KR20160001054A - Method for preparing ester compound using sulfonic acid or sulfonate catalysts - Google Patents
Method for preparing ester compound using sulfonic acid or sulfonate catalysts Download PDFInfo
- Publication number
- KR20160001054A KR20160001054A KR1020140078756A KR20140078756A KR20160001054A KR 20160001054 A KR20160001054 A KR 20160001054A KR 1020140078756 A KR1020140078756 A KR 1020140078756A KR 20140078756 A KR20140078756 A KR 20140078756A KR 20160001054 A KR20160001054 A KR 20160001054A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- nafion
- catalyst
- polyhydric alcohol
- ester compound
- Prior art date
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The present invention provides a process for producing an ester compound, wherein an ester compound is obtained by performing an esterification reaction of a polyhydric alcohol and a fatty acid using any one of a sulfonic acid and a sulfonic acid salt as a catalyst. Thus, it is possible to efficiently produce a multivalent fatty acid ester compound during a short reaction time even in a small amount, because the activity is superior to that of the existing acid catalyst. Further, there is an advantage that the perfluorosulfonic acid catalyst can be easily filtered from the reaction mixture after the esterification reaction, and can be dried and reused.
Description
More particularly, the present invention relates to a process for producing an ester compound by esterification reaction of a polyhydric alcohol and a fatty acid accelerated by a sulfonic acid or sulfonic acid salt catalyst, and to a process for producing an ester compound which can be applied to a lubricant for refrigerator oil, And a method for producing a polyvalent ester compound in an excellent yield in a fast reaction time.
Polyvalent fatty acid ester compounds synthesized from polyhydric alcohols and fatty acids are high-value compounds that can be applied to environment-friendly insulating oil, biodegradable hydraulic operating oil, cosmetic raw materials and the like.
At present, esterification reaction between a polyhydric alcohol and a fatty acid uses a strong acid, a strong alkali, or a phosphoric acid or a sulfonic acid-based catalyst. Therefore, it is difficult to purify the catalyst remaining in the solution after the reaction, and a large amount of high- There is a problem, and a new eco-friendly catalyst process technology is required to improve it.
In addition, the esterification reaction between polyhydric alcohol and fatty acid requires an extended period of time of 20 hours or more because the reaction rate is delayed due to the effect of steric hindrance when the ester group is sequentially formed in the hydroxyl group of the polyhydric alcohol.
Korean Patent Registration No. 2012-0084675 discloses a novel process for producing 3-mercapto (meth) propionic acid by reacting (meth) acrylic acid with thioacetic acid under a catalyst and a process for producing (meth) acrylic acid having a mercapto group Korean Patent Registration No. 2012-0097330 discloses a carboxylic acid ester compound having a mercapto group obtained through an ester reaction between mercaptocarboxylic acid and an alcohol, The esterification reaction is required.
Although various catalysts for esterification have been developed so far, the time of the ester reaction has not been shortened.
DISCLOSURE OF THE INVENTION An object of the present invention is to solve the above-mentioned problems, and an object of the present invention is to solve the above-mentioned problems by using a sulfonic acid or sulfonic acid salt catalyst as a catalyst for the esterification reaction of a polyhydric alcohol and a fatty acid, And a method for producing a polyhydric fatty acid ester compound for use in cosmetic raw materials and the like.
It is also intended to provide a method for easily reusing perfluorosulfonic acid or perfluorosulfonic acid salt catalyst from the reaction mixture after the reaction.
According to an aspect of the present invention,
There is provided a process for producing an ester compound comprising a step of esterifying a polyhydric alcohol and a fatty acid using any one of a sulfonic acid and a sulfonic acid as a catalyst.
The sulfonic acid may be at least one catalyst selected from the group consisting of an alkylsulfonic acid, an arylsulfonic acid, an alkylarylsulfonic acid, an arylalkylsulfonic acid, a trifluoromethanesulfonic acid, and a perfluorosulfonic acid.
The alkyl group of the alkylsulfonic acid may be a linear or branched alkyl group having 1 to 4 carbon atoms.
The aryl group of the arylsulfonic acid may have 6 to 12 carbon atoms.
The alkyl group of the alkylarylsulfonic acid may be a linear or branched alkyl group having 1 to 4 carbon atoms, and the aryl group may have 6 to 12 carbon atoms.
The aryl group of the arylalkylsulfonic acid may have 6 to 12 carbon atoms, and the alkyl group may be a straight-chain or branched alkyl group having 1 to 4 carbon atoms.
The perfluorosulfonic acid may be Nafion in acid form.
The Nafion in the acid form may be any one selected from Nafion N115, Nafion N117, Nafion NR50, Nafion NRE-212, Nafion N324, Nafion R1100, Nafion D520 and Nafion D521.
The sulfonate may be at least one selected from the group consisting of an alkylsulfonate, an arylsulfonate, an alkylarylsulfonate, an arylalkylsulfonate, a trifluoromethanesulfonate, and a perfluorosulfonate.
The perfluorosulfonic acid salt may be in a salt form of Nafion.
Wherein the salt form of Nafion is at least one selected from Nafion N115, Nafion N117, Nafion NR50, Nafion NRE-212, Nafion N324, Nafion R1100, Nafion D520 and Nafion D521, Sc).
The content of the catalyst may be 0.01 to 10 moles per 100 moles of the polyhydric alcohol.
The polyhydric alcohol may contain three or more hydroxyl groups.
The polyhydric alcohol may contain three or four hydroxyl groups.
The polyhydric alcohol may be a C4 to C30 linear or branched polyhydric alcohol.
The fatty acid may be a C4 to C30 linear or branched, saturated or unsaturated fatty acid.
Wherein the fatty acid is selected from the group consisting of 2-ethylhexanoic acid, isononanoic acid, oleic acid, palmitic acid, stearic acid, linoleic acid, ) And linolenic acid. ≪ / RTI >
The esterification reaction can be carried out at a temperature of 150 to 250 ° C.
The perfluorosulfonic acid may be filtered after the esterification reaction, dried and reused.
The perfluorosulfonic acid salt may be filtered after the ester reaction, dried and reused.
According to the method for producing an ester compound using a sulfonic acid or sulfonic acid salt catalyst of the present invention, the activity is excellent as compared with the existing acid catalyst, so that a polyvalent fatty acid ester compound can be efficiently produced in a short reaction time in a small amount, Thereafter, the perfluorosulfonic acid or the perfluorosulfonic acid salt catalyst can be easily filtered and reused from the reaction mixture.
BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a graph showing generation rates of triester according to Examples 1 to 10, Comparative Examples 1 and 2 of the present invention. FIG.
2 is a graph showing generation rates of triestes over time according to Examples 11 to 20, Comparative Example 3 and Comparative Example 4 of the present invention.
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings so that those skilled in the art can easily carry out the present invention.
However, the following description does not limit the present invention to specific embodiments. In the following description of the present invention, detailed description of related arts will be omitted if it is determined that the gist of the present invention may be blurred .
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the terms "comprises ", or" having ", and the like, specify that the presence of stated features, integers, steps, operations, elements, or combinations thereof, But do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, or combinations thereof.
Hereinafter, a method for producing an ester compound using any one of the sulfonic acid and sulfonic acid salt of the present invention as a catalyst will be described.
The method for producing an ester compound of the present invention uses a sulfonic acid or a sulfonic acid salt as a catalyst to esterify a polyhydric alcohol and a fatty acid.
The sulfonic acid may be an alkylsulfonic acid, an arylsulfonic acid, an alkylarylsulfonic acid, an arylalkylsulfonic acid, a trifluoromethanesulfonic acid, or a perfluorosulfonic acid. In addition, the sulfonic acid does not contain rare earth metals and other metals.
The alkyl group of the alkylsulfonic acid may be a linear or branched alkyl group having 1 to 4 carbon atoms.
The aryl group of the arylsulfonic acid may have 6 to 12 carbon atoms.
The alkyl group of the alkylarylsulfonic acid may be a linear or branched alkyl group having 1 to 4 carbon atoms, and the aryl group may have 6 to 12 carbon atoms.
The aryl group of the arylalkylsulfonic acid may have 6 to 12 carbon atoms, and the alkyl group may be a straight-chain or branched alkyl group having 1 to 4 carbon atoms.
The perfluorosulfonic acid may be an acidic Nafion. The Nafion may be Nafion N115, Nafion N117, Nafion NR50, Nafion NRE-212, Nafion N324, Nafion R1100, Nafion D520 and Nafion D521, Lt; / RTI >
The sulfonate may be an alkylsulfonate, an arylsulfonate, an alkylarylsulfonate, an arylalkylsulfonate, a trifluoromethanesulfonate, or a perfluorosulfonate. Wherein the alkyl and aryl groups are the same as described for sulfonic acid.
The perfluorosulfonic acid salt may be in a salt form of Nafion. The salt form of Nafion can be a salt of Nafion N115, Nafion N117, Nafion NR50, Nafion NRE-212, Nafion N324, Nafion R1100, Nafion D520 and Nafion D521 and Scandium (Sc) Preferably Nafion NR-50 and a salt of scandium (Nafion-Sc).
The content of the catalyst is preferably 0.01 to 10 moles, more preferably 0.05 to 5 moles, and still more preferably 0.2 to 2 moles per 100 moles of the polyhydric alcohol.
The polyhydric alcohol is an alcohol containing two or more hydroxyl groups, and the trivalent alcohol is an alcohol containing three hydroxyl groups. The polyhydric alcohol is preferably a trihydric or higher alcohol, and more preferably trihydric or tetravalent alcohols can be used.
Specifically, the polyhydric alcohol may be a compound in which three or four hydroxyl groups in the molecule are symmetrically linked, such as trimethylolpropane and pentaerythritol.
The polyhydric alcohol is preferably C4 to C30 linear or branched polyhydric alcohol. More preferably, it may be C4 to C20, and more preferably C4 to C10.
In addition, the polyhydric alcohol may be a saturated alcohol or an unsaturated alcohol.
Preferably, the fatty acid is a C4 to C30 linear or branched saturated or unsaturated fatty acid. And more preferably a C6 to C28 saturated or unsaturated fatty acid.
Specifically, the fatty acid may be selected from the group consisting of 2-ethylhexanoic acid, isononanoic acid, oleic acid, palmitic acid, stearic acid, linoleic acid, linolenic acid, and the like.
The esterification reaction is preferably carried out at a temperature of 150 to 250 ° C.
In addition, the esterification reaction can be carried out in a solvent-free reaction. However, the scope of the invention is not limited thereto, and organic solvents which can be usually used for an organic reaction can be used alone or in combination.
The reaction time is affected by the reaction temperature, which affects the reaction rate. Therefore, the reaction time can be selected according to the reaction temperature, and preferably, the time taken until the reaction is completed can be selected.
The reaction pressure is selected depending on the reaction temperature and the kind of the reactants, and preferably the normal pressure can be selected.
The Nafion catalyst may be filtered after the ester reaction, dried and reused.
[Example]
Hereinafter, the structure of the present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
Example One: Trifluoromethanesulfonic acid Catalyzed Esterification Reaction (2- EHA use)
1.34 g (10 mmol) of trimethylolpropane (TMP) and 4.75 g (33 mmol, 3.3 equiv) of 2-ethylhexanoic acid, 2-EHA were placed in a 10 mL vial, 9.0 mg of triflic acid catalyst (0.6 mol% of TMP) was added. The reaction mixture was stirred on an oil bath at 180 ° C, and the sample collected over time was diluted with dichloromethane (DCM) and analyzed by GC-MS (Gas Chromatograph / Mass spectrophotometry).
Example 2: Trifluoromethanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that 18.0 mg (1.2 mol% of TMP) of trifluoromethanesulfonic acid catalyst was used.
Example 3: Trifluoromethanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that 3.0 mg (0.2 mol% of TMP) of trifluoromethanesulfonic acid catalyst was used.
Example 4: Methanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that 6.0 mg of methanesulfonic acid catalyst (0.6 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 5: Methanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that 12 mg of methanesulfonic acid catalyst (1.2 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 6: Methanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that 2 mg of methanesulfonic acid catalyst (0.2 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 7: Nafion NR -50 catalyst Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that 25.0 mg of Nafion NR-50 catalyst (0.2 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 8: Nafion NR -50 One reuse of catalyst Esterification reaction
The reaction was carried out in the same manner as in Example 1 except that 5 ml of the reaction mixture after the reaction of Example 7 was replaced with 10 ml of ethyl acetate three times and dried and 25.0 mg of the obtained Nafion NR-50 catalyst was used again instead of the trifluoromethanesulfonic acid catalyst To prepare an ester compound.
Example 9: Nafion NR -50 Re-use of catalyst twice Esterification reaction
The procedure of Example 8 was repeated except that 5 ml of the reaction mixture after the reaction of Example 8 was diluted 3 times with 10 ml of ethyl acetate and dried and 25.0 mg of the obtained Nafion NR-50 catalyst was reused instead of trifluoromethanesulfonic acid catalyst To prepare an ester compound.
Example 10: Nafion - Sc Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 1, except that Nafion NR50 and 25.0 mg of scandium salt catalyst (Nafion-Sc) were used in place of the trifluoromethanesulfonic acid catalyst.
Example 11: Trifluoromethanesulfonic acid Catalyzed Esterification Reaction Decanoic acid use)
1.34 g (10 mmol) of trimethylolpropane (TMP) and 5.68 g (33 mmol, 3.3 equiv) of decanoic acid were placed in a 10 mL vial, Trifluoromethanesulfonic acid catalyst 9.0 mg (0.6 mol% of TMP) was added. The reaction mixture was stirred on an oil bath at 180 ° C, and the sample collected over time was diluted with dichloromethane (DCM) and analyzed by GC-MS (Gas Chromatograph / Mass spectrophotometry).
Example 12: Trifluoromethanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that 18.0 mg (1.2 mol% of TMP) of trifluoromethanesulfonic acid catalyst was used.
Example 13: Trifluoromethanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that 3.0 mg (0.2 mol% of TMP) of trifluoromethanesulfonic acid catalyst was used.
Example 14: Methanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that 6.0 mg of methanesulfonic acid catalyst (0.6 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 15: Methanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that 12 mg of methanesulfonic acid catalyst (1.2 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 16: Methanesulfonic acid Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that 2 mg of methanesulfonic acid catalyst (0.2 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 17: Nafion NR -50 catalyst Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that 25.0 mg of Nafion NR-50 catalyst (0.2 mol% of TMP) was used instead of trifluoromethanesulfonic acid catalyst.
Example 18: Nafion NR -50 One reuse of catalyst Esterification reaction
The procedure of Example 11 was repeated except that 5 ml of the reaction mixture after the reaction of Example 17 was diluted 3 times with 10 ml of ethyl acetate and dried and 25.0 mg of the obtained Nafion NR-50 catalyst was reused instead of trifluoromethanesulfonic acid catalyst To prepare an ester compound.
Example 19: Nafion NR -50 Re-use of catalyst twice Esterification reaction
The procedure of Example 11 was repeated except that 5 ml of the reaction mixture after the reaction of Example 18 was diluted three times with 10 ml of ethyl acetate and dried and 25.0 mg of the obtained Nafion NR-50 catalyst was reused instead of trifluoromethanesulfonic acid catalyst To prepare an ester compound.
Example 20: Nafion - Sc Catalyzed Esterification reaction
An ester compound was prepared in the same manner as in Example 11, except that Nafion NR50 and 25.0 mg of a scandium salt (Nafion-Sc) catalyst were used instead of the trifluoromethanesulfonic acid catalyst.
Comparative Example 1: catalyst-free Esterification Reaction (2- EHA use)
An ester compound was prepared in the same manner as in Example 1, except that the catalyst was not used.
Comparative Example 2: PTSA Catalyzed Esterification Reaction (2- EHA use)
An ester compound was prepared in the same manner as in Example 1, except that 3.8 mg (0.2 mol% of TMP) of a p- toluenesulfonic acid (PTSA) catalyst was used instead of the trifluoromethanesulfonic acid catalyst.
Comparative Example 3: catalyst-free Esterification Reaction Decanoic acid use)
An ester compound was prepared in the same manner as in Example 11, except that the catalyst was not used.
Comparative Example 4: PTSA Catalyzed Esterification Reaction Decanoic acid use)
An ester compound was prepared in the same manner as in Example 11, except that 3.8 mg (0.2 mol% of TMP) of a p- toluenesulfonic acid (PTSA) catalyst was used instead of the trifluoromethanesulfonic acid catalyst.
[Test Example]
GC - MS Analysis
GC-MS analysis of samples collected over time according to Examples 1 to 8, Comparative Examples 1 and 2 (using 2-EHA as a fatty acid), and the production rate of the triester over time is shown in Table 1 and FIG. 1 . In addition, GC-MS analysis of samples collected over time according to Examples 9 to 16, Comparative Example 3 and Comparative Example 4 (using decanoic acid as a fatty acid), and the production rate of triester over time is shown in Tables 2 and 2 Respectively. The production rate of the triester is, in detail, the ratio of the production rate of the triester to the total production rate of the alcohol, monoester, diester and triester.
NR-50 (25 mg)
NR-50 (25 mg)
*unit:%
NR-50 (25 mg)
NR-50 (25 mg)
*unit: %
1 and 2, in the case of Examples 1 to 3 and Examples 11 to 13 using a trifluoromethane sulfonic acid (triflic acid) catalyst, the yield of triester was 80% to 90% after 1 hour of the esterification reaction It can be seen that the reaction is almost completed.
In the case of Examples 4 to 6 and Examples 14 to 16 using a methanesulfonic acid catalyst, the yield of triester was 40% to 50% after 2 hours of the esterification reaction, compared with the PTSA catalyst of Comparative Example 2 and Comparative Example 4 Respectively.
In the case of Example 7 and Example 9 using Nafion NR-50 catalyst, the yield of the triester is 40% to 50% after 1 hour of the esterification reaction but reaches 90% after 8 hours.
In the case of Examples 8, 9, 18, and 19 in which the Nafion NR-50 catalyst was reused once or twice, after 2 hours of the esterification reaction, the yield of triester was close to Examples 7 and 9 And also showed a higher production rate than PTSA catalyst. Therefore, it was found that even when the Nafion NR-50 catalyst was reused, the generation rate of the triester was not significantly different.
In the case of Example 10 and Example 20 using Nafion-Sc catalyst, the formation rate of the triester was about 50% after 2 hours of the esterification reaction, and the production rate was similar to or higher than that of the PTSA catalyst.
On the other hand, in Comparative Examples 1 and 3 in which the catalyst was not used, the triester generation rate did not reach 10% even after 2 hours of reaction, and remained about 30% even after 8 hours had elapsed.
Further, in Comparative Examples 2 and 4 using the PTSA catalyst, the generation rate of triester was about 40% higher than that in the case of not using the catalyst after 2 hours of reaction, but after about 8 hours, the generation rate of triester was about 50% , Indicating a low triester generation rate as compared with the examples of the present invention.
According to the above results, it can be seen that the ester reaction using the sulfonic acid and Nafion catalyst of the present invention is a useful method that can complete the preparation of the ester compound in a very short time as compared with the conventional method and has a high triester generation rate.
Claims (17)
Wherein the sulfonic acid is at least one catalyst selected from the group consisting of an alkylsulfonic acid, an arylsulfonic acid, an alkylarylsulfonic acid, an arylalkylsulfonic acid, a trifluoromethanesulfonic acid, and a perfluorosulfonic acid.
Wherein the alkyl group of the alkylsulfonic acid is a straight chain or branched alkyl group having 1 to 4 carbon atoms, the aryl group of the arylsulfonic acid has 6 to 12 carbon atoms, and the alkyl group of the alkylarylsulfonic acid is a straight or branched alkyl group having 1 to 4 carbon atoms , The aryl group has 6 to 12 carbon atoms, the aryl group of the arylalkylsulfonic acid has 6 to 12 carbon atoms, and the alkyl group is a straight-chain or branched alkyl group having 1 to 4 carbon atoms.
Wherein the perfluorosulfonic acid is Nafion in the form of an acid.
Wherein the acid type Nafion is any one selected from Nafion N115, Nafion N117, Nafion NR50, Nafion NRE-212, Nafion N324, Nafion R1100, Nafion D520 and Nafion D521 ≪ / RTI >
Wherein the sulfonate is at least one catalyst selected from an alkylsulfonate, an arylsulfonate, an alkylarylsulfonate, an arylalkylsulfonate, a trifluoromethanesulfonate, and a perfluorosulfonate. Way.
Wherein the perfluorosulfonic acid salt is a salt-type naphion.
Wherein the salt form of Nafion is at least one selected from Nafion N115, Nafion N117, Nafion NR50, Nafion NRE-212, Nafion N324, Nafion R1100, Nafion D520 and Nafion D521, Sc). ≪ / RTI >
Wherein the content of the catalyst is 0.01 to 10 moles per 100 moles of the polyhydric alcohol ≪ / RTI >
Wherein the polyhydric alcohol comprises three or more hydroxyl groups.
Wherein the polyhydric alcohol comprises three or four hydroxyl groups.
Wherein the polyhydric alcohol is a C4 to C30 linear or branched polyhydric alcohol.
Wherein the fatty acid is a C4 to C30 linear or branched saturated or unsaturated fatty acid.
Wherein the fatty acid is selected from the group consisting of 2-ethylhexanoic acid, isononanoic acid, oleic acid, palmitic acid, stearic acid, linoleic acid, ) And linolenic acid. ≪ RTI ID = 0.0 > 21. < / RTI >
Wherein the esterification reaction is carried out at a temperature of 150 to 250 ° C.
Wherein the perfluorosulfonic acid is subjected to an esterification reaction, followed by filtration, drying and reuse.
Wherein the perfluorosulfonic acid salt is subjected to an esterification reaction, followed by filtration, drying and reuse.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140078756A KR20160001054A (en) | 2014-06-26 | 2014-06-26 | Method for preparing ester compound using sulfonic acid or sulfonate catalysts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020140078756A KR20160001054A (en) | 2014-06-26 | 2014-06-26 | Method for preparing ester compound using sulfonic acid or sulfonate catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20160001054A true KR20160001054A (en) | 2016-01-06 |
Family
ID=55164993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140078756A KR20160001054A (en) | 2014-06-26 | 2014-06-26 | Method for preparing ester compound using sulfonic acid or sulfonate catalysts |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR20160001054A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180059594A (en) * | 2016-11-25 | 2018-06-05 | 여명바이오켐 주식회사 | Synthetic method of Xylitol Sesquicaprylate |
| KR20190082953A (en) * | 2016-11-25 | 2019-07-10 | 아르끄마 프랑스 | Acid composition for treating fatty acids |
| KR20190085541A (en) * | 2016-11-25 | 2019-07-18 | 아르끄마 프랑스 | Acid composition for treating fatty acids |
-
2014
- 2014-06-26 KR KR1020140078756A patent/KR20160001054A/en not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180059594A (en) * | 2016-11-25 | 2018-06-05 | 여명바이오켐 주식회사 | Synthetic method of Xylitol Sesquicaprylate |
| KR20190082953A (en) * | 2016-11-25 | 2019-07-10 | 아르끄마 프랑스 | Acid composition for treating fatty acids |
| KR20190085541A (en) * | 2016-11-25 | 2019-07-18 | 아르끄마 프랑스 | Acid composition for treating fatty acids |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6224570B2 (en) | Process for producing derivatives of β-hydroxycarboxylic acid | |
| US8604227B2 (en) | Process for preparing linear alpha,omega-dicarboxylic diesters | |
| CA2643441A1 (en) | Branched carboxylic acid diesters | |
| KR20160001054A (en) | Method for preparing ester compound using sulfonic acid or sulfonate catalysts | |
| Hu et al. | Facile and efficient hydrolysis of organic halides, epoxides, and esters with water catalyzed by ferric sulfate in a PEG 1000-DAIL [BF 4]/toluene temperature-dependent biphasic system | |
| DE112020003458T5 (en) | Process for the preparation of organic carboxylic acid esters using a combined bidentate arylphosphine ligand catalyst | |
| Fan et al. | Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO 3 | |
| KR20140143392A (en) | METHOD FOR PRODUCING β-ALKOXYPROPIONAMIDE | |
| WO2015186787A1 (en) | Method for producing carboxylic acid anhydride, and method for producing carboxylic acid ester | |
| JP4649645B2 (en) | Process for producing optically active alcohol compounds | |
| KR101374569B1 (en) | Hydroxyphenyl ketone derivatives for enantiomeric amino acid separation and its uses | |
| EP1731498B1 (en) | Method for producing ester and esterification catalyst | |
| KR101602428B1 (en) | Method for preparing glycidol through successive catalytic reaction | |
| Shekarriz et al. | Esterification of carboxylic acids with alcohols under microwave irradiation in the presence of zinc triflate | |
| KR101733387B1 (en) | Method for preparation of organic acid ester | |
| KR100408806B1 (en) | Process for Preparing 3-Hydroxy Propionic Acid and Salt from Exopide Derivative | |
| CN103547558A (en) | Method for producing five-membered ring-containing compound | |
| KR20140142784A (en) | Method for preparing ester compound using metal triflate catalysts | |
| KR20150016544A (en) | Process for the production of 4-alkanoyloxy-2-methylbutanoic acid | |
| CN109912515B (en) | Preparation method of rosuvastatin calcium | |
| JP5530606B2 (en) | Method for producing triphenylene carboxylic acid ester | |
| KR101821796B1 (en) | Method of producing alkylated phenol | |
| WO2017154738A1 (en) | Method for producing optically active amine compound | |
| KR101709670B1 (en) | A Method for Preparation of Ester Compound which Improve the Yield by Using an Acetone | |
| JP4143203B2 (en) | Immobilized acid catalyst |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |