WO2001079190A1 - Method of synthesizing glyceryl mono-esters - Google Patents

Method of synthesizing glyceryl mono-esters Download PDF

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Publication number
WO2001079190A1
WO2001079190A1 PCT/ZA2001/000045 ZA0100045W WO0179190A1 WO 2001079190 A1 WO2001079190 A1 WO 2001079190A1 ZA 0100045 W ZA0100045 W ZA 0100045W WO 0179190 A1 WO0179190 A1 WO 0179190A1
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Prior art keywords
acid
closed
ring
metal salt
expoxide
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PCT/ZA2001/000045
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French (fr)
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Guy Thomas Topping
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Guy Thomas Topping
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Priority to AU63523/01A priority Critical patent/AU6352301A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups

Definitions

  • This invention reiates to the synthesis of glyceryl mono-esters.
  • esteriflcation is used inter alia to produce certain glyceryl mono-esters which are used as lubricants in synthetic plastics such as polypropylene, polyethylene and polyvinyl chloride.
  • mono-esters include glyceryl onostearat ⁇ and glyceryl monooleate.
  • a currently used method of manufacture of these compounds is by the esterificatio ⁇ of glycerol ⁇ 1 ,2,3-propanetrioI) with a fatty acid.
  • glyceryl mono-, di- and tri- esters ere formed.
  • This presents a problem as the ability of the product to act as a lubricant in synthetic plastics is diminished due to the presence of the di- and tri- ester. For this reason, an expensive separation process is required to separate the desired glyceryl mono-ester from the other compounds formed. This separation process greatly increases the cost of the glyceryl mono-ester,
  • Glyceryl p-Aminobenzoate is also synthesized by the esterification of p- aminobe ⁇ zoic acid with glycerol. This compound is used in cosmetic sunscreen preparations. Likewise glycerol monolaurate, which Is used in polishing compounds, and glycerol monoacetate which is used in tanning can be produced by an esterification process based on glyceryl,
  • a method of manufacturing a glycerol monoester which comprises reacting epichlorohydrin with the metal salt of an organic acid to form an ester compound ith a closed expoxide ring, and opening the closed expoxide ring.
  • Said metal salt can be sodium stearate, sodium oleat ⁇ , the sodium salt of p- arninobenzoic acid or sodium acetate.
  • Other salts such as potassium, lithium, magnesium and calcium can be used.
  • Said acid can be a fatty acid, an aliphatic acid or an aromatic carboxyl acid.
  • a method of manufacturing a glycerol mono-ester which comprises reacting epichlorohydrin with the metal salt of an acid selected from lauric acid, myrlstlc acid, palmitic acid, stearic acid, oleic acid, linoleic acid, acetic acid, linolenlc acid, citric acid, ascorbic acid, benzoic acid and p-aminobenzoic acid to form an ester compound with a closed expoxide ring, and thereafter opening the closed expoxide ring using an acid catalysed aqueous solution.
  • an acid selected from lauric acid, myrlstlc acid, palmitic acid, stearic acid, oleic acid, linoleic acid, acetic acid, linolenlc acid, citric acid, ascorbic acid, benzoic acid and p-aminobenzoic acid to form an ester compound with a closed expoxide ring, and thereafter
  • the invention also provides a method which comprises reacting epichlorohydrin with the metal salt of a fatty acid, aliphatic acid or aromatic carboxylic acid as follows:- CH SH-CH. + Na O- CC?-RR ⁇ CClH ⁇ -CH-CH -0-6 ⁇ R + NaCi
  • I a Cl to C30 branch or straight chained aliphatic or aromatic compound, and thereafter opening the closed expoxide ring by acid catalyzation.
  • suitable metal salts are the metal salts of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, lino ⁇ enic acid and p-Aminobenz ⁇ ic acid.
  • the present invention is primarily Intended to synthesize glygeryl monostearate and glyceryl monooleate but other mono stearates can also be synthesized.
  • epichlorohydrin By reacting epichlorohydrin with sodium stearate an epoxide ester is formed which Is the precursor to glyceryl monostearate, and with sodium oieate to form an epoxide ester which is the precursor to glyceryl monooleate.
  • Example 1 a) Glyceryl monostearate. An amount of 284,4g of sodium stearate is weighed out and placed in an Erlenmeyer flask. An excess (250g) of epichlorohydrin Is then added to the reaction vessel. A Dean and Stark apparatus with a drain tap is then attached to the reaction vessel and a Dlmroth condenser is placed on the Dean and Stark apparatus. All ground joints are greased with vacuum grease.
  • the reaction is run under reflux conditions for about two hours at about 100 degrees C but temperatures of above and below this figure can be used.
  • the sodium stearate is not readily soluble in the epichlorohydrin and the reaction can be seen to be going to completion when the stearate is in solution and sodium chloride crystals have formed In the solution.
  • the reaction goes to completion as follows:-
  • the remaining solution is then filtered to remove the sodium chloride crystals using a Buechner funnel and a filter flask.
  • the product thus obtained is not the final product as it has a closed epoxide ring.
  • 250ml of a 2% sulphuric acid solution is added to the filtrate and refl ⁇ xing is continued for a further hour at about 100 degrees C.
  • the reaction is as foltows;-
  • the sodium oieate is not readliy soluble in the epichlorohydrin and the reaction can be seen to be going to completion when the oieate Is in solution and sodium chloride crystals have formed in the solution.
  • the reaction goes to completion as follows:-
  • the remaining solution Is then filtered to remove the sodium chloride crystals using a Buechner funnel and a filter flask.
  • the product thus obtained is not the final product as It has a closed epoxide ring, To open the epoxide ring 250ml of a 2% sulphuric acid solution is added to the filtrate and refluxing is continued for a further hour at about 100 degrees C,
  • the remaining solution is then filtered to remove the sodium chloride crystals using a Buechner funnel and a filter flask.
  • the product thus obtained Is not the final product as it has a closed epoxide ring.
  • 250ml of a 2% sulphuric acid solution Is added to the filtrate and refluxing is continued for a further hour at about 100 degrees C.
  • the reaction is run under reflux conditions for about two hours at about 100 degrees C but temperatures of above and below this figure can be used. Excess epichlorohydrin is allowed to distil off by draining it away through the Dean and Stark apparatus. A vacuum pump can be used to aid in removal of excess epichlorohydrin.
  • the remaining solution is then filtered to remove the sodium chloride crystals using a Bue ⁇ hner funnel and a filter flask.
  • the product thus obtained is not the final product as it has a closed epoxide ring.
  • 250ml of a 2% sulphuric acid solution is added to the filtrate and refluxing is continued for a further hour at about 100 degrees C.
  • Example 4 is raftf-fllu ly nij wu'ljnm l*n' "-ntr>. jn pl ⁇ ra nf thfl gnHii ⁇ m nlfiafa

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention provides a method of manufacturing a glycerol monoester which comprises reacting epichlorohydrin with the metal salt of a fatty acid, an aliphatic acid or an aromatic carboxyl acid to form an ester compound with a closed expoxide ring, and opening the closed expoxide ring by adding acidified water.

Description

Method of synthe^ng glyseryl mono-esters
Field of the invention
This invention reiates to the synthesis of glyceryl mono-esters.
Background to the invention
It Is well known that when organic acids are heated with primary or secondary alcohols an equilibrium condition is established with the ester and water. This process is known as esteriflcation and is used inter alia to produce certain glyceryl mono-esters which are used as lubricants in synthetic plastics such as polypropylene, polyethylene and polyvinyl chloride. These mono-esters include glyceryl onostearatθ and glyceryl monooleate.
A currently used method of manufacture of these compounds is by the esterificatioπ of glycerol {1 ,2,3-propanetrioI) with a fatty acid. During this reaction, glyceryl mono-, di- and tri- esters ere formed. This presents a problem as the ability of the product to act as a lubricant in synthetic plastics is diminished due to the presence of the di- and tri- ester. For this reason, an expensive separation process is required to separate the desired glyceryl mono-ester from the other compounds formed. This separation process greatly increases the cost of the glyceryl mono-ester,
Glyceryl p-Aminobenzoate is also synthesized by the esterification of p- aminobeπzoic acid with glycerol. This compound is used in cosmetic sunscreen preparations. Likewise glycerol monolaurate, which Is used in polishing compounds, and glycerol monoacetate which is used in tanning can be produced by an esterification process based on glyceryl,
Brief summary of the Invention
According to one aspect of the present invention there is provided a method of manufacturing a glycerol monoester which comprises reacting epichlorohydrin with the metal salt of an organic acid to form an ester compound ith a closed expoxide ring, and opening the closed expoxide ring.
Said metal salt can be sodium stearate, sodium oleatθ, the sodium salt of p- arninobenzoic acid or sodium acetate. Other salts such as potassium, lithium, magnesium and calcium can be used.
Said acid can be a fatty acid, an aliphatic acid or an aromatic carboxyl acid.
According to a further aspect of the present invention there is provided a method of manufacturing a glycerol mono-ester which comprises reacting epichlorohydrin with the metal salt of an acid selected from lauric acid, myrlstlc acid, palmitic acid, stearic acid, oleic acid, linoleic acid, acetic acid, linolenlc acid, citric acid, ascorbic acid, benzoic acid and p-aminobenzoic acid to form an ester compound with a closed expoxide ring, and thereafter opening the closed expoxide ring using an acid catalysed aqueous solution.
The invention also provides a method which comprises reacting epichlorohydrin with the metal salt of a fatty acid, aliphatic acid or aromatic carboxylic acid as follows:- CH SH-CH. + Na O- CC?-RR →→ CClHϊ-CH-CH -0-6^ R + NaCi
Where Is a Cl to C30 branch or straight chained aliphatic or aromatic compound, and thereafter opening the closed expoxide ring by acid catalyzation.
Examples of suitable metal salts are the metal salts of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linoϊenic acid and p-Aminobenzαic acid.
Detailed description of he invention
The present invention is primarily Intended to synthesize glygeryl monostearate and glyceryl monooleate but other mono stearates can also be synthesized. By reacting epichlorohydrin with sodium stearate an epoxide ester is formed which Is the precursor to glyceryl monostearate, and with sodium oieate to form an epoxide ester which is the precursor to glyceryl monooleate. By reacting epichlorohydrin with the sodium salt of p-aminobeπzαic acid there is formed an epoxide ester which Is the precursor to glyceryl p-a inobenzoate, In all three cases the epoxide ring is then opened using the acid-catalyzed addition of water. Specific examples of the method are described below:-
Example 1 a) Glyceryl monostearate. An amount of 284,4g of sodium stearate is weighed out and placed in an Erlenmeyer flask. An excess (250g) of epichlorohydrin Is then added to the reaction vessel. A Dean and Stark apparatus with a drain tap is then attached to the reaction vessel and a Dlmroth condenser is placed on the Dean and Stark apparatus. All ground joints are greased with vacuum grease.
The reaction is run under reflux conditions for about two hours at about 100 degrees C but temperatures of above and below this figure can be used.
The sodium stearate is not readily soluble in the epichlorohydrin and the reaction can be seen to be going to completion when the stearate is in solution and sodium chloride crystals have formed In the solution. The reaction goes to completion as follows:-
Figure imgf000005_0001
+ NaCI
Excess epichlorohydrin Is allowed to distil off by draining it away through the Dean and Stark apparatus. A vacuum pump can be used to aid in removal of excess epichlorohydrin.
The remaining solution is then filtered to remove the sodium chloride crystals using a Buechner funnel and a filter flask. The product thus obtained is not the final product as it has a closed epoxide ring. To open the epoxide ring 250ml of a 2% sulphuric acid solution is added to the filtrate and reflυxing is continued for a further hour at about 100 degrees C.
The reaction is as foltows;-
CH -(OH ) -C-O-CH -CH-CH + H O → CHr(CH ) -C-O-CH -C -CH,
Excess water Is drawn off under vacuum to obtain glyceryl monostearate.
b) Glyceryl mono oieate
An amount of 304g of sodium oieate is weighed out and placed in an Erlenmeyer flask. An excess (25Qg) of epichlorohydrin is then added to the reaction vessel. A Dean and Stark apparatus with a drain tap is then attached to the reaction vessel and a Dirnroth condenser is placed on the Dean and Stark apparatus. All ground joints are greased with vacuum grease.
The sodium oieate is not readliy soluble in the epichlorohydrin and the reaction can be seen to be going to completion when the oieate Is in solution and sodium chloride crystals have formed in the solution. The reaction goes to completion as follows:-
CH 1 - H-CH. +
Figure imgf000006_0001
Excess epichlorohydrin is allowed to distil off by draining it away through the Dean and Stark apparatus. A vacuum pump can be used to aid in removal of excess epichlorohydrin,
The remaining solution Is then filtered to remove the sodium chloride crystals using a Buechner funnel and a filter flask.
The product thus obtained is not the final product as It has a closed epoxide ring, To open the epoxide ring 250ml of a 2% sulphuric acid solution is added to the filtrate and refluxing is continued for a further hour at about 100 degrees C,
Figure imgf000007_0001
Excess water is drawn off under vacuum to obtain glyceryl mono oieate,
Example c) Production of Glyceryl p-Aminobenzoate
An amount of 159g of the sodium salt of p-aminobenzoic acid is weighed out and placed in an Ertenmeyer flask. An excess (250g) of epichlorohydrin is then added to the reaction vessel. A Dean and Stark apparatus with a drain tap is then attached to the reaction vessel and a Dimroth condenser Is placed on the Dean and Stark apparatus. Ail ground joints are greased with vacuum grease. The reaction is run under reflux conditions for about two hours at about 100 degrees C. The reaction goes to completion as follows;-
Figure imgf000008_0001
Excess epichlorohydrin is allowed to distil off by όrain g it away through the Dean and Stark apparatus. A vacuum pump can be used to aid in removal of excess epichlorohydrin.
The remaining solution is then filtered to remove the sodium chloride crystals using a Buechner funnel and a filter flask.
The product thus obtained Is not the final product as it has a closed epoxide ring. To open the epoxide ring 250ml of a 2% sulphuric acid solution Is added to the filtrate and refluxing is continued for a further hour at about 100 degrees C.
The reaction is as follows
Figure imgf000008_0002
Excess water is drawn off under vacuum to obtain glyceryl monostearte
Examptø 4 d) Glyceryl acetate. An amount of 82,04g of sodium acetate is weighed out and placed in an Erlenmeyer flask. An excess (250g) of epichlorohydrin is then added to the reaction vessel. A Dean and Stark apparatus with a drain tap is then attached to the reaction vessel and a Dimroth condenser is placed on the Dean and Stark apparatus, Ail ground joints are greased with vacuum grease.
The reaction is run under reflux conditions for about two hours at about 100 degrees C but temperatures of above and below this figure can be used. Excess epichlorohydrin is allowed to distil off by draining it away through the Dean and Stark apparatus. A vacuum pump can be used to aid in removal of excess epichlorohydrin.
The remaining solution is then filtered to remove the sodium chloride crystals using a Bueσhner funnel and a filter flask.
The product thus obtained is not the final product as it has a closed epoxide ring. To open the epoxide ring 250ml of a 2% sulphuric acid solution is added to the filtrate and refluxing is continued for a further hour at about 100 degrees C.
Excess water Is drawn off under vacuum to obtain glyceryl acetate.
Exsynple 5
Example 4 is raftf-fllu ly nij wu'ljnm l*n' "-ntr>. jn plπra nf thfl gnHii ιm nlfiafa

Claims

1. A method of manufacturing a glycerol monoester which comprises reacting epichlorohydrin with the metal salt of an organic acid to form an ester compound with a closed expoxide ring, and opening the closed expoxide ring.
2. A method as claimed in claim 1 , wherein said metal salt is sodium stearate.
3. A method as claimed in claim 1 , wherein said metai salt is a sodium oieate.
4. A method as claimed in claim , wherein said metai salt is the sodium salt of p-amiπobenzoic acid,
5. A method as claimed in claim 1, 2, 3 or 4, herein said acid is a fatty acid, an aliphatic acid or an aromatic carboxyl acid.
6* A method of manufacturing a glycerol monoester which comprises reacting epichlorohydrin with the metal salt of an acid selected from lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolθnic acid, acetic acid, citric acid, ascorbic acid, benzoic acid and p-aminobenzoic acid to form an ester compound with a closed expoxide ring, and thereafter opening the closed expoxide ring using an acid catalysed aqueous solution.
7. A method which comprises reacting epichlorohydrin with the metal salt of a fatty acid, aliphatic acid or aromatic carboxylic acid as fallows;- CH ACH-C PH + Na O-C P-R → C -H- -9CH-CH -O-C P-R + NaCI
Where R is a Ct to C30 branch or straight chained aliphatic or aromatic compound, and thereafter opening the closed expoxide ring by acid catalyzation.
PCT/ZA2001/000045 2000-04-17 2001-04-17 Method of synthesizing glyceryl mono-esters WO2001079190A1 (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100470607B1 (en) * 2002-03-09 2005-02-07 삼광 고하켐 주식회사 Method for preparing highly pure glyceryl monoester
CN103864725A (en) * 2014-03-28 2014-06-18 中南林业科技大学 Eleostearic acid glycidyl ester and preparation method thereof
CN108409569A (en) * 2018-04-13 2018-08-17 山东滨州金盛新材料科技有限责任公司 A kind of aqueous polyglycereol tartaric acid ester compounds and preparation method thereof
CN109851503A (en) * 2019-01-30 2019-06-07 天津现代职业技术学院 A kind of method that water phase prepares citric acid mono fatty acid glyceride
CN110256243A (en) * 2019-07-11 2019-09-20 深圳海王医药科技研究院有限公司 The preparation method of P-hydroxybenzoic acid glyceride

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100470607B1 (en) * 2002-03-09 2005-02-07 삼광 고하켐 주식회사 Method for preparing highly pure glyceryl monoester
CN103864725A (en) * 2014-03-28 2014-06-18 中南林业科技大学 Eleostearic acid glycidyl ester and preparation method thereof
CN108409569A (en) * 2018-04-13 2018-08-17 山东滨州金盛新材料科技有限责任公司 A kind of aqueous polyglycereol tartaric acid ester compounds and preparation method thereof
CN108409569B (en) * 2018-04-13 2021-02-12 山东滨州金盛新材料科技有限责任公司 Water-based polyglycerol fruit ester compound and preparation method thereof
CN109851503A (en) * 2019-01-30 2019-06-07 天津现代职业技术学院 A kind of method that water phase prepares citric acid mono fatty acid glyceride
CN110256243A (en) * 2019-07-11 2019-09-20 深圳海王医药科技研究院有限公司 The preparation method of P-hydroxybenzoic acid glyceride

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