JPS59164749A - α−ケト酸または／およびその塩の製造法 - Google Patents
α−ケト酸または／およびその塩の製造法Info
- Publication number
- JPS59164749A JPS59164749A JP3970183A JP3970183A JPS59164749A JP S59164749 A JPS59164749 A JP S59164749A JP 3970183 A JP3970183 A JP 3970183A JP 3970183 A JP3970183 A JP 3970183A JP S59164749 A JPS59164749 A JP S59164749A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- alkali
- aldehyde
- formula
- alkyl
- 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.)
- Granted
Links
- 150000004716 alpha keto acids Chemical class 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 title description 5
- 239000002253 acid Substances 0.000 claims abstract description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 239000011707 mineral Substances 0.000 claims abstract description 7
- 150000003901 oxalic acid esters Chemical class 0.000 claims abstract description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- -1 oxalate ester Chemical class 0.000 claims description 216
- 238000000034 method Methods 0.000 claims description 19
- 150000001299 aldehydes Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical group CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 235000010755 mineral Nutrition 0.000 claims description 6
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical group CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 5
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical group CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 claims description 4
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 239000001893 (2R)-2-methylbutanal Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical group CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical group [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 150000001340 alkali metals Chemical group 0.000 abstract description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 229910052784 alkaline earth metal Chemical group 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- NIOYUNMRJMEDGI-UHFFFAOYSA-N hexadecanal Chemical compound CCCCCCCCCCCCCCCC=O NIOYUNMRJMEDGI-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QHKABHOOEWYVLI-UHFFFAOYSA-N 3-methyl-2-oxobutanoic acid Chemical compound CC(C)C(=O)C(O)=O QHKABHOOEWYVLI-UHFFFAOYSA-N 0.000 description 3
- 239000001388 3-methyl-2-oxobutanoic acid Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000008206 alpha-amino acids Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- MLVXWWITLGPKNM-UHFFFAOYSA-N 2-butylheptadecanal Chemical compound C(CCC)C(C=O)CCCCCCCCCCCCCCC MLVXWWITLGPKNM-UHFFFAOYSA-N 0.000 description 2
- RACNVJFSQSOKGQ-UHFFFAOYSA-N 2-butylhexanal Chemical compound CCCCC(C=O)CCCC RACNVJFSQSOKGQ-UHFFFAOYSA-N 0.000 description 2
- ONZAWDAAKDTSAU-UHFFFAOYSA-N 3-ethyl-2-oxohexanoic acid Chemical compound CCCC(CC)C(=O)C(O)=O ONZAWDAAKDTSAU-UHFFFAOYSA-N 0.000 description 2
- KFVYOZFUNTZIOL-UHFFFAOYSA-N 3-methyl-2-oxooctanoic acid Chemical compound CCCCCC(C)C(=O)C(O)=O KFVYOZFUNTZIOL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SXIYYZWCMUFWBW-UHFFFAOYSA-N Nonadecanal Chemical compound CCCCCCCCCCCCCCCCCCC=O SXIYYZWCMUFWBW-UHFFFAOYSA-N 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WIQBZDCJCRFGKA-UHFFFAOYSA-M Sodium-3-methyl-2-oxobutyrate Chemical compound [Na+].CC(C)C(=O)C([O-])=O WIQBZDCJCRFGKA-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- FWBUWJHWAKTPHI-UHFFFAOYSA-N icosanal Chemical compound CCCCCCCCCCCCCCCCCCCC=O FWBUWJHWAKTPHI-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- BHVGMUDWABJNRC-UHFFFAOYSA-N (±)-2-methylhexanal Chemical compound CCCCC(C)C=O BHVGMUDWABJNRC-UHFFFAOYSA-N 0.000 description 1
- FXZFFVCJWZTTMX-UHFFFAOYSA-N 1-methylcyclohexane-1-carbaldehyde Chemical compound O=CC1(C)CCCCC1 FXZFFVCJWZTTMX-UHFFFAOYSA-N 0.000 description 1
- OMLOASXVBUNPTN-UHFFFAOYSA-N 2,4-dimethylcyclohexane-1-carbaldehyde Chemical compound CC1CCC(C=O)C(C)C1 OMLOASXVBUNPTN-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- DWNFIQZNEIGHEO-UHFFFAOYSA-N 2-(chloromethyl)butanal Chemical compound CCC(CCl)C=O DWNFIQZNEIGHEO-UHFFFAOYSA-N 0.000 description 1
- ZKPFRIDJMMOODR-UHFFFAOYSA-N 2-Methyloctanal Chemical compound CCCCCCC(C)C=O ZKPFRIDJMMOODR-UHFFFAOYSA-N 0.000 description 1
- JRCSGCPDPGNWNU-UHFFFAOYSA-N 2-butyldecanal Chemical compound CCCCCCCCC(C=O)CCCC JRCSGCPDPGNWNU-UHFFFAOYSA-N 0.000 description 1
- RGJTUSJRUDPKDJ-UHFFFAOYSA-N 2-butyldodecanal Chemical compound CCCCCCCCCCC(C=O)CCCC RGJTUSJRUDPKDJ-UHFFFAOYSA-N 0.000 description 1
- RQZBCUNQDJDCGV-UHFFFAOYSA-N 2-butylheptanal Chemical compound CCCCCC(C=O)CCCC RQZBCUNQDJDCGV-UHFFFAOYSA-N 0.000 description 1
- BCIOZHPKAJXICS-UHFFFAOYSA-N 2-butylhexadecanal Chemical compound CCCCCCCCCCCCCCC(C=O)CCCC BCIOZHPKAJXICS-UHFFFAOYSA-N 0.000 description 1
- SBKAXHHAMODFHB-UHFFFAOYSA-N 2-butylnonadecanal Chemical compound C(CCC)C(C=O)CCCCCCCCCCCCCCCCC SBKAXHHAMODFHB-UHFFFAOYSA-N 0.000 description 1
- NWUCYANQRMAJJA-UHFFFAOYSA-N 2-butylnonanal Chemical compound CCCCCCCC(C=O)CCCC NWUCYANQRMAJJA-UHFFFAOYSA-N 0.000 description 1
- KZWGHUQXRUISMZ-UHFFFAOYSA-N 2-butyloctanal Chemical compound CCCCCCC(C=O)CCCC KZWGHUQXRUISMZ-UHFFFAOYSA-N 0.000 description 1
- HBMJHUZAOSTAGY-UHFFFAOYSA-N 2-butylpentadecanal Chemical compound C(CCC)C(C=O)CCCCCCCCCCCCC HBMJHUZAOSTAGY-UHFFFAOYSA-N 0.000 description 1
- TXMDKSPWMBPYRS-UHFFFAOYSA-N 2-butyltridecanal Chemical compound CCCCCCCCCCCC(C=O)CCCC TXMDKSPWMBPYRS-UHFFFAOYSA-N 0.000 description 1
- YZEGZZUYINZQHB-UHFFFAOYSA-N 2-butylundecanal Chemical compound CCCCCCCCCC(C=O)CCCC YZEGZZUYINZQHB-UHFFFAOYSA-N 0.000 description 1
- SKHCPIFVAAGPHQ-UHFFFAOYSA-N 2-decyloctadecanal Chemical compound CCCCCCCCCCCCCCCCC(C=O)CCCCCCCCCC SKHCPIFVAAGPHQ-UHFFFAOYSA-N 0.000 description 1
- SCKDRLJTOYRCSX-UHFFFAOYSA-N 2-decyltetradecanal Chemical compound CCCCCCCCCCCCC(C=O)CCCCCCCCCC SCKDRLJTOYRCSX-UHFFFAOYSA-N 0.000 description 1
- KYUSUAYEKINLQX-UHFFFAOYSA-N 2-ethyldecanal Chemical compound CCCCCCCCC(CC)C=O KYUSUAYEKINLQX-UHFFFAOYSA-N 0.000 description 1
- ONDFOFWKYWTFMV-UHFFFAOYSA-N 2-ethyldodecanal Chemical compound CCCCCCCCCCC(CC)C=O ONDFOFWKYWTFMV-UHFFFAOYSA-N 0.000 description 1
- JTJHUJKROKHLLW-UHFFFAOYSA-N 2-ethylheptadecanal Chemical compound CCCCCCCCCCCCCCCC(CC)C=O JTJHUJKROKHLLW-UHFFFAOYSA-N 0.000 description 1
- VYABYGNIWIJUAG-UHFFFAOYSA-N 2-ethylhexadecanal Chemical compound CCCCCCCCCCCCCCC(CC)C=O VYABYGNIWIJUAG-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- LTIQXSCCXOWRQE-UHFFFAOYSA-N 2-ethylnonanal Chemical compound CCCCCCCC(CC)C=O LTIQXSCCXOWRQE-UHFFFAOYSA-N 0.000 description 1
- NCDNISXCQQAHDU-UHFFFAOYSA-N 2-ethyloctanal Chemical compound CCCCCCC(CC)C=O NCDNISXCQQAHDU-UHFFFAOYSA-N 0.000 description 1
- HBRJHRSJXKRYQZ-UHFFFAOYSA-N 2-ethylpentadecanal Chemical compound CCCCCCCCCCCCCC(CC)C=O HBRJHRSJXKRYQZ-UHFFFAOYSA-N 0.000 description 1
- OZGRFPZYTKHWMZ-UHFFFAOYSA-N 2-ethylpentanal Chemical compound CCCC(CC)C=O OZGRFPZYTKHWMZ-UHFFFAOYSA-N 0.000 description 1
- HLFSSOUQTFGMFD-UHFFFAOYSA-N 2-ethyltetradecanal Chemical compound CCCCCCCCCCCCC(CC)C=O HLFSSOUQTFGMFD-UHFFFAOYSA-N 0.000 description 1
- MCGQXFHGPRZIFZ-UHFFFAOYSA-N 2-ethyltridecanal Chemical compound CCCCCCCCCCCC(CC)C=O MCGQXFHGPRZIFZ-UHFFFAOYSA-N 0.000 description 1
- PPJRQOPBVSCJCN-UHFFFAOYSA-N 2-ethylundecanal Chemical compound CCCCCCCCCC(CC)C=O PPJRQOPBVSCJCN-UHFFFAOYSA-N 0.000 description 1
- KTSFKUSRYVFNFU-UHFFFAOYSA-N 2-hexyldecanal Chemical compound CCCCCCCCC(C=O)CCCCCC KTSFKUSRYVFNFU-UHFFFAOYSA-N 0.000 description 1
- QCOAIZCMIUWLAO-UHFFFAOYSA-N 2-hexylnonanal Chemical compound CCCCCCCC(C=O)CCCCCC QCOAIZCMIUWLAO-UHFFFAOYSA-N 0.000 description 1
- RRWFWOOATQYYLP-UHFFFAOYSA-N 2-hexyloctanal Chemical compound CCCCCCC(C=O)CCCCCC RRWFWOOATQYYLP-UHFFFAOYSA-N 0.000 description 1
- LBICMZLDYMBIGA-UHFFFAOYSA-N 2-methyldecanal Chemical compound CCCCCCCCC(C)C=O LBICMZLDYMBIGA-UHFFFAOYSA-N 0.000 description 1
- ISZREKMLQKLUDD-UHFFFAOYSA-N 2-methyldodecanal Chemical compound CCCCCCCCCCC(C)C=O ISZREKMLQKLUDD-UHFFFAOYSA-N 0.000 description 1
- PELJVDHIBZLNOC-UHFFFAOYSA-N 2-methylheptadecanal Chemical compound CCCCCCCCCCCCCCCC(C)C=O PELJVDHIBZLNOC-UHFFFAOYSA-N 0.000 description 1
- DHEKCFIOOSCJRW-UHFFFAOYSA-N 2-methylheptanal Chemical compound CCCCCC(C)C=O DHEKCFIOOSCJRW-UHFFFAOYSA-N 0.000 description 1
- CTUHQRWBXMBEPD-UHFFFAOYSA-N 2-methylhexadecanal Chemical compound CCCCCCCCCCCCCCC(C)C=O CTUHQRWBXMBEPD-UHFFFAOYSA-N 0.000 description 1
- SYINEDRCBKSZPF-UHFFFAOYSA-N 2-methylicosanal Chemical compound CCCCCCCCCCCCCCCCCCC(C)C=O SYINEDRCBKSZPF-UHFFFAOYSA-N 0.000 description 1
- IFKLHTZKVHCPMK-UHFFFAOYSA-N 2-methylnonadecanal Chemical compound CCCCCCCCCCCCCCCCCC(C)C=O IFKLHTZKVHCPMK-UHFFFAOYSA-N 0.000 description 1
- MNXNDLQGVDOJQY-UHFFFAOYSA-N 2-methylnonanal Chemical compound CCCCCCCC(C)C=O MNXNDLQGVDOJQY-UHFFFAOYSA-N 0.000 description 1
- TZXFTUHLVMYUGE-UHFFFAOYSA-N 2-methyloctadecanal Chemical compound CCCCCCCCCCCCCCCCC(C)C=O TZXFTUHLVMYUGE-UHFFFAOYSA-N 0.000 description 1
- AULXFJFWCQVVTN-UHFFFAOYSA-N 2-methylpentadecanal Chemical compound CCCCCCCCCCCCCC(C)C=O AULXFJFWCQVVTN-UHFFFAOYSA-N 0.000 description 1
- MJHNFOWITPQFBW-UHFFFAOYSA-N 2-methyltetradecanal Chemical compound CCCCCCCCCCCCC(C)C=O MJHNFOWITPQFBW-UHFFFAOYSA-N 0.000 description 1
- BBBHELVSOCQEHJ-UHFFFAOYSA-N 2-methyltridecanal Chemical compound CCCCCCCCCCCC(C)C=O BBBHELVSOCQEHJ-UHFFFAOYSA-N 0.000 description 1
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 1
- SXJZIUKTSPPFMN-UHFFFAOYSA-N 2-nonyltridecanal Chemical compound CCCCCCCCCCCC(C=O)CCCCCCCCC SXJZIUKTSPPFMN-UHFFFAOYSA-N 0.000 description 1
- OYGRVQCXQURSER-UHFFFAOYSA-N 2-octyldecanal Chemical compound CCCCCCCCC(C=O)CCCCCCCC OYGRVQCXQURSER-UHFFFAOYSA-N 0.000 description 1
- KTABAZHDUBOMSI-UHFFFAOYSA-N 2-octyldodecanal Chemical compound CCCCCCCCCCC(C=O)CCCCCCCC KTABAZHDUBOMSI-UHFFFAOYSA-N 0.000 description 1
- FQPLZGIOMHRNOM-UHFFFAOYSA-N 2-octylundecanal Chemical compound CCCCCCCCCC(C=O)CCCCCCCC FQPLZGIOMHRNOM-UHFFFAOYSA-N 0.000 description 1
- ZVNHILZUTNYFGT-UHFFFAOYSA-N 2-oxohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(=O)C(O)=O ZVNHILZUTNYFGT-UHFFFAOYSA-N 0.000 description 1
- HSZDCONVHXPTFQ-UHFFFAOYSA-N 2-pentyldecanal Chemical compound CCCCCCCCC(C=O)CCCCC HSZDCONVHXPTFQ-UHFFFAOYSA-N 0.000 description 1
- LLWQWSGAPDBSJQ-UHFFFAOYSA-N 2-pentyldodecanal Chemical compound CCCCCCCCCCC(C=O)CCCCC LLWQWSGAPDBSJQ-UHFFFAOYSA-N 0.000 description 1
- QRYMWDVGBCPJKI-UHFFFAOYSA-N 2-pentylheptanal Chemical compound CCCCCC(C=O)CCCCC QRYMWDVGBCPJKI-UHFFFAOYSA-N 0.000 description 1
- DXRZZZFLQMCCFC-UHFFFAOYSA-N 2-pentylnonanal Chemical compound CCCCCCCC(C=O)CCCCC DXRZZZFLQMCCFC-UHFFFAOYSA-N 0.000 description 1
- FYDUJOZFUFRISC-UHFFFAOYSA-N 2-pentyloctanal Chemical compound CCCCCCC(C=O)CCCCC FYDUJOZFUFRISC-UHFFFAOYSA-N 0.000 description 1
- FEFNFOUJRMDJFO-UHFFFAOYSA-N 2-propylheptanal Chemical compound CCCCCC(C=O)CCC FEFNFOUJRMDJFO-UHFFFAOYSA-N 0.000 description 1
- BOYZPZMWHBWEJG-UHFFFAOYSA-N 2-propylnonanal Chemical compound CCCCCCCC(C=O)CCC BOYZPZMWHBWEJG-UHFFFAOYSA-N 0.000 description 1
- BAUHZKXBGXCLBO-UHFFFAOYSA-N 2-propylpentanal Chemical compound CCCC(C=O)CCC BAUHZKXBGXCLBO-UHFFFAOYSA-N 0.000 description 1
- HPPMVYMRKLIGSE-UHFFFAOYSA-N 2-tetradecyloctadecanal Chemical compound CCCCCCCCCCCCCCCCC(C=O)CCCCCCCCCCCCCC HPPMVYMRKLIGSE-UHFFFAOYSA-N 0.000 description 1
- GXIPWLFFBUPIMB-UHFFFAOYSA-N 2-undecylpentadecanal Chemical compound CCCCCCCCCCCCCC(C=O)CCCCCCCCCCC GXIPWLFFBUPIMB-UHFFFAOYSA-N 0.000 description 1
- INZFAIQXPKIALB-UHFFFAOYSA-N 3-(chloromethyl)-2-oxopentanoic acid Chemical compound CCC(CCl)C(C(O)=O)=O INZFAIQXPKIALB-UHFFFAOYSA-N 0.000 description 1
- MIGQGYPWOONPRH-UHFFFAOYSA-N 3-chloro-2-methylpropanal Chemical compound ClCC(C)C=O MIGQGYPWOONPRH-UHFFFAOYSA-N 0.000 description 1
- VLSWCTOZKSNQEH-UHFFFAOYSA-N 3-ethyl-2-oxoheptanoic acid Chemical compound CCCCC(CC)C(=O)C(O)=O VLSWCTOZKSNQEH-UHFFFAOYSA-N 0.000 description 1
- JGCWJLURRTUWTN-UHFFFAOYSA-N 3-methyl-2-oxodecanoic acid Chemical compound CC(C(C(=O)O)=O)CCCCCCC JGCWJLURRTUWTN-UHFFFAOYSA-N 0.000 description 1
- AUOMTDDJZRJEAS-UHFFFAOYSA-N 3-methyl-2-oxododecanoic acid Chemical compound C(CCCCCCCC)C(C(C(=O)O)=O)C AUOMTDDJZRJEAS-UHFFFAOYSA-N 0.000 description 1
- AHTHDNBJQJWWIN-UHFFFAOYSA-N 3-methyl-2-oxoheptanoic acid Chemical compound CCCCC(C)C(=O)C(O)=O AHTHDNBJQJWWIN-UHFFFAOYSA-N 0.000 description 1
- CDIJNTMPAAQIRZ-UHFFFAOYSA-N 3-methyl-2-oxooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(C)C(=O)C(O)=O CDIJNTMPAAQIRZ-UHFFFAOYSA-N 0.000 description 1
- GQJCZRKPEKDTFQ-UHFFFAOYSA-N 4-(2-methylpropyl)cyclohexane-1-carbaldehyde Chemical compound CC(C)CC1CCC(C=O)CC1 GQJCZRKPEKDTFQ-UHFFFAOYSA-N 0.000 description 1
- XKDWAUAURNOHHZ-UHFFFAOYSA-N 4-bromocyclohexane-1-carbaldehyde Chemical compound BrC1CCC(C=O)CC1 XKDWAUAURNOHHZ-UHFFFAOYSA-N 0.000 description 1
- LZRSTUTWNYNSAM-UHFFFAOYSA-N 4-butylcyclohexane-1-carbaldehyde Chemical compound CCCCC1CCC(C=O)CC1 LZRSTUTWNYNSAM-UHFFFAOYSA-N 0.000 description 1
- LVVFZJREXMSAMO-UHFFFAOYSA-N 4-chlorocyclohexane-1-carbaldehyde Chemical compound ClC1CCC(C=O)CC1 LVVFZJREXMSAMO-UHFFFAOYSA-N 0.000 description 1
- GJRARBLKMCCJFO-UHFFFAOYSA-N 4-ethylcyclohexane-1-carbaldehyde Chemical compound CCC1CCC(C=O)CC1 GJRARBLKMCCJFO-UHFFFAOYSA-N 0.000 description 1
- XZUAUDZGDPLDLH-UHFFFAOYSA-N 4-methylcyclohexane-1-carbaldehyde Chemical compound CC1CCC(C=O)CC1 XZUAUDZGDPLDLH-UHFFFAOYSA-N 0.000 description 1
- QFFSAGSUDNLFFK-UHFFFAOYSA-N 4-pentylcyclohexane-1-carbaldehyde Chemical compound CCCCCC1CCC(C=O)CC1 QFFSAGSUDNLFFK-UHFFFAOYSA-N 0.000 description 1
- GLBRWLVEZQRTKY-UHFFFAOYSA-N 4-propan-2-ylcyclohexane-1-carbaldehyde Chemical compound CC(C)C1CCC(C=O)CC1 GLBRWLVEZQRTKY-UHFFFAOYSA-N 0.000 description 1
- OZKLOXFZSOVSRA-UHFFFAOYSA-N 4-propylcyclohexane-1-carbaldehyde Chemical compound CCCC1CCC(C=O)CC1 OZKLOXFZSOVSRA-UHFFFAOYSA-N 0.000 description 1
- MXGRYXNVQNESIN-UHFFFAOYSA-N 4-tert-butylcyclohexane-1-carbaldehyde Chemical compound CC(C)(C)C1CCC(C=O)CC1 MXGRYXNVQNESIN-UHFFFAOYSA-N 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- FEFILKCZUUCBEA-UHFFFAOYSA-N C(CC)C(C=O)CCCCCCCCCCCCC Chemical compound C(CC)C(C=O)CCCCCCCCCCCCC FEFILKCZUUCBEA-UHFFFAOYSA-N 0.000 description 1
- CYAFLKWXILAMCJ-UHFFFAOYSA-N C(CC)C(C=O)CCCCCCCCCCCCCCC Chemical compound C(CC)C(C=O)CCCCCCCCCCCCCCC CYAFLKWXILAMCJ-UHFFFAOYSA-N 0.000 description 1
- LXRZVWSFOXGEQC-UHFFFAOYSA-N CCCCCCCCCCCCCCCCC(CCCC)C=O Chemical compound CCCCCCCCCCCCCCCCC(CCCC)C=O LXRZVWSFOXGEQC-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- INVYSLWXPIEDIQ-UHFFFAOYSA-N cyclobutanecarbaldehyde Chemical compound O=CC1CCC1 INVYSLWXPIEDIQ-UHFFFAOYSA-N 0.000 description 1
- UGBFRCHGZFHSBC-UHFFFAOYSA-N cycloheptanecarbaldehyde Chemical compound O=CC1CCCCCC1 UGBFRCHGZFHSBC-UHFFFAOYSA-N 0.000 description 1
- IGGUWVNICWZJQU-UHFFFAOYSA-N cyclooctanecarbaldehyde Chemical compound O=CC1CCCCCCC1 IGGUWVNICWZJQU-UHFFFAOYSA-N 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 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
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002923 oximes Chemical class 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
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 208000009852 uremia Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3970183A JPS59164749A (ja) | 1983-03-09 | 1983-03-09 | α−ケト酸または／およびその塩の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3970183A JPS59164749A (ja) | 1983-03-09 | 1983-03-09 | α−ケト酸または／およびその塩の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59164749A true JPS59164749A (ja) | 1984-09-17 |
| JPS624377B2 JPS624377B2 (enrdf_load_stackoverflow) | 1987-01-30 |
Family
ID=12560312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3970183A Granted JPS59164749A (ja) | 1983-03-09 | 1983-03-09 | α−ケト酸または／およびその塩の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59164749A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675087A (zh) * | 2012-05-25 | 2012-09-19 | 绍兴民生医药有限公司 | 一种新的α-酮缬氨酸钙的制备方法 |
| CN102701954A (zh) * | 2011-06-13 | 2012-10-03 | 浙江昂利康制药有限公司 | α-酮缬氨酸钙制备方法 |
| CN112062693A (zh) * | 2020-09-23 | 2020-12-11 | 上海吉奉生物科技有限公司 | 一种2-(9h-芴-9-甲氧基羰基氨基)-3-甲基-2-丁烯酸的合成方法 |
-
1983
- 1983-03-09 JP JP3970183A patent/JPS59164749A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102701954A (zh) * | 2011-06-13 | 2012-10-03 | 浙江昂利康制药有限公司 | α-酮缬氨酸钙制备方法 |
| CN102675087A (zh) * | 2012-05-25 | 2012-09-19 | 绍兴民生医药有限公司 | 一种新的α-酮缬氨酸钙的制备方法 |
| CN112062693A (zh) * | 2020-09-23 | 2020-12-11 | 上海吉奉生物科技有限公司 | 一种2-(9h-芴-9-甲氧基羰基氨基)-3-甲基-2-丁烯酸的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS624377B2 (enrdf_load_stackoverflow) | 1987-01-30 |
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