JPH08302008A - 一酸化炭素とオレフィン性不飽和化合物との共重合化方法 - Google Patents

一酸化炭素とオレフィン性不飽和化合物との共重合化方法

Info

Publication number: JPH08302008A
Authority: JP; Japan
Prior art keywords: group; olefinically unsaturated; unsaturated compound; compound; carbon monoxide
Prior art date: 1995-05-11
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.): Pending

Application number

JP13965596A

Other languages

English (en)

Japanese (ja)

Inventor

Frank Baardman

フランク・バールドマン

Jayne Jubb

ジエイン・ジユツブ

Pieter Scheerman

ピーテル・シエアーマン

Rudolf Jacobus Wijngaarden

ルドルフ・ヤコブス・ウイヤーンガアールデン

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

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.)

1995-05-11

Filing date

1996-05-09

Publication date

1996-11-19

1996-05-09 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1996-11-19 Publication of JPH08302008A publication Critical patent/JPH08302008A/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 38
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims abstract description 25
229910002091 carbon monoxide Inorganic materials 0.000 title claims abstract description 25
238000000034 method Methods 0.000 title claims description 36
229910052751 metal Inorganic materials 0.000 claims abstract description 30
239000002184 metal Substances 0.000 claims abstract description 30
239000003054 catalyst Substances 0.000 claims abstract description 28
-1 boron hydrocarbyl compound Chemical class 0.000 claims abstract description 26
229910052796 boron Inorganic materials 0.000 claims abstract description 24
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 24
239000000203 mixture Substances 0.000 claims abstract description 22
229920001577 copolymer Polymers 0.000 claims abstract description 20
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 19
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 18
125000003118 aryl group Chemical group 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052763 palladium Inorganic materials 0.000 claims abstract description 5
239000004711 α-olefin Substances 0.000 claims abstract description 3
239000003085 diluting agent Substances 0.000 claims description 26
239000003446 ligand Substances 0.000 claims description 21
239000000178 monomer Substances 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
238000006116 polymerization reaction Methods 0.000 claims description 15
239000007787 solid Substances 0.000 claims description 13
239000011236 particulate material Substances 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
239000007788 liquid Substances 0.000 claims description 7
238000003756 stirring Methods 0.000 claims description 7
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
239000011574 phosphorus Substances 0.000 claims description 4
229910052787 antimony Inorganic materials 0.000 claims description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
229910052785 arsenic Inorganic materials 0.000 claims description 3
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 abstract description 3
239000000835 fiber Substances 0.000 abstract description 2
239000005022 packaging material Substances 0.000 abstract description 2
239000010408 film Substances 0.000 abstract 1
238000007334 copolymerization reaction Methods 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002245 particle Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000002253 acid Substances 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
230000001186 cumulative effect Effects 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
229920005603 alternating copolymer Polymers 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
238000005315 distribution function Methods 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
230000001976 improved effect Effects 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
239000013618 particulate matter Substances 0.000 description 2
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 2
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
229920001169 thermoplastic Polymers 0.000 description 2
239000004416 thermosoftening plastic Substances 0.000 description 2
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
DCXDVGKTBDNYRX-UHFFFAOYSA-N 1,2-bis(ethylsulfanyl)ethane Chemical compound CCSCCSCC DCXDVGKTBDNYRX-UHFFFAOYSA-N 0.000 description 1
WERZWRCQQURDDW-UHFFFAOYSA-N 1-(2-propylsulfanylethenylsulfanyl)propane Chemical compound CCCSC=CSCCC WERZWRCQQURDDW-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
RJQXUDISZWMFQR-UHFFFAOYSA-N 3-bis(2,4,6-trimethoxyphenyl)phosphanylpropyl-bis(2,4,6-trimethoxyphenyl)phosphane Chemical compound COC1=CC(OC)=CC(OC)=C1P(C=1C(=CC(OC)=CC=1OC)OC)CCCP(C=1C(=CC(OC)=CC=1OC)OC)C1=C(OC)C=C(OC)C=C1OC RJQXUDISZWMFQR-UHFFFAOYSA-N 0.000 description 1
VPJKUEQDABDUJU-UHFFFAOYSA-N 3-bis(2,4-dimethoxyphenyl)phosphanylpropyl-bis(2,4-dimethoxyphenyl)phosphane Chemical compound COC1=CC(OC)=CC=C1P(C=1C(=CC(OC)=CC=1)OC)CCCP(C=1C(=CC(OC)=CC=1)OC)C1=CC=C(OC)C=C1OC VPJKUEQDABDUJU-UHFFFAOYSA-N 0.000 description 1
SXXPTCXIFIOPQF-UHFFFAOYSA-N 3-bis(2-methoxyphenyl)phosphanylpropyl-bis(2-methoxyphenyl)phosphane Chemical group COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CCCP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC SXXPTCXIFIOPQF-UHFFFAOYSA-N 0.000 description 1
ZHXLLVTYKNOSGA-UHFFFAOYSA-N 3-ethylsulfanylpropyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCSCC)C1=CC=CC=C1 ZHXLLVTYKNOSGA-UHFFFAOYSA-N 0.000 description 1
DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
IMEVSAIFJKKDAP-UHFFFAOYSA-N 4-methoxy-2-(4-methoxypyridin-2-yl)pyridine Chemical compound COC1=CC=NC(C=2N=CC=C(OC)C=2)=C1 IMEVSAIFJKKDAP-UHFFFAOYSA-N 0.000 description 1
NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical compound CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229930192627 Naphthoquinone Natural products 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000000071 blow moulding Methods 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000002950 deficient Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 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
WATLWUFSKRFBOD-UHFFFAOYSA-N difluoro(phenyl)borane Chemical compound FB(F)C1=CC=CC=C1 WATLWUFSKRFBOD-UHFFFAOYSA-N 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000012685 gas phase polymerization Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
CXSYDLCMCLCOCA-UHFFFAOYSA-N hexylboronic acid Chemical compound CCCCCCB(O)O CXSYDLCMCLCOCA-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 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
229910052742 iron Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005684 linear copolymer Polymers 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
150000002791 naphthoquinones Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000011368 organic material Substances 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
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 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
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
229960004889 salicylic acid Drugs 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000004071 soot Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-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
BPKXQSLAVGBZEM-UHFFFAOYSA-N tris[3,5-bis(trifluoromethyl)phenyl]borane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(B(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 BPKXQSLAVGBZEM-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

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Polyethers (AREA)

JP13965596A 1995-05-11 1996-05-09 一酸化炭素とオレフィン性不飽和化合物との共重合化方法 Pending JPH08302008A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP95201239		1995-05-11
NL95201239.1		1995-05-11

Publications (1)

Publication Number	Publication Date
JPH08302008A true JPH08302008A (ja)	1996-11-19

Family

ID=8220289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13965596A Pending JPH08302008A (ja)	1995-05-11	1996-05-09	一酸化炭素とオレフィン性不飽和化合物との共重合化方法

Country Status (3)

Country	Link
JP (1)	JPH08302008A (fr)
CA (1)	CA2176200A1 (fr)
DE (1)	DE69603904T2 (fr)

1996
- 1996-05-09 JP JP13965596A patent/JPH08302008A/ja active Pending
- 1996-05-09 DE DE1996603904 patent/DE69603904T2/de not_active Expired - Fee Related
- 1996-05-09 CA CA 2176200 patent/CA2176200A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
CA2176200A1 (fr)	1996-11-12
DE69603904T2 (de)	2000-03-16
DE69603904D1 (de)	1999-09-30

Publication	Publication Date	Title
US5668249A (en)	1997-09-16	Process for the copolymerization of carbon monoxide with an olefinically unsaturated compound
US5905138A (en)	1999-05-18	Process for the preparation of copolymers
US5658982A (en)	1997-08-19	Process for the copolymerization of carbon monoxide with an olefinically unsaturated compound
US5670611A (en)	1997-09-23	Process for the copolymerization of carbon monoxide with an olefinically unsaturated compound
EP0642545B1 (fr)	1999-09-22	Procede de preparation de copolymeres de monoxyde de carbone et de composes non satures d'ethylene
JPH08302008A (ja)	1996-11-19	一酸化炭素とオレフィン性不飽和化合物との共重合化方法
EP0733660B1 (fr)	1999-12-22	Procédé pour la copolymérisation de monoxide de carbone et de composés à insaturation oléfinique
JPH11507966A (ja)	1999-07-13	一酸化炭素とオレフィン性不飽和化合物のコポリマーの製造用触媒組成物及び方法
EP0742242B1 (fr)	1999-08-25	Procédé pour la copolymerisation de monoxyde de carbone avec un composé à insaturation oléfine
EP0702046B1 (fr)	2000-05-24	Procédé pour la copolymérisation du monoxyde de carbone avec un composé à insaturation oléfine
EP0733661B1 (fr)	1999-11-03	Procédé pour la copolymérisation de monoxide de carbone et de composés à insaturation oléfinique
EP0733662A1 (fr)	1996-09-25	Procédé pour la copolymérisation de monoxide de carbone et de composés à insaturation oléfinique
US5723572A (en)	1998-03-03	Process for the preparation of a linear alternating copolymer of carbon monoxide with ethene and another olefinically unsaturated compound
JPH08283404A (ja)	1996-10-29	一酸化炭素とオレフィン性不飽和化合物との共重合化方法
EP0733663B1 (fr)	1999-12-22	Procédé pour la copolymérisation de monoxide de carbone et de composés à insaturation oléfinique
US5741939A (en)	1998-04-21	Process for the copolymerization of carbon monoxide with an olefinically unsaturated compound
EP0792902A2 (fr)	1997-09-03	Procédé pour la préparation de copolymers
EP0877772B1 (fr)	2000-05-10	Procede de preparation de copolymeres
JPH08269191A (ja)	1996-10-15	一酸化炭素とオレフィン系不飽和化合物との共重合方法
US5747638A (en)	1998-05-05	Process for the preparation of a copolymer of carbon monoxide
EP0694049A1 (fr)	1996-01-31	Preparation de copolymeres de monoxyde de carbone
JPH08269192A (ja)	1996-10-15	一酸化炭素とエチレン系不飽和化合物との気相共重合プロセス
WO2000009584A1 (fr)	2000-02-24	Composition catalytique, et procede de preparation de copolymeres de monoxide de carbone et d'un compose non sature en olefines