KR20040058321A - 인 함유 중합체 조성물, 및 히드로시안화, 불포화 니트릴이성질체화 및 히드로포르밀화 반응에서의 그의 용도 - Google Patents
인 함유 중합체 조성물, 및 히드로시안화, 불포화 니트릴이성질체화 및 히드로포르밀화 반응에서의 그의 용도 Download PDFInfo
- Publication number
- KR20040058321A KR20040058321A KR10-2004-7007942A KR20047007942A KR20040058321A KR 20040058321 A KR20040058321 A KR 20040058321A KR 20047007942 A KR20047007942 A KR 20047007942A KR 20040058321 A KR20040058321 A KR 20040058321A
- Authority
- KR
- South Korea
- Prior art keywords
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- formula
- compound
- propenyl
- phosphorus
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- 239000000203 mixture Substances 0.000 title claims abstract description 209
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 95
- 239000011574 phosphorus Substances 0.000 title claims abstract description 84
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 238000005669 hydrocyanation reaction Methods 0.000 title claims description 92
- 238000006317 isomerization reaction Methods 0.000 title claims description 46
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 31
- 150000002825 nitriles Chemical class 0.000 title abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 128
- 238000000034 method Methods 0.000 claims abstract description 113
- 229920000642 polymer Polymers 0.000 claims abstract description 113
- -1 aryl phosphorochloridites Chemical class 0.000 claims abstract description 77
- 150000003254 radicals Chemical class 0.000 claims abstract description 61
- 229910052751 metal Inorganic materials 0.000 claims abstract description 53
- 239000002184 metal Substances 0.000 claims abstract description 53
- 239000003999 initiator Substances 0.000 claims abstract description 48
- 239000000178 monomer Substances 0.000 claims abstract description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 15
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims description 129
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- 239000003446 ligand Substances 0.000 claims description 107
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- 125000000217 alkyl group Chemical group 0.000 claims description 78
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 77
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 76
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 69
- 229910052760 oxygen Inorganic materials 0.000 claims description 69
- 239000001301 oxygen Substances 0.000 claims description 69
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 59
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 57
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 47
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 239000010948 rhodium Substances 0.000 claims description 22
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
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- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 claims description 19
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 17
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- 229910052759 nickel Inorganic materials 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 150000004292 cyclic ethers Chemical class 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 229910052723 transition metal Inorganic materials 0.000 claims description 14
- 150000003624 transition metals Chemical class 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 239000002841 Lewis acid Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
- 150000007517 lewis acids Chemical class 0.000 claims description 13
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 12
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
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- 150000001342 alkaline earth metals Chemical class 0.000 claims description 11
- ZDTQJPVEXIUREJ-UHFFFAOYSA-N dichlorophosphinous acid Chemical compound OP(Cl)Cl ZDTQJPVEXIUREJ-UHFFFAOYSA-N 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052786 argon Inorganic materials 0.000 claims description 10
- 125000004437 phosphorous atom Chemical group 0.000 claims description 10
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 9
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- 229910052703 rhodium Inorganic materials 0.000 claims description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
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- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
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- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/994,135 US6660876B2 (en) | 2001-11-26 | 2001-11-26 | Phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions |
| US09/994,135 | 2001-11-26 | ||
| PCT/US2002/037304 WO2003045552A2 (en) | 2001-11-26 | 2002-11-20 | Polymeric phosphorus-containing compositions and their use in hydrocyanation, unsaturated nitrile isomerization and hydroformylation reactions |
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| KR20040058321A true KR20040058321A (ko) | 2004-07-03 |
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| KR10-2004-7007942A Ceased KR20040058321A (ko) | 2001-11-26 | 2002-11-20 | 인 함유 중합체 조성물, 및 히드로시안화, 불포화 니트릴이성질체화 및 히드로포르밀화 반응에서의 그의 용도 |
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| EP (3) | EP2277623A3 (https=) |
| JP (2) | JP4373786B2 (https=) |
| KR (1) | KR20040058321A (https=) |
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| AU (1) | AU2002348313A1 (https=) |
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| MX (1) | MXPA04004938A (https=) |
| PL (1) | PL370988A1 (https=) |
| WO (1) | WO2003045552A2 (https=) |
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| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| US6844289B2 (en) * | 2003-04-08 | 2005-01-18 | Invista North America S.A.R.L. | Process for the preparation of a nickel/phosphorous ligand catalyst |
| FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
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| EP2614070B1 (en) | 2010-09-07 | 2017-07-26 | Invista Technologies S.à r.l. | Nickel compositions for preparing nickel metal and nickel complexes |
| CN103732323B (zh) * | 2011-06-10 | 2016-09-14 | 因温斯特技术公司 | 用于催化镍-配体配合物的制备的镍形式 |
| US8822577B2 (en) | 2011-11-21 | 2014-09-02 | Bridgestone Sports Co., Ltd. | Rubber composition for golf ball |
| CN104039412B (zh) | 2011-12-21 | 2016-08-24 | 因温斯特技术公司 | 用于减少稳定乳液的萃取溶剂控制 |
| EP2794048B1 (en) | 2011-12-21 | 2022-01-05 | INVISTA Textiles (U.K.) Limited | Extraction solvent control for reducing stable emulsions |
| KR20140127218A (ko) | 2011-12-21 | 2014-11-03 | 인비스타 테크놀러지스 에스.에이 알.엘. | 안정한 에멀젼을 감소시키기 위한 추출 용매 제어 |
| CN105307741B (zh) | 2013-06-20 | 2019-06-18 | 英威达纺织(英国)有限公司 | 用于减少稳定乳液的萃取溶剂控制 |
| US9676800B2 (en) | 2013-06-20 | 2017-06-13 | Invista North America S.A.R.L. | Extraction solvent control for reducing stable emulsions |
| CN105377395B (zh) | 2013-06-20 | 2018-05-29 | 英威达纺织(英国)有限公司 | 用于减少稳定乳液的萃取溶剂控制 |
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| WO2015200630A1 (en) | 2014-06-27 | 2015-12-30 | Invista North America S.A R.L. | Integrated process for nitrile manufacture with enhanced liquid-liquid extraction |
| US9914700B2 (en) | 2014-06-27 | 2018-03-13 | Invista North America S.A R.L. | Enhanced extraction of impurities from mixture comprising nitriles |
| CN106140303B (zh) * | 2015-04-03 | 2018-11-27 | 中国科学院大连化学物理研究所 | 一种含膦有机混聚物-金属多相催化剂及其制备和应用 |
| CN106140302B (zh) * | 2015-04-03 | 2018-11-27 | 中国科学院大连化学物理研究所 | 一种含膦有机混聚物-金属多相催化剂及其方法和应用 |
| EP3144289A1 (en) * | 2015-09-16 | 2017-03-22 | Evonik Technochemie GmbH | [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxyl]-terminated compounds |
| CN112480169A (zh) * | 2020-12-07 | 2021-03-12 | 南雄志一精细化工有限公司 | 一种液体含磷化合物及其应用和制备方法 |
| CN115873221B (zh) * | 2021-12-17 | 2024-06-04 | 浙江新和成股份有限公司 | 一种含磷聚合物及其制备方法和应用 |
| CN116410390B (zh) * | 2021-12-31 | 2024-05-10 | 中国石油天然气股份有限公司 | 有机膦配体聚合物及二齿膦配体共聚物催化剂的制备方法 |
| CN119156371A (zh) * | 2022-08-02 | 2024-12-17 | 英威达纺织(英国)有限公司 | 产生腈的方法和用于此类方法的含磷催化剂 |
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| US6284865B1 (en) * | 1999-09-20 | 2001-09-04 | E. I. Du Pont De Nemours And Company | Polymeric phosphite composition and hydrocyanation of unsaturated organic compounds and the isomerization of unsaturated nitriles |
| WO2002040491A1 (en) * | 2000-11-17 | 2002-05-23 | The Penn State Research Foundation | Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catayltic reactions |
| US8828098B2 (en) | 2006-12-18 | 2014-09-09 | 3M Innovative Properties Company | Extenders for fluorochemical treatment of fibrous substrates |
-
2001
- 2001-11-26 US US09/994,135 patent/US6660876B2/en not_active Expired - Lifetime
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2002
- 2002-11-20 KR KR10-2004-7007942A patent/KR20040058321A/ko not_active Ceased
- 2002-11-20 CN CNB028275357A patent/CN100345635C/zh not_active Expired - Lifetime
- 2002-11-20 JP JP2003547046A patent/JP4373786B2/ja not_active Expired - Lifetime
- 2002-11-20 WO PCT/US2002/037304 patent/WO2003045552A2/en not_active Ceased
- 2002-11-20 PL PL02370988A patent/PL370988A1/xx unknown
- 2002-11-20 EP EP10178209A patent/EP2277623A3/en not_active Withdrawn
- 2002-11-20 DE DE60237781T patent/DE60237781D1/de not_active Expired - Lifetime
- 2002-11-20 AU AU2002348313A patent/AU2002348313A1/en not_active Abandoned
- 2002-11-20 MX MXPA04004938A patent/MXPA04004938A/es active IP Right Grant
- 2002-11-20 EP EP07024054A patent/EP1905511B1/en not_active Expired - Lifetime
- 2002-11-20 EP EP02782340A patent/EP1448298B1/en not_active Expired - Lifetime
- 2002-11-20 BR BRPI0214629-0A patent/BR0214629B1/pt not_active IP Right Cessation
- 2002-11-20 CA CA002468195A patent/CA2468195A1/en not_active Abandoned
- 2002-11-20 AT AT02782340T patent/ATE482028T1/de not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2277623A2 (en) | 2011-01-26 |
| BR0214629B1 (pt) | 2012-08-21 |
| CN100345635C (zh) | 2007-10-31 |
| EP1905511A3 (en) | 2010-01-27 |
| EP1448298A2 (en) | 2004-08-25 |
| JP2009161760A (ja) | 2009-07-23 |
| AU2002348313A8 (en) | 2003-06-10 |
| EP1905511B1 (en) | 2013-03-27 |
| JP2005510547A (ja) | 2005-04-21 |
| JP5265400B2 (ja) | 2013-08-14 |
| MXPA04004938A (es) | 2004-08-11 |
| US6924345B2 (en) | 2005-08-02 |
| ATE482028T1 (de) | 2010-10-15 |
| CA2468195A1 (en) | 2003-06-05 |
| WO2003045552A2 (en) | 2003-06-05 |
| PL370988A1 (en) | 2005-06-13 |
| EP1905511A2 (en) | 2008-04-02 |
| EP1448298B1 (en) | 2010-09-22 |
| US20030144440A1 (en) | 2003-07-31 |
| DE60237781D1 (de) | 2010-11-04 |
| US6660876B2 (en) | 2003-12-09 |
| BR0214629A (pt) | 2004-11-03 |
| JP4373786B2 (ja) | 2009-11-25 |
| EP2277623A3 (en) | 2011-06-08 |
| WO2003045552A3 (en) | 2003-10-30 |
| AU2002348313A1 (en) | 2003-06-10 |
| US20040054105A1 (en) | 2004-03-18 |
| CN1617764A (zh) | 2005-05-18 |
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