JP4295083B2 - アルキリデン置換コハク酸エステルの製法 - Google Patents
アルキリデン置換コハク酸エステルの製法 Download PDFInfo
- Publication number
- JP4295083B2 JP4295083B2 JP2003501828A JP2003501828A JP4295083B2 JP 4295083 B2 JP4295083 B2 JP 4295083B2 JP 2003501828 A JP2003501828 A JP 2003501828A JP 2003501828 A JP2003501828 A JP 2003501828A JP 4295083 B2 JP4295083 B2 JP 4295083B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reaction
- hydrocarbon group
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003890 succinate salts Chemical class 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 48
- 150000003900 succinic acid esters Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 239000012429 reaction media Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001118 alkylidene group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 150000004703 alkoxides Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 9
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical group CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 7
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000003997 cyclic ketones Chemical class 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- -1 alkylidene disubstituted succinic acids Chemical class 0.000 description 16
- 150000002576 ketones Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 239000002002 slurry Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- FSUBDXPWXDGTBG-UHFFFAOYSA-N diethyl 2-propan-2-ylidenebutanedioate Chemical compound CCOC(=O)CC(=C(C)C)C(=O)OCC FSUBDXPWXDGTBG-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 5
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- GSNKRSKIWFBWEG-UHFFFAOYSA-N 3-ethylpentan-2-one Chemical compound CCC(CC)C(C)=O GSNKRSKIWFBWEG-UHFFFAOYSA-N 0.000 description 4
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 4
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 4
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 4
- ULPMRIXXHGUZFA-UHFFFAOYSA-N 4-methylhexan-3-one Chemical compound CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JPJOOTWNILDNAW-UHFFFAOYSA-N 1-cyclobutylethanone Chemical compound CC(=O)C1CCC1 JPJOOTWNILDNAW-UHFFFAOYSA-N 0.000 description 2
- LKENTYLPIUIMFG-UHFFFAOYSA-N 1-cyclopentylethanone Chemical compound CC(=O)C1CCCC1 LKENTYLPIUIMFG-UHFFFAOYSA-N 0.000 description 2
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 2
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 description 2
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 2
- XUPXMIAWKPTZLZ-UHFFFAOYSA-N 4-methylhexan-2-one Chemical compound CCC(C)CC(C)=O XUPXMIAWKPTZLZ-UHFFFAOYSA-N 0.000 description 2
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical compound C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 description 2
- GKAXQJCQMJJHRO-UHFFFAOYSA-N diethyl 2,3-di(propan-2-ylidene)butanedioate Chemical compound CCOC(=O)C(=C(C)C)C(=C(C)C)C(=O)OCC GKAXQJCQMJJHRO-UHFFFAOYSA-N 0.000 description 2
- VLSYDDOOBGXUNE-UHFFFAOYSA-N diethyl 2-(2-ethylhexylidene)butanedioate Chemical compound CCCCC(CC)C=C(C(=O)OCC)CC(=O)OCC VLSYDDOOBGXUNE-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VLNUTKMHYLQCQB-UHFFFAOYSA-N 2,2-dimethylpentan-3-one Chemical compound CCC(=O)C(C)(C)C VLNUTKMHYLQCQB-UHFFFAOYSA-N 0.000 description 1
- BZKQYCPXLCAHHX-UHFFFAOYSA-N 2-ethyl-2-(2-ethylphenyl)-1,3-dioxepane-4,7-dione Chemical compound CCc1ccccc1C1(CC)OC(=O)CCC(=O)O1 BZKQYCPXLCAHHX-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- WIGJJPGCEOSPCN-UHFFFAOYSA-N 3,3-diethyl-7,12-dioxaspiro[5.6]dodecane-8,11-dione Chemical compound C1(CCC(=O)OC2(CCC(CC2)(CC)CC)O1)=O WIGJJPGCEOSPCN-UHFFFAOYSA-N 0.000 description 1
- QQZFWPPTASWDEO-UHFFFAOYSA-N 3-ethoxycarbonyl-4-methylpent-3-enoic acid Chemical compound CCOC(=O)C(=C(C)C)CC(O)=O QQZFWPPTASWDEO-UHFFFAOYSA-N 0.000 description 1
- GYWYASONLSQZBB-UHFFFAOYSA-N 3-methylhexan-2-one Chemical compound CCCC(C)C(C)=O GYWYASONLSQZBB-UHFFFAOYSA-N 0.000 description 1
- AZASWMGVGQEVCS-UHFFFAOYSA-N 4,4-dimethylpentan-2-one Chemical compound CC(=O)CC(C)(C)C AZASWMGVGQEVCS-UHFFFAOYSA-N 0.000 description 1
- BFQJUBYBQLIYJZ-UHFFFAOYSA-N 4,8-dimethylundecan-6-one Chemical compound CCCC(C)CC(=O)CC(C)CCC BFQJUBYBQLIYJZ-UHFFFAOYSA-N 0.000 description 1
- YTRCPWNJUYKWII-UHFFFAOYSA-N C1(CCC(=O)OC(C2CCC(CC2)(CC)CC)O1)=O Chemical compound C1(CCC(=O)OC(C2CCC(CC2)(CC)CC)O1)=O YTRCPWNJUYKWII-UHFFFAOYSA-N 0.000 description 1
- IWMRWSJRBVNREH-UHFFFAOYSA-N C1(CCC(=O)OC2(C(C2CC)CC)O1)=O Chemical compound C1(CCC(=O)OC2(C(C2CC)CC)O1)=O IWMRWSJRBVNREH-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000006600 Stobbe condensation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QCOAPBRVQHMEPF-UHFFFAOYSA-N bis(2-methylpropyl) butanedioate Chemical compound CC(C)COC(=O)CCC(=O)OCC(C)C QCOAPBRVQHMEPF-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- NUKMATKUYJULRD-UHFFFAOYSA-N diethyl 2,3-bis(2-ethylhexylidene)butanedioate Chemical compound C(C)OC(C(C(C(=O)OCC)=CC(CCCC)CC)=CC(CCCC)CC)=O NUKMATKUYJULRD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- VCRYGHPVKURQMM-UHFFFAOYSA-N methane;platinum Chemical compound C.[Pt] VCRYGHPVKURQMM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01202184 | 2001-06-07 | ||
| PCT/EP2002/006097 WO2002098837A1 (en) | 2001-06-07 | 2002-06-04 | Process for preparing alkylidene substituted succinic acid esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004519525A JP2004519525A (ja) | 2004-07-02 |
| JP2004519525A5 JP2004519525A5 (enExample) | 2009-02-26 |
| JP4295083B2 true JP4295083B2 (ja) | 2009-07-15 |
Family
ID=8180433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003501828A Expired - Lifetime JP4295083B2 (ja) | 2001-06-07 | 2002-06-04 | アルキリデン置換コハク酸エステルの製法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6914153B2 (enExample) |
| EP (1) | EP1392638B1 (enExample) |
| JP (1) | JP4295083B2 (enExample) |
| CN (1) | CN100349850C (enExample) |
| BR (1) | BR0205610B1 (enExample) |
| MX (1) | MXPA03001149A (enExample) |
| WO (1) | WO2002098837A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003253336A1 (en) * | 2002-08-05 | 2004-02-25 | Basel Poliolefine Italia S.P.A. | Process for preparing alkylidene-substituted-1,4-dions derivatives |
| JP2006265169A (ja) * | 2005-03-24 | 2006-10-05 | Tokuyama Corp | アルキリデンコハク酸化合物の製造方法 |
| FR2921368B1 (fr) | 2007-09-25 | 2012-10-12 | Pf Medicament | Nouveau procede de synthese de derives anticancereux de (poly) aminoalkylaminoacetamide d'epipodophyllotoxine. |
| US8507628B2 (en) | 2007-10-02 | 2013-08-13 | Fina Technology, Inc. | Propylene based polymers for injection stretch blow molding |
| US9090000B2 (en) * | 2009-03-26 | 2015-07-28 | Fina Technology, Inc. | Injection stretch blow molded articles and random copolymers for use therein |
| KR101114073B1 (ko) * | 2009-12-08 | 2012-02-22 | 삼성토탈 주식회사 | 프로필렌 중합용 고체촉매의 제조 방법 |
| EP2751059B1 (en) | 2011-08-29 | 2015-09-16 | Saudi Basic Industries Corporation | Process for preparing di-substituted succinates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE800227C (de) | 1949-07-27 | 1950-10-17 | Heumann Ludwig & Co Gmbh | Verfahren zur Herstellung von 1, 4-substituierten Butadien-(1, 3)-2, 3-dicarbonsaeureestern |
| US4939288A (en) * | 1989-01-23 | 1990-07-03 | Monsanto Company | Method of preparing (R)-succinic acid derivatives |
| US5900517A (en) | 1995-08-30 | 1999-05-04 | Enichem S.P.A. | Cyclopentadienyl derivatives and process for their preparation |
-
2002
- 2002-06-04 MX MXPA03001149A patent/MXPA03001149A/es active IP Right Grant
- 2002-06-04 BR BRPI0205610-0A patent/BR0205610B1/pt not_active IP Right Cessation
- 2002-06-04 CN CNB028109287A patent/CN100349850C/zh not_active Expired - Lifetime
- 2002-06-04 EP EP02738146.6A patent/EP1392638B1/en not_active Expired - Lifetime
- 2002-06-04 WO PCT/EP2002/006097 patent/WO2002098837A1/en not_active Ceased
- 2002-06-04 JP JP2003501828A patent/JP4295083B2/ja not_active Expired - Lifetime
- 2002-06-04 US US10/343,884 patent/US6914153B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20030181743A1 (en) | 2003-09-25 |
| CN100349850C (zh) | 2007-11-21 |
| JP2004519525A (ja) | 2004-07-02 |
| BR0205610A (pt) | 2003-07-15 |
| CN1512979A (zh) | 2004-07-14 |
| WO2002098837A1 (en) | 2002-12-12 |
| BR0205610B1 (pt) | 2012-08-07 |
| US6914153B2 (en) | 2005-07-05 |
| MXPA03001149A (es) | 2003-06-09 |
| EP1392638B1 (en) | 2016-12-14 |
| EP1392638A1 (en) | 2004-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2262756B1 (en) | Process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates | |
| JP4295083B2 (ja) | アルキリデン置換コハク酸エステルの製法 | |
| EP1433772B2 (en) | Method for producing 2-(alkyl)cycloalkenone | |
| JP2004519525A5 (enExample) | ||
| JP2004203844A (ja) | ２−（アルキリデン）シクロアルカノンの製法 | |
| US6500990B2 (en) | Method for producing jasmonate derivatives and intermediates thereof | |
| JP4407896B2 (ja) | ２−（アルキル）シクロアルケノンの製法 | |
| US7091151B2 (en) | Catalytic system for aldol reactions | |
| JP4464274B2 (ja) | アルキリデン置換−１，４−ジオン誘導体の製造法 | |
| JPWO2010113531A1 (ja) | 高純度末端オレフィン化合物の製造方法 | |
| US10138189B2 (en) | Methods for producing 2,6-dimethyl-1,5-heptadien-3-ol and 2,6-dimethyl-1,5-heptadien-3-yl acetate | |
| JP4464275B2 (ja) | アルキリデン置換−１，４−ジオン誘導体の製造法 | |
| US5981792A (en) | Process for the production of 1-functional allylalcohol carboxylic esters | |
| JP4881312B2 (ja) | シクロペンタンカルボキシレート化合物、その製造のための方法及び中間体並びにその使用 | |
| JP4216248B2 (ja) | ジャスモン酸エステル誘導体及びその中間体の製造法 | |
| US20020198401A1 (en) | Method for producing 2,3,5,6-tetrahalogen-xylylidene compounds | |
| JP3993427B2 (ja) | 脂環式ヒドロキシカルボン酸の製造方法 | |
| JP2018108942A (ja) | アセト酢酸エステルアルカリ塩の製造方法および脂肪族ジケトンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050526 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050526 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080616 |
|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20080623 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080624 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20080630 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080924 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20081001 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20081024 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20081031 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20081111 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090311 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090409 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120417 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4295083 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130417 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140417 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |