JP2004519525A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004519525A5 JP2004519525A5 JP2003501828A JP2003501828A JP2004519525A5 JP 2004519525 A5 JP2004519525 A5 JP 2004519525A5 JP 2003501828 A JP2003501828 A JP 2003501828A JP 2003501828 A JP2003501828 A JP 2003501828A JP 2004519525 A5 JP2004519525 A5 JP 2004519525A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- formula
- substituted
- ketone
- succinate
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
- 150000001875 compounds Chemical class 0.000 description 54
- 238000000034 method Methods 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- 150000003900 succinic acid esters Chemical class 0.000 description 25
- 150000002430 hydrocarbons Chemical group 0.000 description 24
- 239000000047 product Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 239000012429 reaction media Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 13
- 150000002576 ketones Chemical class 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- -1 succinate ester Chemical class 0.000 description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 150000004703 alkoxides Chemical class 0.000 description 9
- 125000001118 alkylidene group Chemical group 0.000 description 9
- 230000032050 esterification Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 8
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical group CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 5
- 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
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229930195735 unsaturated hydrocarbon Natural products 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
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 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
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- XUPXMIAWKPTZLZ-UHFFFAOYSA-N 4-methylhexan-2-one Chemical compound CCC(C)CC(C)=O XUPXMIAWKPTZLZ-UHFFFAOYSA-N 0.000 description 3
- 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
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000003997 cyclic ketones Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 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
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- 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
- GYWYASONLSQZBB-UHFFFAOYSA-N 3-methylhexan-2-one Chemical compound CCCC(C)C(C)=O GYWYASONLSQZBB-UHFFFAOYSA-N 0.000 description 2
- AZASWMGVGQEVCS-UHFFFAOYSA-N 4,4-dimethylpentan-2-one Chemical compound CC(=O)CC(C)(C)C AZASWMGVGQEVCS-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 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
- 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
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000004678 hydrides Chemical class 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
- 230000000737 periodic effect Effects 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
- 239000002994 raw material Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 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
- ARCBZRDYPZWSHF-UHFFFAOYSA-N C1(CCC(=O)OC(C(C(C)C)(CC)CC)O1)=O Chemical compound C1(CCC(=O)OC(C(C(C)C)(CC)CC)O1)=O ARCBZRDYPZWSHF-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
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-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
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 239000000463 material Substances 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
- 150000003254 radicals Chemical class 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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 true JP2004519525A5 (enExample) | 2009-02-26 |
| JP4295083B2 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7550633B2 (en) | Method for the production of isopulegol | |
| JP4295083B2 (ja) | アルキリデン置換コハク酸エステルの製法 | |
| EP3245185B1 (en) | Intermediate compounds for producing perfuming ingredients | |
| JP2004519525A5 (enExample) | ||
| EP1433772B2 (en) | Method for producing 2-(alkyl)cycloalkenone | |
| JP2004203844A (ja) | ２−（アルキリデン）シクロアルカノンの製法 | |
| EP1134210B1 (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 | |
| JPH11228467A (ja) | 飽和アルコールの製造方法 | |
| JP4464274B2 (ja) | アルキリデン置換−１，４−ジオン誘導体の製造法 | |
| EP1577287B1 (en) | Process for producing a cycloalkanone composition | |
| 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 | |
| JPH11171802A (ja) | アルキルビフェニル誘導体の製造法およびその中間体 | |
| US6753444B2 (en) | Method for producing 2,3,5,6-tetrahalogen-xylyidene compounds | |
| 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 | |
| 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 | |
| US6559336B2 (en) | Process for the preparation of 5- and/or 6-substituted-2-hydroxybenzoic acid esters | |
| JP4605766B2 (ja) | アルキリデンシクロペンタノン誘導体の製造法 | |
| EP1368298B1 (en) | Process for the preparation of 5- and/or 6 - substituted - 2 - hydroxy-benzoic acid esters | |
| CN117776882A (zh) | 一种1,3-二羰基化合物的制备方法 | |
| JPS6311344B2 (enExample) |