WO2020165915A1

WO2020165915A1 - A process for the preparation of carboxymethylated alcohol

Info

Publication number: WO2020165915A1
Application number: PCT/IN2020/050133
Authority: WO
Inventors: Bhuvanesh Gupta; Bishwajit Santosh BHATTACHARYA; Rajeev Chauhan; Jitendra Kumar RATHOUR; Gaurav Kumar; Chetna Verma
Original assignee: Gujarat Fluorochemicals Limited; Indian Institute Of Technology Delhi
Priority date: 2019-02-11
Filing date: 2020-02-10
Publication date: 2020-08-20

Abstract

The present invention discloses a process for the preparation of carboxymethylated alcohol, comprising: reacting alcohol, chloroacetic acid and hydroxide in a polar protic solvent, 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 °C, wherein the ratio between the reactants alcohol, chloroacetic acid and hydroxide is 1:1:1-2 and wherein the yield of the reaction is between 65 to 75%.

Description

TITLE

A PROCESS FOR THE PREPARATION OF CARBOXYMETHYLATED

ALCOHOL

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 properties.

BACKGROUND OF THE INVENTION

Fluoropolymers are primarily produced via heterogeneous polymerization reactions, including suspension, emulsion and microemulsion systems. 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 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 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.

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 of non-fluorinated surfactants instead of fluorinated surfactants. Carboxymethylated alcohols represent a class of compounds with potential surfactant like properties.

Various processes for the preparation of carboxymethylated alcohols are disclosed in the prior art.

German patents 975,850 and 2,418,444, describe the process of obtaining alcoholates from alcohol or ether alcohol by reacting with alkali hydroxide followed by carboxy-methylation with sodium chloroacetate. The major drawback of the aforestated processes is the long reaction period of 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 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 1204771 A 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 60-120°C, and under a pressure of about 10-100 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 instructions for carrying out the process are provided. Further, free chloroacetic acid must be metered in the molten state, requiring 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 were 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.

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.

OBJECTIVES OF THE INVENTION

A basic objective of the present invention is to overcome the disadvantages and drawbacks of the known art.

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 of conversion of the reactants.

Another objective of the invention is to provide a process for the carboxymethylation of alcohols in ethanolic medium.

Yet another objective of the invention is to provide a process for the production of carboxymethylated alcohol at ambient temperature. Still another objective of the invention is to provide a carboxymethylated alcohol that is highly pure, shows excellent solubility, conductivity, and surfactant properties.

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.

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 atoms.

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, 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 °C, 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%.

In accordance with another embodiment, the reaction temperature ranges from 25 to 40 °C. 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 between 69 to 71 % and most preferably about 70%. The conductivities of the carboxym ethylated 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 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. In accordance with another embodiment of the invention the polar protic solvent is selected from the group consisting of methanol and ethanol. 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 carboxym ethylated 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 ammonium cation and most preferably sodium cation.

Preferably, the carboxym ethylated alcohol is selected from the group consisting of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2- hexyl)decyloxy]acetate.

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.

Figure 1 . FTIR spectra of (a) Sodium-2-Dodecyloxy acetate and (b) Sodium- 2-[(2-hexyl)decyloxy]acetate. 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 acetate

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 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 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 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 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 alcohol, chloroacetic acid and hydroxide in a polar protic solvent, at a temperature ranging from 25 to 60 °C to afford carboxym ethylated 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 °C.

The reaction sequence is as follows:

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 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 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 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 lithium hydroxide, sodium hydroxide and potassium hydroxide. In a preferred embodiment, the alkali metal hydroxide is sodium hydroxide.

The carboxym ethylated alcohols obtained from the aforestated carboxymethylation reaction are 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 ammonium cation.

Preferably, the carboxymethylated alcohol is either Sodium-2-Dodecyloxy acetate or Sodium-2-[(2-hexyl)decyloxy]acetate.

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 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.

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 basis, and all reagents used in the examples were obtained or are available from the chemical suppliers. The following examples illustrates the basic methodology and versatility of the present invention.

Example 1

Optimization of reactant molar ratios

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 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

Optimization of the reaction time

The carboxymethylation reaction was also carried out for different time intervals. Although the carboxym ethylated 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 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.

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 process and a reaction temperature above 60°C was not advisable due to the presence of ethanol in the reaction mixture. Therefore, the optimized 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 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) 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 carboxymethylation reaction of the present invention.

Example 6

Preparation of Sodium-2-Dodecyloxy acetate

Sodium-2-Dodecyloxy acetate was prepared as follows. Initially, Lauryl alcohol was reacted with sodium hydroxide in ethanol at 30 °C ±2 to form sodium salt of lauryl alcohol. Thereafter, ethanolic solution of chloroacetic acid was added at 30 °C ±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 filtration and washing with ethanol afforded Sodium-2-Dodecyloxy acetate as white shiny powder (Yield: 70%).

Example 7

Preparation of Sodium-2-[(2-hexyl)decyloxy]acetate

Sodium-2-[(2-hexyl)decyloxy]acetate was prepared as follows. Initially, 2- Hexyldecan-1 -ol was reacted with sodium hydroxide in ethanol at 30 °C ±2 to form sodium salt of 2-Hexyldecan-1 -ol. Thereafter, ethanolic solution of chloroacetic acid was added at 40 °C ±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 Sodium- 2-[(2-hexyl)decyloxy]acetate as white shiny powder (Yield: 70%).

Example 8

Physical properties of Sodium-2-Dodecyloxy acetate and Sodium-2-[(2- 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. 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 solubility comparable to commercially available short chain fluorinated surfactants. The aforestated physical properties are presented in Table 1 below.

Table 1

Example 9

FTIR analysis of Sodium-2-Dodecyloxy acetate and Sodium-2-[(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 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 carboxym ethylation of alcohols was confirmed by monitoring the specific ether linkage and carboxylate groups in the structure of carboxym ethylated 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 long 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- 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=0 stretching of the carboxylate ion in regard to its coupling with the other oxygen atom. The peak at 141 1 cm^-1 can be attributed to the stretching of the C-OFI 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 characteristic peaks of carboxylate and ether bond (Figure 1 ) support the formation of a carboxym ethylated alcohol.

Example 10

Thermoqravimetric analysis of Sodium-2-Dodecyloxy acetate and Sodium- 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-lnstruments 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 degradation pattern due to similar structural properties as shown in Figure 2. The initial decomposition of the compounds starts at ~200°C, which indicates dehydration, whereas the second decomposition starts in the range of 300 to 350°C due to the decarboxylation of the surfactants.

Example 11

Differential scanning calorimetry (DSC) analysis of Sodium-2-Dodecyloxy 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 rate of 10K/m in 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 carboxym ethylated alcohols. Sodium-2-Dodecyloxy acetate shows melting at 207°C, whereas Sodium-2-[(2-hexyl)decyloxy]acetate shows the melting at 202°C.

Example 12

MALDI-MS analysis of (a) Sodium-2-Dodecyloxy acetate and (b) Sodium-2- [(2-hexyl)decyloxy]acetate.

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 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 aforestated compounds in ionized form as m/z ratio were observed by MALDI-MS (Figure 4, 5). Various matrices were used in scanning of MALDI- 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 13

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 (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- 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- hexyl)decyloxy]acetate is presented in Table 2.

Table 2

Example 14

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 non- fluorinated surfactant for the emulsion polymerization of fluoro-monomers. Therefore, it was necessary to investigate their surfactant behaviour. Oil-in water emulsion of heptane and water was prepared in a ratio of 9(water):1 (heptane). Without addition of either (a) Sodium-2-Dodecyloxy 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- 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 from the spirit or essential characteristics thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive.

Claims

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 the 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.

3. The process as claimed in claims 1 and 2, wherein the reaction is carried out at a temperature of 25 to 60 °C.

4. The process as claimed in claim 1 , wherein the ratio between the reactants, alcohol, chloroacetic acid and hydroxide is 1 : 1 :1 -2.

5. The process as claimed in claim 1 , wherein the yield of the reaction is between 65 to 75%.

6. The process as claimed in claim 3, wherein the reaction temperature ranges from 25 to 40 °C.

7. The process as claimed in claim 4, wherein the ratio between alcohol, chloroacetic acid and hydroxide is 1 :1 :1.

8. The process as claimed in claim 5, 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 claim 1 , wherein the conductivities of the carboxymethylated alcohols are in the range of 23-25 ms/cm.

10. The process as claimed in claim 1 , wherein the alcohol is selected from the group consisting of lauryl alcohol or 2-Hexyldecan-1 -ol.

1 1 . The process as claimed in claim 1 , wherein the polar protic solvent is selected from the group consisting of methanol or ethanol.

12. The process as claimed in claim 1 , 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 hydroxide.

14. The process as claimed in claim 1 , wherein the carboxymethylated alcohol is represented by the structure R-O-CH₂-C00M, 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.

15. The process as claimed in claim 14, wherein carboxymethylated alcohol is selected from the group consisting of Sodium-2-Dodecyloxy acetate or Sodium-2-[(2-hexyl)decyloxy]acetate.