US3347848A - Process for the production of sucrose esters of fatty acids - Google Patents
Process for the production of sucrose esters of fatty acids Download PDFInfo
- Publication number
- US3347848A US3347848A US470196A US47019665A US3347848A US 3347848 A US3347848 A US 3347848A US 470196 A US470196 A US 470196A US 47019665 A US47019665 A US 47019665A US 3347848 A US3347848 A US 3347848A
- Authority
- US
- United States
- Prior art keywords
- sucrose
- fatty acid
- alkyl ester
- polar solvent
- fatty acids
- 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
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000001959 sucrose esters of fatty acids Substances 0.000 title description 8
- 235000010965 sucrose esters of fatty acids Nutrition 0.000 title description 8
- 229930006000 Sucrose Natural products 0.000 claims description 28
- 239000005720 sucrose Substances 0.000 claims description 28
- 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 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 17
- 239000000194 fatty acid Substances 0.000 claims description 17
- 229930195729 fatty acid Natural products 0.000 claims description 17
- 239000002798 polar solvent Substances 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000005809 transesterification reaction Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000012454 non-polar solvent Substances 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- -1 sucrose ester Chemical class 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000005313 fatty acid group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SKYXZSVBBFFJQQ-UHFFFAOYSA-N 1-methyl-2h-pyrazine Chemical compound CN1CC=NC=C1 SKYXZSVBBFFJQQ-UHFFFAOYSA-N 0.000 description 1
- 229940114069 12-hydroxystearate Drugs 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N n-tetradecanoic acid methyl ester Natural products CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 1
- LIXVMPBOGDCSRM-UHFFFAOYSA-N nonylbenzene Chemical compound CCCCCCCCCC1=CC=CC=C1 LIXVMPBOGDCSRM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- sucrose esters of fatty acids are known and are commercially used as emulsifier-s. More recently, chiefly the sucrose esters of fatty acids having from 12 to 22 carbon atoms and at least one weakly hydrophilic group in the fatty acid chain have gained importance because they are characterized by outstanding detergency characteristics and are readily degraded biologically to absolutely innoxious substances (German patent application Z 10,316).
- Sucrose esters of fatty acids are conventionally prepared by transesterification of lower alkyl esters of fatty acids with sucrose in a polar solvent (see British Patents 809,815 and 826,801), the molar ratio of fatty acid alkyl ester to sucrose being about 3:1 and more.
- Suitable catalysts include above all alkaline compounds, especially potassium carbonate. After completion of the transesterification, the predominant part of the solvent is removed under vacuum. Then a different suitable solvent must be added to prevent decomposition of the sucrose esters by excessively long heating and to precipitate excess sugar. The resultant solution of the sucrose ester must still be washed, and the sucrose ester is left in pure form after evaporation of the extractant.
- Suitable polar solvents which may be used for the purposes of the invention are N-rnethyl morpholine, triethylamine, pyridine, quinoline, pyrazine, N-methylpyrazine, N,N-dimethyl-pyrazine, 2-pyrrolidone, N- methyl-pyrrolidone as well as N,N'-dimethyl formamide and dimethyl sulfoxide which are particularly preferred.
- Suitable solvents for the lower alkyl esters of fatty acids are non-polar solvents boiling between 100 C.
- aromatic and aliphatic hydrocarbons such as toluene, ethyl benzene, gasoline, cyclohexyl benzene, nonyl benzene, ligroin and the like.
- the ratio by weight of polar solvent to the liquid hydrocarbon is desirably 0.5:1 to 5:1, especially 2:1 to 2.5:].
- the process of the invention is generally applicable to the production of sucrose esters of fatty acids. It has been found to be particularly advantageous for the production of the commercially important sucrose esters of fatty acids containing at least one weakly hydrophilic group such as a hydroxyl, carbonyl, oxime or alkoxy group.
- the principle of the process consists in that the sucrose and the catalyst are initially dissolved at moderately elevated temperature of, for example, 70 to 90 C. in the polar solvent. Then the lower alkyl ester of the fatty acid the sucrose ester of which is desired to be prepared, especially the methyl or ethyl ester, is dissolved in the liquid hydrocarbon and the two phases are reacted at temperatures of between 40 and 180 C., especially about to C., while stirring. Initially, the alkyl ester remains almost completely in the hydrocarbon phase. The lower alcohol liberated during the transesterification distils and, at the same time, the dissolving power of the polar solvent for the hydrocarbon increases because the sucrose ester which is formed is better soluble in the polar solvent than the sucrose.
- the new process has the following advantages from the process engineering and economic points of view as compared with known methods: Sucrose and the lower alkyl ester of fatty acid may be fed in a molar ratio of 1:1. Thus, the process is not burdened by excess sugar, and the separation and purification of excess sucrose are eliminated. The total amount of solvent necessary for the transesterification is less than one-half of the quantity previously used. The yield of sucrose ester is increased by about 10% on an average due to the substantially more simple processing and elimination of all additional purification procedures.
- EXAMPLE 2 A mixture of 90 gms. of dimethyl sulfoxide, 50 gms. of gasoline boiling from to C., 30 gms. of sucrose, 27.6 gms. of 12-hydroxymethyl stearate and 0.5 gm. of potassium carbonate catalyst is vigorously stirred for 9 hours at 85 C. under a vacuum of 100 mm. Hg. After having distilled off the solvents, there remains sucrose- 12-hydroxystearate having a surface tension of 38 dynes/ cm. The yield is 96%.
- a process for the production of sucrose mono-esters of fatty acids having from 12 to 22 carbon atoms by transesterification of sucrose with a lower alkyl ester of a fatty acid in inert solvents which comprises (1) forming a liquid two-phase system, a first phase of this system consisting of a solution of said fatty acid alkyl ester in an aliphatic or aromatic hydrocarbon non-polar solvent having a boiling point above 100 C., and a second phase of this system containing said sucrose and potassium carbonate catalyst dissolved in a polar solvent at from 70-90 C., said sucrose and said lower alkyl ester of a fatty acid being present in about a 1:1 mole ratio, (2) stirring the said two phases at a temperature of between 40180 C. while distilling oif lower alcohol liberated by the transesterification reaction, and (3) distilling off the remaining solvents.
- fatty acid alkyl ester is the alkyl ester of a fatty acid having at least one weakly hydrophilic group in the fatty acid chain.
- said weakly hydrophilic group in the fatty acid chain is a hydroxyl, a carbonyl, an oxime or an alkoxy group.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Description
United States Patent 10 Claims. (Cl. 260-234) This invention relates to a process for the production of sucrose esters of fatty acids.
Sucrose esters of fatty acids are known and are commercially used as emulsifier-s. More recently, chiefly the sucrose esters of fatty acids having from 12 to 22 carbon atoms and at least one weakly hydrophilic group in the fatty acid chain have gained importance because they are characterized by outstanding detergency characteristics and are readily degraded biologically to absolutely innoxious substances (German patent application Z 10,316).
Sucrose esters of fatty acids are conventionally prepared by transesterification of lower alkyl esters of fatty acids with sucrose in a polar solvent (see British Patents 809,815 and 826,801), the molar ratio of fatty acid alkyl ester to sucrose being about 3:1 and more. Suitable catalysts include above all alkaline compounds, especially potassium carbonate. After completion of the transesterification, the predominant part of the solvent is removed under vacuum. Then a different suitable solvent must be added to prevent decomposition of the sucrose esters by excessively long heating and to precipitate excess sugar. The resultant solution of the sucrose ester must still be washed, and the sucrose ester is left in pure form after evaporation of the extractant.
This process has the disadvantage, above all when carried out in a commercial scale, that it is extremely complicated and requires a great excess of sucrose and large amounts of the polar solvent. Both the excess sucrose and the solvent must be recovered and re-used to make the process economic. This in turn requires additional purification procedures for both substances with the corresponding expense of equipment.
It is an object of the present invention to provide an improved process for the production of sucrose esters of fatty acids having from 12 to 22 carbon atoms, which comprises effecting the transesterification of sucrose with a lower fatty acid alkyl ester in a liquid two-phase system, one phase of which consists at the beginning of the reaction of a solution of the fatty acid alkyl ester in an aliphatic or aromatic hydrocarbon, and the other phase of which comprises sucrose and, if necessary or desired, the catalyst dissolved in a polar solvent.
Suitable polar solvents which may be used for the purposes of the invention are N-rnethyl morpholine, triethylamine, pyridine, quinoline, pyrazine, N-methylpyrazine, N,N-dimethyl-pyrazine, 2-pyrrolidone, N- methyl-pyrrolidone as well as N,N'-dimethyl formamide and dimethyl sulfoxide which are particularly preferred. Suitable solvents for the lower alkyl esters of fatty acids are non-polar solvents boiling between 100 C. and 200 C., particularly suitable being aromatic and aliphatic hydrocarbons such as toluene, ethyl benzene, gasoline, cyclohexyl benzene, nonyl benzene, ligroin and the like. The ratio by weight of polar solvent to the liquid hydrocarbon is desirably 0.5:1 to 5:1, especially 2:1 to 2.5:].
The process of the invention is generally applicable to the production of sucrose esters of fatty acids. It has been found to be particularly advantageous for the production of the commercially important sucrose esters of fatty acids containing at least one weakly hydrophilic group such as a hydroxyl, carbonyl, oxime or alkoxy group.
The principle of the process consists in that the sucrose and the catalyst are initially dissolved at moderately elevated temperature of, for example, 70 to 90 C. in the polar solvent. Then the lower alkyl ester of the fatty acid the sucrose ester of which is desired to be prepared, especially the methyl or ethyl ester, is dissolved in the liquid hydrocarbon and the two phases are reacted at temperatures of between 40 and 180 C., especially about to C., while stirring. Initially, the alkyl ester remains almost completely in the hydrocarbon phase. The lower alcohol liberated during the transesterification distils and, at the same time, the dissolving power of the polar solvent for the hydrocarbon increases because the sucrose ester which is formed is better soluble in the polar solvent than the sucrose. After a reaction period of 5 to 12 hours and in general of about 8 to 9 hours, the transesterification is completed, and the two solvents are distilled off by increasing the temperature in the reaction mixture or the vaccum applied or by both of these measures and the sucrose ester produced remains in the residue.
The new process has the following advantages from the process engineering and economic points of view as compared with known methods: Sucrose and the lower alkyl ester of fatty acid may be fed in a molar ratio of 1:1. Thus, the process is not burdened by excess sugar, and the separation and purification of excess sucrose are eliminated. The total amount of solvent necessary for the transesterification is less than one-half of the quantity previously used. The yield of sucrose ester is increased by about 10% on an average due to the substantially more simple processing and elimination of all additional purification procedures.
EXAMPLE 1 Sucrose in an amount of 51.5 gms. (0.15 mole) was dissolved with 0.5 gm. of potassium carbonate in 120 gms. of dimethyl sulfoxide at 85 C. At the same time, a solution of 0.15 mole of 12-hydroxymethyl stearate in 50 gms. of cyclohexyl benzene was prepared and the two phases were then vigorously stirred for 9 hours at 85 C. under vacuum. Then the two solvents were distilled off under vacuum. The residue consisted of the sucrose ester of 12-hydroxystearic acid. The yield is more than The product may be used directly as such as the active detergent component of detergent compositions and lowers the surface tension of water of 10 deg. German hardness to 38 dynes/ cm.
EXAMPLE 2 A mixture of 90 gms. of dimethyl sulfoxide, 50 gms. of gasoline boiling from to C., 30 gms. of sucrose, 27.6 gms. of 12-hydroxymethyl stearate and 0.5 gm. of potassium carbonate catalyst is vigorously stirred for 9 hours at 85 C. under a vacuum of 100 mm. Hg. After having distilled off the solvents, there remains sucrose- 12-hydroxystearate having a surface tension of 38 dynes/ cm. The yield is 96%.
Corresponding yields are obtained when transesterifying myristic acid or lauric acid methyl ester with sucrose.
What is claimed is:
l. A process for the production of sucrose mono-esters of fatty acids having from 12 to 22 carbon atoms by transesterification of sucrose with a lower alkyl ester of a fatty acid in inert solvents, which comprises (1) forming a liquid two-phase system, a first phase of this system consisting of a solution of said fatty acid alkyl ester in an aliphatic or aromatic hydrocarbon non-polar solvent having a boiling point above 100 C., and a second phase of this system containing said sucrose and potassium carbonate catalyst dissolved in a polar solvent at from 70-90 C., said sucrose and said lower alkyl ester of a fatty acid being present in about a 1:1 mole ratio, (2) stirring the said two phases at a temperature of between 40180 C. while distilling oif lower alcohol liberated by the transesterification reaction, and (3) distilling off the remaining solvents.
2. The process of claim 1, wherein the ratio by weight of said polar solvent to said non-polar solvent is from 0.521 to 5:1.
3. The process of claim 2, wherein the ratio by weight of said polar solvent to said non-polar solvent is from 2:1 to 25:1.
4. The process of claim 1, wherein said fatty acid alkyl ester is the alkyl ester of a fatty acid having at least one weakly hydrophilic group in the fatty acid chain.
5. The process of claim 1, wherein said polar solvent is dimethyl sulfoxide.
6. The process of claim 1, wherein said polar solvent is dimethyl formamide.
7. The process of claim 4, wherein said weakly hydrophilic group in the fatty acid chain is a hydroxyl, a carbonyl, an oxime or an alkoxy group.
References Cited UNITED STATES PATENTS 2,948,716 8/1960 Davis 260234 3,054,789 9/1962 DAmato 260234 3,251,829 5/1966 Hagge et a1. 260-234 FOREIGN PATENTS 826,801 1/ 1960 Great Britain. 859,305 1/1961 Great Britain.
LEWIS GOTTS, Primary Examiner.
JAMES O. THOMAS, 111., Examiner.
J. R. BROWN, Assistant Examiner.
Claims (1)
1. A PROCESS FOR THE PRODUCTION OF SUCROSE MONO-ESTERS OF FATTY ACIDS HAVING FROM 12 TO 22 CARBON ATOMS BY TRANSESTERIFICATION OF SUCROSE WITH A LOWER ALKYL ESTER OF A FATTY ACID IN INERT SOLVENTS, WHICH COMPRISES (1) FORMING A LIQUID TWO-PHASE SYSTEM, A FIRST PHASE OF THIS SYSTEM CONSISTING OF A SOLUTION OF SAID FATTY ACID ALKYL ESTER IN AN ALIPHATIC OR AROMATIC HYDROCARBON NON-POLAR SOLVENT HAVING A BOILING POINT ABOVE 100*C., AND A SECOND PHASE OF THIS SYSTEM CONTAINING SAID SUCROSE AND POTASSIUM CARBONATE CATALYST DISSOLVED IN A POLAR SOLVENT AT FROM 70-90*C., SAID SUCROSE AND SAID LOWER ALKYL ESTER OF A FATTY ACID BEING PRESENT IN ABOUT A 1:1 MOLE RATIO, (2) STIRRING THE SAID TWO PHASES AT A TEMPERATURE OF BETWEEN 40-180*C. WHILE DISTILLING OFF LOWER ALCOHOL LIBERATED BY THE TRANSESTERIFICATION REACTION, AND (3) DISTILLING OFF THE REMAINING SOLVENTS.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ0010963 | 1964-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3347848A true US3347848A (en) | 1967-10-17 |
Family
ID=7621628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US470196A Expired - Lifetime US3347848A (en) | 1964-07-08 | 1965-07-07 | Process for the production of sucrose esters of fatty acids |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3347848A (en) |
| DE (1) | DE1518251A1 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5070313A (en) * | 1973-10-30 | 1975-06-11 | ||
| US3951945A (en) * | 1973-05-15 | 1976-04-20 | B.V. Chemie Combinatie Amsterdam C.C.A. | Method for the preparation of esters of polyalcohols |
| US3991186A (en) * | 1974-08-14 | 1976-11-09 | Nippon Shinyaku Co., Ltd. | Steryl-β-D-glucoside ester pharmaceutical compositions and method of use |
| US4363763A (en) * | 1980-02-25 | 1982-12-14 | The Procter & Gamble Company | Polyol esters of alpha-hydroxy carboxylic acids |
| US4469635A (en) * | 1980-12-24 | 1984-09-04 | The Procter & Gamble Company | Polyol esters of alpha-hydroxy carboxylic 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 |
| US5453498A (en) * | 1992-02-12 | 1995-09-26 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Process for production of high-monoester sucrose higher 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 |
| US5767257A (en) * | 1996-07-19 | 1998-06-16 | The Procter & Gamble Company | Methods for producing polyol fatty acid polyesters using atmospheric or superatmospheric pressure |
| US5945529A (en) * | 1996-07-19 | 1999-08-31 | The Procter & Gamble Company | Synthesis of polyol fatty acid polyesters using column with inert gas stripping |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB826801A (en) * | 1957-08-29 | 1960-01-20 | Distillers Co Yeast Ltd | Recovery of sucrose esters |
| US2948716A (en) * | 1956-04-12 | 1960-08-09 | Trevor C M Davis | Purification of sugar esters |
| GB859305A (en) * | 1958-07-01 | 1961-01-18 | Distillers Co Yeast Ltd | Production of sucrose esters |
| US3054789A (en) * | 1959-02-06 | 1962-09-18 | Ledoga Spa | Process for the preparation of pure sucrose esters |
| US3251829A (en) * | 1963-03-21 | 1966-05-17 | Bayer Ag | Process for the separation of unreacted sugars from reaction mixtures obtained in the production of sugar fatty acid esters from sugars and fatty acid alkyl esters |
-
1964
- 1964-07-08 DE DE19641518251 patent/DE1518251A1/en active Pending
-
1965
- 1965-07-07 US US470196A patent/US3347848A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948716A (en) * | 1956-04-12 | 1960-08-09 | Trevor C M Davis | Purification of sugar esters |
| GB826801A (en) * | 1957-08-29 | 1960-01-20 | Distillers Co Yeast Ltd | Recovery of sucrose esters |
| GB859305A (en) * | 1958-07-01 | 1961-01-18 | Distillers Co Yeast Ltd | Production of sucrose esters |
| US3054789A (en) * | 1959-02-06 | 1962-09-18 | Ledoga Spa | Process for the preparation of pure sucrose esters |
| US3251829A (en) * | 1963-03-21 | 1966-05-17 | Bayer Ag | Process for the separation of unreacted sugars from reaction mixtures obtained in the production of sugar fatty acid esters from sugars and fatty acid alkyl esters |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3951945A (en) * | 1973-05-15 | 1976-04-20 | B.V. Chemie Combinatie Amsterdam C.C.A. | Method for the preparation of esters of polyalcohols |
| JPS5070313A (en) * | 1973-10-30 | 1975-06-11 | ||
| JPS5821637B2 (en) * | 1973-10-30 | 1983-05-02 | 三菱化学株式会社 | Seizouhouhou |
| US3991186A (en) * | 1974-08-14 | 1976-11-09 | Nippon Shinyaku Co., Ltd. | Steryl-β-D-glucoside ester pharmaceutical compositions and method of use |
| US4363763A (en) * | 1980-02-25 | 1982-12-14 | The Procter & Gamble Company | Polyol esters of alpha-hydroxy carboxylic acids |
| US4469635A (en) * | 1980-12-24 | 1984-09-04 | The Procter & Gamble Company | Polyol esters of alpha-hydroxy carboxylic 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 |
| 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 |
| US5453498A (en) * | 1992-02-12 | 1995-09-26 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Process for production of high-monoester sucrose higher fatty acid esters |
| US5767257A (en) * | 1996-07-19 | 1998-06-16 | The Procter & Gamble Company | Methods for producing polyol fatty acid polyesters using atmospheric or superatmospheric pressure |
| US5945529A (en) * | 1996-07-19 | 1999-08-31 | The Procter & Gamble Company | Synthesis of polyol fatty acid polyesters using column with inert gas stripping |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1518251A1 (en) | 1969-07-24 |
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