US2893990A - Process for producing sugar esters - Google Patents
Process for producing sugar esters Download PDFInfo
- Publication number
- US2893990A US2893990A US552281A US55228155A US2893990A US 2893990 A US2893990 A US 2893990A US 552281 A US552281 A US 552281A US 55228155 A US55228155 A US 55228155A US 2893990 A US2893990 A US 2893990A
- Authority
- US
- United States
- Prior art keywords
- sucrose
- esters
- grams
- ester
- employed
- 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 53
- 230000008569 process Effects 0.000 title claims description 47
- 150000002148 esters Chemical class 0.000 title description 53
- 239000005720 sucrose Substances 0.000 claims description 115
- 229930006000 Sucrose Natural products 0.000 claims description 112
- 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 103
- 239000000194 fatty acid Substances 0.000 claims description 45
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 43
- 229930195729 fatty acid Natural products 0.000 claims description 43
- 150000004665 fatty acids Chemical class 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 20
- 150000001720 carbohydrates Chemical class 0.000 claims description 15
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 claims description 15
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 104
- 239000000243 solution Substances 0.000 description 49
- -1 fatty-acid esters Chemical class 0.000 description 31
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000003599 detergent Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- QIZPVNNYFKFJAD-UHFFFAOYSA-N 1-chloro-2-prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1Cl QIZPVNNYFKFJAD-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229940035023 sucrose monostearate Drugs 0.000 description 11
- WXOMTJVVIMOXJL-BOBFKVMVSA-A O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O WXOMTJVVIMOXJL-BOBFKVMVSA-A 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000005690 diesters Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 10
- 229940071160 cocoate Drugs 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 235000019197 fats Nutrition 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000003240 coconut oil Substances 0.000 description 6
- 235000019864 coconut oil Nutrition 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 5
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 229960005382 phenolphthalein Drugs 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000003760 tallow Substances 0.000 description 5
- 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 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- KGUHOFWIXKIURA-VQXBOQCVSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl dodecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCC)O[C@@H]1O[C@@]1(CO)[C@@H](O)[C@H](O)[C@@H](CO)O1 KGUHOFWIXKIURA-VQXBOQCVSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 4
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229940032085 sucrose monolaurate Drugs 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000008231 carbon dioxide-free water Substances 0.000 description 3
- 235000019868 cocoa butter Nutrition 0.000 description 3
- 229940110456 cocoa butter Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000002070 germicidal effect Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010408 sweeping Methods 0.000 description 3
- 239000000606 toothpaste Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000273930 Brevoortia tyrannus Species 0.000 description 2
- 241000252203 Clupea harengus Species 0.000 description 2
- 101100348017 Drosophila melanogaster Nazo gene Proteins 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000283222 Physeter catodon Species 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000000022 bacteriostatic agent Substances 0.000 description 2
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 235000019621 digestibility Nutrition 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 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 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 159000000011 group IA salts Chemical class 0.000 description 2
- 235000019514 herring Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000010699 lard oil Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
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- 210000004400 mucous membrane Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 230000035484 reaction time Effects 0.000 description 2
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
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- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
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- AGUBCDYYAKENKG-YVNJGZBMSA-N Ethyl abietate Chemical compound C1CC(C(C)C)=CC2=CC[C@H]3[C@@](C(=O)OCC)(C)CCC[C@]3(C)[C@H]21 AGUBCDYYAKENKG-YVNJGZBMSA-N 0.000 description 1
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- CBSOFSBFHDQRLV-UHFFFAOYSA-N N-methylbenzylamine hydrochloride Chemical compound [Cl-].C[NH2+]CC1=CC=CC=C1 CBSOFSBFHDQRLV-UHFFFAOYSA-N 0.000 description 1
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- 208000002193 Pain Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- OVXRPXGVKBHGQO-UHFFFAOYSA-N abietic acid methyl ester Natural products C1CC(C(C)C)=CC2=CCC3C(C(=O)OC)(C)CCCC3(C)C21 OVXRPXGVKBHGQO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- LAUPTJWHHKNSCT-UHFFFAOYSA-M benzyl-hexadecyl-dimethylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 LAUPTJWHHKNSCT-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 1
- 229960000228 cetalkonium chloride Drugs 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000009826 distribution 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
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100001032 irritation of the eye Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OVXRPXGVKBHGQO-UYWIDEMCSA-N methyl (1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound C1CC(C(C)C)=CC2=CC[C@H]3[C@@](C(=O)OC)(C)CCC[C@]3(C)[C@H]21 OVXRPXGVKBHGQO-UYWIDEMCSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- SPIPDAOQETVHEZ-UHFFFAOYSA-J pentasodium;phosphonato phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O SPIPDAOQETVHEZ-UHFFFAOYSA-J 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000004391 petroleum recovery Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- GZCWPZJOEIAXRU-UHFFFAOYSA-N tin zinc Chemical compound [Zn].[Sn] GZCWPZJOEIAXRU-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010698 whale oil Substances 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
- B23K5/00—Gas flame welding
- B23K5/02—Seam welding
- B23K5/06—Welding longitudinal seams
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/04—Water-soluble compounds
- C11D3/06—Phosphates, including polyphosphates
Definitions
- the present invention relates to a novel process for producing esters of sucrose or raflinose and fatty acids having from about 6 to 30 carbon atoms and to the esters obtained thereby.
- the monoand di-esters of the invention may be employed in producing poultry, cattle and swine rations to improve the digestibility of such rations.
- esters of the present invention maybe employed for secondary oil for petroleum recovery whereby aqueous whereby solutions of these esters are used to displace residual oil from the underground rock and thereby permit more efficient recovery of petroleum from the ground,
- the product obtained issubstantially a mono-ester. If one mole of sucrose is employed with two moles ,of a fattyacid ester of a volatile alcohol, the product is essentially a di-ester of sucrose.
- By using largeenough ratios of non-sucrose ester it is possible to provide esters ofsucrose in which several hydroxyls are esterified.
- the resulting dimethylformamide solution was further distilled in vacuo to a thick syrup, which was precipitated with acetone.
- the acetone solution was evaporated, producing a residue which was composed of 22 grams (0.036 mole) of relatively pure sucrose mono-stearate, having a melting point of about 5253 C.; M1 +33.2, for an absolute yield of 24.6% based upon the amount of distearin employed in the reaction.
- the unreacted sucrose obtained above was filtered and dried to be used in subsequent processes. Pure sucrose monostearate was found to have a melting point of 5253 C.
- Example VI A solution was prepared by dissolving about 70 grams (0.208 mole) of sucrose in 400 ml. of N,N-dimethylformamide. With the resulting solution was mixed 92 grams (0.14 mole) of tristearin dissolved in 400 ml. of dimethylformamide. The mixture was placed in a pressure bomb along with 3 grams of trisodium phosphate. The bomb was heated for about 8 hours at a temperature of C. One-half of the dimethylformamide was removed by distillation and the resulting sucrose monostearate was recovered as in Example II. The quantity of recovered substantially-pure sucrose mono-stearate indicated a conversion yield of about 29%.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL111638D NL111638C (enrdf_load_stackoverflow) | 1955-12-12 | ||
| US552281A US2893990A (en) | 1955-12-12 | 1955-12-12 | Process for producing sugar esters |
| FR1146644D FR1146644A (fr) | 1955-12-12 | 1956-01-06 | Nouveaux esters de saccharides et d'acides gras, leur procédé de préparation et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US552281A US2893990A (en) | 1955-12-12 | 1955-12-12 | Process for producing sugar esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2893990A true US2893990A (en) | 1959-07-07 |
Family
ID=24204671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US552281A Expired - Lifetime US2893990A (en) | 1955-12-12 | 1955-12-12 | Process for producing sugar esters |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2893990A (enrdf_load_stackoverflow) |
| FR (1) | FR1146644A (enrdf_load_stackoverflow) |
| NL (1) | NL111638C (enrdf_load_stackoverflow) |
Cited By (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2951015A (en) * | 1957-07-02 | 1960-08-30 | Pfizer & Co C | Aqueous readily injectable therapeutic compositions containing water-insoluble penicillin and sucrose dilaurate |
| US2992082A (en) * | 1958-06-24 | 1961-07-11 | Eastman Kodak Co | Anti-sludging hydrocarbon fuel oils |
| US2997491A (en) * | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing partial fatty esters of inositol |
| US2997493A (en) * | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing straight chain hexitol fatty esters |
| US2997490A (en) * | 1959-05-08 | 1961-08-22 | Procter & Gamble | Method for preparing fatty esters |
| US2999023A (en) * | 1959-05-08 | 1961-09-05 | Drew & Co Inc E F | Confectionary coating compositions |
| US2999858A (en) * | 1956-09-18 | 1961-09-12 | Robert S Aries | Preparation of sucrose monoesters |
| US3023183A (en) * | 1959-06-29 | 1962-02-27 | Cuban American Sugar Company | Esterification |
| US3024229A (en) * | 1957-07-26 | 1962-03-06 | Bayer Ag | Preparation of ester salts of di and trisaccharides |
| US3053677A (en) * | 1959-11-12 | 1962-09-11 | Eastman Kodak Co | Petroleum wax for paper coatings |
| US3054789A (en) * | 1959-02-06 | 1962-09-18 | Ledoga Spa | Process for the preparation of pure sucrose esters |
| US3061629A (en) * | 1958-11-19 | 1962-10-30 | Celanese Corp | Dialkyl sulfoxide in preparation of isocyanate-polyol adduct |
| US3096324A (en) * | 1960-08-24 | 1963-07-02 | Eastman Kodak Co | Process for manufacturing sugar esters |
| US3141012A (en) * | 1960-06-01 | 1964-07-14 | North American Sugar Ind Inc | Recovering solid polyhydric alcohols from transesterification reaction masses |
| DE1200276B (de) * | 1959-10-08 | 1965-09-09 | Bayer Ag | Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker |
| US3219484A (en) * | 1961-08-07 | 1965-11-23 | Colonial Sugar Refining Co | Process for the purification of sugars and their derivatives |
| DE1205510B (de) * | 1961-09-12 | 1965-11-25 | Ledoga Spa | Verfahren zur quantitativen Abtrennung von reinen Rohrzuckermono- bzw. -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen |
| DE1205511B (de) * | 1961-10-31 | 1965-11-25 | Ledoga Spa | Verfahren zur Trennung von Rohrzuckermono- und -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen |
| US3231562A (en) * | 1959-05-21 | 1966-01-25 | Dainippon Seito Kabushiki Kais | Process for recovering unreacted sucrose from reaction solution of fatty acid sucrose ester |
| 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 |
| 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 |
| US3476598A (en) * | 1966-05-10 | 1969-11-04 | Varney Chem Corp | Sucrose based surfactants as aids in sugar refining and sugar crystallization processes |
| US3480616A (en) * | 1966-04-06 | 1969-11-25 | Nebraska State | Esterification of polyhydric compounds in the presence of transparent emulsifying agent |
| US3481881A (en) * | 1965-02-06 | 1969-12-02 | Boehme Chem Fab Kg | Soap or detergent rinsing agent |
| US3867301A (en) * | 1971-09-11 | 1975-02-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| US3872020A (en) * | 1971-09-14 | 1975-03-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| US3954976A (en) * | 1973-12-14 | 1976-05-04 | The Procter & Gamble Company | Pharmaceutical compositions for inhibiting absorption of cholesterol |
| JPS5244803A (en) * | 1976-08-24 | 1977-04-08 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| US4087371A (en) * | 1971-12-23 | 1978-05-02 | Grillo-Werke Aktiengesellschaft | Method of preventing incrustation on heated surfaces, and composition for the practice of the method |
| WO1980000452A1 (en) * | 1978-08-30 | 1980-03-20 | Quimica Milen Sa | Non-polluting detergent composition containing soap and sucrose esters |
| US4241054A (en) * | 1978-12-08 | 1980-12-23 | The Procter & Gamble Company | Detoxifying lipophilic toxins |
| US4259202A (en) * | 1979-02-27 | 1981-03-31 | Toyo Contact Lens Co., Ltd. | Cleaning and preservative solution for contact lenses |
| US4306062A (en) * | 1979-05-24 | 1981-12-15 | Talres Development (N.A.) N.V. | Process for the preparation of sucrose monoesters |
| US4379755A (en) * | 1978-08-10 | 1983-04-12 | Nihon Surfactant Industry Co., Ltd. | Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom |
| US4395365A (en) * | 1980-09-08 | 1983-07-26 | Nissan Motor Co., Ltd. | Metal cleaning composition containing a fatty acid succrose ester and other detergent components |
| US4496547A (en) * | 1981-12-25 | 1985-01-29 | Mitsui Toatsu Chemicals, Inc. | Saccharide fatty acid ester for bloat-prevention or bloat-treatment |
| 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 |
| US4686205A (en) * | 1983-07-07 | 1987-08-11 | Ralston Purina Company | Intake limiting feed for animals containing sucrose octaacetate |
| US4806632A (en) * | 1986-12-29 | 1989-02-21 | The Procter & Gamble Company | Process for the post-hydrogenation of sucrose polyesters |
| US4822875A (en) * | 1986-12-17 | 1989-04-18 | The Procter & Gamble Company | Sucrose polyesters which behave like cocoa butters |
| US4865848A (en) * | 1987-02-26 | 1989-09-12 | Alza Corporation | Skin permeation enhancer compositions using sucrose esters |
| US4877871A (en) * | 1988-06-14 | 1989-10-31 | Nabisco Brands, Inc. | Synthesis of sucrose polyester |
| US4927920A (en) * | 1988-11-15 | 1990-05-22 | Nebraska Department Of Economic Development, State Of Nebraska, U.S.A. | Sugar ester synthesis |
| US4940586A (en) * | 1987-02-26 | 1990-07-10 | Alza Corporation | Skin permeation enhancer compositions using sucrose esters |
| US4942054A (en) * | 1987-05-13 | 1990-07-17 | Curtice-Burns, Inc. | Process for producing low calorie foods from alkyl glycoside fatty acid polyesters |
| WO1990011285A1 (en) * | 1989-03-17 | 1990-10-04 | Nebraska Department Of Economic Development, State Of Nebraska | Separation and purification of sugar esters |
| US4962092A (en) * | 1987-05-06 | 1990-10-09 | The Procter & Gamble Company | Compositions for treating duodenal ulcers |
| US5006648A (en) * | 1986-07-23 | 1991-04-09 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing partial polyol fatty acid esters |
| USRE33885E (en) * | 1975-11-03 | 1992-04-14 | The Procter & Gamble Company | Compositions for inhibiting absorption of cholesterol |
| USRE33996E (en) * | 1976-02-12 | 1992-07-14 | The Procter & Gamble Company | Compositions for treating hypercholesterolemia |
| USRE34617E (en) * | 1976-02-12 | 1994-05-24 | The Procter & Gamble Company | Vitaminized compositions for treating hypercholesterolemia |
| WO1994022919A1 (en) * | 1993-04-07 | 1994-10-13 | Alko Group Ltd. | Applications and methods for the preparation of fatty acid esters of polysaccharides |
| EP0346845B1 (en) * | 1988-06-14 | 1994-12-14 | Mitsubishi Chemical Corporation | Process for producing sucrose fatty acid polyester |
| US5424420A (en) * | 1993-10-05 | 1995-06-13 | Kraft Foods, Inc. | Method for preparing saccharide polyesters by transesterification |
| US5440027A (en) * | 1993-10-05 | 1995-08-08 | Kraft General Foods, Inc. | Method for preparing saccharide fatty acid polyesters by transesterification |
| US5439697A (en) * | 1993-09-09 | 1995-08-08 | The Pillsbury Company | Low-fat spreadable compositions |
| 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 |
| US5559226A (en) * | 1991-04-12 | 1996-09-24 | The Procter & Gamble Company | Process for making polyol fatty acid polyesters having oxidative stability |
| US5596085A (en) * | 1995-04-11 | 1997-01-21 | Kraft Foods, Inc. | Method for preparing polyol fatty acid polyesters by transesterification |
| US5756716A (en) * | 1995-06-07 | 1998-05-26 | Kimball Chase Tech. Ltd. | Sugar-ester manufacturing process |
| WO1998054276A1 (en) * | 1997-05-30 | 1998-12-03 | Oded Broshi | An edible, pleasant tasting, bubble making composition |
| US5968566A (en) * | 1996-05-14 | 1999-10-19 | Mlp Operating Company | Refrigerated yeast-raised pizza dough |
| US6121440A (en) * | 1998-01-29 | 2000-09-19 | The Procter & Gamble Company | Process for synthesis of polyol fatty acid polyesters |
| US6497898B1 (en) | 1993-10-07 | 2002-12-24 | Kanebo Ltd | Surfactant, and an emulsion-type cosmetic composition and a lipsome containing said surfactant |
| US20040063928A1 (en) * | 2001-01-18 | 2004-04-01 | Jo In-Ho | Preparation of aliphatic acid ester of carbohydrate |
| US20070259084A1 (en) * | 2006-05-04 | 2007-11-08 | Gaonkar Anilkumar G | Coffee-Derived Surfactants |
| US7304153B1 (en) | 1990-09-11 | 2007-12-04 | The Procter And Gamble Co. | Polyol polyester synthesis |
| US20130312975A1 (en) * | 2012-05-23 | 2013-11-28 | Basf Se | Process for Water Wetting Oil-Wet Surfaces |
| WO2018045248A1 (en) * | 2016-09-01 | 2018-03-08 | Hs Manufacturing Group Llc | Methods for biobased derivatization of cellulosic surfaces |
| KR20190069016A (ko) * | 2017-12-11 | 2019-06-19 | 주식회사 비제이바이오켐 | 당류계 지방산 에스테르 제조방법 |
| US10717917B2 (en) | 2016-06-24 | 2020-07-21 | Croda, Inc. | Method and composition for asphaltene dispersion |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1158486B (de) * | 1959-02-06 | 1963-12-05 | Ledoga Spa | Verfahren zur Herstellung von reinen Saccharosemono- bzw. -diestern langkettiger, gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen bzw. deren Mischungen |
| FR2540511B1 (fr) * | 1983-02-04 | 1985-08-09 | Henkel France | Composition liquide de nettoyage, ainsi que procede de nettoyage a partir de cette composition |
| JPH0662659B2 (ja) * | 1988-04-18 | 1994-08-17 | 第一工業製薬株式会社 | ショ糖脂肪酸エステルを含む反応混合物の処理方法 |
| FR2670493A1 (fr) * | 1990-12-13 | 1992-06-19 | Isochem Sa | Nouveaux composes monoesters du saccharose tels que les 2-0-acylsaccharoses et les 6-0-acylsaccharoses, ainsi que leurs procedes de synthese. |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1959590A (en) * | 1932-03-22 | 1934-05-22 | Hercules Powder Co Ltd | Fatty acid esters of carbohydrates and method for producing |
| US2147241A (en) * | 1937-08-14 | 1939-02-14 | Corn Prod Refining Co | Production of fatty acid esters from starch factory byproducts |
| US2399959A (en) * | 1942-07-02 | 1946-05-07 | Procter & Gamble | Process of producing esters |
| US2586897A (en) * | 1948-07-03 | 1952-02-26 | Victor Chemical Works | Detergent composition |
| US2594453A (en) * | 1950-04-01 | 1952-04-29 | Monsanto Chemicals | Detergent compositions |
| US2602789A (en) * | 1949-08-23 | 1952-07-08 | Joseph H Schwartz | Ether-esters of polyhydroxy compounds |
| US2700022A (en) * | 1952-07-15 | 1955-01-18 | California Research Corp | Sugar ester-containing lubricant compositions |
-
0
- NL NL111638D patent/NL111638C/xx active
-
1955
- 1955-12-12 US US552281A patent/US2893990A/en not_active Expired - Lifetime
-
1956
- 1956-01-06 FR FR1146644D patent/FR1146644A/fr not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1959590A (en) * | 1932-03-22 | 1934-05-22 | Hercules Powder Co Ltd | Fatty acid esters of carbohydrates and method for producing |
| US2147241A (en) * | 1937-08-14 | 1939-02-14 | Corn Prod Refining Co | Production of fatty acid esters from starch factory byproducts |
| US2399959A (en) * | 1942-07-02 | 1946-05-07 | Procter & Gamble | Process of producing esters |
| US2586897A (en) * | 1948-07-03 | 1952-02-26 | Victor Chemical Works | Detergent composition |
| US2602789A (en) * | 1949-08-23 | 1952-07-08 | Joseph H Schwartz | Ether-esters of polyhydroxy compounds |
| US2594453A (en) * | 1950-04-01 | 1952-04-29 | Monsanto Chemicals | Detergent compositions |
| US2700022A (en) * | 1952-07-15 | 1955-01-18 | California Research Corp | Sugar ester-containing lubricant compositions |
Cited By (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2999858A (en) * | 1956-09-18 | 1961-09-12 | Robert S Aries | Preparation of sucrose monoesters |
| US2951015A (en) * | 1957-07-02 | 1960-08-30 | Pfizer & Co C | Aqueous readily injectable therapeutic compositions containing water-insoluble penicillin and sucrose dilaurate |
| US3024229A (en) * | 1957-07-26 | 1962-03-06 | Bayer Ag | Preparation of ester salts of di and trisaccharides |
| US2992082A (en) * | 1958-06-24 | 1961-07-11 | Eastman Kodak Co | Anti-sludging hydrocarbon fuel oils |
| US3061629A (en) * | 1958-11-19 | 1962-10-30 | Celanese Corp | Dialkyl sulfoxide in preparation of isocyanate-polyol adduct |
| US3054789A (en) * | 1959-02-06 | 1962-09-18 | Ledoga Spa | Process for the preparation of pure sucrose esters |
| US2997490A (en) * | 1959-05-08 | 1961-08-22 | Procter & Gamble | Method for preparing fatty esters |
| US2999023A (en) * | 1959-05-08 | 1961-09-05 | Drew & Co Inc E F | Confectionary coating compositions |
| US3231562A (en) * | 1959-05-21 | 1966-01-25 | Dainippon Seito Kabushiki Kais | Process for recovering unreacted sucrose from reaction solution of fatty acid sucrose ester |
| US3023183A (en) * | 1959-06-29 | 1962-02-27 | Cuban American Sugar Company | Esterification |
| US2997493A (en) * | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing straight chain hexitol fatty esters |
| US2997491A (en) * | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing partial fatty esters of inositol |
| US3251827A (en) * | 1959-10-08 | 1966-05-17 | Bayer Ag | Process for the production of sugar esters |
| DE1200276B (de) * | 1959-10-08 | 1965-09-09 | Bayer Ag | Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker |
| US3053677A (en) * | 1959-11-12 | 1962-09-11 | Eastman Kodak Co | Petroleum wax for paper coatings |
| US3141012A (en) * | 1960-06-01 | 1964-07-14 | North American Sugar Ind Inc | Recovering solid polyhydric alcohols from transesterification reaction masses |
| US3096324A (en) * | 1960-08-24 | 1963-07-02 | Eastman Kodak Co | Process for manufacturing sugar esters |
| US3219484A (en) * | 1961-08-07 | 1965-11-23 | Colonial Sugar Refining Co | Process for the purification of sugars and their derivatives |
| DE1205510B (de) * | 1961-09-12 | 1965-11-25 | Ledoga Spa | Verfahren zur quantitativen Abtrennung von reinen Rohrzuckermono- bzw. -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen |
| DE1205511B (de) * | 1961-10-31 | 1965-11-25 | Ledoga Spa | Verfahren zur Trennung von Rohrzuckermono- und -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen |
| 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 |
| 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 |
| DE1270021B (de) * | 1963-03-21 | 1968-06-12 | Bayer Ag | Verfahren zur Abtrennung nicht-umgesetzter Zucker aus dem bei der Herstellung von Zuckerfettsaeureestern aus Fettsaeurealkylestern und ueberschuessigen Mengen an Zuckernin Dimethylformamid, Dimethylacetamid, Dialkylsulfoxyd oder Butyrolacton erhaltenenReaktionsgemisch |
| US3481881A (en) * | 1965-02-06 | 1969-12-02 | Boehme Chem Fab Kg | Soap or detergent rinsing agent |
| US3480616A (en) * | 1966-04-06 | 1969-11-25 | Nebraska State | Esterification of polyhydric compounds in the presence of transparent emulsifying agent |
| US3476598A (en) * | 1966-05-10 | 1969-11-04 | Varney Chem Corp | Sucrose based surfactants as aids in sugar refining and sugar crystallization processes |
| US3867301A (en) * | 1971-09-11 | 1975-02-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| US3872020A (en) * | 1971-09-14 | 1975-03-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| US4087371A (en) * | 1971-12-23 | 1978-05-02 | Grillo-Werke Aktiengesellschaft | Method of preventing incrustation on heated surfaces, and composition for the practice of the method |
| US3954976A (en) * | 1973-12-14 | 1976-05-04 | The Procter & Gamble Company | Pharmaceutical compositions for inhibiting absorption of cholesterol |
| USRE33885E (en) * | 1975-11-03 | 1992-04-14 | The Procter & Gamble Company | Compositions for inhibiting absorption of cholesterol |
| USRE33996E (en) * | 1976-02-12 | 1992-07-14 | The Procter & Gamble Company | Compositions for treating hypercholesterolemia |
| USRE34617E (en) * | 1976-02-12 | 1994-05-24 | The Procter & Gamble Company | Vitaminized compositions for treating hypercholesterolemia |
| JPS5244803A (en) * | 1976-08-24 | 1977-04-08 | Dai Ichi Kogyo Seiyaku Co Ltd | Detergent compositions |
| US4379755A (en) * | 1978-08-10 | 1983-04-12 | Nihon Surfactant Industry Co., Ltd. | Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom |
| WO1980000452A1 (en) * | 1978-08-30 | 1980-03-20 | Quimica Milen Sa | Non-polluting detergent composition containing soap and sucrose esters |
| US4241054A (en) * | 1978-12-08 | 1980-12-23 | The Procter & Gamble Company | Detoxifying lipophilic toxins |
| US4259202A (en) * | 1979-02-27 | 1981-03-31 | Toyo Contact Lens Co., Ltd. | Cleaning and preservative solution for contact lenses |
| US4306062A (en) * | 1979-05-24 | 1981-12-15 | Talres Development (N.A.) N.V. | Process for the preparation of sucrose monoesters |
| US4395365A (en) * | 1980-09-08 | 1983-07-26 | Nissan Motor Co., Ltd. | Metal cleaning composition containing a fatty acid succrose ester and other detergent components |
| US4496547A (en) * | 1981-12-25 | 1985-01-29 | Mitsui Toatsu Chemicals, Inc. | Saccharide fatty acid ester for bloat-prevention or bloat-treatment |
| 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 |
| US4686205A (en) * | 1983-07-07 | 1987-08-11 | Ralston Purina Company | Intake limiting feed for animals containing sucrose octaacetate |
| US5006648A (en) * | 1986-07-23 | 1991-04-09 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing partial polyol fatty acid esters |
| US5071975A (en) * | 1986-07-23 | 1991-12-10 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing polyol fatty acid polyesters |
| US4822875A (en) * | 1986-12-17 | 1989-04-18 | The Procter & Gamble Company | Sucrose polyesters which behave like cocoa butters |
| US4806632A (en) * | 1986-12-29 | 1989-02-21 | The Procter & Gamble Company | Process for the post-hydrogenation of sucrose polyesters |
| US4865848A (en) * | 1987-02-26 | 1989-09-12 | Alza Corporation | Skin permeation enhancer compositions using sucrose esters |
| US4940586A (en) * | 1987-02-26 | 1990-07-10 | Alza Corporation | Skin permeation enhancer compositions using sucrose esters |
| US4962092A (en) * | 1987-05-06 | 1990-10-09 | The Procter & Gamble Company | Compositions for treating duodenal ulcers |
| 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 |
| US4942054A (en) * | 1987-05-13 | 1990-07-17 | Curtice-Burns, Inc. | Process for producing low calorie foods from alkyl glycoside fatty acid polyesters |
| US4877871A (en) * | 1988-06-14 | 1989-10-31 | Nabisco Brands, Inc. | Synthesis of sucrose polyester |
| EP0346845B1 (en) * | 1988-06-14 | 1994-12-14 | Mitsubishi Chemical Corporation | Process for producing sucrose fatty acid polyester |
| US4927920A (en) * | 1988-11-15 | 1990-05-22 | Nebraska Department Of Economic Development, State Of Nebraska, U.S.A. | Sugar ester synthesis |
| WO1990011285A1 (en) * | 1989-03-17 | 1990-10-04 | Nebraska Department Of Economic Development, State Of Nebraska | Separation and purification of sugar esters |
| US4983731A (en) * | 1989-03-17 | 1991-01-08 | Nebraska Department Of Economic Development | Separation and purification of sugar esters |
| US7304153B1 (en) | 1990-09-11 | 2007-12-04 | The Procter And Gamble Co. | Polyol polyester synthesis |
| US5559226A (en) * | 1991-04-12 | 1996-09-24 | The Procter & Gamble Company | Process for making polyol fatty acid polyesters having oxidative stability |
| 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 |
| AU691805B2 (en) * | 1993-04-07 | 1998-05-28 | Valtion Teknillinen Tutkimuskeskus | Applications and methods for the preparation of fatty acid esters of polysaccharides |
| US5589577A (en) * | 1993-04-07 | 1996-12-31 | Alko Group Ltd. | Applications and methods for the preparation of fatty acid esters of polysaccharides |
| WO1994022919A1 (en) * | 1993-04-07 | 1994-10-13 | Alko Group Ltd. | Applications and methods for the preparation of fatty acid esters of polysaccharides |
| US5439697A (en) * | 1993-09-09 | 1995-08-08 | The Pillsbury Company | Low-fat spreadable compositions |
| US5440027A (en) * | 1993-10-05 | 1995-08-08 | Kraft General Foods, Inc. | Method for preparing saccharide fatty acid polyesters by transesterification |
| US5424420A (en) * | 1993-10-05 | 1995-06-13 | Kraft Foods, Inc. | Method for preparing saccharide polyesters by transesterification |
| US20090098172A1 (en) * | 1993-10-07 | 2009-04-16 | Kao Corporation | Surfactant, and emulsion cosmetic and liposome each containing the same |
| US6497898B1 (en) | 1993-10-07 | 2002-12-24 | Kanebo Ltd | Surfactant, and an emulsion-type cosmetic composition and a lipsome containing said surfactant |
| US20040022819A1 (en) * | 1993-10-07 | 2004-02-05 | Takeshi Ikemoto | Surfactant, and an emulsion-type cosmetic composition and a liposome containing said surfactant |
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| US5756716A (en) * | 1995-06-07 | 1998-05-26 | Kimball Chase Tech. Ltd. | Sugar-ester manufacturing process |
| US5968566A (en) * | 1996-05-14 | 1999-10-19 | Mlp Operating Company | Refrigerated yeast-raised pizza dough |
| US6056983A (en) * | 1997-05-30 | 2000-05-02 | Broshi; Oded | Edible pleasant tasting bubble making composition |
| WO1998054276A1 (en) * | 1997-05-30 | 1998-12-03 | Oded Broshi | An edible, pleasant tasting, bubble making composition |
| US6121440A (en) * | 1998-01-29 | 2000-09-19 | The Procter & Gamble Company | Process for synthesis of polyol fatty acid polyesters |
| US20040063928A1 (en) * | 2001-01-18 | 2004-04-01 | Jo In-Ho | Preparation of aliphatic acid ester of carbohydrate |
| US20090252850A1 (en) * | 2006-05-04 | 2009-10-08 | Gaonkar Anilkumar G | Coffee-Derived Surfactants |
| JP2007297628A (ja) * | 2006-05-04 | 2007-11-15 | Kraft Foods Holdings Inc | コーヒーから誘導される界面活性剤 |
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| US20130312975A1 (en) * | 2012-05-23 | 2013-11-28 | Basf Se | Process for Water Wetting Oil-Wet Surfaces |
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| US10717917B2 (en) | 2016-06-24 | 2020-07-21 | Croda, Inc. | Method and composition for asphaltene dispersion |
| WO2018045248A1 (en) * | 2016-09-01 | 2018-03-08 | Hs Manufacturing Group Llc | Methods for biobased derivatization of cellulosic surfaces |
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| KR20190069016A (ko) * | 2017-12-11 | 2019-06-19 | 주식회사 비제이바이오켐 | 당류계 지방산 에스테르 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1146644A (fr) | 1957-11-13 |
| NL111638C (enrdf_load_stackoverflow) |
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