provided. Further, free
chloroacetic acid must be metered in the molten state, requiring
4
considerable expenditure for heatable containers, pumps, and pipelines.
Therefore, use of aqueous chloroacetic acid is preferable, as disclosed in
CA 1204771 A1. However, the reaction was carried out in biphasic system
and the resultant product was obtained as a biphasic solution wherein
exhaustive steps of phase separation followed by product separation wer5 e
required.
Dutch Patent 64534, reported that the presence of water has negative effect
on the carboxymethylation reaction. Similar observations was reported in
German Patent 2,418,444 and Japanese Patent Sho-50-24 215.
10
Therefore, there exists a need in the art to design a reaction protocol for
carboxymethylation of alcohol which is free from the initial presence of
water, economically feasible and easy to handle.
15 OBJECTIVES OF THE INVENTION
A basic objective of the present invention is to overcome the disadvantages
and drawbacks of the known art.
20 An objective of the present invention is to provide a process for the
production of carboxymethylated alcohol in a single step.
Another objective of the present invention to provide a process for the
production of carboxymethylated alcohols in a short time, with high degree
25 of conversion of the reactants.
Another objective of the invention is to provide a process for the
carboxymethylation of alcohols in ethanolic medium.
30 Yet another objective of the invention is to provide a process for the
production of carboxymethylated alcohol at ambient temperature.
5
Still another objective of the invention is to provide a carboxymethylated
alcohol that is highly pure, shows excellent solubility, conductivity, and
surfactant properties.
5
SUMMARY OF THE INVENTION
The present invention relates to a process for carboxymethylation of
alcohols that is easy to perform, more economical, single step, affords high
product yield and is amenable to large scale industrial production.
10
In accordance with an embodiment of the invention, there is provided a
process for the preparation of carboxymethylated alcohol, comprising
reacting alcohol, chloroacetic acid and hydroxide in a polar protic solvent;
wherein the alcohol is represented by the structure R-OH, R being a linear
or branched hydrocarbon chain having 6 to 36 carbon atoms15 .
In accordance with another embodiment of the invention there is provided a
process for the preparation of carboxymethylated alcohol, comprising
reacting alcohol, chloroacetic acid and hydroxide in a polar protic solvent,
20 wherein the reaction time is in the range of 10 to 30 min, wherein the
reaction is carried out at a temperature of 25 to 60 oC, wherein the ratio
between the reactants, namely alcohol, chloroacetic acid and hydroxide is
1:1:1-2 and wherein the yield of the reaction is between 65 to 75%.
25 In accordance with another embodiment, the reaction temperature ranges
from 25 to 40 oC. Preferably, the ratio between the reactants alcohol,
chloroacetic acid and hydroxide is 1:1:1.
Preferably the yield of the reaction is between 68 to 72%, more preferably
30 between 69 to 71% and most preferably about 70%.
6
The conductivities of the carboxymethylated alcohols prepared by the above
process are in the range of 23-25 ms/cm.
In accordance with an embodiment of the invention, the alcohol is
represented by the structure R-OH, R being a linear or branche5 d
hydrocarbon chain having 6 to 36 carbon atoms. Preferably, the alcohol is
selected from the group consisting of lauryl alcohol and 2-Hexyldecan-1-ol.
In accordance with another embodiment of the invention the polar protic
solvent is selected from the group consisting of methanol and ethanol.
10 Preferably, the hydroxide is an alkali metal hydroxide, alkaline earth metal
hydroxide or ammonium hydroxide, more preferably an alkali metal
hydroxide and most preferably sodium hydroxide.
In accordance with still another embodiment of the invention, the
15 carboxymethylated alcohol is represented by the structure R-O-CH2-
COOM, R being a linear or branched hydrocarbon chain having 6 to 36
carbon atoms and M is a cation selected from alkali metal cation, alkaline
earth metal cation and ammonium cation. More preferably, M is selected
from the group consisting of sodium cation, potassium cation and
20 ammonium cation and most preferably sodium cation.
Preferably, the carboxymethylated alcohol is selected from the group
consisting of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
hexyl)decyloxy]acetate.
25
BRIEF DESCRIPTION OF THE ACCOMPANYING DRAWINGS
The above and other features, aspects, and advantages of the subject
matter will be better understood with regard to the following description and
accompanying drawings.
30 Figure 1. FTIR spectra of (a) Sodium-2-Dodecyloxy acetate and (b) Sodium-
2-[(2-hexyl)decyloxy]acetate.
7
Figure 2. TGA thermogram of (a) Sodium-2-Dodecyloxy acetate and (b)
Sodium-2-[(2-hexyl)decyloxy]acetate.
Figure 3. DSC thermogram of (a) Sodium-2-Dodecyloxy acetate and (b)
Sodium-2-[(2-hexyl)decyloxy]acetate.
Figure 4. MALDI-MS of Sodium-2-Dodecyloxy acetat5 e
Figure 5. MALDI-MS of Sodium-2-[(2-hexyl)decyloxy]acetate
DETAILED DESCRIPTION OF THE INVENTION
Discussed below are some representative embodiments of the present
invention. The invention in its broader aspects is not limited to the specific
10 details and representative methods. Illustrative examples are described in
this section in connection with the embodiments and methods provided.
It is to be noted that, as used in the specification, the singular forms "a,"
"an," and "the" include plural referents unless the context clearly dictates
otherwise. Thus, for example, reference to a composition containing “a
15 compound” includes a mixture of two or more compounds. It should also be
noted that the term "or” is generally employed in its sense including “and/or”
unless the content clearly dictates otherwise.
The expression of various quantities in terms of “%” or “% w/w” means the
20 percentage by weight of the total solution or composition unless otherwise
specified.
All cited references are incorporated herein by reference in their entireties.
Citation of any reference is not an admission regarding any determination
25 as to its availability as prior art to the claimed invention.
The present invention pertains to a process for the synthesis of
carboxymethylated alcohols. A simple, easy and single-step protocol was
implemented for the synthesis as follows. The process comprises reacting
30 alcohol, chloroacetic acid and hydroxide in a polar protic solvent, at a
8
temperature ranging from 25 to 60 oC to afford carboxymethylated alcohols
in yields ranging from 65 to 75%, preferably from 68 to 72%, more preferably
from 69 to 71% and most preferably about 70%. Preferably, the reaction
temperature ranges from 25 to 45 oC.
The reaction sequence is as follow5 s:
R-OH + MOH  R-OM + H2O
R-OM + ClCH2COOH + MOH  ROCH2COOM
10 R = linear or branched hydrocarbon chain having 6 to 36 carbon atoms,
M = cation selected from alkali metal cation, alkaline earth metal cation and
ammonium cation
Typically, the reaction time ranges from 10 to 30 min, and the ratio between
15 the reactants, namely alcohol, chloroacetic acid and hydroxide is 1:1:1-2
respectively. In a preferred embodiment, the ratio between the reactants
alcohol, chloroacetic acid and hydroxide is 1:1:1 respectively.
The alcohols useful in the present invention are represented by the
20 structure- R-OH, R being a linear or branched hydrocarbon chain having 6
to 36 carbon atoms. Preferably, the alcohol is selected from the group
consisting of lauryl alcohol and 2-Hexyldecan-1-ol. The carboxymethylation
reaction is preferably carried out in a polar protic solvent, which is selected
from the group consisting of methanol and ethanol. In a preferred
25 embodiment, the carboxymethylation reaction is carried out in ethanol.
Hydroxides useful for the carboxymethylation reaction include alkali metal
hydroxide, alkaline earth metal hydroxide or ammonium hydroxide.
Examples of alkali metal hydroxides useful in the present invention include
9
lithium hydroxide, sodium hydroxide and potassium hydroxide. In a
preferred embodiment, the alkali metal hydroxide is sodium hydroxide.
The carboxymethylated alcohols obtained from the aforestated
carboxymethylation reaction are represented by the structure- R-O-CH25 -
COOM, R being a linear or branched hydrocarbon chain having 6 to 36
carbon atoms and M is a cation selected from alkali metal cation, alkaline
earth metal cation and ammonium cation. More preferably, M is selected
from the group consisting of sodium cation, potassium cation and
10 ammonium cation.
Preferably, the carboxymethylated alcohol is either Sodium-2-Dodecyloxy
acetate or Sodium-2-[(2-hexyl)decyloxy]acetate.
15 For carrying out the carboxymethylation reaction, the alcohol was reacted
with hydroxide in ethanol to form the corresponding alcoholate. Thereafter,
the alcoholate was reacted with chloroacetic acid in ethanol to afford a white
precipitate of carboxymethylated alcohol. The various reaction parameters
such as reactant ratio, reaction time and reaction temperature were
20 optimized and are presented in the examples below. Finally, the product was
isolated by vacuum filtration as white shiny powder. Physical and chemical
properties of the carboxymethylated alcohols were analyzed by various
characterizing techniques and are described below in suitable examples.
25 The present invention is more particularly described in the following
examples that are intended as illustration only, since numerous
modifications and variations within the scope of the present invention will be
apparent to those of skill in the art. Unless otherwise noted, all parts,
percentages, and ratios reported in the following examples are on a weight
30 basis, and all reagents used in the examples were obtained or are available
from the chemical suppliers.
10
The following examples illustrates the basic methodology and versatility of
the present invention.
Example 1
Optimization of reactant molar ratio5 s
In general, equimolar mixtures of starting alcohol (lauryl alcohol or 2-hexyl
1-decanol), chloroacetic acid and sodium hydroxide were employed. The
carboxymethylation reaction was carried out by varying the reactant molar
ratios. The optimized reactant ratio for the carboxymethylation reaction was
10 1:1:1 for alcohol, chloroacetic acid and sodium hydroxide respectively. The
maximum yield afforded was ~70% for both Sodium-2-Dodecyloxy acetate
and Sodium-2-[(2-hexyl)decyloxy]acetate.
Example 2
15 Optimization of the reaction time
The carboxymethylation reaction was also carried out for different time
intervals. Although the carboxymethylated alcohol was formed immediately,
the influence of reaction time on the yield of the reaction was studied. The
reaction time was varied from 10 min to 2 h, however, the yield of the product
20 did not show any noticeable increase with increase in reaction time beyond
30 min. Therefore, the optimized reaction time for the carboxymethylation
reaction was 30 min, and the maximum yield was ~70% for both Sodium-2-
Dodecyloxy acetate and Sodium-2-[(2-hexyl)decyloxy]acetate respectively.
25 Example 3
Optimization of the reaction temperature
The reaction was also performed at different temperatures. The reaction
was ordinarily conducted at ambient or slightly elevated temperatures in the
range of 25 to 60°C. Below 25°C, the reaction was too slow for a commercial
30 process and a reaction temperature above 60°C was not advisable due to
the presence of ethanol in the reaction mixture. Therefore, the optimized
11
temperature for the carboxymethylation reaction was 40°C and the
maximum yield obtained was ~70% for both Sodium-2-Dodecyloxy acetate
and Sodium-2-[(2-hexyl)decyloxy]acetate respectively.
Example 5 4
Optimization of the solvent
Water, ethanol and their combinations were utilized as solvents for the
carboxymethylation of alcohols. In case of water, the reaction was sluggish
due to the insolubility of fatty alcohols (lauryl alcohol and 2-hexyl-1-decanol)
10 in water and existence of two immiscible phases in the reaction mixture. In
case of ethanol, the reaction was facile as all the reactants were soluble in
ethanol to form a single phase. The reaction was also carried out in a binary
mixture of water and ethanol, however, the reaction did not proceed as
expected. Therefore, ethanol is a preferred solvent for the
15 carboxymethylation reaction of the present invention.
Example 5
Preparation of Sodium-2-Dodecyloxy acetate
Sodium-2-Dodecyloxy acetate was prepared as follows. Initially, Lauryl
20 alcohol was reacted with sodium hydroxide in ethanol at 30 oC ±2 to form
sodium salt of lauryl alcohol. Thereafter, ethanolic solution of chloroacetic
acid was added at 30 oC ±2 to afford white precipitate of Sodium-2-
Dodecyloxy acetate. The reaction was over in 30 minutes and lauryl alcohol,
chloroacetic and sodium hydroxide were used in a ratio of 1:1:1. Vacuum
25 filtration and washing with ethanol afforded Sodium-2-Dodecyloxy acetate
as white shiny powder (Yield: 70%).
Example 6
Preparation of Sodium-2-[(2-hexyl)decyloxy]acetate
30 Sodium-2-[(2-hexyl)decyloxy]acetate was prepared as follows. Initially, 2-
Hexyldecan-1-ol was reacted with sodium hydroxide in ethanol at 30 oC ±2
12
to form sodium salt of 2-Hexyldecan-1-ol. Thereafter, ethanolic solution of
chloroacetic acid was added at 40 oC ±2 to afford white precipitate of
Sodium-2-[(2-hexyl)decyloxy]acetate. The reaction was over in 30 minutes
and 2-Hexyldecan-1-ol, chloroacetic and sodium hydroxide were used in a
ratio of 1:1:1. Vacuum filtration and washing with ethanol afforded Sodium5 -
2-[(2-hexyl)decyloxy]acetate as white shiny powder (Yield: 70%).
Example 7
Physical properties of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
10 hexyl)decyloxy]acetate
Physical properties of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
hexyl)decyloxy]acetate were compared with that of commercially available
short chain fluorinated surfactants. Both Sodium-2-Dodecyloxy acetate and
Sodium-2-[(2-hexyl)decyloxy]acetate were white in colour, and odourless.
15 Both Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
hexyldecyloxy)]acetate show excellent purity. Purity of the above
compounds was analyzed by titration method. The conductivity of Sodium-
2-Dodecyloxy acetate and Sodium-2-[(2-hexyl)decyloxy]acetate was
observed in the range of 23-25 ms/cm. They also exhibited excellent
20 solubility comparable to commercially available short chain fluorinated
surfactants. The aforestated physical properties are presented in Table 1
below.
25
30
13
Table 1
Example 8
FTIR analysis of Sodium-2-Dodecyloxy acetate and Sodium-2-[(5 2-
hexyl)decyloxy]acetate.
The functional group interactions and formation of new linkages in both
Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-hexyl)decyloxy]acetate
were investigated by FTIR techniques. The spectra were recorded by using
10 Nicolet-6700 by potassium bromide disk technique, in the range of 4000–
400 cm−1 with a resolution of 4 cm-1 and averaged over 64 scans. The
DESCRIPTIONS UNIT
Sodium-2-
Dodecyloxy
acetate
Sodium-2-[(2-
hexyldecyloxy)]ace
tate
Method/Remarks
Appearance - White powder White powder Visually
Odour - Odourless Odourless -
pH (5% Soln) - 8.38 7.32 pH Mater
Conductivity ms/cm 23.90 23.50 Comparable to
commercially
available short
chain fluorinated
surfactants
Purity % 99.23 98.89 Titration method
Density g/mol 0.9998 0.9996 -
Solubility g/sec 5 / 30 5 / 45 Comparable to
commercially
available short
chain fluorinated
surfactants
14
carboxymethylation of alcohols was confirmed by monitoring the specific
ether linkage and carboxylate groups in the structure of carboxymethylated
alcohols.
FTIR spectra of (a) Sodium-2-Dodecyloxy acetate and (b) Sodium-2-[(2-
hexyl)decyloxy]acetate is presented in Figure 1. The backbone of the lon5 g
alkyl chain present in the carboxylated alcohol, which is inherited from lauryl
alcohol and 2-hexyl-1-decanol appears at 2941 cm-1 and 3006 cm-1. This
was higher compared to 2858 cm-1 and 2922 cm- for lauryl alcohol. Similar
observations were made in the case of Sodium-2-[(2-
10 hexyldecyloxy)]acetate. The characteristic strong peak in both Sodium-2-
Dodecyloxy acetate and Sodium-2-[(2-hexyl)decyloxy]acetate appeared at
1619 cm-1 and 1630 cm-1 respectively (Figure 1), which can be attributed to
the C=O stretching of the carboxylate ion in regard to its coupling with the
other oxygen atom. The peak at 1411 cm-1 can be attributed to the stretching
15 of the C-OH band which on deprotonation gets shifted to higher energy.
There is an appearance of new peak at 1257 cm-1 and 1245 cm-1 in Sodium-
2-Dodecyloxy acetate and Sodium-2-[(2-hexyl)decyloxy]acetate
respectively, which can be attributed to the newly formed ether linkage in
the product after carboxymethylation of respective alcohols. The
20 characteristic peaks of carboxylate and ether bond (Figure 1) support the
formation of a carboxymethylated alcohol.
Example 9
Thermogravimetric analysis of Sodium-2-Dodecyloxy acetate and Sodium-
25 2-[(2-hexyl)decyloxy]acetate.
The thermal behaviour of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
hexyl)decyloxy]acetate was investigated by Thermogravimetric analysis
using TA-Instruments in the range of 50 to 600°C at a heating rate of
10°C/min under nitrogen. Both the compounds show similar two-step
30 degradation pattern due to similar structural properties as shown in Figure
2. The initial decomposition of the compounds starts at ~200°C, which
15
indicates dehydration, whereas the second decomposition starts in the
range of 300 to 350°C due to the decarboxylation of the surfactants.
Example 10
Differential scanning calorimetry (DSC) analysis of Sodium-2-Dodecylo5 xy
acetate and Sodium-2-[(2-hexyl)decyloxy]acetate.
In the present invention the DSC analysis of Sodium-2-Dodecyloxy acetate
and Sodium-2-[(2-hexyl)decyloxy]acetate was carried out by using
Universal V4.5A TA Instrument in the range of -50 to 300°C at the heating
10 rate of 10K/min under nitrogen. DSC thermograms of both the compounds
are shown in Figure 3. Both thermograms show similar phase change w.r.t
temperature due to the presence of fatty long alkyl chains of hydrocarbons
in the above carboxymethylated alcohols. Sodium-2-Dodecyloxy acetate
shows melting at 207°C, whereas Sodium-2-[(2-hexyl)decyloxy]acetate
15 shows the melting at 202°C.
Example 11
MALDI-MS analysis of (a) Sodium-2-Dodecyloxy acetate and (b) Sodium-2-
[(2-hexyl)decyloxy]acetate.
20 MALDI coupled Mass spectroscopy analysis was carried out for the
molecular weight determination of Sodium-2-Dodecyloxy acetate and
Sodium-2-[(2-hexyl)decyloxy]acetate. The instrument, Bruker
UltrafleXtreme MALDI-TOF/TOF Mass Spectrometer, was used in a
scanning speed of 2 kHz in TOF mode. MALDI-MS spectra of the above
25 compounds in positive ion mode were recorded in water and the mass
spectra of the compounds displayed intact molecular ion peaks.
Theoretically calculated molecular weight of Sodium-2-Dodecyloxy acetate
is ~266 g/mol and the molecular weight of Sodium-2-[(2-
hexyl)decyloxy]acetate is ~323 g/mol. The molecular weights of the
30 aforestated compounds in ionized form as m/z ratio were observed by
MALDI-MS (Figure 4, 5). Various matrices were used in scanning of MALDI16
MS and various peaks at different intensity were observed. But the peak at
maxima indicates the actual molecular weight of the compound in ionized
state as m/z ratio.
Example 5 12
Elemental analysis of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
hexyl)decyloxy]acetate
The elemental analysis of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
hexyl)decyloxy]acetate was carried out by energy dispersive X-ray analysis
10 (EDX) RONTEC’s EDX Model QuanTax 200 (SDD technology, USA). The
samples were placed on an aluminum sample stub and coated with carbon
using Auto-Fine Coater JFC-1600 (Joel, USA Inc., USA). The EDX spectrum
showed individual energy peaks for different elements present in the
sample. Both Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
15 hexyl)decyloxy]acetate showed identical characteristic peaks. Distinctive
energy peaks at around 0.2 keV indicate the characteristic peaks for carbon
and oxygen. Another important characteristic peak at ~1 keV was observed
in both the compounds which indicate the presence of sodium. The EDX
pattern of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2-
20 hexyl)decyloxy]acetate is presented in Table 2.
Table 2
17
Example 13
Surfactant behaviour of (a) Sodium-2-Dodecyloxy acetate and (b) Sodium-
2-[(2-hexyl)decyloxy]acetate
Both (a) Sodium-2-Dodecyloxy acetate and (b) Sodium-2-[(2-
hexyl)decyloxy]acetate are intended for use as a hydrocarbon based non5 -
fluorinated surfactant for the emulsion polymerization of fluoro-monomers.
Therefore, it was necessary to investigate their surfactant behaviour. Oil-inwater
emulsion of heptane and water was prepared in a ratio of
9(water):1(heptane). Without addition of either (a) Sodium-2-Dodecyloxy
10 acetate or (b) Sodium-2-[(2-hexyl)decyloxy]acetate the heptane water
mixture showed two distinct layers of solvents. But after addition of either
(a) Sodium-2-Dodecyloxy acetate or (b) Sodium-2-[(2-
hexyl)decyloxy]acetate a one phase solution was obtained. Although both
(a) Sodium-2-Dodecyloxy acetate and (b) Sodium-2-[(2-
15 hexyl)decyloxy]acetate are mild compared to other conventionally used
surfactants, above 6%, both compounds exhibit excellent surfactant
behavior.
The invention may be embodied in other specific forms without departing
20 from the spirit or essential characteristics thereof. The present embodiments
are therefore to be considered in all respects as illustrative and not
restrictive.

We Claim:
1. A process for the preparation of carboxymethylated alcohol,
comprising reacting alcohol, chloroacetic acid and hydroxide in a
polar protic solvent; wherein the alcohol is represented by th5 e
structure R-OH, R being a linear or branched hydrocarbon chain
having 6 to 36 carbon atoms.
2. The process as claimed in claim 1, wherein the reaction time is in the
range of 10 to 30 min.
10 3. The process as claimed in claims 1 and 2, wherein the reaction is
carried out at a temperature of 25 to 60 oC.
4. The process as claimed in claims 1 to 3, wherein the ratio between
the reactants, alcohol, chloroacetic acid and hydroxide is 1:1:1-2.
5. The process as claimed in claims 1 to 4, wherein the yield of the
15 reaction is between 65 to 75%.
6. The process as claimed in claims 3 to 5, wherein the reaction
temperature ranges from 25 to 40 oC.
7. The process as claimed in claims 4 to 6, wherein the ratio between
alcohol, chloroacetic acid and hydroxide is 1:1:1.
20 8. The process as claimed in claims 5 to 7, wherein the yield of the
reaction is between 68 to 72%, preferably between 69 to 71% and
more preferably 70%.
9. The process as claimed in claims 1 to 8, wherein the conductivities
of the carboxymethylated alcohols are in the range of 23-25 ms/cm.
25 10.The process as claimed in claims 1 to 9, wherein the alcohol is
selected from the group consisting of lauryl alcohol or 2-Hexyldecan-
1-ol.
11.The process as claimed in claims 1 to 10, wherein the polar protic
solvent is selected from the group consisting of methanol or ethanol.
19
12.The process as claimed in claims 1 to 11, wherein the hydroxide is
an alkali metal hydroxide, alkaline earth metal hydroxide or
ammonium hydroxide.
13.The process as claimed in claim 12, wherein the alkali metal
hydroxide is sodium hydroxide5 .
14.The process as claimed in claims 1 to 13, wherein the
carboxymethylated alcohol is represented by the structure R-O-CH2-
COOM, R being a linear or branched hydrocarbon chain having 6 to
36 carbon atoms and M is a cation selected from alkali metal cation,
10 alkaline earth metal cation and ammonium cation.
15. The process as claimed in claims 1 to 14, wherein carboxymethylated
alcohol is selected from the group consisting of Sodium-2-
Dodecyloxy acetate or Sodium-2-[(2-hexyl)decyloxy]acetate.