NO852293L - Fremgangsmaate til fremstilling av fettsyreestere av kortkjedede alkoholer. - Google Patents
Fremgangsmaate til fremstilling av fettsyreestere av kortkjedede alkoholer.Info
- Publication number
- NO852293L NO852293L NO852293A NO852293A NO852293L NO 852293 L NO852293 L NO 852293L NO 852293 A NO852293 A NO 852293A NO 852293 A NO852293 A NO 852293A NO 852293 L NO852293 L NO 852293L
- Authority
- NO
- Norway
- Prior art keywords
- acid
- alcohol
- glyceride
- reaction
- glycerol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 13
- 239000002253 acid Substances 0.000 title description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 37
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 29
- 229930195729 fatty acid Natural products 0.000 claims abstract description 29
- 239000000194 fatty acid Substances 0.000 claims abstract description 29
- -1 fatty acid esters Chemical class 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 14
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 238000005191 phase separation Methods 0.000 claims abstract description 8
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 4
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 102
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000009833 condensation Methods 0.000 claims description 13
- 230000005494 condensation Effects 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- 230000007306 turnover Effects 0.000 claims 1
- 239000003925 fat Substances 0.000 description 27
- 235000019197 fats Nutrition 0.000 description 27
- 239000003760 tallow Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 235000021588 free fatty acids Nutrition 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 210000000577 adipose tissue Anatomy 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- 229920000715 Mucilage Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- BZUNJUAMQZRJIP-UHFFFAOYSA-N 15-hydroxypentadecanoic acid Chemical compound OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 description 2
- UGAGPNKCDRTDHP-UHFFFAOYSA-N 16-hydroxyhexadecanoic acid Chemical compound OCCCCCCCCCCCCCCCC(O)=O UGAGPNKCDRTDHP-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical compound CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 238000011049 filling Methods 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
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000010460 hemp oil Substances 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 2
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-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
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 description 1
- YKHVVNDSWHSBPA-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienoic acid Chemical compound CCCCC\C=C\C=C\C(O)=O YKHVVNDSWHSBPA-BLHCBFLLSA-N 0.000 description 1
- MUCMKTPAZLSKTL-UHFFFAOYSA-N (3RS)-3-hydroxydodecanoic acid Natural products CCCCCCCCCC(O)CC(O)=O MUCMKTPAZLSKTL-UHFFFAOYSA-N 0.000 description 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- UBEIMDKGOYBUKT-FLIQGJDUSA-N 1,2,3-trilinolenoylglycerol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC UBEIMDKGOYBUKT-FLIQGJDUSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
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- MUMWRBGBCHMKOL-UHFFFAOYSA-N 12-hexyloctadecanoic acid Chemical class CCCCCCC(CCCCCC)CCCCCCCCCCC(O)=O MUMWRBGBCHMKOL-UHFFFAOYSA-N 0.000 description 1
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical class CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
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- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- SAOSCTYRONNFTC-UHFFFAOYSA-N 2-methyl-decanoic acid Chemical class CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 1
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- BVUBANAQPIROHS-UHFFFAOYSA-N 3,3-dimethyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(C)(C)CC(O)=O BVUBANAQPIROHS-UHFFFAOYSA-N 0.000 description 1
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- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- XSXIVVZCUAHUJO-UHFFFAOYSA-N Homo-gamma-linoleic acid Natural products CCCCCC=CCC=CCCCCCCCCCC(O)=O XSXIVVZCUAHUJO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 239000005639 Lauric acid Substances 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
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 244000057114 Sapium sebiferum Species 0.000 description 1
- 235000005128 Sapium sebiferum Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
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- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- YDZIJQXINJLRLL-UHFFFAOYSA-N alpha-hydroxydodecanoic acid Natural products CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 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
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- 229940114079 arachidonic acid Drugs 0.000 description 1
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- 150000007514 bases Chemical class 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- MXSHHHVKQWTICU-UHFFFAOYSA-M cesium;dodecanoate Chemical compound [Cs+].CCCCCCCCCCCC([O-])=O MXSHHHVKQWTICU-UHFFFAOYSA-M 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
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- 150000001875 compounds Chemical class 0.000 description 1
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- 238000007906 compression Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
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- 230000008021 deposition Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
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- 230000001804 emulsifying effect Effects 0.000 description 1
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- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 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
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
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- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
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- 150000004678 hydrides Chemical class 0.000 description 1
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- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
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- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 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
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 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
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- PAWGRNGPMLVJQH-ZHACJKMWSA-N trans-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C\C(O)=O PAWGRNGPMLVJQH-ZHACJKMWSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- MAYCICSNZYXLHB-UHFFFAOYSA-N tricaproin Chemical compound CCCCCC(=O)OCC(OC(=O)CCCCC)COC(=O)CCCCC MAYCICSNZYXLHB-UHFFFAOYSA-N 0.000 description 1
- 229940093609 tricaprylin Drugs 0.000 description 1
- PHYFQTYBJUILEZ-WUOFIQDXSA-N trielaidin Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C\CCCCCCCC)COC(=O)CCCCCCC\C=C\CCCCCCCC PHYFQTYBJUILEZ-WUOFIQDXSA-N 0.000 description 1
- 229940113164 trimyristin Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- NMOHFBPSMIYLGY-UHFFFAOYSA-L zinc;2-dodecylbenzenesulfonate Chemical group [Zn+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O NMOHFBPSMIYLGY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843421217 DE3421217A1 (de) | 1984-06-07 | 1984-06-07 | Verfahren zur herstellung von fettsaeureestern kurzkettiger alkohole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852293L true NO852293L (no) | 1985-12-09 |
Family
ID=6237842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852293A NO852293L (no) | 1984-06-07 | 1985-06-06 | Fremgangsmaate til fremstilling av fettsyreestere av kortkjedede alkoholer. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4668439A (xx) |
| EP (1) | EP0164643B1 (xx) |
| JP (1) | JPS611640A (xx) |
| KR (1) | KR910008370B1 (xx) |
| CN (1) | CN85106282A (xx) |
| AT (1) | ATE46532T1 (xx) |
| AU (1) | AU569570B2 (xx) |
| BR (1) | BR8502693A (xx) |
| CA (1) | CA1247130A (xx) |
| DD (1) | DD232913A5 (xx) |
| DE (2) | DE3421217A1 (xx) |
| DK (1) | DK254685A (xx) |
| ES (1) | ES8604094A1 (xx) |
| MX (1) | MX160996A (xx) |
| MY (1) | MY100687A (xx) |
| NO (1) | NO852293L (xx) |
| NZ (1) | NZ212308A (xx) |
| PH (1) | PH21080A (xx) |
| PT (1) | PT80603B (xx) |
| SU (1) | SU1402250A3 (xx) |
| ZA (1) | ZA854288B (xx) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3515403A1 (de) * | 1985-04-29 | 1986-10-30 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur katalytischen umesterung von fettsaeureglyceriden mit niederen alkanolen |
| DE3707563A1 (de) * | 1987-03-10 | 1988-09-22 | Klaus Dr Ing Scharmer | Verfahren zur alkoholyse von fettsaeureglyceriden und vorrichtung zum durchfuehren des verfahrens |
| US5019668A (en) * | 1988-06-14 | 1991-05-28 | Palm Oil Research & Development Board | Recovery of carotenoids |
| BE1006287A3 (fr) * | 1992-04-30 | 1994-07-12 | Gheorghiu Mihail | Procede de fabrication d'esters methyliques d'acides gras a partir d'une huile ou graisse naturelle, esters methyliques tels qu'ainsi obtenus et leur utilisation. |
| FR2698101B1 (fr) * | 1992-11-19 | 1995-01-06 | Arceau Huileries | Procédé de transestérification catalytique de corps gras d'origine végétale ou animale et procédé de récupération des produits obtenus. |
| EP0654528A1 (fr) * | 1993-11-22 | 1995-05-24 | Mihail Gheorghiu | Procédé de fabrication d'esters méthyliques d'acides gras à partir d'une huile ou graisse naturelle, esters méthyliques tels qu'ainsi obtenus et leur utilisation |
| US5532392A (en) * | 1994-01-13 | 1996-07-02 | Gheorghiu; Mihail | Process for the preparation of methyl fatty acid esters starting from natural oil or fat, methyl esters obtained in this way and use thereof |
| US5491226A (en) * | 1994-04-06 | 1996-02-13 | Procter & Gamble Company | Process for preparing polyol polyesters having low levels of triglycerides |
| US5844111A (en) * | 1995-06-07 | 1998-12-01 | The Procter & Gamble Company | Method for purifying an inert gas while preparing lower alkyl esters |
| US5648483A (en) * | 1995-06-07 | 1997-07-15 | The Procter & Gamble Company | Continuous transesterification method for preparing polyol polyesters |
| DE19537235A1 (de) * | 1995-10-06 | 1997-04-10 | Haarmann & Reimer Gmbh | Verfahren zur Herstellung von trans-2,cis-4-Decadiensäureethylester |
| US5730029A (en) * | 1997-02-26 | 1998-03-24 | The Lubrizol Corporation | Esters derived from vegetable oils used as additives for fuels |
| US6007856A (en) * | 1997-08-08 | 1999-12-28 | The Procter & Gamble Company | Oil-in-water dispersions of β-carotene and other carotenoids stable against oxidation prepared from water-dispersible beadlets having high concentrations of carotenoid |
| US6965043B1 (en) | 1997-11-10 | 2005-11-15 | Procter + Gamble Co. | Process for making high purity fatty acid lower alkyl esters |
| WO1999024387A1 (en) * | 1997-11-10 | 1999-05-20 | The Procter & Gamble Company | A process for making high purity fatty acid lower alkyl esters |
| US6127560A (en) * | 1998-12-29 | 2000-10-03 | West Central Cooperative | Method for preparing a lower alkyl ester product from vegetable oil |
| US6849581B1 (en) | 1999-03-30 | 2005-02-01 | Bj Services Company | Gelled hydrocarbon compositions and methods for use thereof |
| US6407272B1 (en) * | 1999-07-14 | 2002-06-18 | Arizona Chemical Company | Secondary alcohol esters of hydroxyacids and uses thereof |
| US20020035282A1 (en) * | 2000-03-06 | 2002-03-21 | Suppes Galen J. | Carbonate catalyzed alcoholysis of triglycerides |
| AU2001261890A1 (en) * | 2000-05-15 | 2001-11-26 | J. Richard Gapes | Transesterification of fats |
| JP2002241786A (ja) * | 2000-12-15 | 2002-08-28 | Sumitomo Chem Co Ltd | 植物の種子および／または果実から脂肪酸エステルを製造する方法 |
| US6965044B1 (en) | 2001-07-06 | 2005-11-15 | Iowa State University Research Foundation | Method of converting free fatty acids to fatty acid methyl esters with small excess of methanol |
| WO2003042343A1 (de) * | 2001-11-16 | 2003-05-22 | Gapes Richard J | Veresterung von fettsäuren in ölen |
| KR100556337B1 (ko) * | 2002-02-05 | 2006-03-03 | 주식회사 가야에너지 | 단일단계 연속공정을 통한 고순도 지방산 알킬에스테르의제조방법 |
| US7145026B2 (en) * | 2002-04-12 | 2006-12-05 | Biodiesel Technologies, Inc. | Continuous transesterification process |
| PT1534659E (pt) * | 2002-08-23 | 2008-07-03 | Richard Gapes | Transesterificação e esterificação de ácidos gordos e triglicéridos por dispersão e processo de dispersão para a produção de ésteres metílicos de ácidos gordos |
| US7871448B2 (en) * | 2003-01-27 | 2011-01-18 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US7806945B2 (en) * | 2003-01-27 | 2010-10-05 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US9725397B2 (en) | 2003-01-27 | 2017-08-08 | REG Seneca, LLC | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| US8088183B2 (en) * | 2003-01-27 | 2012-01-03 | Seneca Landlord, Llc | Production of biodiesel and glycerin from high free fatty acid feedstocks |
| AU2003282270B2 (en) * | 2003-11-24 | 2009-08-27 | Council Of Scientific And Industrial Research | An improved process for the preparation of bio-diesel |
| US20050108927A1 (en) * | 2003-11-24 | 2005-05-26 | Council Of Scientific And Industrial Research Of Rafi Marg | Process for the preparation of bio-diesel |
| JP2005206770A (ja) * | 2004-01-19 | 2005-08-04 | Ics Kk | 脂肪酸エステルの製造方法及び脂肪酸エステルを含む燃料 |
| JP4849387B2 (ja) * | 2004-07-12 | 2012-01-11 | アイシーエス株式会社 | 油脂類を原料とする脂肪酸エステルの製造方法 |
| DE102004044660A1 (de) | 2004-09-15 | 2006-03-30 | Siegfried Prof. Dr. Peter | Verfahren zur Umesterung von Fetten und Ölen biologischen Ursprungs mittels Alkoholyse unter Verwendung spezieller Kohlensäuresalze |
| JP2006249066A (ja) * | 2005-02-14 | 2006-09-21 | Ics Kk | 気液反応効率の向上方法 |
| JP4963011B2 (ja) * | 2005-03-01 | 2012-06-27 | 花王株式会社 | 脂肪酸低級アルキルエステルの製造方法 |
| WO2006121021A1 (ja) * | 2005-05-13 | 2006-11-16 | Toray Industries, Inc. | 脂肪酸エステルの製造方法およびグリセリンの製造方法 |
| AT502218B1 (de) * | 2005-07-25 | 2010-09-15 | Bdi Biodiesel Internat Ag | Verfahren zur herstellung von carbonsäurealkylestern |
| CN100439474C (zh) * | 2005-09-30 | 2008-12-03 | 中国科学院山西煤炭化学研究所 | 高酸值油脂同时酯化酯交换制备生物柴油的方法 |
| US7624878B2 (en) * | 2006-02-16 | 2009-12-01 | Nalco Company | Fatty acid by-products and methods of using same |
| US7837891B2 (en) * | 2006-02-16 | 2010-11-23 | Nalco Company | Fatty acid by-products and methods of using same |
| US20070218183A1 (en) * | 2006-03-14 | 2007-09-20 | Bunge Oils, Inc. | Oil composition of conjugated linoleic acid |
| JP2008031400A (ja) * | 2006-06-29 | 2008-02-14 | Ics Kk | 油脂類を原料とする脂肪酸エステルの製造方法 |
| WO2008071041A1 (fr) * | 2006-12-15 | 2008-06-19 | China Petroleum & Chemical Corporation | Procédé de préparation de biodiesel |
| US8288573B2 (en) * | 2006-12-15 | 2012-10-16 | China Petroleum & Chemical Corporation | Process for preparing a bio-diesel |
| US20080282606A1 (en) * | 2007-04-16 | 2008-11-20 | Plaza John P | System and process for producing biodiesel |
| WO2010098697A1 (ru) * | 2009-02-24 | 2010-09-02 | Закрытое Акционерное Общество Научно-Исследовательский Институт "Pocбиo" | Способ получения биодизельного топлива |
| US8907113B2 (en) * | 2009-07-25 | 2014-12-09 | Aicardo Roa-Espinosa | Enhanced biodiesel process |
| US20110021807A1 (en) * | 2009-07-25 | 2011-01-27 | Soil Net Llc | Enhanced biodiesel process |
| US9540590B2 (en) * | 2013-05-29 | 2017-01-10 | Polyvalor, Limited Partnership | Process and system for producing a fatty acid alkyl ester |
| US9957464B2 (en) | 2013-06-11 | 2018-05-01 | Renewable Energy Group, Inc. | Methods and devices for producing biodiesel and products obtained therefrom |
| US9328054B1 (en) | 2013-09-27 | 2016-05-03 | Travis Danner | Method of alcoholisis of fatty acids and fatty acid gyicerides |
| US9476009B2 (en) * | 2015-03-05 | 2016-10-25 | Drexel University | Acidic methanol stripping process that reduces sulfur content of biodiesel from waste greases |
| KR102062333B1 (ko) | 2016-06-02 | 2020-01-03 | 유성민 | 지방산 메틸 또는 에틸 에스테르를 제조하기 위한 고체 촉매 및 이를 이용한 지방산 메틸 또는 에틸 에스테르 제조방법 |
| FR3077299B1 (fr) * | 2018-02-01 | 2020-10-30 | Tropical Essence Sdn Bhd | Additif pour huile a base de triglycerides |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2177407A (en) * | 1936-09-21 | 1939-10-24 | Du Pont | Alcoholysis of glycerides |
| US2383632A (en) * | 1942-10-17 | 1945-08-28 | Colgate Palmolive Peet Co | Process of treating fatty glycerides |
| US2383614A (en) * | 1942-10-17 | 1945-08-28 | Colgate Palmolive Peet Co | Treatment of fatty glycerides |
| US2378007A (en) * | 1942-10-30 | 1945-06-12 | Procter & Gamble | Process of modifying the molecular structure of oils and fats |
| US2447186A (en) * | 1945-01-01 | 1948-08-17 | Photo Technical Corp | Producing lower alkyl esters |
| GB634411A (en) * | 1946-07-16 | 1950-03-22 | Unilever Ltd | Method of treating low-grade fatty stock to form alkyl esters therefrom |
| US2494366A (en) * | 1947-07-15 | 1950-01-10 | Nopco Chem Co | Production of fatty esters |
-
1984
- 1984-06-07 DE DE19843421217 patent/DE3421217A1/de not_active Withdrawn
-
1985
- 1985-05-29 AT AT85106561T patent/ATE46532T1/de not_active IP Right Cessation
- 1985-05-29 DE DE8585106561T patent/DE3573131D1/de not_active Expired
- 1985-05-29 EP EP85106561A patent/EP0164643B1/de not_active Expired
- 1985-06-04 SU SU853901006A patent/SU1402250A3/ru active
- 1985-06-05 BR BR8502693A patent/BR8502693A/pt unknown
- 1985-06-05 US US06/741,639 patent/US4668439A/en not_active Expired - Fee Related
- 1985-06-05 NZ NZ212308A patent/NZ212308A/en unknown
- 1985-06-05 KR KR1019850003920A patent/KR910008370B1/ko not_active IP Right Cessation
- 1985-06-05 PT PT80603A patent/PT80603B/pt not_active IP Right Cessation
- 1985-06-05 DD DD85277054A patent/DD232913A5/de not_active IP Right Cessation
- 1985-06-05 ES ES543917A patent/ES8604094A1/es not_active Expired
- 1985-06-05 PH PH32367A patent/PH21080A/en unknown
- 1985-06-06 NO NO852293A patent/NO852293L/no unknown
- 1985-06-06 AU AU43392/85A patent/AU569570B2/en not_active Ceased
- 1985-06-06 DK DK254685A patent/DK254685A/da not_active Application Discontinuation
- 1985-06-06 JP JP60121624A patent/JPS611640A/ja active Pending
- 1985-06-06 ZA ZA854288A patent/ZA854288B/xx unknown
- 1985-06-06 CA CA000483296A patent/CA1247130A/en not_active Expired
- 1985-06-06 MX MX205565A patent/MX160996A/es unknown
- 1985-08-20 CN CN198585106282A patent/CN85106282A/zh active Pending
-
1987
- 1987-09-22 MY MYPI87001853A patent/MY100687A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3421217A1 (de) | 1985-09-05 |
| ATE46532T1 (de) | 1989-10-15 |
| JPS611640A (ja) | 1986-01-07 |
| DE3573131D1 (en) | 1989-10-26 |
| DK254685A (da) | 1985-12-08 |
| AU569570B2 (en) | 1988-02-04 |
| PT80603A (de) | 1985-07-01 |
| US4668439A (en) | 1987-05-26 |
| SU1402250A3 (ru) | 1988-06-07 |
| EP0164643A3 (en) | 1987-01-28 |
| PH21080A (en) | 1987-07-10 |
| CN85106282A (zh) | 1987-02-18 |
| BR8502693A (pt) | 1986-02-12 |
| ES543917A0 (es) | 1986-01-16 |
| PT80603B (de) | 1987-04-23 |
| DK254685D0 (da) | 1985-06-06 |
| DD232913A5 (de) | 1986-02-12 |
| MX160996A (es) | 1990-06-29 |
| EP0164643A2 (de) | 1985-12-18 |
| AU4339285A (en) | 1985-12-12 |
| NZ212308A (en) | 1988-05-30 |
| CA1247130A (en) | 1988-12-20 |
| KR910008370B1 (ko) | 1991-10-12 |
| MY100687A (en) | 1991-01-17 |
| KR860000238A (ko) | 1986-01-27 |
| ZA854288B (en) | 1986-01-29 |
| ES8604094A1 (es) | 1986-01-16 |
| EP0164643B1 (de) | 1989-09-20 |
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