US3558597A - Process for the production of sugar esters - Google Patents
Process for the production of sugar esters Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- sugar
- fatty acid
- mol
- acid ester
- sucrose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 235000000346 sugar Nutrition 0.000 title description 33
- 238000000034 method Methods 0.000 title description 14
- 150000002148 esters Chemical class 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 20
- 229930195729 fatty acid Natural products 0.000 abstract description 20
- 239000000194 fatty acid Substances 0.000 abstract description 20
- 238000005809 transesterification reaction Methods 0.000 abstract description 12
- 239000003054 catalyst Substances 0.000 abstract description 11
- 239000006227 byproduct Substances 0.000 abstract description 6
- 239000012429 reaction media Substances 0.000 abstract description 4
- 239000012442 inert solvent Substances 0.000 abstract description 3
- 150000004665 fatty acids Chemical class 0.000 abstract description 2
- -1 fatty acid ester Chemical class 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 8
- 229930006000 Sucrose Natural products 0.000 description 8
- 239000005720 sucrose Substances 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 4
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229940032007 methylethyl ketone Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940114926 stearate Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- QIZPVNNYFKFJAD-UHFFFAOYSA-N 1-chloro-2-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1Cl QIZPVNNYFKFJAD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229940114930 potassium stearate Drugs 0.000 description 2
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 2
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940035023 sucrose monostearate Drugs 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 150000004043 trisaccharides Chemical class 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FWNZKPKGBYWNJO-KVVVOXFISA-N (z)-octadec-9-enoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FWNZKPKGBYWNJO-KVVVOXFISA-N 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- KGUHOFWIXKIURA-VQXBOQCVSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl dodecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCC)O[C@@H]1O[C@@]1(CO)[C@@H](O)[C@H](O)[C@@H](CO)O1 KGUHOFWIXKIURA-VQXBOQCVSA-N 0.000 description 1
- FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 229940032085 sucrose monolaurate Drugs 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
Definitions
- 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.
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0043039 | 1967-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3558597A true US3558597A (en) | 1971-01-26 |
Family
ID=7025205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US746292A Expired - Lifetime US3558597A (en) | 1967-08-04 | 1968-07-22 | Process for the production of sugar esters |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3558597A (enrdf_load_stackoverflow) |
| BE (1) | BE719016A (enrdf_load_stackoverflow) |
| CH (1) | CH510614A (enrdf_load_stackoverflow) |
| DE (1) | DE1643795A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1575350A (enrdf_load_stackoverflow) |
| GB (1) | GB1188614A (enrdf_load_stackoverflow) |
| NL (1) | NL6810494A (enrdf_load_stackoverflow) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5024210A (enrdf_load_stackoverflow) * | 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 (enrdf_load_stackoverflow) * | 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 (zh) * | 2013-07-29 | 2013-10-23 | 柳州爱格富食品科技股份有限公司 | 蔗糖酯的制备方法 |
| CN111187310A (zh) * | 2020-01-17 | 2020-05-22 | 常州工学院 | 一种海藻糖脂肪酸酯的工业制备方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50142507A (enrdf_load_stackoverflow) * | 1974-05-02 | 1975-11-17 | ||
| JPS5917120B2 (ja) * | 1974-10-02 | 1984-04-19 | ユニチカ株式会社 | シヨ糖エステルの製造方法 |
| US4839164A (en) * | 1987-02-24 | 1989-06-13 | Estee Lauder, Inc. | Trehalose containing cosmetic composition and method of using it |
| DE4015733A1 (de) * | 1990-05-16 | 1991-11-21 | Grillo Werke Ag | Verfahren zur loesungsmittelfreien herstellung von mono- und/oder diestern des (alpha)-d-methylglukosids |
| EP4398732A1 (en) * | 2021-09-09 | 2024-07-17 | Apeel Technology, Inc. | Compounds and formulations for protective coatings on products such as agricultural products |
-
1967
- 1967-08-04 DE DE19671643795 patent/DE1643795A1/de active Pending
-
1968
- 1968-07-22 US US746292A patent/US3558597A/en not_active Expired - Lifetime
- 1968-07-24 NL NL6810494A patent/NL6810494A/xx unknown
- 1968-08-02 FR FR1575350D patent/FR1575350A/fr not_active Expired
- 1968-08-02 CH CH1160968A patent/CH510614A/de unknown
- 1968-08-02 GB GB37035/68A patent/GB1188614A/en not_active Expired
- 1968-08-02 BE BE719016D patent/BE719016A/xx unknown
Cited By (27)
| 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 (enrdf_load_stackoverflow) * | 1973-03-16 | 1975-03-15 | ||
| US3996206A (en) * | 1973-03-16 | 1976-12-07 | Tate & Lyle Limited | Process of making sucrose esters |
| US3963699A (en) * | 1974-01-10 | 1976-06-15 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters |
| JPS5165704A (enrdf_load_stackoverflow) * | 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 |
| US5071975A (en) * | 1986-07-23 | 1991-12-10 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing polyol fatty acid polyesters |
| 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 |
| US4806632A (en) * | 1986-12-29 | 1989-02-21 | The Procter & Gamble Company | Process for the post-hydrogenation of sucrose polyesters |
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| WO1992003060A1 (en) * | 1987-05-13 | 1992-03-05 | Curtice-Burns, Inc. | Saccharide 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 |
| 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 (zh) * | 2013-07-29 | 2013-10-23 | 柳州爱格富食品科技股份有限公司 | 蔗糖酯的制备方法 |
| CN103360434B (zh) * | 2013-07-29 | 2016-05-04 | 柳州爱格富食品科技股份有限公司 | 蔗糖酯的制备方法 |
| CN111187310A (zh) * | 2020-01-17 | 2020-05-22 | 常州工学院 | 一种海藻糖脂肪酸酯的工业制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1643795A1 (de) | 1971-07-01 |
| BE719016A (enrdf_load_stackoverflow) | 1969-02-03 |
| NL6810494A (enrdf_load_stackoverflow) | 1969-02-06 |
| CH510614A (de) | 1971-07-31 |
| GB1188614A (en) | 1970-04-22 |
| FR1575350A (enrdf_load_stackoverflow) | 1969-07-18 |
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