US3558597A - Process for the production of sugar esters - Google Patents

Process for the production of sugar esters Download PDF

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Publication number
US3558597A
US3558597A US746292A US3558597DA US3558597A US 3558597 A US3558597 A US 3558597A US 746292 A US746292 A US 746292A US 3558597D A US3558597D A US 3558597DA US 3558597 A US3558597 A US 3558597A
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sugar
fatty acid
mol
acid ester
sucrose
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US746292A
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Hanswilli Von Brachel
Manfred Schon
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Cassella Farbwerke Mainkur AG
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Cassella Farbwerke Mainkur AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids

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  • This invention relates to an improvement in the production of sugar esters via transeste'rification of sugars with fatty acid esters.
  • the conventional prior art transesterification process is carried out in the presence of an inert solvent reaction medium such as dimethyl formamide or dimethyl sulfoxide in the presence of any one of the well known basic transesten'fication catalysts.
  • This prior art process suffers from the disadvantage of requiring the use of specialized solvents which are slightly toxic, as well as the necessity of solvent removal after completion of the reaction.
  • such a process requires the use of a three fold excess of sugar reactant in order to obtain sugar monoesters of commercial significance.
  • the present invention is based on the unexpected discovery that it is possible to eliminate the prior art required inert reaction medium under conditions which do not require the use of a three fold excess of sugar reactant and yet obtain a high yield of commercially significant sugar monoesters.
  • the process of the present invention for producing sugar esters by transesterification of a sugar with a fatty acid ester comprises heating said reactants in the presence of a catalytic amount of a basic transesterification catalyst under pressure and temperature conditions which eliminate alcohol by-product and produce readily recoverable sugar ester.
  • a catalytic amount of a basic transesterification catalyst under pressure and temperature conditions which eliminate alcohol by-product and produce readily recoverable sugar ester.
  • from about 0.5 to about 3 mols of sugar reactant are employed per mol of fatty acid ester and the temperature involved ranges from 100 to 170 C. at a pressure of from about 0.1 to about 500 mm. Hg.
  • transesterification process of the present invention it is carried out in the presence of the usual or known basic transesterification catalyst at a temperature of from 100 to 170 C. and at a pressure within the range of from about, 0.1 to about 500 mm. Hg, the choice of the temperature employed dictating a pressure within said range distills 01f resultant alcohol by-product.
  • the preferred't emperature is from 130 to 160 C. and the preferred pressure is from 1 to 15 mm. Hg.
  • the reaction time is not critical aspect of the present invention other than it is" determinative of percentage yields obtained. In general, it ranges from 3 to 24 hours, most reaction conditions having run their course in from about 5 to hours.
  • sucrose and trehalose typify the disaccharides and raffinose is a typical trisaccharide.
  • the preferred fatty acid esters for the process of the present invention include the lower alkyl esters of saturated or unsaturated fatty acids or hydroxy fatty acids having 12-18 carbon atoms.
  • particularly important fatty acid esters include the methyl, ethyl, propyLhydroxypropyl, and glycerol esters of laun'c, myristic, palmitic, stearic, hydroxy stearic, o1eic,”ricinenic, linoleicand ricinoleic.
  • the fatty acid esters present in talloil, coconut oil and soybean oil are of major interest from the standpoint of product identity.
  • any of the conventional basic transesterification catalysts used in the prior art process may also be employed in the present process.
  • catalytic amounts thereof range from about 0.5 to 20% by weight based on the amount of fatty acid ester reactant.
  • Typical preferred catalysts include the alkali metal salts of weak acids, alkali metal hydroxides and alkali metal alcoholates of lower alkanols.
  • the preferred basic catalyst is potassium carbonate.
  • the molar ratio of sugar to fatty acid ester employed in the present invention ranges between about 0.5 and 3 mols of sugar to 1 mol of fatty acid ester.
  • the preferred ratio is from about 0.8 to about 1.2 mols of sugar per mol of fatty'acid ester employed.
  • the sugar ester product of the present invention comprises a mixture of esters. Depending upon the choice of reactant ratio, fatty acid ester identity and the catalyst employed, these mixtures comprise monoand diesters in varying proportions, the monoester being the predominant product present. Depending upon the choice of reactants, ratios thereof and other reaction conditions, the yields" obtained, based on the monoester, range from about 60 to of theory.
  • sugar esters of the type produced by the present invention are useful as biologically decomposable emulsifiers in food processing, the pharmaceutical industry and in cosmetics.
  • EXAMPLE 1 34.2 g. (0.1 mol) sucrose, 29.9 g. (0.1 mol) methyl stearate and 4.5 g. potassium carbonate are heated with stirring at to 15 mm. Hg, with about 3 g. methanol distilling off during the course of. 8 hours.
  • the resultant reaction mixture that contains, apart from sugar stearate, unreacted sugar, methyl stearate, potassium carbonate and potassium stearate, is boiled with 200 "cc. methylethyl ketone after the addition of 4 cc. glacial acetic acid (in order to convert potassium stearate into stearic acid), and while hot, undissolved sugar and potassium acetate are filtered off with suction.
  • Saponification value calculated- Monostearate 92 Distearate 128 Found 105 having a saponification value of 109 can be isolated.
  • a process for producing sugar. esters by transesterification of a sugar with a fatty acid ester which comprises heating a mixture consisting of a catalytic amount of a basic transesterification catalyst, from about 0.5 to about 3 mols of a sugar selected from the group consisting of sucrose, trehalose and raflinose and 1 mol of a fatty acid ester which is a lower alkyl ester of a saturated or unsaturated fatty acid or hydroxy fatty acid having 12 to 18 carbon atoms at a temperature of from 100 to C. and at a pressure within the range of from about 0.1 to about 500 mm. Hg to distilloff resulting alcohol byproduct and recovering resulting sugar ester.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

TRANSESTERIFICATION OF SUGAR WITH A FATTY ACID ESTER IN THE PRESENCE OF A BASIC TRANSETERIFICATION CATALYST AT TEMPERATURE AND PRESSURE CONDITIONS DESIGNED TO DISTILL OFF ALCHOL BY-PRODUCT AND THEREBY ELIMINATE THE NEED OF AN INERT SOLVENT REACTION MEDIUM AND ITS INHERENT DISADVANTAGES.

Description

United States Patent Int. Cl. corc 69/32 U.S. Cl. 260-234 4 Claims ABSTRACT OF THE DISCLOSURE Transesterification of sugar with a fatty acid ester in the presence of a basic transesterification catalyst at temperature and pressure conditions designed to distill off alcohol by-product and thereby eliminate the need of an inert solvent reaction medium and its inherent disadvantages.
BACKGROUND OF THE INVENTION This invention relates to an improvement in the production of sugar esters via transeste'rification of sugars with fatty acid esters. The conventional prior art transesterification process is carried out in the presence of an inert solvent reaction medium such as dimethyl formamide or dimethyl sulfoxide in the presence of any one of the well known basic transesten'fication catalysts. This prior art process suffers from the disadvantage of requiring the use of specialized solvents which are slightly toxic, as well as the necessity of solvent removal after completion of the reaction. Moreover, such a process requires the use of a three fold excess of sugar reactant in order to obtain sugar monoesters of commercial significance. The present invention is based on the unexpected discovery that it is possible to eliminate the prior art required inert reaction medium under conditions which do not require the use of a three fold excess of sugar reactant and yet obtain a high yield of commercially significant sugar monoesters.
SUMMARY OF THE INVENTION The process of the present invention for producing sugar esters by transesterification of a sugar with a fatty acid ester comprises heating said reactants in the presence of a catalytic amount of a basic transesterification catalyst under pressure and temperature conditions which eliminate alcohol by-product and produce readily recoverable sugar ester. In general, from about 0.5 to about 3 mols of sugar reactant are employed per mol of fatty acid ester and the temperature involved ranges from 100 to 170 C. at a pressure of from about 0.1 to about 500 mm. Hg.
DETAILED DESCRIPTION OF THE INVENTION In accordance with the transesterification process of the present invention, it is carried out in the presence of the usual or known basic transesterification catalyst at a temperature of from 100 to 170 C. and at a pressure within the range of from about, 0.1 to about 500 mm. Hg, the choice of the temperature employed dictating a pressure within said range distills 01f resultant alcohol by-product. The preferred't emperature is from 130 to 160 C. and the preferred pressure is from 1 to 15 mm. Hg. The reaction time is not critical aspect of the present invention other than it is" determinative of percentage yields obtained. In general, it ranges from 3 to 24 hours, most reaction conditions having run their course in from about 5 to hours.
Although all sugars are susceptible to the transesterification process of the instant invention, disaccharides and trisaccharides are generally preferred since they yield the more commercially significant products. Sucrose and trehalose typify the disaccharides and raffinose is a typical trisaccharide.
The preferred fatty acid esters for the process of the present invention include the lower alkyl esters of saturated or unsaturated fatty acids or hydroxy fatty acids having 12-18 carbon atoms. Examples of particularly important fatty acid esters include the methyl, ethyl, propyLhydroxypropyl, and glycerol esters of laun'c, myristic, palmitic, stearic, hydroxy stearic, o1eic,"ricinenic, linoleicand ricinoleic. Additionally, the fatty acid esters present in talloil, coconut oil and soybean oil are of major interest from the standpoint of product identity.
Any of the conventional basic transesterification catalysts used in the prior art process may also be employed in the present process. In general, catalytic amounts thereof range from about 0.5 to 20% by weight based on the amount of fatty acid ester reactant. Typical preferred catalysts include the alkali metal salts of weak acids, alkali metal hydroxides and alkali metal alcoholates of lower alkanols. The preferred basic catalyst is potassium carbonate.
The molar ratio of sugar to fatty acid ester employed in the present invention ranges between about 0.5 and 3 mols of sugar to 1 mol of fatty acid ester. The preferred ratio is from about 0.8 to about 1.2 mols of sugar per mol of fatty'acid ester employed.
Recovery of the product of the instant invention is in accordance with conventional techniques of the prior art. It is helpful to boil the crude reaction product in methylethyl ketone, chloroform or acetone in the presence of a small amount of acid for the purpose of converting the fatty acid salt by-products to fatty acids. Thereafter, unreacted sugar may be removed from the hot solution by suction filtration. Upon further cooling, the desired sugar ester product separates out as a solid from the filtrate.
The sugar ester product of the present invention comprises a mixture of esters. Depending upon the choice of reactant ratio, fatty acid ester identity and the catalyst employed, these mixtures comprise monoand diesters in varying proportions, the monoester being the predominant product present. Depending upon the choice of reactants, ratios thereof and other reaction conditions, the yields" obtained, based on the monoester, range from about 60 to of theory.
As is known by those in the art, sugar esters of the type produced by the present invention are useful as biologically decomposable emulsifiers in food processing, the pharmaceutical industry and in cosmetics.
The following examples are for the purpose of illustrating the present invention but are not limiting to the scope thereof. The precentages referred to therein are by weight and the temperatures are in degrees centigrade.
EXAMPLE 1 34.2 g. (0.1 mol) sucrose, 29.9 g. (0.1 mol) methyl stearate and 4.5 g. potassium carbonate are heated with stirring at to 15 mm. Hg, with about 3 g. methanol distilling off during the course of. 8 hours.
The resultant reaction mixture that contains, apart from sugar stearate, unreacted sugar, methyl stearate, potassium carbonate and potassium stearate, is boiled with 200 "cc. methylethyl ketone after the addition of 4 cc. glacial acetic acid (in order to convert potassium stearate into stearic acid), and while hot, undissolved sugar and potassium acetate are filtered off with suction. When cooling down, sugar stearate in the form of a light brown powder precipitates from the filtrate. Yield: 42 g. ('=69% of the theoretical referred to sucrose monostearate).
Saponification value: calculated- Monostearate 92 Distearate 128 Found 105 having a saponification value of 109 can be isolated.
EXAMPLE 2 34.2 g. (0.1 mol) sucrose, 21.4 g. (0.1 mol) methyl laurate and 4.5 g. potassium carbonate are heated with stirring in vacuo at 140 to 145/ 15 mm. Hg for 12 hours,
about 3 g. methanol being distilled off. The crude product is boiled with 200 cc. acetone after the addition of 4 cc. glacialacetic acid, then filtered off with suction, and the sugar ester which is separated from the filtrate is filtered olf with suction at 32.6 g. sugar ester (=62.2% of the theoretical referred to sucrose monolaurate) are ob- 'tained.
Saponification value: calculated- Monolaurate 107 Dilaurate 159 Found 106 EXAMPLE 3 Under the conditions given in Example 1 and employing 34.2 g. (0.1 mol) sucrose, 59.8 g. (0.2 mols) methyl stearate and 4.5 g. potassium carbonate, about 6 g. methanol distilled off. After boiling the crude product, with 200 cc. methyl-ethyl ketone and 4 cc. glacial acetic acid, a crude product is obtained from which 70.2 g. sucrose distearate (=80% of the theoretical) having a saponification value of 128 can be isolated.
EXAMPLE 4 34.2 g. (0.1 mol) sucrose, 34.3 g. (0.1 mol) 1,2-propanediol monostearate and 4.5 g. potassium carbonate are 4 heated with stirring at -145 1 mm. 'Hg. About 7.5 cc. 1,2-propanediol distills off in the course of '8 hours. After working up as described in Example 1, 45.4 g. sugar stearate (=74.5% of the theoretical referred to sucrose monostearate) having a saponification value of 103 are obtained.
If the 1,2-propanediol monostearate of this example is replaced with 0.1 mol 1,2-propanediol monooleate (43.1 g.), a sucrose oleate having similar properties is obtained.
What is claimed is:
1. A process for producing sugar. esters by transesterification of a sugar with a fatty acid ester which comprises heating a mixture consisting of a catalytic amount of a basic transesterification catalyst, from about 0.5 to about 3 mols of a sugar selected from the group consisting of sucrose, trehalose and raflinose and 1 mol of a fatty acid ester which is a lower alkyl ester of a saturated or unsaturated fatty acid or hydroxy fatty acid having 12 to 18 carbon atoms at a temperature of from 100 to C. and at a pressure within the range of from about 0.1 to about 500 mm. Hg to distilloff resulting alcohol byproduct and recovering resulting sugar ester.
2. The process of claim 1 wherein from about 0.8 to about 1.2 mols of sugar to 1 mol of fatty acid ester are employed.
3. The process of claim 2 wherein said heating is conducted for from about 3 to about 24 hours.
4. The process of claim 1 wherein said sugar is sucrose, said fatty acid ester is methyl stearate, methyl laurate or 1,2-propanediol monostearate and said catalyst is potassium carbonate.
References Cited UNITED STATES PATENTS 2,831,855 4/1958 Martin 260234 2,999,858 9/196l Curtis 260234 3,251,827 5/1966 Schnell et a1 260234 LEWIS GOTTS, Primary Examiner J. .R. BROWN, Assistant Examiner
US746292A 1967-08-04 1968-07-22 Process for the production of sugar esters Expired - Lifetime US3558597A (en)

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5024210A (en) * 1973-03-16 1975-03-15
US3956278A (en) * 1972-11-06 1976-05-11 Krems-Chemie Gesellschaft M.B.H. Novel mixed partial esters of carbohydrates
JPS5165704A (en) * 1974-10-17 1976-06-07 Tate & Lyle Ltd
US3963699A (en) * 1974-01-10 1976-06-15 The Procter & Gamble Company Synthesis of higher polyol fatty acid polyesters
US4298730A (en) * 1979-12-19 1981-11-03 Talres Development (N.A.) N.V. Process for the production of a surfactant containing sucrose esters
US4517360A (en) * 1983-06-23 1985-05-14 The Procter & Gamble Company Synthesis of higher polyol fatty acid polyesters using carbonate catalysts
US4518772A (en) * 1983-06-23 1985-05-21 The Proctor & Gamble Company Synthesis of higher polyol fatty acid polyesters using high soap:polyol ratios
US4778881A (en) * 1985-01-24 1988-10-18 Cooperatieve Vereniging Suiker Unie U.A. Method for the preparation of esters of a non-reducing sugar and one or more fatty acids
US4806632A (en) * 1986-12-29 1989-02-21 The Procter & Gamble Company Process for the post-hydrogenation of sucrose polyesters
US4942054A (en) * 1987-05-13 1990-07-17 Curtice-Burns, Inc. Process for producing low calorie foods from alkyl glycoside fatty acid polyesters
US4973489A (en) * 1987-05-13 1990-11-27 Curtice Burns, Inc. Polysaccaride fatty acid polyester fat substitutes
US4983731A (en) * 1989-03-17 1991-01-08 Nebraska Department Of Economic Development Separation and purification of sugar esters
US5006648A (en) * 1986-07-23 1991-04-09 Van Den Bergh Foods Co., Division Of Conopco Inc. Process for preparing partial polyol fatty acid esters
US5550220A (en) * 1987-05-13 1996-08-27 Curtice-Burns, Inc. Alkyl glycoside fatty acid polyester fat substitute food compositions and process to produce the same
US5559226A (en) * 1991-04-12 1996-09-24 The Procter & Gamble Company Process for making polyol fatty acid polyesters having oxidative stability
US6121440A (en) * 1998-01-29 2000-09-19 The Procter & Gamble Company Process for synthesis of polyol fatty acid polyesters
US20040022819A1 (en) * 1993-10-07 2004-02-05 Takeshi Ikemoto Surfactant, and an emulsion-type cosmetic composition and a liposome containing said surfactant
US7304153B1 (en) 1990-09-11 2007-12-04 The Procter And Gamble Co. Polyol polyester synthesis
CN103360434A (en) * 2013-07-29 2013-10-23 柳州爱格富食品科技股份有限公司 Preparation method of sucrose ester
CN111187310A (en) * 2020-01-17 2020-05-22 常州工学院 Industrial preparation method of trehalose fatty acid ester

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50142507A (en) * 1974-05-02 1975-11-17
JPS5917120B2 (en) * 1974-10-02 1984-04-19 ユニチカ株式会社 Method for producing sucrose ester
US4839164A (en) * 1987-02-24 1989-06-13 Estee Lauder, Inc. Trehalose containing cosmetic composition and method of using it
DE4015733A1 (en) * 1990-05-16 1991-11-21 Grillo Werke Ag Mono and/or di:ester(s) of alpha D-methyl-glucoside prepn. - by solvent-free process in presence of carrier impregnated with basic catalyst and poly:carboxylic acid soap

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956278A (en) * 1972-11-06 1976-05-11 Krems-Chemie Gesellschaft M.B.H. Novel mixed partial esters of carbohydrates
JPS5024210A (en) * 1973-03-16 1975-03-15
US3996206A (en) * 1973-03-16 1976-12-07 Tate & Lyle Limited Process of making sucrose esters
JPS546526B2 (en) * 1973-03-16 1979-03-29
US3963699A (en) * 1974-01-10 1976-06-15 The Procter & Gamble Company Synthesis of higher polyol fatty acid polyesters
JPS5165704A (en) * 1974-10-17 1976-06-07 Tate & Lyle Ltd
US4032702A (en) * 1974-10-17 1977-06-28 Tate & Lyle Limited Production of surface active material
US4298730A (en) * 1979-12-19 1981-11-03 Talres Development (N.A.) N.V. Process for the production of a surfactant containing sucrose esters
US4517360A (en) * 1983-06-23 1985-05-14 The Procter & Gamble Company Synthesis of higher polyol fatty acid polyesters using carbonate catalysts
US4518772A (en) * 1983-06-23 1985-05-21 The Proctor & Gamble Company Synthesis of higher polyol fatty acid polyesters using high soap:polyol ratios
US4778881A (en) * 1985-01-24 1988-10-18 Cooperatieve Vereniging Suiker Unie U.A. Method for the preparation of esters of a non-reducing sugar and one or more fatty acids
US5006648A (en) * 1986-07-23 1991-04-09 Van Den Bergh Foods Co., Division Of Conopco Inc. Process for preparing partial polyol fatty acid esters
US5071975A (en) * 1986-07-23 1991-12-10 Van Den Bergh Foods Co., Division Of Conopco Inc. Process for preparing polyol fatty acid polyesters
US4806632A (en) * 1986-12-29 1989-02-21 The Procter & Gamble Company Process for the post-hydrogenation of sucrose polyesters
US4942054A (en) * 1987-05-13 1990-07-17 Curtice-Burns, Inc. Process for producing low calorie foods from alkyl glycoside fatty acid polyesters
US4973489A (en) * 1987-05-13 1990-11-27 Curtice Burns, Inc. Polysaccaride fatty acid polyester fat substitutes
US5550220A (en) * 1987-05-13 1996-08-27 Curtice-Burns, Inc. Alkyl glycoside fatty acid polyester fat substitute food compositions and process to produce the same
WO1992003060A1 (en) * 1987-05-13 1992-03-05 Curtice-Burns, Inc. Saccharide fatty acid polyester fat substitutes
US4983731A (en) * 1989-03-17 1991-01-08 Nebraska Department Of Economic Development Separation and purification of sugar esters
US7304153B1 (en) 1990-09-11 2007-12-04 The Procter And Gamble Co. Polyol polyester synthesis
US5559226A (en) * 1991-04-12 1996-09-24 The Procter & Gamble Company Process for making polyol fatty acid polyesters having oxidative stability
US20040022819A1 (en) * 1993-10-07 2004-02-05 Takeshi Ikemoto Surfactant, and an emulsion-type cosmetic composition and a liposome containing said surfactant
US20070292462A1 (en) * 1993-10-07 2007-12-20 Kao Corporation Surfactant, and an emulsion-type cosmetic composition and a liposome containing said surfactant
US20090098172A1 (en) * 1993-10-07 2009-04-16 Kao Corporation Surfactant, and emulsion cosmetic and liposome each containing the same
US6121440A (en) * 1998-01-29 2000-09-19 The Procter & Gamble Company Process for synthesis of polyol fatty acid polyesters
CN103360434A (en) * 2013-07-29 2013-10-23 柳州爱格富食品科技股份有限公司 Preparation method of sucrose ester
CN103360434B (en) * 2013-07-29 2016-05-04 柳州爱格富食品科技股份有限公司 The preparation method of sucrose ester
CN111187310A (en) * 2020-01-17 2020-05-22 常州工学院 Industrial preparation method of trehalose fatty acid ester

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BE719016A (en) 1969-02-03
DE1643795A1 (en) 1971-07-01
GB1188614A (en) 1970-04-22
CH510614A (en) 1971-07-31
FR1575350A (en) 1969-07-18

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