JPS6328118B2 - - Google Patents
Info
- Publication number
- JPS6328118B2 JPS6328118B2 JP1750081A JP1750081A JPS6328118B2 JP S6328118 B2 JPS6328118 B2 JP S6328118B2 JP 1750081 A JP1750081 A JP 1750081A JP 1750081 A JP1750081 A JP 1750081A JP S6328118 B2 JPS6328118 B2 JP S6328118B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- sugar alcohol
- acid ester
- producing
- reaction
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 136
- 239000000194 fatty acid Substances 0.000 claims description 136
- 229930195729 fatty acid Natural products 0.000 claims description 136
- -1 fatty acid ester Chemical class 0.000 claims description 115
- 150000005846 sugar alcohols Chemical class 0.000 claims description 52
- 238000006136 alcoholysis reaction Methods 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 29
- 239000002585 base Substances 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 22
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 21
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 12
- 239000000600 sorbitol Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 235000010355 mannitol Nutrition 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- 229930195725 Mannitol Natural products 0.000 claims description 5
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 claims description 5
- 239000000845 maltitol Substances 0.000 claims description 5
- 235000010449 maltitol Nutrition 0.000 claims description 5
- 229940035436 maltitol Drugs 0.000 claims description 5
- 239000000594 mannitol Substances 0.000 claims description 5
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 4
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- OXQKEKGBFMQTML-UHFFFAOYSA-N alpha-Glucoheptitol Chemical compound OCC(O)C(O)C(O)C(O)C(O)CO OXQKEKGBFMQTML-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000832 lactitol Substances 0.000 claims description 2
- 235000010448 lactitol Nutrition 0.000 claims description 2
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 claims description 2
- 229960003451 lactitol Drugs 0.000 claims description 2
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 46
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 26
- 239000003760 tallow Substances 0.000 description 22
- 239000007795 chemical reaction product Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 229960002920 sorbitol Drugs 0.000 description 20
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 235000015278 beef Nutrition 0.000 description 15
- 235000011187 glycerol Nutrition 0.000 description 14
- 150000005690 diesters Chemical class 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 238000004445 quantitative analysis Methods 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- 244000060011 Cocos nucifera Species 0.000 description 5
- 235000013162 Cocos nucifera Nutrition 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004386 Erythritol Substances 0.000 description 4
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 4
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 4
- 235000019414 erythritol Nutrition 0.000 description 4
- 229940009714 erythritol Drugs 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 230000008719 thickening Effects 0.000 description 4
- 239000000811 xylitol Substances 0.000 description 4
- 235000010447 xylitol Nutrition 0.000 description 4
- 229960002675 xylitol Drugs 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 3
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical group 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 2
- IMPKVMRTXBRHRB-MBMOQRBOSA-N (+)-quercitol Chemical compound O[C@@H]1C[C@@H](O)[C@H](O)C(O)[C@H]1O IMPKVMRTXBRHRB-MBMOQRBOSA-N 0.000 description 1
- UHGGERUQGSJHKR-VCDGYCQFSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;octadecanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCCCCCCCC(O)=O UHGGERUQGSJHKR-VCDGYCQFSA-N 0.000 description 1
- KAKVFSYQVNHFBS-UHFFFAOYSA-N (5-hydroxycyclopenten-1-yl)-phenylmethanone Chemical compound OC1CCC=C1C(=O)C1=CC=CC=C1 KAKVFSYQVNHFBS-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-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
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FBXFSONDSA-N Allitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-FBXFSONDSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-altritol Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OXQKEKGBFMQTML-WAHCGKIUSA-N Perseitol Natural products OC[C@H](O)[C@H](O)C(O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-WAHCGKIUSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- FQCKMBLVYCEXJB-MNSAWQCASA-L atorvastatin calcium Chemical compound [Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 FQCKMBLVYCEXJB-MNSAWQCASA-L 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 239000008103 glucose Substances 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
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229940002661 lipitor Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 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
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- OXQKEKGBFMQTML-BIVRFLNRSA-N perseitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-BIVRFLNRSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229950011392 sorbitan stearate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
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æ³ã«é¢ãããDETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing sugar alcohol fatty acid esters.
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ãã®ã§ããã More specifically, the present invention relates to a method for producing a sugar alcohol fatty acid ester by alcoholysing a sugar alcohol and a fatty acid ester in the presence of a base catalyst.
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åºãçšéãæãã極ããŠæçšãªååç©ã§ããã Sugar alcohol fatty acid esters have excellent surface activity, good biodegradability, and high safety, so they are used as additives for foods, cosmetics, pharmaceuticals, feed, and resins, metal processing oils, rust preventives, It is an extremely useful compound that has a wide range of uses such as textile oils.
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ãã Conventionally, methods for producing sugar alcohol fatty acid esters include (1) reacting sugar alcohols with fatty acid chlorides or fatty acid anhydrides, and (2) dehydrating sugar alcohols and fatty acids in the presence of a base catalyst or an acid catalyst. (3) sugar alcohol and fatty acid lower alkyl esters such as fatty acid methyl esters and fatty acid ethyl esters, and fatty acid esters such as fatty acid glycerides, in the presence or absence of a solvent capable of dissolving both, in trace amounts ( Methods of alcoholysis using a base catalyst (about 0.1 to 1.0% by weight based on the total amount of sugar alcohol and fatty acid ester) are known, but each method has the following drawbacks.
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ãåé¿ãåŸãªãã That is, in the first method, since fatty acid chlorides and fatty acid anhydrides are expensive, it is generally extremely disadvantageous to implement industrially, except in the case of specific sugar alcohol fatty acid esters such as sugar alcohol lower fatty acid esters. be. Also, the second method usually uses 200 to 250
Since it is necessary to carry out the reaction at a high temperature of °C, the main product is fatty acid ester of the sugar alcohol dehydration cyclization product, which has a cyclic ether skeleton and is produced by intramolecular dehydration and ring closure of the sugar alcohol itself. It has a fatal flaw in that the yield of fatty acid ester is extremely low. in particular,
For example, when sorbitol and fatty acids are reacted,
Large amounts of sorbitan fatty acid ester and sorbide fatty acid ester are produced, and only a small amount of sorbitol fatty acid ester is produced. Although it is possible to increase the production rate of sorbitol fatty acid ester to a certain extent by improving the catalyst and reaction conditions, even in this case it is not possible to avoid considerable by-product of sorbitan fatty acid ester and sorbide fatty acid ester.
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倧ã®çç±ãšãªã€ãŠããã In addition, the third method uses methanol, ethanol,
It is relatively highly reactive, such as propylene glycol and glycerin, and has extremely high or relatively high solubility in fatty acid esters such as fatty acid lower alkyl esters and fatty acid glycerides, and during alcoholysis, Alternatively, it is an extremely useful method for alcohols that do not easily cause side reactions such as dehydration condensation between molecules, and is widely practiced industrially. However, alcohols that have unique properties such as sugar alcohols having 4 to 9 hydroxyl groups, which are the target of the method of the present invention, have extremely low solubility in fatty acid esters, have poor reactivity, and are easy to undergo dehydration and ring closure. Generally, it is necessary to perform alcoholysis in the presence of a special solvent that can dissolve both sugar alcohols and fatty acid esters, which increases production and purification costs. There is a risk that the solvent used during alcoholysis may remain in the product. Therefore, it cannot be said that it is an industrially advantageous method. In any case, conventional methods for producing sugar alcohol fatty acid esters have various drawbacks, and even though sugar alcohol fatty acid esters have excellent performance and high safety, they are not widely used. This is the biggest reason.
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åºããæ¬çºæãå®æãããã«è³ã€ãã As a result of intensive studies to overcome the deficiencies of conventional methods, the present inventors have discovered that when producing sugar alcohol fatty acid esters by reacting sugar alcohols and fatty acid esters in the presence of a base catalyst to carry out alcoholysis, By using a base catalyst in an amount within a specific range that is significantly increased from the amount used in the past, the compatibility of sugar alcohols and fatty acid esters was unexpectedly improved, making it possible to use sugar alcohols with 4 to 9 hydroxyl groups. In this case, the reaction can proceed smoothly under mild conditions without the use of solvents, which were previously thought to be essential in this type of reaction. The present inventors have discovered that it is now possible to almost completely suppress the production of sugar alcohols, and that the desired sugar alcohol fatty acid ester can be produced with high selectivity, leading to the completion of the present invention.
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žãšã¹ãã«ã®è£œé æ¹æ³ã§ããã The present invention uses a sugar alcohol having 4 to 9 hydroxyl groups and a fatty acid ester in the presence of a basic catalyst of 3 to 15% by weight based on the total amount of the sugar alcohol and fatty acid ester, using substantially a solvent. This is a method for producing a sugar alcohol fatty acid ester, which is characterized in that alcoholysis is carried out without any alcoholysis.
次ã«æ¬çºæã詳现ã«èª¬æããã Next, the present invention will be explained in detail.
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ããŒã«çã䜿çšããããšãã§ããã The sugar alcohol used in the present invention is a type of polyhydric alcohol having 4 to 9 hydroxyl groups,
Specifically, erythritol having 4 hydroxyl groups,
Tetritols such as threitol, pentitols such as lipitor, arabitol, and xylitol having 5 hydroxyl groups, hexitols such as allitol, sorbitol, mannitol, dulcitol, ideitol, and altritol having 6 hydroxyl groups, boremitol having 7 hydroxyl groups, Typical examples include heptitols such as sedoheptitol and perseitol, maltitol and lactitol each having nine hydroxyl groups. Further, cyclic sugar alcohols such as inositol, sucillitol, quercitol, etc. can also be used.
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æå©ã«äœ¿çšãåŸãç³ã¢ã«ã³ãŒã«ã®äžã€ã§ããã Among them, sorbitol and mannitol are produced in large quantities by hydrogenating glucose and mannose, respectively, in the presence of a nickel catalyst.
In addition, it is produced at a low cost, so it is one of the sugar alcohols that can be most advantageously used in the present invention.
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䜿çšããããšãå¯èœã§ããã Most of these sugar alcohols have optical isomers, and any of the D-form, L-form, and DL-form can be used.
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ã«ããžãšã¹ãã«ã®ãããã䜿çšã§ããã On the other hand, as the fatty acid ester, an ester of a fatty acid and a monovalent to trivalent alcohol is used.
Specifically, fatty acid esters of lower monohydric alcohols such as methanol, ethanol, isopropanol, ethylene glycol mono-lower alkyl ether, carbitol (diethylene glycol mono-lower alkyl ether), lower monohydric alcohols such as ethylene glycol, propylene glycol, butanediol, etc.
Typical examples include fatty acid esters of alcohols, fatty acid esters of lower trihydric alcohols such as glycerin, and trimethylolpropane. Among them, glycerin fatty acid esters are available in large quantities and at low cost as fats such as beef tallow, hydrogenated beef tallow, palm oil, palm kernel oil, coconut oil, olive oil, soybean oil, rapeseed oil, cottonseed oil, linseed oil, castor oil, lard, and fish oil. It is one of the fatty acid esters that can be most preferably used in the present invention. There are three types of glycerin fatty acid esters: glycerin monofatty acid esters (monoglycerides), glycerin difatty acid esters (diglycerides), and glycerin trifatty acid esters (triglycerides). Monoglycerides and diglycerides can also be used. The same applies to other lower trihydric alcohol fatty acid esters, and both monoesters and diesters can be used in the case of lower dihydric alcohol fatty acid esters.
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žã§ãå·®æ¯ããªãã In addition, the fatty acid component constituting the fatty acid ester is not particularly limited, but from the viewpoint of the usefulness of the final sugar alcohol fatty acid ester, fatty acids having about 6 to 24 carbon atoms are usually most suitable. . These fatty acid components may be either saturated fatty acids or unsaturated fatty acids, and their carbon chains are not limited to linear ones, but branched ones can also be used. Note that a fatty acid having a substituent such as a hydroxyl group may also be used.
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žçãäŸç€ºããããšãã§ããã Typical examples of these fatty acids include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid,
Examples include elaidic acid, arachidic acid, behenic acid, and lignoceric acid.
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ã䜵çšããããšãå¯èœã§ããã Note that the sugar alcohols and fatty acid esters mentioned above do not necessarily need to be used alone, and two or more of each can be used in combination.
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ãé«ããªãåŸåã瀺ãã In addition, the usage ratio of sugar alcohol and fatty acid ester depends on the type, molecular weight, etc. of the sugar alcohol and fatty acid ester, and the average degree of substitution of the target sugar alcohol fatty acid ester, i.e., monoester, diester,
Although it varies depending on the composition ratio of triester, etc., usually sugar alcohol: fatty acid ester = 5 to 70:30
-95 weight ratio, more preferably 10-60:40-90 weight ratio, most preferably 15-55:45-85 weight ratio is suitable. Generally, as the amount of sugar alcohol used increases,
The average degree of substitution of sugar alcohol fatty acid esters tends to be lower, and the production rate of sugar alcohol monofatty acid esters tends to be higher.
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äŸã§ããã Next, the base catalyst used in the present invention includes alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate, alkaline earth metal carbonates such as magnesium carbonate, calcium carbonate, and barium carbonate, lithium hydroxide, and hydroxide. Alkali metal hydroxides such as sodium and potassium hydroxide, alkaline earth metal hydroxides such as magnesium hydroxide, calcium hydroxide, and barium hydroxide, sodium oxide,
oxides of alkali metals or alkaline earth metals such as magnesium oxide, calcium oxide, and barium oxide; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; ammonium salts such as ammonium carbonate and ammonium bicarbonate;
sodium methylate, sodium ethylate,
Alcoholates such as potassium methylate and potassium butyrate, sodium acetate, potassium acetate, fatty acid salts such as soaps, triethylamine, tributylamine, laurylamine, 1,8-diazabicyclo[5.4.0]undecene-7, 1,4 ,5,
6-tetrahydropyrimidine, formamidine,
Typical examples include organic bases such as N-ethylmorpholine.
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ç¹ã«å¥œãŸããã Among them, alkali metal carbonates and alkali metal hydroxides exhibit particularly excellent catalytic effects, are inexpensive, and are easy to handle, so they are among the basic catalysts that can be most preferably used in the present invention. Furthermore, when both of the above catalysts are used together, the catalytic effect is further improved, so
Particularly preferred.
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æ¯çãå¢å€§ããçºã奜ãŸãããªãã If the amount of the base catalyst used is less than the above range, the catalytic effect will be extremely insufficient, and the affinity between the sugar alcohol and fatty acid ester, which originally have poor compatibility, will hardly be improved, which is not preferable. . or,
Even if the base catalyst is used in an amount larger than the upper limit of the above range, no significant advantage will be exhibited; on the contrary, the viscosity of the reaction mass during alcoholysis will increase significantly, making stirring difficult, or the conversion of fatty acid esters to fatty acids This is undesirable because the ratio of saponification reactions in which salts (so-called soaps) are produced as by-products increases.
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ã奜ãŸããçµæãåŸãããã The optimum amount of the base catalyst to be used varies depending on the type of sugar alcohol, fatty acid ester, and base catalyst, reaction temperature, etc., but in general, the optimum amount is 5 to 10% by weight based on the total amount of sugar alcohol and fatty acid ester. Favorable results are obtained.
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ãããã A sugar alcohol fatty acid ester is produced by performing alcoholysis using the above-mentioned sugar alcohol, fatty acid ester, and base catalyst.
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°C, more preferably 100 to 170 °C, most preferably
A temperature of about 110 to 150°C is good.
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é²è¡ãããããšãå¯èœã§ããã If the temperature is below the lower limit of the above range, the reaction rate will drop significantly, and if the temperature is higher than the upper limit, side reactions such as intramolecular dehydration ring closure reaction of sugar alcohols will tend to proceed, resulting in sugar alcohol fatty acid esters. Both are undesirable because they lead to a decrease in yield and deterioration of quality. Although the reaction can give satisfactory results even under normal pressure, it is possible to remove the alcohols produced by the alcoholysis reaction from the reaction system by keeping it under reduced pressure or by blowing inert gas such as nitrogen gas. If removed, the reaction can proceed in a more desirable direction.
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ããšãå¯èœã§ããã Various methods can be used to carry out the above-mentioned alcoholysis, such as a method in which a sugar alcohol, a fatty acid ester, and a base catalyst are simultaneously charged into a reactor to carry out the alcoholysis; After charging both the ester and the base catalyst into the reactor and carrying out the saponification reaction to some extent,
It is possible to arbitrarily adopt a method in which alcoholysis is carried out by charging sugar alcohol, or a method in which only fatty acid ester is charged into the reactor in advance, and then sugar alcohol and base catalyst are simultaneously charged and alcoholysis is carried out. It is possible.
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ã®ãããã®æ¹åŒããæ¡çšããããšãå¯èœã§ããã The reactor is usually a tank reactor equipped with a heating device and a stirring device, or a tube reactor, etc.
Of course, it is also possible to use other types of reactors. Furthermore, if necessary, a cooling device or a device for maintaining the inside of the reactor at reduced pressure may be installed. Further, the alcoholysis reaction can be carried out in a batch manner, a semi-batch manner, or a continuous manner.
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ã®é²è¡ç¶æ³ãçµç¹ãæ£ç¢ºã«ç¥ãããšãã§ããã The time required for the alcoholysis reaction varies depending on the type and ratio of sugar alcohol, fatty acid ester, and base catalyst used, reaction temperature, reaction pressure, type of reactor, etc., but it usually ranges from 10 minutes to 20 hours. Preferably 30 minutes to 15 hours, most preferably 1 to 15 hours.
Approximately 10 hours is appropriate. The viscosity of the reaction mass tends to increase as the reaction progresses, so by measuring changes in the viscosity of the reaction mass, it is possible to roughly know the progress of the reaction and the end point.
Further, by analyzing the remaining amount of unreacted raw materials and the content of products in the reaction mass using gas chromatography, liquid chromatography, etc., it is also possible to accurately know the progress status and end point of the reaction.
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è¡ããã In the method of the present invention, in addition to the production reaction of sugar alcohol fatty acid ester by alcoholysis of sugar alcohol and fatty acid ester with a base catalyst,
A reaction for producing fatty acid salts, that is, soaps, by the saponification reaction of the fatty acid ester and the base catalyst also proceeds at the same time.
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ãã The latter saponification reaction has the effect of improving the compatibility of the sugar alcohol and fatty acid ester, which originally have little compatibility, and promoting the reaction for producing the sugar alcohol fatty acid ester. Therefore, it is also effective to add separately synthesized soaps at the beginning of the reaction, and in this case it is also possible to reduce the amount of the base catalyst.
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žãšã¹ãã«ãååŸããããšãã§ããã In addition to sugar alcohol fatty acid esters, the reaction products obtained by the method of the present invention include soaps,
Contains unreacted sugar alcohol, unreacted fatty acid ester, unreacted base catalyst, etc. This reaction product can be used as it is for various purposes, but unreacted raw materials and by-products other than the sugar alcohol fatty acid ester in the reaction product can be extracted, converted to other derivatives, or
It can be easily removed by known methods such as filtration and crystallization, and ultimately a highly purified sugar alcohol fatty acid ester can be obtained.
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ããªãã®ã倧ããªç¹åŸŽã®äžã€ã§ããã The sugar alcohol fatty acid ester obtained by the method of the present invention is characterized by an extremely high proportion of low-substitution sugar alcohol fatty acid esters, that is, monoesters and diesters, which have the highest utility value. Another major feature is that almost no fatty acid ester is produced in the dehydrated cyclized sugar alcohol, which has a cyclic ether core produced by intramolecular dehydration and cyclization of the sugar alcohol itself.
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ãšãã§ããçºãç£æ¥äžæ¥µããŠæçšã§ããã As detailed above, according to the present invention, high quality sugar alcohol fatty acid esters can be produced using inexpensive sugar alcohols and fatty acid esters as main raw materials under mild conditions and without using substantially any solvent. It is industrially extremely useful because it can be produced with high selectivity and economically.
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çã«èª¬æããã The present invention will be explained in more detail below using Examples and Comparative Examples.
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äœïŒæ·¡è€è²ïŒãšãªã€ããExample 1 150 g of D-sorbitol, 350 g of beef tallow, and 25 g of potassium carbonate were placed in the glass reactor equipped with a stirrer in 1, and an alcoholysis reaction was carried out at 150°C.
After about 1 hour had passed after the start of the reaction, the reaction mass began to bubble and gradually thicken, and there was a noticeable tendency for the entire reaction mass to become homogeneous. After a total of 5 hours of reaction, the reaction mass became a fairly viscous and homogeneous liquid (light brown color).
æçµçã«510ïœã®åå¿çæç©ãåŸãã Finally, 510 g of reaction product was obtained.
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æ€åºãããã«éããªãã€ãã The reaction product solidified upon cooling to room temperature, becoming a slightly sticky solid. Quantitative analysis of the reaction product using gas chromatography after trimethylsilyl etherification showed that 42.3% by weight of sorbitol tallow fatty acid ester (monoester/diester = 68/32 weight ratio) and potassium tallow fatty acid.
18.7% by weight, beef tallow fatty acid glyceride 21.5% by weight
(total amount of mono-, di-, and triglycerides), unreacted D-sorbitol, glycerin, etc. were 17.5% by weight, and only trace amounts of sorbitan tallow fatty acid ester were detected.
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éããªãã€ããComparative Example 1 An alcoholysis reaction was carried out at 150° C. in the same manner as in Example 1 using 150 g of D-sorbitol, 350 g of beef tallow, and 10 g of potassium carbonate. About 3 hours after the start of the reaction, the reaction mass tended to bubble slightly, but no thickening or homogenization of the reaction mass was observed, and when stirring was stopped, it turned into a liquid phase and an extremely viscous semi-solid. Immediate separation into two phases was observed. Thereafter, the reaction was continued for a total of 10 hours, but the reaction was stopped because there was almost no tendency for thickening or homogenization of the reaction mass. A portion of the liquid phase portion and semi-solid phase portion (liquid phase portion/semi-solid phase portionâ7/3 weight ratio) in the reaction mass was sampled and analyzed by gas chromatography, and it was found that most of the liquid phase portion was was beef tallow fatty acid triglyceride, and some beef tallow fatty acid diglyceride and beef tallow fatty acid monoglyceride were also detected. In addition, the semi-solid phase was mainly composed of D-sorbitol, and some potassium tallow fatty acid was also detected. However, only a small amount of sorbitol tallow fatty acid ester was detected in the semi-solid phase.
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The alcoholysis reaction was carried out at 125°C. From about 20 minutes after the start of the alcoholysis reaction, the reaction mass became noticeably prone to bubbling, thickening, and homogenization. As a result of carrying out the alcoholysis reaction for a total of 4 hours, the reaction mass became a viscous homogeneous liquid (white), and 515 g of a reaction product was finally obtained.
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As a result of quantitative analysis using a method similar to total amount), unreacted sorbitol, glycerin, etc.
The amount was 23.1% by weight, and no sorbitan coconut fatty acid ester was detected.
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ãã€ããExample 3 400 g of hydrogenated beef tallow and 5 g of sodium hydroxide were charged into the same reactor as in Example 1, and the saponification reaction was carried out at 110°C for 1 hour. Then, 20 g of potassium carbonate was charged, and then D- 100 g of sorbitol was gradually charged over 1 hour. About 30 minutes after the start of charging D-sorbitol, bubbling, thickening, and homogenization of the reaction mass were observed. After charging D-sorbitol, the alcoholysis reaction was carried out at 110â for another 7 hours, resulting in the reaction mass becoming a viscous homogeneous liquid (white, which becomes a hard solid when cooled to room temperature) and finally weighing 508g. A reaction product was obtained. Quantitative analysis of the reaction product in the same manner as in Example 1 revealed that sorbitol hydrogenated beef tallow fatty acid ester was 35.4% by weight (monoester/diester/triester = 60/38/2 weight ratio) and hydrogenated beef tallow fatty acid salt was 20.3% by weight. Weight% (total amount of sodium salt and potassium salt), hydrogenated beef tallow fatty acid glyceride 37.1% by weight (total amount of mono-, di-, and triglyceride), unreacted D
-Sorbitol, glycerin, etc. were 7.2% by weight, and sorbitan tallow fatty acid ester was not detected.
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Prepare 200g and 300g of methyl stearate,
After dehydrating and drying for 30 minutes at 120°C and 30 mmHgabs, 20 g of sodium methylate and 20 g of sodium carbonate were added, and alcoholysis reaction was carried out at 120°C and 10 mmHgabs for 3 hours. As the alcoholysis reaction progressed, methanol distilled out and was collected in a trap cooled in a dry ice-acetone bath.
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ããåå¿çæç©480ïœãåŸãããã The reaction mass finally became a viscous homogeneous liquid (white, solidified to a hard solid when cooled to room temperature). 480 g of reaction product was obtained.
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žãšã¹ãã«ã¯æ€åºãããªãã€ãã As a result of quantitative analysis of the reaction product in the same manner as in Example 1, it was found that sorbitol stearate
48.5% by weight (monoester/diester = 71/29
(weight ratio), sodium stearate was 25.0% by weight, and the remainder was unreacted D-sorbitol, unreacted methyl stearate, and others. Moreover, sorbitan stearate was not detected.
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ããèèªé
žãšã¹ãã«ã¯æ€åºãããªãã€ããExample 5 Using the same reactor as in Example 1, an alcoholysis reaction was carried out under exactly the same conditions as in Example 2, except that 225 g of D-mannitol was used instead of D-sorbitol. The reaction mass became a viscous homogeneous liquid (white, solidified when cooled to room temperature), and 513 g of reaction product was finally obtained. As a result of quantitative analysis of the reaction product in the same manner as in Example 1,
Mannitol coconut fatty acid ester 41.7% by weight
(monoester/diester = 71/29 weight ratio), coconut fatty acid potassium 23.1% by weight, coconut fatty acid glyceride 10.5% by weight (total amount of mono-, di-, and triglycerides), unreacted D-mannitol, glycerin, etc. 24.7% by weight. , mannitan coconut fatty acid ester was not detected.
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200mlã®æ¹ææ©ä»ã¬ã©ã¹è£œåå¿åšã«ïŒ€âãã³ã
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ããåèšïŒæéåå¿ãè¡ãªããç²çš ãªåäžæ¶²ç¶å
å¿çæç©ïŒçœè²ã宀枩è¿å·åŽãããšåºåïŒ101ïœ
ãåŸããExample 6 In a 200 ml glass reactor equipped with a stirrer, 40 g of D-mannitol, 30 g of lauric acid triglyceride, 30 g of lauric acid monoglyceride, and 3 potassium carbonate were added.
g was charged, and the allurisis reaction was carried out at 130°C. After about 5 minutes had passed from the start of the reaction, the reaction mass began to foam violently and tend to thicken and become more uniform. The reaction was carried out for a total of 2 hours, and 101 g of a viscous homogeneous liquid reaction product (white, solidified when cooled to room temperature)
I got it.
åå¿çæç©ãå®æœäŸïŒãšåæ§ã®æ¹æ³ã§å®éåæ
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žãšã¹ãã«40.1
ééïŒ
ïŒã¢ããšã¹ãã«ïŒãžãšã¹ãã«ïŒ81ïŒ19éé
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ž
ã°ãªã»ãªã29.5ééïŒ
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žãšã¹ãã«ã¯æ€åºãããªãã€ãã As a result of quantitative analysis of the reaction product in the same manner as in Example 1, mannitol lauric acid ester 40.1
Weight% (monoester/diester = 81/19 weight ratio), potassium laurate 9.1% by weight, lauric acid glyceride 29.5% by weight (total amount of mono-, di-, and triglycerides), unreacted D-mannitol, glycerin, etc. 21.3% by weight and mannitan laurate was not detected.
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žã«ãªãŠã 12ïœãä»èŸŒã¿125
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è¿å·åŽãããšåºåïŒãåŸããExample 7 In a reactor similar to Example 6, erythritol 25
125 g, prepared with 75 g of beef tallow and 12 g of potassium carbonate.
The alcoholysis reaction was carried out at .degree. C. for 3 hours to obtain 107 g of an extremely viscous homogeneous liquid reaction product (light brown in color, which solidified when cooled to room temperature).
åå¿çæç©ãå®æœäŸïŒãšåæ§ã®æ¹æ³ã§å®éåæ
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38.7ééïŒ
ïŒã¢ããšã¹ãã«ïŒãžãšã¹ãã«ïŒ71ïŒ29
ééæ¯ïŒãçèèèªé
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ã³ã°ãªã»ãªã³ä»ã§ãã€ãã As a result of quantitative analysis of the reaction product in the same manner as in Example 1, it was found that erythritol beef tallow fatty acid ester
38.7% by weight (monoester/diester = 71/29
weight ratio), beef tallow fatty acid potassium is 33.0% by weight,
The remainder was tallow fatty acid glyceride (a mixture of mono-, di-, and triglycerides), unreacted erythritol, glycerin, and the like.
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å®æœäŸïŒãšåæ§ã®åå¿åšã«ãã·ãªããŒã«40ïœã
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ä»èŸŒã¿ã150âã10mmïœã§ïŒæéã¢ã«ã³ãŒãªã·
ã¹åå¿ãè¡ãªããç²çš ãªåäžæ¶²ç¶ã®åå¿çæç©95
ïœïŒæ·¡é»è²ã宀枩è¿å·åŽãããšåºåïŒãåŸããExample 8 In a reactor similar to Example 6, 40 g of xylitol was added.
60 g of methyl palmitate and 4 g of potassium carbonate were charged, and an alcoholysis reaction was carried out at 150°C and 10 mmHg for 2 hours to produce a viscous homogeneous liquid reaction product95.
g (pale yellow, solidified upon cooling to room temperature) was obtained.
å®æœäŸïŒãšåæ§ã®æ¹æ³ã§å®éåæããçµæãã
ã·ãªããŒã«ãã«ããã³é
žãšã¹ãã«52.3ééïŒ
ïŒã¢
ããšã¹ãã«ïŒãžãšã¹ãã«ïŒ73ïŒ27ééæ¯ïŒããã«
ããã³é
žã«ãªãŠã 15.8ééïŒ
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å¿ãã·ãªããŒã«ãæªåå¿ãã«ããã³é
žã¡ãã«ä»ã§
ãã€ãã As a result of quantitative analysis using the same method as in Example 1, it was found that xylitol palmitate ester was 52.3% by weight (monoester/diester = 73/27 weight ratio), potassium palmitate was 15.8% by weight, and the rest was unreacted xylitol and unreacted. It contained methyl palmitate and others.
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é
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ãã«ãããŒã«åã³ã°ãªã»ãªã³ä»ã§ãã€ããExample 9 65 g of palm oil and 2 g of potassium hydroxide were placed in the same reactor as in Example 6, and a saponification reaction was carried out at 130°C for 30 minutes. Then, 35 g of maltitol and 4 g of potassium carbonate were added, and the mixture was heated at 130°C. The alcoholysis reaction was carried out for 4 hours. 103 g of a viscous, homogeneous liquid reaction product (pale yellow, solidified upon cooling to room temperature) was obtained. As a result of quantitative analysis using the same method as in Example 1, 40.5% by weight of maltitol palm fatty acid ester (monoester/diester/triester =
67/29/4 weight ratio), palm fatty acid potassium 22.1
The remainder was palm fatty acid glyceride (a mixture of mono-, di- and triglycerides), unreacted maltitol, glycerin, etc.
Claims (1)
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ãšã¹ãã«ã®è£œé æ¹æ³ã ïŒïŒ å¡©åºè§Šåªãã¢ã«ã«ãªéå±çé žå¡©ã§ããç¹èš±
è«æ±ã®ç¯å²ç¬¬ïŒé ãåã¯ç¬¬ïŒïŒé èšèŒã®ç³ã¢ã«ã³
ãŒã«èèªé žãšã¹ãã«ã®è£œé æ¹æ³ã ïŒïŒ å¡©åºè§ŠåªãšããŠã¢ã«ã«ãªéå±çé žå¡©ãšã¢ã«
ã«ãªéå±æ°Žé žåç©ã䜵çšããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒ
é ãåã¯ç¬¬ïŒïŒé èšèŒã®ç³ã¢ã«ã³ãŒã«èèªé žãšã¹
ãã«ã®è£œé æ¹æ³ã ïŒïŒ 90ä¹è³180âã®æž©åºŠã§ã¢ã«ã³ãŒãªã·ã¹ãã
ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®ç³ã¢ã«ã³ãŒã«èèªé ž
ãšã¹ãã«ã®è£œé æ¹æ³ã[Scope of Claims] 1. A sugar alcohol having 4 to 9 hydroxyl groups and a fatty acid ester are substantially dissolved in a solvent in the presence of a base catalyst of 3 to 15% by weight based on the total amount of the sugar alcohol and fatty acid ester. A method for producing a sugar alcohol fatty acid ester, characterized by carrying out alcoholysis without using. 2. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is hexitol. 3. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 2, wherein the sugar alcohol is sorbitol. 4. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 2, wherein the sugar alcohol is mannitol. 5. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is pentitol. 6. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is tetritol. 7. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is heptitol. 8. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is maltitol. 9. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is lactitol. 10. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the fatty acid ester is an ester of a fatty acid having 6 to 24 carbon atoms and a monovalent to trivalent alcohol. 11. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 10, wherein the fatty acid ester is a fatty acid glyceride. 12. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the base catalyst is an alkali metal base catalyst. 13. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 12, wherein the base catalyst is an alkali metal carbonate. 14 Claim 1 in which an alkali metal carbonate and an alkali metal hydroxide are used together as a base catalyst
The method for producing a sugar alcohol fatty acid ester according to item 1 or 12. 15. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein alcoholysis is carried out at a temperature of 90 to 180°C.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1750081A JPS57133197A (en) | 1981-02-10 | 1981-02-10 | Manufacture of sugar alcohol fatty acid ester |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1750081A JPS57133197A (en) | 1981-02-10 | 1981-02-10 | Manufacture of sugar alcohol fatty acid ester |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57133197A JPS57133197A (en) | 1982-08-17 |
JPS6328118B2 true JPS6328118B2 (en) | 1988-06-07 |
Family
ID=11945705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1750081A Granted JPS57133197A (en) | 1981-02-10 | 1981-02-10 | Manufacture of sugar alcohol fatty acid ester |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57133197A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011207987A (en) * | 2010-03-29 | 2011-10-20 | Sumitomo Chemical Co Ltd | Processing stabilizer for resin, resin composition containing the same, and method for improving processing stability of resin |
JP2011207990A (en) * | 2010-03-29 | 2011-10-20 | Sumitomo Chemical Co Ltd | Processing stabilizer for resin, resin composition containing the same, and method for improving processing stability of resin |
-
1981
- 1981-02-10 JP JP1750081A patent/JPS57133197A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57133197A (en) | 1982-08-17 |
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