CS118891A2 - Catalictic mixtures - Google Patents

Catalictic mixtures Download PDF

Info

Publication number: CS118891A2
Authority: CS; Czechoslovakia
Prior art keywords: group; bisphosphine; bis; catalytic; mixture
Prior art date: 1990-04-27

Application number

CS911188A

Other languages

Czech (cs)

English (en)

Inventor

Johanes Jacobus Keijsper

Der Made Alexander Willem Van

Original Assignee

Shell Int Research

Priority date (The priority date 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 date listed.)

1990-04-27

Filing date

1991-04-25

Publication date

1991-12-17

1991-04-25 Application filed by Shell Int Research filed Critical Shell Int Research

1991-12-17 Publication of CS118891A2 publication Critical patent/CS118891A2/cs

Links

239000000203 mixture Substances 0.000 title claims description 63
-1 methoxyl substituent Chemical group 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 32
229920000642 polymer Polymers 0.000 claims description 30
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 25
229910002091 carbon monoxide Inorganic materials 0.000 claims description 25
230000003197 catalytic effect Effects 0.000 claims description 25
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
238000004519 manufacturing process Methods 0.000 claims description 19
229910052751 metal Inorganic materials 0.000 claims description 15
239000002184 metal Substances 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
230000000737 periodic effect Effects 0.000 claims description 13
229910052763 palladium Inorganic materials 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004437 phosphorous atom Chemical group 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000000178 monomer Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
HIQNEJUMZTWMLW-UHFFFAOYSA-N 2-(bromomethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(CBr)C(C)=C1 HIQNEJUMZTWMLW-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000005082 alkoxyalkenyl group Chemical group 0.000 claims 1
150000004676 glycans Chemical class 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
229920001282 polysaccharide Polymers 0.000 claims 1
239000005017 polysaccharide Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 32
229920001897 terpolymer Polymers 0.000 description 30
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 18
239000005977 Ethylene Substances 0.000 description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 13
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 10
239000001294 propane Substances 0.000 description 10
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
150000001450 anions Chemical class 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
XFUUFBLWGWFPHO-UHFFFAOYSA-N [3-bromo-2-(bromomethyl)propyl]benzene Chemical compound BrCC(CBr)CC1=CC=CC=C1 XFUUFBLWGWFPHO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
230000035484 reaction time Effects 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
LODRGECCKZZTEQ-UHFFFAOYSA-N 2-benzylpropane-1,3-diol Chemical compound OCC(CO)CC1=CC=CC=C1 LODRGECCKZZTEQ-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
BPBDZXFJDMJLIB-UHFFFAOYSA-N 2-phenylpropane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=C1 BPBDZXFJDMJLIB-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
HVELAOQZAFXLRD-UHFFFAOYSA-N 1,3-dibromopropan-2-yloxymethylbenzene Chemical compound BrCC(CBr)OCC1=CC=CC=C1 HVELAOQZAFXLRD-UHFFFAOYSA-N 0.000 description 4
GIHLNZRKIMYHEE-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)pentane Chemical compound CCCC(CBr)CBr GIHLNZRKIMYHEE-UHFFFAOYSA-N 0.000 description 4
UXWURUWEMZGZES-UHFFFAOYSA-N 2-(1,3-dibromopropan-2-yloxymethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(COC(CBr)CBr)C(C)=C1 UXWURUWEMZGZES-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
KTITXCBEQVXBCV-UHFFFAOYSA-N [2-benzyl-3-bis(2-methoxyphenyl)phosphanylpropyl]-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC(CC=1C=CC=CC=1)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC KTITXCBEQVXBCV-UHFFFAOYSA-N 0.000 description 4
239000012280 lithium aluminium hydride Substances 0.000 description 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
QRNSGEFSAXCAKE-UHFFFAOYSA-N 1,3-dibromopropan-2-ylbenzene Chemical compound BrCC(CBr)C1=CC=CC=C1 QRNSGEFSAXCAKE-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
CVTBEWNXYIMNBC-UHFFFAOYSA-N [3-bis(2-methoxyphenyl)phosphanyl-2-phenylmethoxypropyl]-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC(OCC=1C=CC=CC=1)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC CVTBEWNXYIMNBC-UHFFFAOYSA-N 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
229910000073 phosphorus hydride Inorganic materials 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
PKBFVTXNGGQGPP-UHFFFAOYSA-N 2-[bis(2-methoxyphenyl)phosphanylmethyl]pentyl-bis(2-methoxyphenyl)phosphane Chemical compound C=1C=CC=C(OC)C=1P(C=1C(=CC=CC=1)OC)CC(CCC)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC PKBFVTXNGGQGPP-UHFFFAOYSA-N 0.000 description 2
FZHZPYGRGQZBCV-UHFFFAOYSA-N 2-propylpropane-1,3-diol Chemical compound CCCC(CO)CO FZHZPYGRGQZBCV-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
229930040373 Paraformaldehyde Natural products 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
ZGZXNTFQFNCLAX-UHFFFAOYSA-N [3-bis(2-methoxyphenyl)phosphanyl-2-[(2,4,6-trimethylphenyl)methoxy]propyl]-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC(OCC=1C(=CC(C)=CC=1C)C)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC ZGZXNTFQFNCLAX-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000003977 halocarboxylic acids Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
229960002523 mercuric chloride Drugs 0.000 description 2
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
229920002866 paraformaldehyde Polymers 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JHOWMCBSVKWDGJ-UHFFFAOYSA-N 1,3-dichloro-2-(ethoxymethoxy)propane Chemical compound CCOCOC(CCl)CCl JHOWMCBSVKWDGJ-UHFFFAOYSA-N 0.000 description 1
229940005561 1,4-benzoquinone Drugs 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
PNZNRRLYMLDCQJ-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(CCBr)C(C)=C1 PNZNRRLYMLDCQJ-UHFFFAOYSA-N 0.000 description 1
REDMBNQXBOTRET-UHFFFAOYSA-N 2-hydroxy-2-phenylbutanedioic acid Chemical compound OC(=O)CC(O)(C(O)=O)C1=CC=CC=C1 REDMBNQXBOTRET-UHFFFAOYSA-N 0.000 description 1
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
NYHPDWYNFJIBTJ-UHFFFAOYSA-N [3-bis(2-methoxyphenyl)phosphanyl-2-(ethoxymethoxy)propyl]-bis(2-methoxyphenyl)phosphane Chemical compound C=1C=CC=C(OC)C=1P(C=1C(=CC=CC=1)OC)CC(OCOCC)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC NYHPDWYNFJIBTJ-UHFFFAOYSA-N 0.000 description 1
PUKSHJDYPYXUKZ-UHFFFAOYSA-N [3-bis(2-methoxyphenyl)phosphanyl-2-phenylpropyl]-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC(C=1C=CC=CC=1)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC PUKSHJDYPYXUKZ-UHFFFAOYSA-N 0.000 description 1
BKHJHGONWLDYCV-UHFFFAOYSA-N [C]=O.[C] Chemical compound [C]=O.[C] BKHJHGONWLDYCV-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
RXGLFOLVJOKHPX-UHFFFAOYSA-N bis(2-methoxyphenyl)-propylphosphane Chemical compound C=1C=CC=C(OC)C=1P(CCC)C1=CC=CC=C1OC RXGLFOLVJOKHPX-UHFFFAOYSA-N 0.000 description 1
HFEAMIKDDWKNAG-UHFFFAOYSA-N bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1PC1=CC=CC=C1OC HFEAMIKDDWKNAG-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910021386 carbon form Inorganic materials 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
238000005086 pumping Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-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
IIOSDXGZLBPOHD-UHFFFAOYSA-N tris(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC IIOSDXGZLBPOHD-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5027—Polyphosphines
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5077—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure P-Metal, including R2P-M+
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Crystallography & Structural Chemistry (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Inorganic Chemistry (AREA)
Polyethers (AREA)
Catalysts (AREA)

CS911188A 1990-04-27 1991-04-25 Catalictic mixtures CS118891A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL9001019		1990-04-27

Publications (1)

Publication Number	Publication Date
CS118891A2 true CS118891A2 (en)	1991-12-17

Family

ID=19857024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911188A CS118891A2 (en)	1990-04-27	1991-04-25	Catalictic mixtures

Country Status (18)

Country	Link
US (1)	US5171832A (tr)
EP (1)	EP0454270B1 (tr)
JP (1)	JPH04227726A (tr)
KR (1)	KR910018414A (tr)
CN (1)	CN1034946C (tr)
AU (1)	AU631309B2 (tr)
BR (1)	BR9101666A (tr)
CA (1)	CA2041256A1 (tr)
CS (1)	CS118891A2 (tr)
DE (1)	DE69100774T2 (tr)
ES (1)	ES2061158T3 (tr)
FI (1)	FI912017A7 (tr)
HU (1)	HUT57238A (tr)
MY (1)	MY105449A (tr)
PL (1)	PL290030A1 (tr)
RU (1)	RU2060259C1 (tr)
TR (1)	TR24942A (tr)
ZA (1)	ZA913120B (tr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2274252A (en) *	1992-12-15	1994-07-20	Shell Int Research	Catalyst system and co-polymerization process
EP0702046B1 (en) *	1994-09-15	2000-05-24	Shell Internationale Researchmaatschappij B.V.	Process for the copolymerization of carbon monoxide with an olefinically unsaturated compound
DE19829520A1 (de) *	1998-07-02	2000-01-05	Basf Ag	Katalysatorsysteme auf der Basis von Übergangsmetallkomplexen für die Kohlenmonoxidcopolymerisation in einem wässrigen Medium
US6852662B2 (en) *	1998-07-02	2005-02-08	Basf Aktiengesellschaft	Catalyst systems based on transition metal complexes for carbon monoxide copolymerization in an aqueous medium
DE19846053A1 (de) *	1998-10-07	2000-04-13	Basf Ag	Verfahren zur Herstellung von linearen, alternierenden Kohlenmonoxidcopolymeren
KR100789141B1 (ko)	2006-12-28	2007-12-28	주식회사 효성	폴리케톤의 제조방법
JP6118318B2 (ja)	2011-07-21	2017-04-19	ジーイー・ヘルスケア・リミテッド	前駆体化合物及びその製造方法
KR101832850B1 (ko)	2015-09-09	2018-02-27	이재권	3,3-비스-[비스-(2-메톡시페닐)포스파닐메틸]-1,5-디옥시-스파이로[5,5]운데칸 및 그의 유도체 제조방법

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3694412A (en) *	1971-03-04	1972-09-26	Shell Oil Co	Process for preparing interpolymers of carbon monoxide in the presence of aryl phosphine-palladium halide complex
US4331818A (en) *	1980-03-19	1982-05-25	The Procter & Gamble Company	Chiral phospine ligand
EP0121965B1 (en) *	1983-04-06	1989-12-27	Shell Internationale Researchmaatschappij B.V.	Process for the preparation of polyketones
NL8403035A (nl) *	1984-10-05	1986-05-01	Shell Int Research	Werkwijze ter bereiding van polyketonen.
IN166314B (tr) *	1985-08-29	1990-04-07	Shell Int Research
IN171627B (tr) *	1986-08-26	1992-11-28	Shell Int Research
NL8602164A (nl) *	1986-08-26	1988-03-16	Shell Int Research	Katalysatorcomposities.
CA1333619C (en) *	1987-06-24	1994-12-20	Johannes Adrianus Van Doorn	Catalyst compositions
US4933311A (en) *	1987-06-24	1990-06-12	Shell Oil Company	Polymerization process
DE3883724T2 (de) *	1987-12-11	1994-04-28	Showa Denko Kk	Verfahren zur Herstellung von Aminen vom Allyltyp.
US5010172A (en) *	1989-01-20	1991-04-23	Shell Oil Company	Polymerization of carbon monoxide/olefin with tertiary monophosphine or secondary monophosphine oxide
EP0380162B1 (en) *	1989-01-26	1995-04-12	Shell Internationale Researchmaatschappij B.V.	Catalyst compositions

1991
- 1991-04-12 US US07/684,109 patent/US5171832A/en not_active Expired - Fee Related
- 1991-04-24 KR KR1019910006611A patent/KR910018414A/ko not_active Withdrawn
- 1991-04-24 AU AU75907/91A patent/AU631309B2/en not_active Ceased
- 1991-04-25 ZA ZA913120A patent/ZA913120B/xx unknown
- 1991-04-25 HU HU911389A patent/HUT57238A/hu unknown
- 1991-04-25 MY MYPI91000710A patent/MY105449A/en unknown
- 1991-04-25 RU SU914895259A patent/RU2060259C1/ru active
- 1991-04-25 PL PL29003091A patent/PL290030A1/xx unknown
- 1991-04-25 BR BR919101666A patent/BR9101666A/pt not_active IP Right Cessation
- 1991-04-25 DE DE91201007T patent/DE69100774T2/de not_active Expired - Fee Related
- 1991-04-25 ES ES91201007T patent/ES2061158T3/es not_active Expired - Lifetime
- 1991-04-25 EP EP91201007A patent/EP0454270B1/en not_active Expired - Lifetime
- 1991-04-25 CA CA002041256A patent/CA2041256A1/en not_active Abandoned
- 1991-04-25 JP JP3122576A patent/JPH04227726A/ja active Pending
- 1991-04-25 FI FI912017A patent/FI912017A7/fi not_active Application Discontinuation
- 1991-04-25 CN CN91102637A patent/CN1034946C/zh not_active Expired - Fee Related
- 1991-04-25 CS CS911188A patent/CS118891A2/cs unknown
- 1991-05-07 TR TR91/0386A patent/TR24942A/tr unknown

Also Published As

Publication number	Publication date
FI912017L (fi)	1991-10-28
CN1056108A (zh)	1991-11-13
EP0454270B1 (en)	1993-12-15
CN1034946C (zh)	1997-05-21
EP0454270A1 (en)	1991-10-30
DE69100774T2 (de)	1994-04-28
ZA913120B (en)	1992-02-26
FI912017A0 (fi)	1991-04-25
CA2041256A1 (en)	1991-10-28
KR910018414A (ko)	1991-11-30
AU631309B2 (en)	1992-11-19
AU7590791A (en)	1991-11-28
US5171832A (en)	1992-12-15
BR9101666A (pt)	1991-12-10
JPH04227726A (ja)	1992-08-17
TR24942A (tr)	1992-07-01
MY105449A (en)	1994-10-31
HU911389D0 (en)	1991-10-28
DE69100774D1 (de)	1994-01-27
FI912017A7 (fi)	1991-10-28
RU2060259C1 (ru)	1996-05-20
HUT57238A (en)	1991-11-28
ES2061158T3 (es)	1994-12-01
PL290030A1 (en)	1992-08-24

Publication	Publication Date	Title
KR970004932B1 (ko)	1997-04-10	신규한 촉매 조성물, 그를 사용하여 중합체를 제조하는 방법 및 그로부터 제조된 중합체
CA1336910C (en)	1995-09-05	Catalytic composition for the polymerisation of carbon monoxide with an olefin based on a palladium compound and a diphosphine
JP2618004B2 (ja)	1997-06-11	触媒組成物
US4940683A (en)	1990-07-10	Polymerization process
CS118891A2 (en)	1991-12-17	Catalictic mixtures
EP0526949A1 (en)	1993-02-10	Catalyst compositions suitable for the preparation of polymers of carbon monoxide and alpha-olefins
JPH05194727A (ja)	1993-08-03	一酸化炭素とオレフィン性不飽和化合物とのポリマー製造用触媒組成物
JP2643977B2 (ja)	1997-08-25	置換ジアリールホスファイドの製造
EP0456317B1 (en)	1993-08-25	Catalyst compositions and polymerization process, hexakisphosphines and hexahalo compounds
EP0408155B1 (en)	1995-10-11	Catalyst compositions for the preparation of polymers of carbon monoxide with olefinically unsaturated compounds
EP1192205A1 (en)	2002-04-03	Catalyst composition and use thereof
JP2862610B2 (ja)	1999-03-03	触媒組成物
US5229343A (en)	1993-07-20	Polymerization process