DE2412374C3 - Verfahren zur Herstellung eines oberflächenaktiven Produktes durch Umesterung von Saccharose mit einem Triglycerid - Google Patents
Verfahren zur Herstellung eines oberflächenaktiven Produktes durch Umesterung von Saccharose mit einem TriglyceridInfo
- Publication number
- DE2412374C3 DE2412374C3 DE2412374A DE2412374A DE2412374C3 DE 2412374 C3 DE2412374 C3 DE 2412374C3 DE 2412374 A DE2412374 A DE 2412374A DE 2412374 A DE2412374 A DE 2412374A DE 2412374 C3 DE2412374 C3 DE 2412374C3
- Authority
- DE
- Germany
- Prior art keywords
- sucrose
- reaction
- transesterification
- product
- 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
- 229930006000 Sucrose Natural products 0.000 title claims description 86
- 239000005720 sucrose Substances 0.000 title claims description 85
- 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 title claims description 81
- 238000000034 method Methods 0.000 title claims description 61
- 230000008569 process Effects 0.000 title claims description 30
- 238000005809 transesterification reaction Methods 0.000 title claims description 26
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 36
- 239000003760 tallow Substances 0.000 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 15
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 2
- 229960004793 sucrose Drugs 0.000 description 83
- 238000006243 chemical reaction Methods 0.000 description 76
- 239000000047 product Substances 0.000 description 50
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- 239000000203 mixture Substances 0.000 description 32
- 238000003756 stirring Methods 0.000 description 20
- 239000004094 surface-active agent Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 description 17
- -1 fatty acid chlorides Chemical class 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 210000002374 sebum Anatomy 0.000 description 11
- 150000003626 triacylglycerols Chemical class 0.000 description 11
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 10
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 125000005456 glyceride group Chemical group 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 238000004140 cleaning Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 235000019482 Palm oil Nutrition 0.000 description 5
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- 235000012343 cottonseed oil Nutrition 0.000 description 5
- 239000002385 cottonseed oil Substances 0.000 description 5
- 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 5
- 239000000944 linseed oil Substances 0.000 description 5
- 235000021388 linseed oil Nutrition 0.000 description 5
- 239000002540 palm oil Substances 0.000 description 5
- 150000003445 sucroses Chemical class 0.000 description 5
- 235000019483 Peanut oil Nutrition 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- 239000000312 peanut oil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000220317 Rosa Species 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000005908 glyceryl ester group Chemical group 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AFSHUZFNMVJNKX-UHFFFAOYSA-N 1,2-di-(9Z-octadecenoyl)glycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCCCCCCCC AFSHUZFNMVJNKX-UHFFFAOYSA-N 0.000 description 2
- AFSHUZFNMVJNKX-LLWMBOQKSA-N 1,2-dioleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC AFSHUZFNMVJNKX-LLWMBOQKSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 2
- 235000021552 granulated sugar Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 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
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-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
- 206010010219 Compulsions Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- UPWGQKDVAURUGE-UHFFFAOYSA-N glycerine monooleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC(CO)CO UPWGQKDVAURUGE-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 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
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical group 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 238000005406 washing Methods 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
-
- 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
- Y10S516/06—Protein or carboxylic compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Saccharide Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Catalysts (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1279473A GB1399053A (en) | 1973-03-16 | 1973-03-16 | Process for the production of surface active agents comprising sucrose esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2412374A1 DE2412374A1 (de) | 1974-09-19 |
| DE2412374B2 DE2412374B2 (de) | 1978-02-16 |
| DE2412374C3 true DE2412374C3 (de) | 1978-10-12 |
Family
ID=10011273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2412374A Expired DE2412374C3 (de) | 1973-03-16 | 1974-03-15 | Verfahren zur Herstellung eines oberflächenaktiven Produktes durch Umesterung von Saccharose mit einem Triglycerid |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3996206A (enExample) |
| JP (1) | JPS546526B2 (enExample) |
| AR (1) | AR200180A1 (enExample) |
| AT (1) | AT336551B (enExample) |
| AU (1) | AU473796B2 (enExample) |
| BE (1) | BE812369A (enExample) |
| BR (1) | BR7402031D0 (enExample) |
| CA (1) | CA1016939A (enExample) |
| CH (1) | CH585765A5 (enExample) |
| DE (1) | DE2412374C3 (enExample) |
| ES (1) | ES424369A1 (enExample) |
| FR (1) | FR2221436B1 (enExample) |
| GB (1) | GB1399053A (enExample) |
| GT (1) | GT197538679A (enExample) |
| IE (1) | IE39074B1 (enExample) |
| IT (1) | IT1009292B (enExample) |
| KE (1) | KE2593A (enExample) |
| MY (1) | MY7600028A (enExample) |
| NL (1) | NL163792C (enExample) |
| NO (1) | NO137827C (enExample) |
| SE (1) | SE411747B (enExample) |
| SU (1) | SU576954A3 (enExample) |
| ZA (1) | ZA741483B (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1499989A (en) * | 1974-10-17 | 1978-02-01 | Tate & Lyle Ltd | Production of a surface active material containing sucrose esters |
| GB1593856A (en) * | 1976-11-17 | 1981-07-22 | Gist Brocades Nv | Process for the treatment of fruit and vegetables |
| FR2463152A1 (fr) * | 1979-08-16 | 1981-02-20 | Rhone Poulenc Ind | Procede de preparation de sucroglycerides |
| IE50028B1 (en) * | 1979-12-19 | 1986-02-05 | Tate & Lyle Plc | Process for the production of a surfactant containing sucrose esters |
| JPS58110515A (ja) * | 1981-12-25 | 1983-07-01 | Mitsui Toatsu Chem Inc | 鼓脹症の予防剤、又は治療剤 |
| CA1195323A (en) * | 1982-04-12 | 1985-10-15 | Leonard F. Vander Burgh | Glycosidic surfactants |
| JPS59122408A (ja) * | 1982-12-28 | 1984-07-14 | Mitsubishi Chem Ind Ltd | 薬害軽減剤 |
| 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 |
| FR2548185B1 (fr) * | 1983-06-29 | 1986-03-21 | Agrifurane Sa | Procede de preparation d'esters furanniques par reaction de transesterification |
| 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 |
| JPS61189289A (ja) * | 1985-02-15 | 1986-08-22 | Dai Ichi Kogyo Seiyaku Co Ltd | 高置換度シヨ糖脂肪酸エステルの製造法 |
| JPS624298A (ja) * | 1985-06-27 | 1987-01-10 | Dai Ichi Kogyo Seiyaku Co Ltd | 高置換度シヨ糖脂肪酸エステルの製造法 |
| NL8601904A (nl) * | 1986-07-23 | 1988-02-16 | Unilever Nv | Werkwijze voor de bereiding van polyol-vetzuurpolyesters. |
| US4806632A (en) * | 1986-12-29 | 1989-02-21 | The Procter & Gamble Company | Process for the post-hydrogenation of sucrose polyesters |
| US4889656A (en) * | 1987-10-30 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluorides and derivatives thereof |
| EP0320043B1 (en) * | 1987-12-11 | 1994-04-13 | Unilever N.V. | Process for the synthesis of polyol fatty acid esters |
| DE4015733A1 (de) * | 1990-05-16 | 1991-11-21 | Grillo Werke Ag | Verfahren zur loesungsmittelfreien herstellung von mono- und/oder diestern des (alpha)-d-methylglukosids |
| AU8538891A (en) | 1990-09-11 | 1992-03-30 | Procter & Gamble Company, The | Polyol polyester synthesis |
| DE4103681C2 (de) * | 1991-02-07 | 1994-11-24 | Grillo Werke Ag | Derivate von Disaccharidalkoholen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE4212155A1 (de) * | 1992-04-10 | 1993-10-14 | Henkel Kgaa | Verfahren zur Herstellung von Polyol-Fettsäure-Partialestern |
| NL9302126A (nl) * | 1993-12-07 | 1995-07-03 | Meern Bv Engelhard De | Werkwijze voor het interesterificeren van triglycerides. |
| US5491226A (en) * | 1994-04-06 | 1996-02-13 | Procter & Gamble Company | Process for preparing polyol polyesters having low levels of triglycerides |
| US5585506A (en) * | 1994-07-22 | 1996-12-17 | Lonza Inc. | One phase production of polyglycerol esters |
| US5705147A (en) * | 1995-09-18 | 1998-01-06 | Stepan Company | Methods and compositions for conditioning skin and hair |
| DE19542303C2 (de) | 1995-11-14 | 1998-03-26 | Suedzucker Ag | Acylierte Saccharosemonocarbonsäuren |
| WO1997042826A1 (en) * | 1996-05-14 | 1997-11-20 | Mlp Operating Company | Refrigerated yeast-raised pizza dough |
| US5767257A (en) * | 1996-07-19 | 1998-06-16 | The Procter & Gamble Company | Methods for producing polyol fatty acid polyesters using atmospheric or superatmospheric pressure |
| DE19717968A1 (de) * | 1997-04-28 | 1998-10-29 | Henkel Kgaa | Verfahren zur Herstellung von Kohlenhydratpartialestern |
| DE69908104T2 (de) * | 1998-03-23 | 2004-04-01 | The Procter & Gamble Company, Cincinnati | Herstellung von hochveresterten polyol-fettsäurepolyestern |
| CA2474599A1 (en) * | 2002-01-30 | 2003-08-07 | Sigma Coatings B.V. | Polysaccharide esters and their use as binders in coatings |
| US8877735B2 (en) * | 2004-08-31 | 2014-11-04 | The Procter & Gamble Company | Alkoxylated sucrose esters composition |
| GB0423972D0 (en) * | 2004-10-28 | 2004-12-01 | Vincent Processes Ltd | Process for the production of esters of sugars and sugar derivatives |
| GB0608512D0 (en) * | 2006-04-28 | 2006-06-07 | Vincent Processes Ltd | Process for the production of esters of sugars and sugar derivatives |
| WO2012053017A1 (en) | 2010-10-19 | 2012-04-26 | Istituto Di Ricerca Protos | Enzyme-catalyzed process for the preparation of sugar 6 -e sters |
| CN102060881B (zh) * | 2011-01-14 | 2013-02-27 | 中国林业科学研究院林产化学工业研究所 | 一种由木本油脂制备高品位蔗糖脂肪酸酯的方法 |
| CN103130844A (zh) * | 2013-03-07 | 2013-06-05 | 广西云鹏工贸有限责任公司 | 制糖工艺用消泡剂蔗糖脂肪酸酯合成工艺 |
| EP3031443A1 (de) | 2014-12-12 | 2016-06-15 | Basf Se | Zusammensetzung enthaltend Kohlehydratpartialester |
| CN112375107A (zh) * | 2020-10-30 | 2021-02-19 | 广西大学 | 一种蔗糖酯的制备方法 |
| CN112915565B (zh) * | 2021-03-04 | 2022-04-08 | 安徽金禾实业股份有限公司 | 一种旋转式蔗糖-6-酯连续生产设备及生产方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US355897A (en) * | 1887-01-11 | Sectional metallic sole | ||
| DE1200276B (de) * | 1959-10-08 | 1965-09-09 | Bayer Ag | Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker |
| US3248381A (en) * | 1961-11-21 | 1966-04-26 | Ledoga Spa | Process for the preparation of watersoluble and water-insoluble sucrose esters and products obtained thereby |
| NL145278B (nl) * | 1966-04-06 | 1975-03-17 | Nebraska State | Werkwijze ter uitvoering van een heresteringsreactie tussen een vloeibare polyhydrische alcohol en een hydrofobe ester van een vetzuur met lange keten. |
| JPS4523534Y1 (enExample) * | 1966-06-25 | 1970-09-17 | ||
| 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 |
| US3714144A (en) * | 1969-05-29 | 1973-01-30 | Us Agriculture | Process for the production of sucrose esters of fatty acids |
| BE757846A (fr) * | 1969-10-23 | 1971-04-01 | Dai Ichi Kogyo Seiyaku Cy Ltd | Procede de synthese d'esters de saccharose d'acides gras |
-
1973
- 1973-03-16 GB GB1279473A patent/GB1399053A/en not_active Expired
-
1974
- 1974-03-06 US US05/448,695 patent/US3996206A/en not_active Expired - Lifetime
- 1974-03-07 ZA ZA00741483A patent/ZA741483B/xx unknown
- 1974-03-13 IT IT67740/74A patent/IT1009292B/it active
- 1974-03-14 JP JP2864374A patent/JPS546526B2/ja not_active Expired
- 1974-03-14 AT AT213674A patent/AT336551B/de not_active IP Right Cessation
- 1974-03-14 FR FR7408639A patent/FR2221436B1/fr not_active Expired
- 1974-03-15 IE IE567/74A patent/IE39074B1/xx unknown
- 1974-03-15 BE BE142059A patent/BE812369A/xx not_active IP Right Cessation
- 1974-03-15 DE DE2412374A patent/DE2412374C3/de not_active Expired
- 1974-03-15 CA CA195,145A patent/CA1016939A/en not_active Expired
- 1974-03-15 AU AU66728/74A patent/AU473796B2/en not_active Expired
- 1974-03-15 SU SU7402008030A patent/SU576954A3/ru active
- 1974-03-15 BR BR2031/74A patent/BR7402031D0/pt unknown
- 1974-03-15 SE SE7403520A patent/SE411747B/xx unknown
- 1974-03-16 ES ES424369A patent/ES424369A1/es not_active Expired
- 1974-03-18 AR AR252834A patent/AR200180A1/es active
- 1974-03-18 CH CH371274A patent/CH585765A5/xx not_active IP Right Cessation
- 1974-03-18 NO NO740945A patent/NO137827C/no unknown
- 1974-03-18 NL NL7403627.A patent/NL163792C/xx not_active IP Right Cessation
-
1975
- 1975-10-10 GT GT197538679A patent/GT197538679A/es unknown
- 1975-12-22 KE KE2593*UA patent/KE2593A/xx unknown
-
1976
- 1976-12-31 MY MY197628A patent/MY7600028A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE39074L (en) | 1974-09-16 |
| MY7600028A (en) | 1976-12-31 |
| US3996206A (en) | 1976-12-07 |
| NO137827C (no) | 1978-05-03 |
| FR2221436A1 (enExample) | 1974-10-11 |
| NO137827B (no) | 1978-01-23 |
| ATA213674A (de) | 1976-09-15 |
| JPS5024210A (enExample) | 1975-03-15 |
| DE2412374A1 (de) | 1974-09-19 |
| IE39074B1 (en) | 1978-08-02 |
| GT197538679A (es) | 1977-04-02 |
| AU6672874A (en) | 1975-10-16 |
| KE2593A (en) | 1976-01-09 |
| AU473796B2 (en) | 1976-07-01 |
| SE411747B (sv) | 1980-02-04 |
| NL163792C (nl) | 1980-10-15 |
| ZA741483B (en) | 1975-02-26 |
| DE2412374B2 (de) | 1978-02-16 |
| ES424369A1 (es) | 1976-10-16 |
| CH585765A5 (enExample) | 1977-03-15 |
| IT1009292B (it) | 1976-12-10 |
| CA1016939A (en) | 1977-09-06 |
| NO740945L (no) | 1974-09-17 |
| FR2221436B1 (enExample) | 1979-01-05 |
| NL163792B (nl) | 1980-05-16 |
| NL7403627A (enExample) | 1974-09-18 |
| BR7402031D0 (pt) | 1974-11-19 |
| BE812369A (fr) | 1974-07-01 |
| GB1399053A (en) | 1975-06-25 |
| JPS546526B2 (enExample) | 1979-03-29 |
| SU576954A3 (ru) | 1977-10-15 |
| AT336551B (de) | 1977-05-10 |
| AR200180A1 (es) | 1974-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2412374C3 (de) | Verfahren zur Herstellung eines oberflächenaktiven Produktes durch Umesterung von Saccharose mit einem Triglycerid | |
| DE2546716C3 (de) | Verfahren zur Herstellung eines oberflächenaktiven Produktes | |
| DE2946565C2 (enExample) | ||
| EP0708813B1 (de) | Verfahren zur herstellung von fettsäurealkylestern | |
| DE3107318A1 (de) | Verfahren zur herstellung hochwertiger fettsaeureester | |
| DE69018413T2 (de) | Verfahren zum Raffinieren organischer Lösungsmittel enthaltende rohe Produkte aus einem Polyol-Fettsäure-Veresterungsgemisch. | |
| EP1322588A1 (de) | Verfahren zur herstellung von fettsäurealkylestern | |
| DE2051766B2 (de) | Verfahren zur Herstellung von Saccharose-Fettsäureestern | |
| DE3881503T2 (de) | Verfahren zur herstellung von polyol-fettsaeure-estern. | |
| DE3889084T2 (de) | Verfahren zur Herstellung von Polyol-Fettsäureester. | |
| DE1277237B (de) | Verfahren zur Herstellung von oberflaechenaktiven Stoffen aus Alkoholen, Fettsaeureestern und Alkylenoxyden | |
| DE69811676T2 (de) | Verfahren zur verminderung des gehaltes an langkettigen gesättigten fettsäuren in fettsäurezusammensetzungen | |
| DE3545056C2 (enExample) | ||
| DE69028759T2 (de) | Verfahren zur Raffinierung von Seife enthaltendem Rohprodukt aus einem Polyol-Fettsäure-Veresterungsgemisch | |
| DE69511435T2 (de) | Fraktionierung von triglyceridölen | |
| DE68927618T2 (de) | Verfahren zur Herstellung von Polyol-Fettsäure-Polyestern | |
| EP0885898B1 (de) | Verfahren zur Herstellung von Saccharosefettsäureestern | |
| DE69226445T2 (de) | Verfahren zur Herstellungvon Polyol-Fettsaurepolyestern | |
| DE3030553A1 (de) | Verfahren zur herstellung von sucroglyzeriden | |
| CH426452A (de) | Verfahren zur Herstellung von Fetten, insbesondere von Speisefetten mit einem vom Ausgangsmaterial abweichenden Schmelzverhalten | |
| DE69020309T2 (de) | Verfahren zur Transveresterung von Triglyceriden. | |
| EP0728176B1 (de) | Verfahren zur herstellung von fettsäureniedrigalkylestern | |
| EP1811951B1 (de) | Verfahren zur herstellung von kohlenhydratpartialestern | |
| DE10259157A1 (de) | Verfahren zur Herstellung von konjugierter Linolsäure | |
| EP0065267A2 (de) | Verfahren zur Herstellung von Carbonsäureestern von Anhydrohexiten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |