DE2546716C3 - Verfahren zur Herstellung eines oberflächenaktiven Produktes - Google Patents
Verfahren zur Herstellung eines oberflächenaktiven ProduktesInfo
- Publication number
- DE2546716C3 DE2546716C3 DE2546716A DE2546716A DE2546716C3 DE 2546716 C3 DE2546716 C3 DE 2546716C3 DE 2546716 A DE2546716 A DE 2546716A DE 2546716 A DE2546716 A DE 2546716A DE 2546716 C3 DE2546716 C3 DE 2546716C3
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- cane sugar
- transesterification
- acid
- oil
- 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
Links
- 238000000034 method Methods 0.000 title claims description 49
- 230000008569 process Effects 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title description 6
- 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 42
- 229930006000 Sucrose Natural products 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 19
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 238000005809 transesterification reaction Methods 0.000 claims description 14
- 125000005907 alkyl ester group Chemical group 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003626 triacylglycerols Chemical class 0.000 claims description 6
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- -1 fatty acid ester Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- 229960004793 sucrose Drugs 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000002253 acid Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- 235000021388 linseed oil Nutrition 0.000 description 4
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 229940073769 methyl oleate Drugs 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 239000000312 peanut oil Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 208000020442 loss of weight Diseases 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 108010002493 Arachin Proteins 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-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
- 230000009965 odorless effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000004760 silicates Chemical group 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 230000009967 tasteless effect Effects 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/002—Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/02—Organic and inorganic agents containing, except water
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Saccharide Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45122/74A GB1499989A (en) | 1974-10-17 | 1974-10-17 | Production of a surface active material containing sucrose esters |
| GB1622275 | 1975-04-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2546716A1 DE2546716A1 (de) | 1976-04-29 |
| DE2546716B2 DE2546716B2 (de) | 1981-04-09 |
| DE2546716C3 true DE2546716C3 (de) | 1983-11-17 |
Family
ID=26251906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2546716A Expired DE2546716C3 (de) | 1974-10-17 | 1975-10-17 | Verfahren zur Herstellung eines oberflächenaktiven Produktes |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4032702A (en, 2012) |
| JP (1) | JPS5165704A (en, 2012) |
| AR (1) | AR212161A1 (en, 2012) |
| AT (1) | AT347410B (en, 2012) |
| BR (1) | BR7506830A (en, 2012) |
| CA (1) | CA1045130A (en, 2012) |
| CH (1) | CH606074A5 (en, 2012) |
| CU (1) | CU34398A (en, 2012) |
| DE (1) | DE2546716C3 (en, 2012) |
| DK (1) | DK142148B (en, 2012) |
| ES (1) | ES441908A2 (en, 2012) |
| FR (1) | FR2288143A2 (en, 2012) |
| GB (1) | GB1499989A (en, 2012) |
| IE (1) | IE42171B1 (en, 2012) |
| IT (1) | IT1048249B (en, 2012) |
| NL (1) | NL172761B (en, 2012) |
| NO (1) | NO140983C (en, 2012) |
| SE (1) | SE430339B (en, 2012) |
| SU (1) | SU906383A3 (en, 2012) |
| TR (1) | TR18880A (en, 2012) |
| ZA (1) | ZA756573B (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1593856A (en) * | 1976-11-17 | 1981-07-22 | Gist Brocades Nv | Process for the treatment of fruit and vegetables |
| JPS6037085B2 (ja) * | 1978-09-22 | 1985-08-24 | 花王株式会社 | 棒状化粧料 |
| JPS5547610A (en) * | 1978-09-29 | 1980-04-04 | Kao Corp | Hair cosmetic |
| JPS6026368B2 (ja) * | 1978-09-29 | 1985-06-24 | 花王株式会社 | 粉末圧縮型化粧料 |
| JPS6037086B2 (ja) * | 1978-09-26 | 1985-08-24 | 花王株式会社 | 化粧料 |
| JPS6037087B2 (ja) * | 1978-09-28 | 1985-08-24 | 花王株式会社 | 化粧料 |
| EP0010975B1 (en) * | 1978-11-06 | 1983-05-18 | TATE & LYLE PUBLIC LIMITED COMPANY | Gramophone record composition and gramophone records produced therefrom |
| EP0011419A1 (en) * | 1978-11-09 | 1980-05-28 | TATE & LYLE PUBLIC LIMITED COMPANY | P.V.C. compositions for extrusion moulding |
| IE50028B1 (en) * | 1979-12-19 | 1986-02-05 | Tate & Lyle Plc | Process for the production of a surfactant containing sucrose esters |
| US4518772A (en) * | 1983-06-23 | 1985-05-21 | The Proctor & Gamble Company | Synthesis of higher polyol fatty acid polyesters using high soap:polyol ratios |
| US4517360A (en) * | 1983-06-23 | 1985-05-14 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters using carbonate catalysts |
| JPS6115893A (ja) * | 1984-06-29 | 1986-01-23 | Dai Ichi Kogyo Seiyaku Co Ltd | シヨ糖脂肪酸エステルの精製法 |
| NL8601904A (nl) * | 1986-07-23 | 1988-02-16 | Unilever Nv | Werkwijze voor de bereiding van polyol-vetzuurpolyesters. |
| JPS63179884A (ja) * | 1987-01-17 | 1988-07-23 | Mitsubishi Kasei Corp | シヨ糖脂肪酸エステルの製造方法 |
| ATE143664T1 (de) * | 1989-12-21 | 1996-10-15 | Unilever Nv | Verfahren zur raffinierung von seife enthaltendem rohprodukt aus einem polyol-fettsäure- veresterungsgemisch |
| ES2095326T3 (es) | 1990-09-11 | 1997-02-16 | Procter & Gamble | Sintesis de poliesteres de poliol. |
| CA2111479C (en) * | 1991-04-12 | 1998-07-07 | Robert J. Sarama | Process for improving oxidative stability of polyol fatty acid polyesters |
| 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 |
| CA2263104C (en) * | 1996-08-08 | 2003-06-17 | Roger Stephen Berger | Polyol polyester synthesis |
| US6121440A (en) * | 1998-01-29 | 2000-09-19 | The Procter & Gamble Company | Process for synthesis of polyol fatty acid polyesters |
| AU4911300A (en) * | 1999-06-01 | 2000-12-18 | Astion Development Aps | A method of producing organic emulsifiers and organic surfactants, products produced by said method, and the use of such products |
| GB0608512D0 (en) | 2006-04-28 | 2006-06-07 | Vincent Processes Ltd | Process for the production of esters of sugars and sugar derivatives |
| EP3031443A1 (de) | 2014-12-12 | 2016-06-15 | Basf Se | Zusammensetzung enthaltend Kohlehydratpartialester |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1200276B (de) * | 1959-10-08 | 1965-09-09 | Bayer Ag | Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker |
| DE1643795A1 (de) * | 1967-08-04 | 1971-07-01 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Zuckerestern |
| US3597417A (en) * | 1968-07-23 | 1971-08-03 | Procter & Gamble | Process for the preparation of fatty acid esters of sugar glycosides |
| DE2004899C2 (de) * | 1969-02-05 | 1984-07-26 | Dai-Ichi Kogyo Seiyaku Co.,Ltd., Kyoto | Verfahren zur Abtrennung von Verunreinigungen aus Saccharosefettsäureester-Rohprodukten |
| US3714144A (en) * | 1969-05-29 | 1973-01-30 | Us Agriculture | Process for the production of sucrose esters of fatty acids |
| GB1399053A (en) * | 1973-03-16 | 1975-06-25 | Tate & Lyle Ltd | Process for the production of surface active agents comprising sucrose esters |
-
1974
- 1974-10-17 GB GB45122/74A patent/GB1499989A/en not_active Expired
-
1975
- 1975-04-18 TR TR18880A patent/TR18880A/xx unknown
- 1975-10-15 US US05/622,495 patent/US4032702A/en not_active Expired - Lifetime
- 1975-10-15 AR AR260811A patent/AR212161A1/es active
- 1975-10-16 SE SE7511612A patent/SE430339B/xx unknown
- 1975-10-16 DK DK465675AA patent/DK142148B/da not_active IP Right Cessation
- 1975-10-16 IT IT69587/75A patent/IT1048249B/it active
- 1975-10-16 NO NO753492A patent/NO140983C/no unknown
- 1975-10-17 DE DE2546716A patent/DE2546716C3/de not_active Expired
- 1975-10-17 CA CA237,872A patent/CA1045130A/en not_active Expired
- 1975-10-17 ZA ZA00756573A patent/ZA756573B/xx unknown
- 1975-10-17 CH CH1354075A patent/CH606074A5/xx not_active IP Right Cessation
- 1975-10-17 FR FR7531806A patent/FR2288143A2/fr active Granted
- 1975-10-17 NL NLAANVRAGE7512252,A patent/NL172761B/xx not_active IP Right Cessation
- 1975-10-17 AT AT793375A patent/AT347410B/de not_active IP Right Cessation
- 1975-10-17 JP JP50124459A patent/JPS5165704A/ja active Pending
- 1975-10-17 IE IE2270/75A patent/IE42171B1/en unknown
- 1975-10-17 BR BR7506830A patent/BR7506830A/pt unknown
- 1975-10-17 SU SU752184053A patent/SU906383A3/ru active
- 1975-10-17 ES ES441908A patent/ES441908A2/es not_active Expired
- 1975-11-12 CU CU34398A patent/CU34398A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK142148C (en, 2012) | 1981-02-02 |
| DK465675A (en, 2012) | 1976-04-18 |
| AR212161A1 (es) | 1978-05-31 |
| NO753492L (en, 2012) | 1976-04-21 |
| ATA793375A (de) | 1978-05-15 |
| IT1048249B (it) | 1980-11-20 |
| CU34398A (en, 2012) | 1977-06-08 |
| CH606074A5 (en, 2012) | 1978-10-13 |
| CA1045130A (en) | 1978-12-26 |
| IE42171L (en) | 1976-04-17 |
| TR18880A (tr) | 1977-10-13 |
| US4032702A (en) | 1977-06-28 |
| FR2288143B2 (en, 2012) | 1979-02-02 |
| FR2288143A2 (fr) | 1976-05-14 |
| SE7511612L (sv) | 1976-04-20 |
| NL172761B (nl) | 1983-05-16 |
| SU906383A3 (ru) | 1982-02-15 |
| JPS5165704A (en, 2012) | 1976-06-07 |
| AT347410B (de) | 1978-12-27 |
| NO140983C (no) | 1979-12-19 |
| AU8582875A (en) | 1977-04-21 |
| ZA756573B (en) | 1976-09-29 |
| IE42171B1 (en) | 1980-06-18 |
| BR7506830A (pt) | 1976-08-31 |
| NO140983B (no) | 1979-09-10 |
| SE430339B (sv) | 1983-11-07 |
| NL7512252A (nl) | 1976-04-21 |
| DE2546716A1 (de) | 1976-04-29 |
| ES441908A2 (es) | 1977-07-01 |
| GB1499989A (en) | 1978-02-01 |
| DK142148B (da) | 1980-09-08 |
| DE2546716B2 (de) | 1981-04-09 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8263 | Opposition against grant of a patent | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |