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A Process For The Preparation Of 2 Butoxyethyl Chloroacetate

Abstract: ABSTRACT A PROCESS FOR THE PREPARATION OF 2-BUTOXYETHYL CHLOROACETATE The present disclosure relates to a process for the preparation of 2-butoxyethyl chloroacetate. The fluid medium and the catalyst used in the process of the present disclosure can be recovered and recycled thereby making the process environment friendly as well as economical. The process of the present disclosure provides 2-butoxyethyl chloroacetate with a comparatively high purity and high yield.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
18 February 2022
Publication Number
10/2022
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
dewan@rkdewanmail.com
Parent Application
Patent Number
Legal Status
Grant Date
2024-10-30
Renewal Date

Applicants

GHARDA CHEMICALS LIMITED
D-1/2, MIDC, Lote Parshuram, Taluka Khed, Ratnagiri-415722, Maharashtra, India

Inventors

1. SHENOY Diwakar K
c/o, GHARDA CHEMICALS LIMITED, D-1/2, MIDC, Lote Parshuram, Taluka Khed, Ratnagiri 415722, Maharashtra, India
2. SHET, Laxminarayan S
c/o, GHARDA CHEMICALS LIMITED, D-1/2, MIDC, Lote Parshuram, Taluka Khed, Ratnagiri 415722, Maharashtra, India
3. SAMANGADKAR, Yatin S
c/o, GHARDA CHEMICALS LIMITED, D-1/2, MIDC, Lote Parshuram, Taluka Khed, Ratnagiri 415722, Maharashtra, India
4. THASALE, Sandesh S
c/o, GHARDA CHEMICALS LIMITED, D-1/2, MIDC, Lote Parshuram, Taluka Khed, Ratnagiri 415722, Maharashtra, India
5. SALVI, Manoj V
c/o, GHARDA CHEMICALS LIMITED, D-1/2, MIDC, Lote Parshuram, Taluka Khed, Ratnagiri 415722, Maharashtra, India

Specification

Claims:WE CLAIM:
1. A process for preparing 2-butoxyethyl chloroacetate, said process comprising the following steps:
i. reacting butyl cellosolve with mono chloro acetic acid in a predetermined molar ratio in the presence of a catalyst in a fluid medium to obtain a reaction mixture;
ii. heating said reaction mixture at a first predetermined temperature and simultaneously removing water to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, said fluid medium, unreacted butyl cellosolve, unreacted mono chloro acetic acid and said catalyst;
iii. fractionally distilling said first product mixture at a second pre-determined temperature to recover said fluid medium and said unreacted butyl cellosolve, to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, said unreacted mono chloro acetic acid and said catalyst; and
iv. vacuum distilling said second product mixture at a third predetermined temperature and at a predetermined pressure to obtain 2-butoxyethyl chloroacetate and a residual mass containing said catalyst and said unreacted mono chloroacetic acid.
2. The process as claimed in claim 1, wherein said recovered fluid medium along with said unreacted butyl cellosolve and said residual mass containing said catalyst and said unreacted mono chloroacetic acid are recycled to a next batch.
3. The process as claimed in claim 1, wherein said predetermined molar ratio of said butyl cellosolve to said mono chloroacetic acid is in the range of 1:0.5 to 1:1.
4. The process as claimed in claim 1, wherein said catalyst is selected from the group consisting of para toluene sulfonic acid (PTSA) and methane sulphonic acid.
5. The process as claimed in claim 1, wherein said catalyst is present in an amount in the range of 1 mole% to 2 mole% with respect to the amount of butyl cellosolve.
6. The process as claimed in claim 1, wherein said fluid medium is selected from the group consisting of toluene, n-hexane, cyclohexane, benzene and chlorobenzene.
7. The process as claimed in claim 1, wherein said first predetermined temperature is in the range of 50 °C to 130 °C, said second predetermined temperature is in the range of 90 °C to 130 °C and said third predetermined temperature is in the range of 100 °C to 120 °C.
8. The process as claimed in claim 1, wherein said predetermined pressure is in the range of 4 mmHg to 5 mmHg.
9. The process as claimed in claim 1, wherein a yield of 2-Butoxyethyl chloroacetate is in the range of 90 mole% to 99 mole% and a purity is in the range of 98 % to 99.9 %.
Dated this 18th day of February, 2022

_______________________________
MOHAN RAJKUMAR DEWAN, IN/PA – 25
of R.K.DEWAN & CO.
Authorized Agent of Applicant
, Description:FIELD
The present disclosure relates to a process for the preparation of 2-Butoxyethyl chloroacetate.
BACKGROUND
The background information herein below relates to the present disclosure but is not necessarily prior art.
Triclopyr-butotyl is an organic compound in the pyridine group that is used as a systemic foliar herbicide and fungicide. Triclopyr-butotyl is used to control broadleaf weeds and to control rust diseases on crops. The chemical name of Triclopyr-butotyl is 2-[(3,5,6-trichloro-2-pyridinyl)oxy]acetic acid 2-butoxyethyl ester and has the following chemical structure:

Triclopyr-butotyl
2-Butoxyethyl chloroacetate is an important intermediate used for the preparation of Triclopyr-butotyl-butotyl. Conventionally, the process of preparing 2-Butoxyethyl chloroacetate involves catalytic esterification of butyl cellosolve and mono chloro acetic acid by using mineral acid as a catalyst. However, various impurities/by-products are formed during the conventional processes. Further, the use of mineral acids on a large scale production/reaction is not convenient due to the corrosive nature of the mineral acids.
There is, therefore, felt a need to provide a process for preparing 2-Butoxyethyl chloroacetate that mitigates the aforestated drawbacks or at least provides a useful alternative.
OBJECTS
Some of the objects of the present disclosure, which at least one embodiment herein satisfies, are as follows:
It is an object of the present disclosure to ameliorate one or more problems of the prior art or to at least provide a useful alternative.
An object of the present disclosure is to provide a process for the preparation of 2-Butoxyethyl chloroacetate.
Another object of the present disclosure is to provide a process for the preparation of 2-Butoxyethyl chloroacetate with high yield and high purity.
Yet another object of the present disclosure is to provide a process for the preparation of 2-Butoxyethyl chloroacetate that is environment friendly.
Still another object of the present disclosure is to provide a simple and cost-efficient process for the preparation of 2-Butoxyethyl chloroacetate.
Other objects and advantages of the present disclosure will be more apparent from the following description, which is not intended to limit the scope of the present disclosure.
SUMMARY
The present disclosure relates to a process for the preparation of 2-Butoxyethyl chloroacetate. The process comprises reacting butyl cellosolve with mono chloro acetic acid in a predetermined molar ratio in the presence of a catalyst in a fluid medium to obtain a reaction mixture. The reaction mixture is heated at a first predetermined temperature and simultaneously water is removed to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, the fluid medium, unreacted butyl cellosolve, unreacted mono chloro acetic acid and catalyst. The first product mixture is fractionally distilled at a second pre-determined temperature to recover the fluid medium and the unreacted butyl cellosolve and to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and the catalyst. The second product mixture is vacuum distilled at a third predetermined temperature and at a predetermined pressure to obtain 2-butoxyethyl chloroacetate and a residual mass containing the catalyst and unreacted mono chloroacetic acid. The unreacted butyl cellosolve, unreacted mono chloro acetic acid, the fluid medium and the catalyst are recovered and recycled in the next batch.
DETAILED DESCRIPTION
The present disclosure relates to a process for the preparation of 2-Butoxyethyl chloroacetate.
Embodiments are provided so as to thoroughly and fully convey the scope of the present disclosure to the person skilled in the art. Numerous details are set forth, relating to specific components, and methods, to provide a complete understanding of embodiments of the present disclosure. It will be apparent to the person skilled in the art that the details provided in the embodiments should not be construed to limit the scope of the present disclosure. In some embodiments, well-known processes, well-known apparatus structures, and well-known techniques are not described in detail.
The terminology used, in the present disclosure, is only for the purpose of explaining a particular embodiment and such terminology shall not be considered to limit the scope of the present disclosure. As used in the present disclosure, the forms "a,” "an," and "the" may be intended to include the plural forms as well, unless the context clearly suggests otherwise. The terms "comprises," "comprising," “including,” and “having,” are open ended transitional phrases and therefore specify the presence of stated features, integers, steps, operations, elements, modules, units and/or components, but do not forbid the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. The particular order of steps disclosed in the method and process of the present disclosure is not to be construed as necessarily requiring their performance as described or illustrated. It is also to be understood that additional or alternative steps may be employed.
As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed elements.
The terms first, second, third, etc., should not be construed to limit the scope of the present disclosure as the aforementioned terms may be only used to distinguish one element, component, region, layer or section from another component, region, layer or section. Terms such as first, second, third etc., when used herein do not imply a specific sequence or order unless clearly suggested by the present disclosure.
Triclopyr-butotyl is a synthetic herbicide used to control both broadleaf and woody plants. Broadleaf weeds often controlled with triclopyr-butotyl include nettles, docks, brambles, and woody plants. Triclopyr-butotyl affects the actively growing plants by mimicking a specific type of plant growth hormone, known as an auxin. Plants rapidly take in Triclopyr-butotyl through leaves and roots and lead to plant death. After absorbing the herbicide, the plants die slowly i.e. within weeks.
2-Butoxyethyl chloroacetate is an important intermediate in the preparation of Triclopyr-butotyl. Conventionally, the process of preparing 2-Butoxyethyl chloroacetate involves catalytic esterification of butyl cellosolve and mono chloro acetic acid by using mineral acid as a catalyst. However, various impurities/by-products are formed during the conventional processes. Further, the use of mineral acids on a large scale production/reaction is not convenient due to the corrosive nature of the mineral acids.
The present disclosure provides a process for the preparation of 2-Butoxyethyl chloroacetate which is simple, provides 2-Butoxyethyl chloroacetate in high yield and high purity and is environment friendly.
The present disclosure provides a process for the preparation of 2-Butoxyethyl chloroacetate.
2-Butoxyethyl chloroacetate is represented below as Formula I.

Formula-I
Chemical formula: C8H15ClO3
Molar mass: 194.65
The process for the preparation of 2-Butoxyethyl chloroacetate comprises the following steps:
i. reacting butyl cellosolve with mono chloro acetic acid in a predetermined molar ratio in the presence of a catalyst in a fluid medium to obtain a reaction mixture;
ii. heating the reaction mixture at a first predetermined temperature and simultaneously removing water to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, the fluid medium, unreacted butyl cellosolve, unreacted mono chloro acetic acid and the catalyst;
iii. fractionally distilling the first product mixture at a second pre-determined temperature to recover said fluid medium and the unreacted butyl cellosolve, to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, the unreacted mono chloro acetic acid and the catalyst; and
iv. vacuum distilling the second product mixture at a third predetermined temperature and at a predetermined pressure to obtain 2-butoxyethyl chloroacetate and a residual mass containing the catalyst and the unreacted mono chloroacetic acid.
The process is described in detail herein below:
In a first step, butyl cellosolve is reacted with mono chloro acetic acid in a predetermined molar ratio in the presence of a catalyst in a fluid medium to obtain a reaction mixture.
In an embodiment of the present disclosure, the predetermined molar ratio of the butyl cellosolve to the mono chloro acetic acid is in the range of 1:0.5 to 1:1. In an exemplary embodiment of the present disclosure, the molar ratio of the butyl cellosolve to the mono chloro acetic acid is 1:0.9.
The catalyst is selected from the group consisting of para toluene sulfonic acid (PTSA) and methane sulphonic acid. In an exemplary embodiment of the present disclosure, the catalyst is para toluene sulfonic acid (PTSA).
The catalyst is present in an amount in the range of 1 mole% to 2 mole% with respect to the amount of butyl cellosolve. In an exemplary embodiment of the present disclosure, the amount of the catalyst is 1 mole% with respect to the amount of butyl cellosolve.
The fluid medium is selected from the group consisting of toluene, n-hexane, cyclohexane, benzene and chlorobenzene. In an exemplary embodiment of the present disclosure, the fluid medium is toluene. In another exemplary embodiment of the present disclosure, the fluid medium is n-hexane.
In a second step, the reaction mixture is heated at a first predetermined temperature and simultaneously water is removed to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, the fluid medium, unreacted butyl cellosolve, unreacted mono chloro acetic acid and the catalyst.
The first predetermined temperature is in the range of 50 °C to 130 °C. In an exemplary embodiment of the present disclosure, the first predetermined temperature is 86 °C. In another exemplary embodiment of the present disclosure, the first predetermined temperature is 65 °C.
In an embodiment of the present disclosure, the simultaneous removal of water from the reaction mixture is done by azeotropic distillation.
In a third step, the first product mixture is fractionally distilled at a second pre-determined temperature to recover the fluid medium and the unreacted butyl cellosolve, to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and the catalyst.
The second pre-determined temperature is in the range of 90 °C to 130 °C. In an exemplary embodiment of the present disclosure, the second predetermined temperature is 130 °C. In another exemplary embodiment of the present disclosure, the second predetermined temperature is 125 °C. In still another exemplary embodiment of the present disclosure, the second predetermined temperature is 95 °C.
In accordance with an embodiment of the present disclosure, during the fractional distillation of the first product mixture, traces of 2-Butoxy chloroacetate is also distilled out along with the fluid medium and the unreacted butyl cellosolve.
The fluid medium, the unreacted butyl cellosolve and 2-Butoxy chloroacetate are recycled and used in the next batch thereby making the process economical and environment friendly.
In a fourth step, the second product mixture is vacuum distilled at a third predetermined temperature at a predetermined pressure to obtain 2-butoxyethyl chloroacetate and a residual mass containing the catalyst and the unreacted mono chloroacetic acid.
The third pre-determined temperature is in the range of 100 °C to 120 °C. In an exemplary embodiment of the present disclosure, the third predetermined temperature is 110 °C.
The pre-determined pressure is in the range of 4 mmHg to 5 mmHg. In an exemplary embodiment of the present disclosure, the pre-determined pressure is 4.5 mmHg.
In accordance with an embodiment of the present disclosure, the residual mass containing the catalyst and the unreacted mono chloroacetic acid is recycled and used in the next batch, thus, making the process economical and environment friendly.
The process of the present disclosure is simple, economical, environment friendly and suitable for industrial applications. The unreacted starting materials, the fluid medium and the catalysts are recovered and recycled in the next batch that makes the process of the present disclosure economical and environment friendly.
The yield of 2-butoxyethyl chloroacetate obtained by the process of the present disclosure is in the range of 90 mole% to 98 mole%. The purity of 2-butoxyethyl chloroacetate obtained by the process of the present disclosure is 98.0 % to 99.9 %.
The foregoing description of the embodiments has been provided for purposes of illustration and is not intended to limit the scope of the present disclosure. Individual components of a particular embodiment are generally not limited to that particular embodiment but are interchangeable. Such variations are not to be regarded as a departure from the present disclosure, and all such modifications are considered to be within the scope of the present disclosure.
The present disclosure is further described in light of the following experiments which are set forth for illustration purpose only and not to be construed for limiting the scope of the disclosure. The following experiments can be scaled up to industrial/commercial scale and the results obtained can be extrapolated to the industrial scale.
EXPERIMENTAL DETAILS
Example 1: Preparation of 2-butoxyethyl chloroacetate by using toluene as a fluid medium in accordance with the present disclosure
In 4 neck round bottom flask with Dean and Stark apparatus, double coil condenser, overhead stirrer and reaction temperature indicator, 129.8 g of butyl cellosolve and 94.5 g of mono chloro acetic acid were charged and reacted in the presence of 2.5 g of para toluene sulfonic acid (PTSA) in 100 ml toluene to obtain a reaction mixture. The reaction mixture was heated at 86 °C and simultaneously water was removed through the Dean and Stark system to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, toluene, unreacted butyl cellosolve, unreacted mono chloro acetic acid and para toluene sulfonic acid. After complete removal of water (18ml), the first product mixture was fractionally distilled at 130 °C to recover toluene, and unreacted butyl cellosolve, to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and the para toluene sulfonic acid. Small fraction of 2-butoxyethyl chloroacetate was also distilled out along with toluene and unreacted butyl cellosolve. The second product mixture was vacuum distilled at 110 °C and at a pressure of 4.5 mmHg to obtain 2-butoxyethyl chloroacetate and a residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid. Residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid was recycled and used in the next batch.
The purity of 2-butoxyethyl chloroacetate was 99.0 % and the yield was 91.0 mole %.
Example 2: Preparation of 2-butoxyethyl chloroacetate by using the recovered unreacted reactants, solvent and catalyst of Example 1
In the above reaction set up with residual mass containing para toluene sulfonic acid and unreacted mono chloroacetic acid of Example 1, 121.5 g butyl cellosolve, 94.5 g mono chloro acetic acid, recovered toluene, unreacted butyl cellosolve and small fraction of 2-butoxyethyl chloroacetate of example 1 were added to obtain a reaction mixture. The reaction mixture was heated at 86 °C and simultaneously water was removed through the Dean and Stark system to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, toluene, unreacted butyl cellosolve, unreacted mono chloro acetic acid and para toluene sulfonic acid. After complete removal of water (18ml), the first product mixture was fractionally distilled at 125 °C to recover toluene, and unreacted butyl cellosolve, to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and para toluene sulfonic acid. Small fraction of 2-butoxyethyl chloroacetate was also distilled out along with toluene and unreacted butyl cellosolve. Recovered toluene and butyl cellosolve was recycled in the next batch. The second product mixture was vacuum distilled at 110 °C and at 4.5 mmHg to obtain 2-butoxyethyl chloroacetate and a residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid. Residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid was recycled and used in the next batch.
The purity of 2-butoxyethyl chloroacetate was 99.2 % and the yield was 97.0 mole %.
Example 3: Preparation of 2-butoxyethyl chloroacetate by using the recovered unreacted reactants, solvent and catalyst of Example 2
In the above reaction set up with residual mass containing para toluene sulfonic acid and unreacted mono chloroacetic acid of Example 2, 121.5 g butyl cellosolve, 94.5 g mono chloro acetic acid, recovered toluene, unreacted butyl cellosolve and small fraction of 2-butoxyethyl chloroacetate of example 2 were added to obtain a reaction mixture. The reaction mixture was heated at 86 °C and simultaneously water was removed through the Dean and Stark system to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, toluene, unreacted butyl cellosolve, unreacted mono chloro acetic acid and para toluene sulfonic acid. After complete removal of water, the first product mixture was fractionally distilled at 130 °C to recover toluene, and unreacted butyl cellosolve and to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and para toluene sulfonic acid. Small fraction of 2-butoxyethyl chloroacetate was also distilled out along with toluene and unreacted butyl cellosolve. Recovered toluene and butyl cellosolve was recycled in the next batch. The second product mixture was vacuum distilled at 115 °C and at 4.5 mmHg to obtain 2-butoxyethyl chloroacetate and a residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid. Residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid was recycled and used in the next batch.
The purity of 2-butoxyethyl chloroacetate was 99.5 % and the yield was 97.0 m %.
Example 4: Preparation of 2-butoxyethyl chloroacetate using n-hexane as a fluid medium in accordance with the present disclosure
In a 4 neck round bottom flask with Dean and Stark apparatus, double coil condenser, overhead stirrer and reaction temperature indicator 129.8 g butyl cellosolve and 94.5 g mono chloro acetic acid were charged and reacted in the presence of 2.5 g of para toluene sulfonic acid in 100 ml n-hexane to obtain a reaction mixture. The reaction mixture was heated at 65 °C and simultaneously water was removed through the Dean and Stark system to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, n-hexane, unreacted butyl cellosolve, unreacted mono chloro acetic acid and para toluene sulfonic acid. After complete removal of water (18ml) the first product mixture was fractionally distilled at 95 °C to recover n-hexane, and unreacted butyl cellosolve and to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and the catalyst. Small fraction of 2-butoxyethyl chloroacetate was also distilled out along with n-hexane and unreacted butyl cellosolve. The second product mixture was vacuum distilled at 115 °C and at 4.5 mmHg to obtain 2-butoxyethyl chloroacetate and a residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid. Residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid was recycled and used in the next batch.
The purity of 2-butoxyethyl chloroacetate was 99.2 % and the yield was 93.0 mole %.
Example 5: Preparation of 2-butoxyethyl chloroacetate by using the recovered unreacted reactants, solvent and catalyst of Example 4
In the above reaction set up with residual mass containing para toluene sulfonic acid and unreacted mono chloroacetic acid of Example 4, 121.5 g butyl cellosolve, 94.5 g mono chloro acetic acid, recovered n-hexane, unreacted butyl cellosolve and small fraction of 2-butoxyethyl chloroacetate of example 4 were added to obtain a reaction mixture. The reaction mixture was heated at 65 °C and simultaneously water was removed through the Dean and Stark system to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, n-hexane, unreacted butyl cellosolve, unreacted mono chloro acetic acid and para toluene sulfonic acid. The first product mixture was fractionally distilled at 95 °C to recover n-hexane, and unreacted butyl cellosolve and to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and para toluene sulfonic acid. Small fraction of 2-butoxyethyl chloroacetate was also distilled out along with n-hexane and unreacted butyl cellosolve. Recovered n-hexane and butyl cellosolve was recycled in the next batch. The second product mixture was vacuum distilled at 110 °C and at 4-5mm Hg to obtain 2-butoxyethyl chloroacetate and a residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid. Residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid was recycled and used in the next batch.
The purity of 2-butoxyethyl chloroacetate was 99.0 % and the yield was 97.5 mole %.
Example 6: Preparation of 2-butoxyethyl chloroacetate by using the recovered unreacted reactants, solvent and catalyst of Example 5
In the above reaction set up with residual mass containing para toluene sulfonic acid and unreacted mono chloroacetic acid of Example 5, 121.5g butyl cellosolve, 94.5g mono chloro acetic acid, recovered n-hexane, unreacted butyl cellosolve and small fraction of 2-butoxyethyl chloroacetate of example 5 were added to obtain a reaction mixture. The reaction mixture was heated at 65 °C and simultaneously water was removed through the Dean and Stark system to obtain a first product mixture comprising 2-butoxyethyl chloroacetate, n-hexane, unreacted butyl cellosolve, unreacted mono chloro acetic acid and para toluene sulfonic acid. The first product mixture was fractionally distilled at 95 °C to recover n-hexane, and unreacted butyl cellosolve and to obtain a second product mixture comprising 2-butoxyethyl chloroacetate, unreacted mono chloro acetic acid and para toluene sulfonic acid. Small fraction of 2-butoxyethyl chloroacetate was also distilled out along with n-hexane and unreacted butyl cellosolve. Recovered n-hexane and butyl cellosolve was recycled in the next batch. The second product mixture was vacuum distilled at 110 °C and at 4-5mm Hg to obtain 2-butoxyethyl chloroacetate and a residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid. Residual mass containing the para toluene sulfonic acid and the unreacted mono chloroacetic acid was recycled and used in the next batch.
The purity of 2-butoxyethyl chloroacetate was 99.4 % and the yield was 97.3 mole %.
TECHNICAL ADVANCEMENTS
The present disclosure described hereinabove has several technical advantages including, but not limited to, the realization of a process for the preparation of 2-butoxyethyl chloroacetate, that:
? is environment friendly, as solvents, reactants and catalyst are recycled;
? is simple, efficient, and economical; and
? provides 2-butoxyethyl chloroacetate in high yield and high purity.
The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the following description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skill in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
The foregoing description of the specific embodiments so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.
The use of the expression “at least” or “at least one” suggests the use of one or more elements or ingredients or quantities, as the use may be in the embodiment of the invention to achieve one or more of the desired objects or results. While certain embodiments of the inventions have been described, these embodiments have been presented by way of example only, and are not intended to limit the scope of the inventions. Variations or modifications to the formulation of this invention, within the scope of the invention, may occur to those skilled in the art upon reviewing the disclosure herein. Such variations or modifications are well within the spirit of this invention.
The numerical values given for various physical parameters, dimensions and quantities are only approximate values and it is envisaged that the values higher than the numerical value assigned to the physical parameters, dimensions and quantities fall within the scope of the invention unless there is a statement in the specification to the contrary.
Any discussion of documents, acts, materials, devices, articles or the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.
The numerical values given for various physical parameters, dimensions, and quantities are only approximate values and it is envisaged that the values higher than the numerical value assigned to the physical parameters, dimensions and quantities fall within the scope of the invention unless there is a statement in the specification to the contrary.
While considerable emphasis has been placed herein on the specific features of the preferred embodiment, it will be appreciated that many additional features can be added and that many changes can be made in the preferred embodiment without departing from the principles of the disclosure. These and other changes in the preferred embodiment of the disclosure will be apparent to those skilled in the art from the disclosure herein, whereby it is to be distinctly understood that the foregoing descriptive matter is to be interpreted merely as illustrative of the disclosure and not as a limitation.

Documents

Application Documents

# Name Date
1 202221008650-IntimationOfGrant30-10-2024.pdf 2024-10-30
1 202221008650-STATEMENT OF UNDERTAKING (FORM 3) [18-02-2022(online)].pdf 2022-02-18
2 202221008650-PatentCertificate30-10-2024.pdf 2024-10-30
2 202221008650-REQUEST FOR EARLY PUBLICATION(FORM-9) [18-02-2022(online)].pdf 2022-02-18
3 202221008650-PROOF OF RIGHT [18-02-2022(online)].pdf 2022-02-18
3 202221008650-AMMENDED DOCUMENTS [26-07-2024(online)].pdf 2024-07-26
4 202221008650-POWER OF AUTHORITY [18-02-2022(online)].pdf 2022-02-18
4 202221008650-CLAIMS [26-07-2024(online)].pdf 2024-07-26
5 202221008650-FORM-9 [18-02-2022(online)].pdf 2022-02-18
5 202221008650-FER_SER_REPLY [26-07-2024(online)].pdf 2024-07-26
6 202221008650-FORM 13 [26-07-2024(online)].pdf 2024-07-26
6 202221008650-FORM 1 [18-02-2022(online)].pdf 2022-02-18
7 202221008650-MARKED COPIES OF AMENDEMENTS [26-07-2024(online)].pdf 2024-07-26
7 202221008650-DECLARATION OF INVENTORSHIP (FORM 5) [18-02-2022(online)].pdf 2022-02-18
8 202221008650-FORM-26 [24-07-2024(online)].pdf 2024-07-24
8 202221008650-COMPLETE SPECIFICATION [18-02-2022(online)].pdf 2022-02-18
9 202221008650-FORM 3 [06-07-2024(online)].pdf 2024-07-06
9 202221008650-FORM 3 [18-04-2023(online)].pdf 2023-04-18
10 202221008650-FER.pdf 2024-01-29
10 202221008650-Request Letter-Correspondence [19-04-2023(online)].pdf 2023-04-19
11 202221008650-FORM 3 [28-12-2023(online)].pdf 2023-12-28
11 202221008650-Power of Attorney [19-04-2023(online)].pdf 2023-04-19
12 202221008650-Covering Letter [19-04-2023(online)].pdf 2023-04-19
12 202221008650-FORM 18 [18-08-2023(online)].pdf 2023-08-18
13 202221008650-CORRESPONDENCE(IPO)(WIPO DAS)-08-05-2023.pdf 2023-05-08
14 202221008650-Covering Letter [19-04-2023(online)].pdf 2023-04-19
14 202221008650-FORM 18 [18-08-2023(online)].pdf 2023-08-18
15 202221008650-FORM 3 [28-12-2023(online)].pdf 2023-12-28
15 202221008650-Power of Attorney [19-04-2023(online)].pdf 2023-04-19
16 202221008650-FER.pdf 2024-01-29
16 202221008650-Request Letter-Correspondence [19-04-2023(online)].pdf 2023-04-19
17 202221008650-FORM 3 [18-04-2023(online)].pdf 2023-04-18
17 202221008650-FORM 3 [06-07-2024(online)].pdf 2024-07-06
18 202221008650-COMPLETE SPECIFICATION [18-02-2022(online)].pdf 2022-02-18
18 202221008650-FORM-26 [24-07-2024(online)].pdf 2024-07-24
19 202221008650-MARKED COPIES OF AMENDEMENTS [26-07-2024(online)].pdf 2024-07-26
19 202221008650-DECLARATION OF INVENTORSHIP (FORM 5) [18-02-2022(online)].pdf 2022-02-18
20 202221008650-FORM 13 [26-07-2024(online)].pdf 2024-07-26
20 202221008650-FORM 1 [18-02-2022(online)].pdf 2022-02-18
21 202221008650-FORM-9 [18-02-2022(online)].pdf 2022-02-18
21 202221008650-FER_SER_REPLY [26-07-2024(online)].pdf 2024-07-26
22 202221008650-POWER OF AUTHORITY [18-02-2022(online)].pdf 2022-02-18
22 202221008650-CLAIMS [26-07-2024(online)].pdf 2024-07-26
23 202221008650-PROOF OF RIGHT [18-02-2022(online)].pdf 2022-02-18
23 202221008650-AMMENDED DOCUMENTS [26-07-2024(online)].pdf 2024-07-26
24 202221008650-REQUEST FOR EARLY PUBLICATION(FORM-9) [18-02-2022(online)].pdf 2022-02-18
24 202221008650-PatentCertificate30-10-2024.pdf 2024-10-30
25 202221008650-IntimationOfGrant30-10-2024.pdf 2024-10-30
25 202221008650-STATEMENT OF UNDERTAKING (FORM 3) [18-02-2022(online)].pdf 2022-02-18

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