CA1153945A - Process for the production of a surfactant containing sucrose esters - Google Patents
Process for the production of a surfactant containing sucrose estersInfo
- Publication number
- CA1153945A CA1153945A CA000356985A CA356985A CA1153945A CA 1153945 A CA1153945 A CA 1153945A CA 000356985 A CA000356985 A CA 000356985A CA 356985 A CA356985 A CA 356985A CA 1153945 A CA1153945 A CA 1153945A
- Authority
- CA
- Canada
- Prior art keywords
- soap
- sucrose
- weight
- process according
- starting mixture
- 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 abstract description 62
- 230000008569 process Effects 0.000 title claims abstract description 56
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 22
- 150000003445 sucroses Chemical class 0.000 title description 14
- 238000004519 manufacturing process Methods 0.000 title description 11
- 239000005720 sucrose Substances 0.000 claims abstract description 138
- 229930006000 Sucrose Natural products 0.000 claims abstract description 137
- 239000000344 soap Substances 0.000 claims abstract description 135
- 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 abstract description 111
- 239000000203 mixture Substances 0.000 claims abstract description 89
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 30
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000011591 potassium Substances 0.000 claims abstract description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 27
- 239000000194 fatty acid Substances 0.000 claims abstract description 27
- 229930195729 fatty acid Natural products 0.000 claims abstract description 27
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 27
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 25
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 150000005690 diesters Chemical class 0.000 claims abstract description 15
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 51
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 38
- 125000005456 glyceride group Chemical group 0.000 claims description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 description 60
- 239000000047 product Substances 0.000 description 43
- -1 sucrose ester Chemical class 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 239000003760 tallow Substances 0.000 description 17
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 229960001947 tripalmitin Drugs 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000004703 alkoxides Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000009884 interesterification Methods 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 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
- 239000000843 powder Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- JEIJBKDXJPNHGD-UHFFFAOYSA-N chloroform;pyridine Chemical compound ClC(Cl)Cl.C1=CC=NC=C1 JEIJBKDXJPNHGD-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000002860 competitive effect Effects 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 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 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-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
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D10/00—Compositions of detergents, not provided for by one single preceding group
- C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7943762 | 1979-12-19 | ||
| GB7943762 | 1979-12-19 | ||
| GB8014370 | 1980-05-01 | ||
| GB8014370 | 1980-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1153945A true CA1153945A (en) | 1983-09-20 |
Family
ID=26273922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000356985A Expired CA1153945A (en) | 1979-12-19 | 1980-07-25 | Process for the production of a surfactant containing sucrose esters |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4298730A (enExample) |
| EP (1) | EP0031191B1 (enExample) |
| KR (1) | KR830003571A (enExample) |
| AR (1) | AR222567A1 (enExample) |
| AU (1) | AU534287B2 (enExample) |
| BR (1) | BR8005556A (enExample) |
| CA (1) | CA1153945A (enExample) |
| CU (1) | CU35315A (enExample) |
| DE (1) | DE3060918D1 (enExample) |
| DK (1) | DK370880A (enExample) |
| ES (1) | ES494692A0 (enExample) |
| FI (1) | FI802734A7 (enExample) |
| GR (1) | GR69950B (enExample) |
| IE (1) | IE50028B1 (enExample) |
| IL (1) | IL60716A0 (enExample) |
| NO (1) | NO802549L (enExample) |
| NZ (1) | NZ194465A (enExample) |
| OA (1) | OA06636A (enExample) |
| PT (1) | PT71737B (enExample) |
| YU (1) | YU216380A (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| GB8514975D0 (en) * | 1985-06-13 | 1985-07-17 | Sempernova Plc | Compositions |
| NL8601904A (nl) * | 1986-07-23 | 1988-02-16 | Unilever Nv | Werkwijze voor de bereiding van polyol-vetzuurpolyesters. |
| GB8800087D0 (en) * | 1988-01-05 | 1988-02-10 | Unilever Plc | Process for synthesis of polyol fatty acid polyesters |
| JPH0667955B2 (ja) * | 1989-05-09 | 1994-08-31 | 第一工業製薬株式会社 | 粉末状高ｈｌｂショ糖脂肪酸エステルの製造法 |
| DE69123595T3 (de) * | 1990-09-11 | 2004-09-30 | The Procter & Gamble Company, Cincinnati | Verfahren zur herstellung von polyolpolyestern |
| JP3164820B2 (ja) | 1990-09-11 | 2001-05-14 | ザ、プロクター、エンド、ギャンブル、カンパニー | より低レベルの二脂肪族ケトンおよびβ−ケトエステルを含む高エステル化ポリオール脂肪酸ポリエステルを得るための改良法 |
| JP3068648B2 (ja) * | 1991-04-12 | 2000-07-24 | ザ、プロクター、エンド、ギャンブル、カンパニー | ポリオール脂肪酸ポリエステルの酸化安定性の改善方法 |
| US5872245A (en) * | 1992-09-30 | 1999-02-16 | Optima Technologies Group | Continuous process for the synthesis of sucrose fatty acid esters |
| US5681948A (en) * | 1995-03-06 | 1997-10-28 | Kraft Foods, Inc. | Two-stage method for preparing polyol fatty acid polyesters |
| US5596085A (en) * | 1995-04-11 | 1997-01-21 | Kraft Foods, Inc. | Method for preparing polyol fatty acid polyesters by transesterification |
| US5705147A (en) * | 1995-09-18 | 1998-01-06 | Stepan Company | Methods and compositions for conditioning skin and hair |
| AU3122897A (en) * | 1996-05-14 | 1997-12-05 | 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 |
| US5945529A (en) * | 1996-07-19 | 1999-08-31 | The Procter & Gamble Company | Synthesis of polyol fatty acid polyesters using column with inert gas stripping |
| CN1230963A (zh) * | 1996-08-08 | 1999-10-06 | 普罗克特和甘保尔公司 | 多元醇多酯的合成 |
| US6121440A (en) * | 1998-01-29 | 2000-09-19 | The Procter & Gamble Company | Process for synthesis of polyol fatty acid polyesters |
| BR9908994A (pt) * | 1998-03-23 | 2000-12-12 | Procter & Gamble | Sìntese de poliésteres de ácido graxo de poliol superior por transesterificação |
| US20030130348A1 (en) * | 2001-11-16 | 2003-07-10 | Strohmaier George K. | Polyunsaturated oil saponification |
| US7098352B2 (en) * | 2001-11-16 | 2006-08-29 | Virtus Nutrition Llc | Calcium salt saponification of polyunsaturated oils |
| EP1765964A4 (en) * | 2004-04-30 | 2007-11-07 | SYNTHESIS OF METALLIC SALTS OF MONOVALENT AND DIVALENT POLYUNSATURATED FATTY ACIDS | |
| 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 |
| US8575333B2 (en) * | 2006-09-14 | 2013-11-05 | Bahram Memarzadeh | Halogenated alkyl di- and trisaccharides, pharmaceutical formulations, diagnostic kits and methods of treatment |
| EP2097488B1 (en) * | 2006-12-29 | 2018-04-18 | Sherwin-Williams Luxembourg Investment Management Company S.à r.l. | Pretreatment and stain system |
| CN102093438A (zh) * | 2010-11-22 | 2011-06-15 | 柳州爱格富食品科技股份有限公司 | 利用旋转薄膜酯交换连续反应器合成蔗糖多酯的工艺 |
| CN102533454B (zh) * | 2011-12-31 | 2013-04-10 | 柳州高通食品化工有限公司 | 一种蔗糖酯的生产方法及其在调制油脂专用抗氧化剂中的应用 |
| DK2820112T3 (en) | 2012-02-28 | 2017-09-11 | Petroliam Nasional Berhad | PROCEDURE FOR PREPARING POLYOLS AND APPLICATIONS THEREOF |
| JP6133908B2 (ja) | 2012-02-28 | 2017-05-24 | ペトロリアム ナショナル ブルハドＰｅｔｒｏｌｉａｍ Ｎａｓｉｏｎａｌ Ｂｅｒｈａｄ | 潤滑油の物質組成および生成方法 |
| CN104302614B (zh) | 2012-02-28 | 2017-03-08 | 马来西亚国家石油公司 | 用于生物润滑剂和生物聚合物的生物多元醇及其制备方法 |
| WO2013129910A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhard | Composition of matter polyols for polyurethane applications |
| WO2013129907A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad (Petronas) | Method for the production of esters and uses thereof |
| CN102850413A (zh) * | 2012-05-29 | 2013-01-02 | 常州大学 | 一种制备蔗糖脂肪酸酯的方法 |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2970962A (en) * | 1958-02-11 | 1961-02-07 | Sugar Res Foundation Inc | Novel detergent compositions |
| DE1200276B (de) * | 1959-10-08 | 1965-09-09 | Bayer Ag | Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker |
| 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. |
| DE1643795A1 (de) * | 1967-08-04 | 1971-07-01 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von Zuckerestern |
| 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 |
| GB1399927A (en) * | 1971-09-11 | 1975-07-02 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| GB1399053A (en) * | 1973-03-16 | 1975-06-25 | Tate & Lyle Ltd | Process for the production of surface active agents comprising sucrose esters |
| US3963699A (en) * | 1974-01-10 | 1976-06-15 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters |
| GB1499989A (en) * | 1974-10-17 | 1978-02-01 | Tate & Lyle Ltd | Production of a surface active material containing sucrose esters |
| NO142306C (no) * | 1975-04-18 | 1980-07-30 | Tate & Lyle Ltd | Fremgangsmaate til rensing av et fast stoff i form av et omestringsprodukt frembrakt ved reaksjon mellom sukrose og minst ett fettsyretriglycerid |
-
1980
- 1980-07-24 IE IE1546/80A patent/IE50028B1/en unknown
- 1980-07-25 CA CA000356985A patent/CA1153945A/en not_active Expired
- 1980-07-28 NZ NZ194465A patent/NZ194465A/xx unknown
- 1980-07-31 US US06/174,277 patent/US4298730A/en not_active Expired - Lifetime
- 1980-07-31 IL IL60716A patent/IL60716A0/xx unknown
- 1980-08-01 AU AU60988/80A patent/AU534287B2/en not_active Ceased
- 1980-08-13 EP EP80302785A patent/EP0031191B1/en not_active Expired
- 1980-08-13 DE DE8080302785T patent/DE3060918D1/de not_active Expired
- 1980-08-15 AR AR282186A patent/AR222567A1/es active
- 1980-08-25 PT PT71737A patent/PT71737B/pt unknown
- 1980-08-29 FI FI802734A patent/FI802734A7/fi unknown
- 1980-08-29 DK DK370880A patent/DK370880A/da not_active Application Discontinuation
- 1980-08-29 NO NO802549A patent/NO802549L/no unknown
- 1980-08-29 YU YU02163/80A patent/YU216380A/xx unknown
- 1980-08-30 GR GR62774A patent/GR69950B/el unknown
- 1980-09-01 ES ES494692A patent/ES494692A0/es active Granted
- 1980-09-01 BR BR8005556A patent/BR8005556A/pt unknown
- 1980-09-05 CU CU8035315A patent/CU35315A/es unknown
- 1980-09-25 KR KR1019800003743A patent/KR830003571A/ko active Pending
- 1980-10-07 OA OA57230A patent/OA06636A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL60716A0 (en) | 1980-09-16 |
| ES8106538A1 (es) | 1981-07-16 |
| US4298730A (en) | 1981-11-03 |
| GR69950B (enExample) | 1982-07-22 |
| IE50028B1 (en) | 1986-02-05 |
| NZ194465A (en) | 1982-12-21 |
| EP0031191B1 (en) | 1982-10-06 |
| KR830003571A (ko) | 1983-06-21 |
| DE3060918D1 (en) | 1982-11-11 |
| AR222567A1 (es) | 1981-05-29 |
| AU534287B2 (en) | 1984-01-19 |
| CU35315A (en) | 1982-03-28 |
| PT71737B (en) | 1981-06-15 |
| AU6098880A (en) | 1981-06-25 |
| PT71737A (en) | 1980-09-01 |
| ES494692A0 (es) | 1981-07-16 |
| DK370880A (da) | 1981-06-20 |
| NO802549L (no) | 1981-06-22 |
| OA06636A (fr) | 1981-08-31 |
| IE801546L (en) | 1981-06-19 |
| YU216380A (en) | 1983-10-31 |
| BR8005556A (pt) | 1981-06-23 |
| FI802734A7 (fi) | 1981-06-19 |
| EP0031191A1 (en) | 1981-07-01 |
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