JP4183618B2 - ジホスフィン - Google Patents
ジホスフィン Download PDFInfo
- Publication number
- JP4183618B2 JP4183618B2 JP2003534439A JP2003534439A JP4183618B2 JP 4183618 B2 JP4183618 B2 JP 4183618B2 JP 2003534439 A JP2003534439 A JP 2003534439A JP 2003534439 A JP2003534439 A JP 2003534439A JP 4183618 B2 JP4183618 B2 JP 4183618B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- diphosphine
- decyl
- phospha
- trioxatricyclo
- 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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- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 title claims description 48
- 229910052698 phosphorus Inorganic materials 0.000 claims description 57
- -1 2 -phosphatricyclo [3.3.1.1 {3,7}] decyl group Chemical group 0.000 claims description 48
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 25
- 229910052763 palladium Inorganic materials 0.000 claims description 25
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 24
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 23
- 238000005810 carbonylation reaction Methods 0.000 claims description 19
- 230000006315 carbonylation Effects 0.000 claims description 17
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000001993 dienes Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000001273 butane Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 9
- 150000002941 palladium compounds Chemical class 0.000 claims description 9
- 125000004437 phosphorous atom Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 4
- IREINSNPXVMWID-UHFFFAOYSA-N ethyl-[(1,3,5,7-tetramethyl-2,4,6-trioxatricyclo[3.3.1.13,7]decan-8-yl)methyl]phosphane Chemical compound CC12C(C3(CC(OC(C1)(O3)C)(O2)C)C)CPCC IREINSNPXVMWID-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims description 4
- RFXAVEPWLRRSLE-UHFFFAOYSA-N CC12C(C3(CC(OC(C1)(O3)C)(O2)C)C)CPCCC Chemical compound CC12C(C3(CC(OC(C1)(O3)C)(O2)C)C)CPCCC RFXAVEPWLRRSLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 20
- 150000001450 anions Chemical class 0.000 description 12
- HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 2
- MBIZFBDREVRUHY-UHFFFAOYSA-N 2,6-Dimethoxybenzoic acid Chemical compound COC1=CC=CC(OC)=C1C(O)=O MBIZFBDREVRUHY-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical class NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- UIRWNAVHKJFQQG-UHFFFAOYSA-N 1,1,1,3,3,5,5,5-octafluoropentane-2,4-dione Chemical compound FC(F)(F)C(=O)C(F)(F)C(=O)C(F)(F)F UIRWNAVHKJFQQG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 description 1
- DJXHXILQRDQZGU-UHFFFAOYSA-N 2-phosphatricyclo[3.3.1.13,7]decane Chemical group C1C(P2)CC3CC1CC2C3 DJXHXILQRDQZGU-UHFFFAOYSA-N 0.000 description 1
- KRMWJAMEOOZEQN-UHFFFAOYSA-N 3-phosphanylbutan-2-ylphosphane Chemical compound CC(P)C(C)P KRMWJAMEOOZEQN-UHFFFAOYSA-N 0.000 description 1
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 1
- VOAXSDYMVCZQHO-UHFFFAOYSA-N 4-phosphanylbutylphosphane Chemical compound PCCCCP VOAXSDYMVCZQHO-UHFFFAOYSA-N 0.000 description 1
- DQVXKBASSJKPAY-UHFFFAOYSA-N 5-phosphanylpentylphosphane Chemical group PCCCCCP DQVXKBASSJKPAY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- YRRTUCFPJHHYHO-UHFFFAOYSA-N CC(C(=O)O)=CCC.CC(CC(=O)O)CC Chemical compound CC(C(=O)O)=CCC.CC(CC(=O)O)CC YRRTUCFPJHHYHO-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- SHCSFZHSNSGTOP-UHFFFAOYSA-N Methyl 4-pentenoate Chemical compound COC(=O)CCC=C SHCSFZHSNSGTOP-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229910008449 SnF 2 Inorganic materials 0.000 description 1
- 150000001260 acyclic compounds Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- YIYBQIKDCADOSF-ARJAWSKDSA-N cis-pent-2-enoic acid Chemical compound CC\C=C/C(O)=O YIYBQIKDCADOSF-ARJAWSKDSA-N 0.000 description 1
- UIUWNILCHFBLEQ-IHWYPQMZSA-N cis-pent-3-enoic acid Chemical compound C\C=C/CC(O)=O UIUWNILCHFBLEQ-IHWYPQMZSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- QAMFBRUWYYMMGJ-UHFFFAOYSA-N hexafluoroacetylacetone Chemical compound FC(F)(F)C(=O)CC(=O)C(F)(F)F QAMFBRUWYYMMGJ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- MBAHGFJTIVZLFB-SNAWJCMRSA-N methyl (e)-pent-2-enoate Chemical compound CC\C=C\C(=O)OC MBAHGFJTIVZLFB-SNAWJCMRSA-N 0.000 description 1
- KJALUUCEMMPKAC-ONEGZZNKSA-N methyl (e)-pent-3-enoate Chemical compound COC(=O)C\C=C\C KJALUUCEMMPKAC-ONEGZZNKSA-N 0.000 description 1
- MBAHGFJTIVZLFB-PLNGDYQASA-N methyl (z)-pent-2-enoate Chemical compound CC\C=C/C(=O)OC MBAHGFJTIVZLFB-PLNGDYQASA-N 0.000 description 1
- KJALUUCEMMPKAC-ARJAWSKDSA-N methyl (z)-pent-3-enoate Chemical compound COC(=O)C\C=C/C KJALUUCEMMPKAC-ARJAWSKDSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
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Description
R1>P−R2−PR3R4
[但し、R1が、無置換又は置換の2−ホスファトリシクロ[3.3.1.1{3,7}]デシル基を表し、R2が架橋基を表し、R3及びR4が、それぞれ相互に独立して1〜20個の炭素原子を有する1価の基を表すか、あるいは一緒になって2〜20個の炭素原子を有する2価の基を形成する。]
で表されるジホスフィンを使用することにより活性度を増加させることができることが、特許文献3に記載されており、公知である。R2について記載された特定の例としては、1,2−エタン及び1,3−プロパン基のみが挙げられている。特許文献3に示された例によれば、このようなジホスフィンは、エチレン、プロペン、α−C14−オレフィン及び3−メチルペンタノエート(ペンテン酸メチル)のカルボニル化において高い活性又は選択性をもたらすようである。しかしながら、このような組成物を、1,3−ブタジエン等の共役ジエンの場合に使用すると、その選択性が前述の特許文献1におけるより遙かに悪くなる。
[但し、R 1 が、それが結合するリン原子と共に、2−ホスファトリシクロ[3.3.1.1{3,7}]デシル基、又は1個以上の炭素原子がヘテロ原子と置換された前記基の誘導体を形成する2価の基を表し、
R 2 、R 3 が、それぞれ相互に独立して1〜20個の原子を有するアルキル、アリール、ヘテロアリール、ヘテロヒドロカルビル、又はアルコキシを表すか、あるいはR 2 及びR 3 が一緒になって1,5−ペンチレン、1,6−へキシレン、1,3−シクロオクチレン、1,4−シクロオクチレンを形成するか、又はR 2 及びR 3 が共に結合するリン原子と一緒になって、2−ホスファトリシクロ[3.3.1.1{3,7}]デシル基を形成し、そして
nが4又は5を表す。]
で表されるジホスフィン又はこれらの混合物、カルボニル化触媒として好適で且つパラジウム又はパラジウム化合物及びこのようなジホスフィンを含む組成物、そしてこのような組成物の存在下に共役ジエンをカルボニル化する方法により達成されることを見出した。
(I)パラジウム又はパラジウム化合物及び
(II)前記のジホスフィンの1種
を含んでいる。
によって図で表すことができる。
を含む有機化合物である。
107gのジフェニルエーテル、20mlのメタノール、20mlのブタジエン、0.5ミリモルのパラジウム、1ミリモルの1,4−P,P’−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタン及び30ミリモルの2,4,6−トリメチル安息香酸を、窒素雰囲気下、磁気スターラを備えたオートクレーブ(270ml)内に投入した。オートクレーブを閉じ、40バールの一酸化炭素で加圧し、そして150℃に加熱した。この温度に到達した後、さらに一酸化炭素を導入することにより、圧力を10時間一定に維持した。オートクレーブを冷却、ガス抜きした後、反応溶液を取り出した。その溶液は、パラジウムの析出のない透明な黄色溶液であった。種々の生成物の転化率及び選択率を、溶液のGC分析により測定した。
1ミリモルの1,4−P,P’−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタンの代わりに1ミリモルの1,3−P,P’−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)プロパンを用いて実施例1を繰り返した。反応溶液は、パラジウムの析出のない透明な黄色であった。
1ミリモルの1,4−P,P’−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタンの代わりに1ミリモルの1,4−ビス(ジフェニルホスフィノ)ブタンを用いて実施例1を繰り返した。反応後、反応混合物は黒色のパラジウム析出物を含むものであった。
1ミリモルの1,4−P,P’−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタンの代わりに1ミリモルの1,3−ビス(ジシクロヘキシルホスフィノ)エタンを用いて実施例1を繰り返した。反応後の反応溶液は、パラジウムの析出のない透明な黄色であった。
1ミリモルの1,4−P,P’−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタンの代わりに1ミリモルの1,3−ビス(1,5−シクロオクチレンホスフィノ)プロパンを用いて実施例1を繰り返した。反応後、反応混合物は黒色のパラジウム析出物を含むものであった。
Claims (13)
- 式:
R2、R3が、それぞれ相互に独立して1〜20個の原子を有するアルキル、アリール、ヘテロアリール、ヘテロヒドロカルビル、又はアルコキシを表すか、あるいはR 2 及びR 3 が一緒になって1,5−ペンチレン、1,6−へキシレン、1,3−シクロオクチレン、1,4−シクロオクチレンを形成するか、又はR 2 及びR 3 が共に結合するリン原子と一緒になって、2−ホスファトリシクロ[3.3.1.1{3,7}]デシル基を形成し、そして
nが4又は5を表す。]
で表されるジホスフィン又はこれらの混合物。 - R1が、1位、3位、5位及び7位の1以上の位置で1〜20個の原子を有する1価の基R4で置換され、R 4 が、メチル、トリフルオロメチル、エトキシ、フェニル及び4−ドデシルフェニルから構成される群から選択された基である請求項1に記載のジホスフィン。
- R1が、1位、3位、5位及び7位の各位置で、基R 4 で置換され、R 4 が、メチル、トリフルオロメチル、エトキシ、フェニル及び4−ドデシルフェニルから構成される群から選択された基である請求項1又は2に記載のジホスフィン。
- R1が、骨格に酸素又はイオウを含んでいる請求項1〜3のいずれかに記載のジホスフィン。
- R1が、2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキソアダマンチル基である請求項1〜4のいずれかに記載のジホスフィン。
- R2及びR3が一緒になって請求項1〜5のいずれかに記載の基R 1 を形成する請求項1〜5のいずれかに記載のジホスフィン。
- nが4である請求項1〜6のいずれかに記載のジホスフィン。
- nが5である請求項1〜6のいずれかに記載のジホスフィン。
- 1,4−P,P'−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタン、1,4−P,P'−ジペルフルオロ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタン、1,4−P,P'−ジ(2−ホスファ−1,3,5,7−テトラ(トリフルオロメチル)−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ブタンから構成される群から選択される請求項1に記載のジホスフィン。
- 1,5−P,P'−ジ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ペンタン、1,5−P,P'−ジペルフルオロ(2−ホスファ−1,3,5,7−テトラメチル−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ペンタン、1,5−P,P'−ジ(2−ホスファ−1,3,5,7−テトラ(トリフルオロメチル)−6,9,10−トリオキサトリシクロ[3.3.1.1{3,7}]デシル)ペンタンから構成される群から選択される請求項1に記載のジホスフィン。
- カルボニル化触媒として好適で、且つ
(I)パラジウム又はパラジウム化合物及び
(II)請求項1〜10に記載のジホスフィン
を含む組成物。 - 液相中で、ヒドロキシル含有化合物の存在下に共役ジエンをカルボニル化することによりアルキレンカルボン酸又はその誘導体を製造する方法であって、
上記カルボニル化を、カルボニル化触媒として好適で、且つ
(I)パラジウム又はパラジウム化合物及び
(II)請求項1〜10に記載のジホスフィン
を含む組成物の存在下に行うことを特徴とする方法。 - 共役ジエンとして1,3−ブタジエンを用いて、ペンテン酸又はその誘導体を得る請求項12に記載の方法。
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DE10148712A DE10148712A1 (de) | 2001-10-02 | 2001-10-02 | Diphosphin |
PCT/EP2002/010798 WO2003031457A1 (de) | 2001-10-02 | 2002-09-26 | Diphosphin |
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JP2005504850A JP2005504850A (ja) | 2005-02-17 |
JP4183618B2 true JP4183618B2 (ja) | 2008-11-19 |
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EP (1) | EP1434781B1 (ja) |
JP (1) | JP4183618B2 (ja) |
KR (1) | KR100881534B1 (ja) |
CN (1) | CN1297562C (ja) |
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DE (2) | DE10148712A1 (ja) |
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US20060235241A1 (en) * | 2003-05-22 | 2006-10-19 | Eit Drent | Process for the carbonylation of a conuugated diene |
JP2007524697A (ja) * | 2004-02-26 | 2007-08-30 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | 共役ジエンのカルボニル化のためのプロセス |
US7265242B2 (en) | 2004-02-26 | 2007-09-04 | Shell Oil Company | Process for the carbonylation of ethylenically or acetylenically unsaturated compounds |
BRPI0507918A (pt) * | 2004-02-26 | 2007-07-10 | Shell Int Research | processo para a carbonilação de compostos insaturados, composição de catalisador, e, ligando de difosfina bidentado assimétrico |
FR2943061B1 (fr) * | 2009-03-13 | 2011-02-25 | Rhodia Operations | Composes organophosphores, systemes catalytiques comprenant ces composes et procede d'hydrocyanation ou d'hydroformylation utilisant ces systemes catalytiques |
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WO2003031457A1 (de) | 2003-04-17 |
MXPA04002504A (es) | 2004-05-31 |
US7074965B2 (en) | 2006-07-11 |
CN1297562C (zh) | 2007-01-31 |
AR036635A1 (es) | 2004-09-22 |
US20040249216A1 (en) | 2004-12-09 |
CN1564825A (zh) | 2005-01-12 |
ES2269810T3 (es) | 2007-04-01 |
MY134246A (en) | 2007-11-30 |
DE10148712A1 (de) | 2003-04-17 |
EP1434781B1 (de) | 2006-07-26 |
BR0212590A (pt) | 2004-10-13 |
CA2461920A1 (en) | 2003-04-17 |
EP1434781A1 (de) | 2004-07-07 |
KR100881534B1 (ko) | 2009-02-05 |
DE50207666D1 (de) | 2006-09-07 |
JP2005504850A (ja) | 2005-02-17 |
KR20050030885A (ko) | 2005-03-31 |
ATE334134T1 (de) | 2006-08-15 |
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