JP5260662B2 - リシノール酸からメチル7−オキソヘプタノエートとウンデシレン酸とを同時に製造する方法 - Google Patents
リシノール酸からメチル7−オキソヘプタノエートとウンデシレン酸とを同時に製造する方法 Download PDFInfo
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- JP5260662B2 JP5260662B2 JP2010525403A JP2010525403A JP5260662B2 JP 5260662 B2 JP5260662 B2 JP 5260662B2 JP 2010525403 A JP2010525403 A JP 2010525403A JP 2010525403 A JP2010525403 A JP 2010525403A JP 5260662 B2 JP5260662 B2 JP 5260662B2
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- Prior art keywords
- acid
- methyl
- oxoheptanoate
- ricinoleic
- hydroxy
- 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 - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 42
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 title claims abstract description 26
- 229960003656 ricinoleic acid Drugs 0.000 title claims abstract description 26
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 title claims abstract description 26
- NJVFYRBRYZXABC-UHFFFAOYSA-N methyl 7-oxoheptanoate Chemical compound COC(=O)CCCCCC=O NJVFYRBRYZXABC-UHFFFAOYSA-N 0.000 title claims abstract description 19
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 229960002703 undecylenic acid Drugs 0.000 title claims abstract description 12
- 238000000855 fermentation Methods 0.000 claims abstract description 12
- 230000004151 fermentation Effects 0.000 claims abstract description 12
- -1 methyl diester Chemical class 0.000 claims abstract description 12
- ANLABNUUYWRCRP-UHFFFAOYSA-N 1-(4-nitrophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1(C#N)CCCC1 ANLABNUUYWRCRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 7
- 241000894006 Bacteria Species 0.000 claims abstract description 6
- 241000233866 Fungi Species 0.000 claims abstract description 6
- 238000005336 cracking Methods 0.000 claims abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 27
- FSNCDMCRKUCPBS-UHFFFAOYSA-N 7-hydroxyoctadec-9-enedioic acid Chemical compound OC(=O)CCCCCC(O)CC=CCCCCCCCC(O)=O FSNCDMCRKUCPBS-UHFFFAOYSA-N 0.000 claims description 7
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 claims description 5
- 238000006268 reductive amination reaction Methods 0.000 claims description 5
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims 1
- 229960002684 aminocaproic acid Drugs 0.000 claims 1
- 230000032050 esterification Effects 0.000 abstract description 5
- 238000005886 esterification reaction Methods 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 11
- 239000004359 castor oil Substances 0.000 description 10
- 235000019438 castor oil Nutrition 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 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 10
- 230000008569 process Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- 241000222178 Candida tropicalis Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- LCAVRNOMCURXMM-UHFFFAOYSA-N methyl tridec-12-enoate Chemical compound COC(=O)CCCCCCCCCCC=C LCAVRNOMCURXMM-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- PZRZUJZXSTZDBZ-UHFFFAOYSA-N 11-bromoundec-10-enoic acid Chemical compound OC(=O)CCCCCCCCC=CBr PZRZUJZXSTZDBZ-UHFFFAOYSA-N 0.000 description 2
- OOFMTFUTWFAVGC-UHFFFAOYSA-N 7-oxoheptanoic acid Chemical compound OC(=O)CCCCCC=O OOFMTFUTWFAVGC-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- GGDWDKDPRJFMHD-ZXYUVVQBSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(e,3r)-3-hydroxy-4-methoxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(OC)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC GGDWDKDPRJFMHD-ZXYUVVQBSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229950000086 mexiprostil Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 238000005949 ozonolysis reaction Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-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
- UKIDUMMXBQMTKO-UHFFFAOYSA-N 1-methyl-1-nitro-2-nitrosoguanidine Chemical compound [O-][N+](=O)N(C)C(=N)NN=O UKIDUMMXBQMTKO-UHFFFAOYSA-N 0.000 description 1
- PARCICAYFORNPH-UHFFFAOYSA-N 12-tridecenoic acid Chemical compound OC(=O)CCCCCCCCCCC=C PARCICAYFORNPH-UHFFFAOYSA-N 0.000 description 1
- ZNJKLGAQBVTJPN-UHFFFAOYSA-N 14-hydroxyicos-9-enedioic acid Chemical compound OC(=O)CCCCCC(O)CCCC=CCCCCCCCC(O)=O ZNJKLGAQBVTJPN-UHFFFAOYSA-N 0.000 description 1
- HASUJDLTAYUWCO-UHFFFAOYSA-N 2-aminoundecanoic acid Chemical compound CCCCCCCCCC(N)C(O)=O HASUJDLTAYUWCO-UHFFFAOYSA-N 0.000 description 1
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 description 1
- POVLCORPALZSFB-UHFFFAOYSA-N 3-hydroxyoctadec-9-enedioic acid Chemical compound OC(=O)CC(O)CCCCCC=CCCCCCCCC(O)=O POVLCORPALZSFB-UHFFFAOYSA-N 0.000 description 1
- KSWRZJNADSIDKV-UHFFFAOYSA-N 8-amino-3-hydroxynaphthalene-1,6-disulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 KSWRZJNADSIDKV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XKGDWZQXVZSXAO-ADYSOMBNSA-N Ricinoleic Acid methyl ester Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC XKGDWZQXVZSXAO-ADYSOMBNSA-N 0.000 description 1
- XKGDWZQXVZSXAO-SFHVURJKSA-N Ricinolsaeure-methylester Natural products CCCCCC[C@H](O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-SFHVURJKSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 239000004959 Rilsan Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PWGQHOJABIQOOS-UHFFFAOYSA-N copper;dioxido(dioxo)chromium Chemical compound [Cu+2].[O-][Cr]([O-])(=O)=O PWGQHOJABIQOOS-UHFFFAOYSA-N 0.000 description 1
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- AKAVKRSUSVIDIM-UHFFFAOYSA-N icos-11-en-7-ol Chemical compound OC(CCCCCC)CCCC=CCCCCCCCC AKAVKRSUSVIDIM-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- KDHIOWQSFJTRQG-UHFFFAOYSA-N methyl 7-(5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=CCCC1=O KDHIOWQSFJTRQG-UHFFFAOYSA-N 0.000 description 1
- KISVAASFGZJBCY-UHFFFAOYSA-N methyl undecenate Chemical compound COC(=O)CCCCCCCCC=C KISVAASFGZJBCY-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 1
- UVMYOBBALQKLKK-UHFFFAOYSA-N nonadecene Natural products CCCCCCCCCCCC=CCCCCCC UVMYOBBALQKLKK-UHFFFAOYSA-N 0.000 description 1
- SBLKVIQSIHEQOF-UHFFFAOYSA-N octadec-9-enedioic acid Chemical compound OC(=O)CCCCCCCC=CCCCCCCCC(O)=O SBLKVIQSIHEQOF-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 229940127293 prostanoid Drugs 0.000 description 1
- 150000003814 prostanoids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- XKGDWZQXVZSXAO-UHFFFAOYSA-N ricinoleic acid methyl ester Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-UHFFFAOYSA-N 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
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Description
(a) リシノール酸をバクテリア、イーストまたは真菌を用いた発酵で7-ヒドロキシ-9-オクタデセン二酸を作り、
(b) 段階(a)で得られた7- ヒドロキシ-9- オクタデセン二酸をエステル化して対応するメチルジエステルを形成し、
(c) 段階(b)で得られた生成物を高温クラッキングしてメチルウンデシレネートとメチル7- オキソヘプタノエートとの混合物を形成し、
(d) 段階(c)で得られたメチルウンデシレネートとメチル7-オキソヘプタノエートとを分離し、
(e) 段階(d)で得られたメチルウンデシレネートを加水分解してウンデシレン酸を形成する。
(f) 段階(e)で得られたウンデシレン酸とHBrとを反応させて11-ブロムウンデシレン酸を形成し、
(g) 段階(f)で得られた11-ブロムウンデシレン酸をアムモニアと反応させて11-アミノウンデカン酸を形成する。
(a) レステロル酸をバクテリア、イーストまたは真菌による発酵で7-ヒドロキシ-11-エイコセン二酸を作り、
(b) 段階(a)で得られた7-ヒドロキシ-11-エイコセン二酸をエステル化して、対応するメチルジエステルを形成し、
(c) 段階(b)で得られた生成物を高温クラッキングして、メチル12-トリデセノエートとメチル7-オキソヘプタノエートとの混合物を形成し、
(d) 段階(c)で得られたメチル12- トリデセノエートとメチル7-オキソヘプタノエートとを分離し、
(e) 段階(d)で得られたメチル12-トリデセノエートを加水分解して12- トリデセン酸の形にする。
以下、リシノール酸を使用した本発明方法の実施例を示すが、本発明が下記実施例に限定されるものではない。
段階(a) リシノール酸の発酵
この実施例ではイースト株をリシノール酸を含む媒体中で培養した。その後、混合物を120℃で15分間殺菌した。培養物は30℃に維持した。pHを7〜7.5に維持するために水酸化ナトリウム溶液を連続的に加えた。48時間培養した後にジエチルエーテルで抽出してヒドロキシル化された不飽和二酸を回収した。この手順を使用して7-ヒドロキシ-9-オクタドデセン二酸を得た。
実施例2
段階(b) 7-ヒドロキシ-9-オクタ−ドデセン二酸のエステル化
上記で得られた二酸を酸触媒とメタノールとの存在下でエステル化してメチル・ジエステルにした。ワコーから提供された硫酸ジルコニアの不均質酸触媒の存在下およびメタノールの存在下で1gの二酸を使用した。平衡に達するまで反応液を150℃に加熱し、過剰なメタノールを蒸留分離した。この実験条件で7-ヒドロキシ-9-オクタデセン二酸からメチルジエステルを得ることができた。
実施例3
段階(c) ジエステルの熱クラッキング
上記メチルジエステルの熱分解を管状炉中で500℃で15秒の滞在時間で実行した。260℃でジエステルを揮発させた後に600℃に加熱した水蒸気と混合する。この反応で生じた流れをまず最初に一連の熱交換で凝縮して温度を約150℃に下げる。それから沈澱によって水を分離する。得られた生成物を連続蒸留塔で分別する。上記の実験的条件下でウンデシレン酸のメチルエステル、7-オキソヘプタン酸のエステル、リシノール酸から生じるその他のジエステルの画分を回収できた。未変換物は反応装置の入口で分離した後に再循環できる。
本発明方法の段階(d)、(e)および(f)は当業者の公知の従来段階であるので例示しない。
実施例4
メチル7-オキソヘプタン酸エステルの還元アミノ化
磁気攪拌機を備えたオートクレーブ中に、1gのクロム酸銅触媒と、8gの7-オキソヘプタン酸のメチルエステルと、30gのエタノールと、30gのアムモニアとを導入する。その後、水素を80バールの圧力で導入する。その後、オートクレーブを1時間以上かけて150℃に加熱し、この温度で2時間維持する。濾過して触媒を除去し、溶剤を除去した後に製品を分析した。上記の実験条件で7-アミノヘプタン酸のメチルエステルが得られた。このエステルを加水分解すると7-アミノヘプタン酸が形成できる。加水分解はジャケット付きの反応装置中で25℃で30分の滞在時間で実行した。メタノールは精製後にエステル化段階へ再循環できた。
Claims (3)
- 連続した下記の(a)〜(e)段階から成るリシノール酸の変換方法:
(a) リシノール酸をバクテリア、イーストまたは真菌を用いた発酵で7-ヒドロキシ-9-オクタデセン二酸を作り、
(b) 段階(a)で得られた7- ヒドロキシ-9- オクタデセン二酸をエステル化して対応するメチルジエステルを形成し、
(c) 段階(b)で得られたせ生成物を高温クラッキングしてメチルウンデシレネートとメチル7- オキソヘプタノエートとの混合物を形成し、
(d) 段階(c)で得られたメチルウンデシレネートとメチル7-オキソヘプタノエートとを分離し、
(e) 段階(d)で得られたメチルウンデシレネートを加水分解してウンデシレン酸を形成する。 - 下記の(f)と(g)の段階をさらに有する請求項1に記載の方法:
(f) 段階(e)で得られたウンデシレン酸とHBrとを反応させて11-ブロムウンデカン酸を形成し、
(g) 段階(f)で得られた11-ブロムウンデカン酸をアムモニアと反応させて11-アミノウンデカン酸を形成する。 - 下記の段階をさらに有する請求項1または2に記載の方法:
段階(d)で得られたメチル7-オキソヘプタノエートを還元アミノ化する段階と、
それに続く加水分解によって7-アミノヘプタン酸を形成する段階。
Applications Claiming Priority (3)
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FR0757696 | 2007-09-20 | ||
FR0757696A FR2921364B1 (fr) | 2007-09-20 | 2007-09-20 | Procede de coproduction de 7-oxoheptanoate de methyle et d'acide undecylenique a partir d'acide ricinoleique |
PCT/FR2008/051666 WO2009047446A2 (fr) | 2007-09-20 | 2008-09-17 | Procede de coproduction de 7-oxoheptanoate de methyle et d'acide undecylenique a partir d'acide ricinoleique |
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JP2010539227A JP2010539227A (ja) | 2010-12-16 |
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US (1) | US20100203600A1 (ja) |
EP (1) | EP2188380B1 (ja) |
JP (1) | JP5260662B2 (ja) |
CN (1) | CN101868551B (ja) |
AT (1) | ATE509115T1 (ja) |
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FR2942628B1 (fr) | 2009-03-02 | 2011-07-01 | Arkema France | Procede de production d'ester d'acide ricinoleique par transesterification enzymatique selective |
KR101280951B1 (ko) | 2011-05-17 | 2013-07-02 | 서울대학교산학협력단 | 11-아미노운데카논산 또는 그의 에스터 유도체의 제조방법 |
MY166083A (en) | 2011-06-17 | 2018-05-24 | Invista Tech Sarl | Use of hydrolases to increase monomer content in waste stream |
US9650653B2 (en) | 2011-06-30 | 2017-05-16 | Invista North America S.A.R.L. | Bioconversion process for producing nylon-7, nylon-7,7 and polyesters |
CN102417447B (zh) * | 2011-10-31 | 2014-04-30 | 广西亿康药业股份有限公司 | 十一烯酸的生产方法 |
US9102960B2 (en) | 2011-12-16 | 2015-08-11 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage |
US9102958B2 (en) | 2011-12-16 | 2015-08-11 | Invista North America S.á.r.l. | Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage |
BR112014015077A2 (pt) * | 2011-12-21 | 2020-10-27 | Invista Technologies S.A.R.L. | método para produzir um alcano di- ou trifuncional |
EP2706117A1 (en) * | 2012-09-07 | 2014-03-12 | Basf Se | Process for preparing sebacic acid |
EP2931907A2 (en) | 2012-12-14 | 2015-10-21 | Invista Technologies S.A R.L. | METHODS OF PRODUCING 7-CARBON CHEMICALS VIA CoA-DEPENDENT CARBON CHAIN ELONGATION ASSOCIATED WITH CARBON STORAGE |
CN105026570A (zh) | 2012-12-31 | 2015-11-04 | 英威达技术有限责任公司 | 通过氧化裂解从长链脂肪酸生产7-碳化学物的方法 |
CN105408487A (zh) | 2012-12-31 | 2016-03-16 | 英威达技术有限责任公司 | 通过甲酯保护的碳链延伸生产7碳化学物的方法 |
WO2014105796A2 (en) | 2012-12-31 | 2014-07-03 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via aromatic compounds |
US9738911B2 (en) | 2012-12-31 | 2017-08-22 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via pyruvate and succinate semialdehyde aldol condensation |
US9637764B2 (en) | 2012-12-31 | 2017-05-02 | Invista North America S.A.R.L. | Methods of producing 7-carbon chemicals via carbon chain elongation associated with cyclohexane carboxylate synthesis |
CN105189764A (zh) | 2012-12-31 | 2015-12-23 | 英威达技术有限责任公司 | 通过与辅酶b合成相关的c1碳链延伸生产7-碳化学物的方法 |
US9580733B2 (en) | 2012-12-31 | 2017-02-28 | Invista North America S.A.R.L. | Methods of producing 6-carbon chemicals via methyl-ester shielded carbon chain elongation |
CN103113224A (zh) * | 2013-01-05 | 2013-05-22 | 六安市晖润粉末新材料有限公司 | 一种十一烯酸甲酯裂解制备反应装置及裂解工艺 |
US9745607B2 (en) | 2014-05-15 | 2017-08-29 | Invista North America S.A.R.L. | Methods of producing 6-carbon chemicals using 2,6-diaminopimelate as precursor to 2-aminopimelate |
WO2015195611A2 (en) | 2014-06-16 | 2015-12-23 | Invista Technologies S.À.R.L. | Methods, reagents and cells for biosynthesizing compound |
BR112016029375A2 (pt) | 2014-06-16 | 2017-10-17 | Invista Tech Sarl | métodos, reagentes e células para biossintetizar compostos |
US9938543B2 (en) | 2014-06-16 | 2018-04-10 | Invista North America S.A.R.L. | Methods, reagents and cells for biosynthesizing glutarate methyl ester |
EP3155108A1 (en) | 2014-06-16 | 2017-04-19 | Invista Technologies S.à.r.l. | Methods, reagents and cells for biosynthesizing compounds |
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US2807633A (en) * | 1955-01-21 | 1957-09-24 | Organico S A | Pyrolysis of ricinoleates |
US3823070A (en) * | 1971-12-23 | 1974-07-09 | Hasegawa T Co Ltd | Process for producing a straight chain dicarboxylic acid,an omega-hydroxy fatty acid,and an omega-1-keto fatty acid |
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US5952517A (en) * | 1997-02-14 | 1999-09-14 | Caschem, Inc. | Method for preparing cleaved products from castor oil or derivatives thereof |
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US6569670B2 (en) * | 1999-09-30 | 2003-05-27 | Cognis Corporation | Fermentation process |
US20020061566A1 (en) * | 2000-03-20 | 2002-05-23 | Eirich L. Dudley | Biooxidation capabilities of candida sp |
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US7050956B2 (en) * | 2001-04-30 | 2006-05-23 | Hewlett-Packard Development Company, L.P. | Method and apparatus for morphological modeling of complex systems to predict performance |
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JP2010539227A (ja) | 2010-12-16 |
BRPI0816947A2 (pt) | 2014-10-29 |
CN101868551A (zh) | 2010-10-20 |
CN101868551B (zh) | 2013-07-10 |
FR2921364B1 (fr) | 2009-11-06 |
EP2188380B1 (fr) | 2011-05-11 |
FR2921364A1 (fr) | 2009-03-27 |
WO2009047446A2 (fr) | 2009-04-16 |
US20100203600A1 (en) | 2010-08-12 |
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