CN1255415C - 用于二烯烃的氢氰化和非共轭2－烷基－3－单烯烃腈的异构化的多齿亚磷酸酯配体和镍催化剂组合物 - Google Patents
用于二烯烃的氢氰化和非共轭2－烷基－3－单烯烃腈的异构化的多齿亚磷酸酯配体和镍催化剂组合物 Download PDFInfo
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- CN1255415C CN1255415C CNB031368573A CN03136857A CN1255415C CN 1255415 C CN1255415 C CN 1255415C CN B031368573 A CNB031368573 A CN B031368573A CN 03136857 A CN03136857 A CN 03136857A CN 1255415 C CN1255415 C CN 1255415C
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- alkyl
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- hydrocyanation
- isomerization
- catalyst
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- 238000005669 hydrocyanation reaction Methods 0.000 title abstract description 35
- 238000006317 isomerization reaction Methods 0.000 title abstract description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000003446 ligand Substances 0.000 claims abstract description 19
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012018 catalyst precursor Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052759 nickel Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 abstract description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 48
- 239000003054 catalyst Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- -1 diene compounds Chemical class 0.000 description 17
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 14
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- 150000002825 nitriles Chemical class 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
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- PMJHHCWVYXUKFD-PLNGDYQASA-N (3z)-penta-1,3-diene Chemical compound C\C=C/C=C PMJHHCWVYXUKFD-PLNGDYQASA-N 0.000 description 1
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 1
- KBVDKMYIVHHRON-UHFFFAOYSA-N 2-ethenylpentanenitrile Chemical compound CCCC(C=C)C#N KBVDKMYIVHHRON-UHFFFAOYSA-N 0.000 description 1
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- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 244000292604 Salvia columbariae Species 0.000 description 1
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- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- 238000004364 calculation method Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
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- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
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- 238000007333 cyanation reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-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
- 229920001778 nylon Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 229910052725 zinc Inorganic materials 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
- C07F9/6571—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 and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl 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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- 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
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
- B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
-
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5402397P | 1997-07-29 | 1997-07-29 | |
| US60/054023 | 1997-07-29 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98807514A Division CN1117728C (zh) | 1997-07-29 | 1998-07-23 | 二烯烃的氢氰化和非共轭2－烷基－3－单烯烃腈的异构化 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1515576A CN1515576A (zh) | 2004-07-28 |
| CN1255415C true CN1255415C (zh) | 2006-05-10 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| CNB031368573A Expired - Fee Related CN1255415C (zh) | 1997-07-29 | 1998-07-23 | 用于二烯烃的氢氰化和非共轭2－烷基－3－单烯烃腈的异构化的多齿亚磷酸酯配体和镍催化剂组合物 |
| CN98807514A Expired - Fee Related CN1117728C (zh) | 1997-07-29 | 1998-07-23 | 二烯烃的氢氰化和非共轭2－烷基－3－单烯烃腈的异构化 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98807514A Expired - Fee Related CN1117728C (zh) | 1997-07-29 | 1998-07-23 | 二烯烃的氢氰化和非共轭2－烷基－3－单烯烃腈的异构化 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5981772A (https=) |
| EP (1) | EP1000021B1 (https=) |
| JP (1) | JP2002509550A (https=) |
| KR (1) | KR100545279B1 (https=) |
| CN (2) | CN1255415C (https=) |
| BR (1) | BR9810820B1 (https=) |
| CA (1) | CA2291443A1 (https=) |
| DE (1) | DE69808481T2 (https=) |
| ID (1) | ID23785A (https=) |
| MY (1) | MY125853A (https=) |
| TW (1) | TW527339B (https=) |
| WO (1) | WO1999006357A1 (https=) |
| ZA (1) | ZA986369B (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6307107B1 (en) * | 1999-09-20 | 2001-10-23 | E.I. Du Pont De Nemours And Company | Hydroformylation of acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes |
| KR100714324B1 (ko) * | 1999-09-20 | 2007-05-04 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 다좌 포스파이트 리간드, 및 이를 함유하는 촉매 조성물 |
| BR0014567A (pt) | 1999-09-20 | 2002-06-18 | Du Pont | Processo de hidrocianação, ligante de fosfito multidentado e composição de catalisador |
| US6515161B1 (en) * | 1999-09-20 | 2003-02-04 | E. I. Du Pont De Nemours And Company | Hydroformylation process utilizing multidentate phosphite ligands |
| US6380421B1 (en) * | 1999-09-20 | 2002-04-30 | E. I. Du Pont De Nemours And Company | Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions |
| DE10038037A1 (de) * | 2000-08-02 | 2002-04-18 | Basf Ag | Zur Herstellung von Nitrilen geeigneter Katalysator und Verfahren zur Herstellung von Nitrilen |
| AU2002216719A1 (en) * | 2000-11-17 | 2002-05-27 | The Penn State Research Foundation | Ortho substituted chiral phosphines and phosphinites and their use in asymmetriccatayltic reactions |
| FR2819250B1 (fr) * | 2001-01-05 | 2004-12-03 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
| DE10136488A1 (de) * | 2001-07-27 | 2003-02-06 | Basf Ag | Ni(O) enthaltendes Katalysatorsystem |
| DE10150285A1 (de) * | 2001-10-12 | 2003-04-17 | Basf Ag | Phosphonite |
| AR036636A1 (es) * | 2001-10-12 | 2004-09-22 | Basf Ag | Fosfonita i, su uso como ligando en complejos de metal de transicion, dichos complejos, procedimiento para la obtencion de estos ultimos, uso de complejos de metal transitorio como catalizador y procedimientos para la adicion de acido cianhidrico a un doble enlace olefinico y para la isomerizacion d |
| DE10150286A1 (de) * | 2001-10-12 | 2003-04-17 | Basf Ag | Phosphinite |
| US6660876B2 (en) * | 2001-11-26 | 2003-12-09 | E. I. Du Pont De Nemours And Company | Phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions |
| AR038161A1 (es) * | 2002-01-24 | 2004-12-29 | Basf Ag | Procedimiento para separar acidos de mezclas de reaccion quimicas con la ayuda de liquidos ionicos |
| EP1344770A1 (en) * | 2002-03-12 | 2003-09-17 | E.I. du Pont de Nemours and Company | Process for the hydrocyanation of butadiene |
| FR2842196B1 (fr) * | 2002-07-15 | 2006-01-13 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
| FR2842195B1 (fr) * | 2002-07-15 | 2005-12-02 | Rhodia Polyamide Intermediates | Procede de fabrication de composes nitrile a partir de composes a insaturation ethylenique |
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| US6897329B2 (en) * | 2003-01-14 | 2005-05-24 | Invista North America S.A.R.L. | Process for the preparation of nickel/phosphorous ligand catalyst for olefin hydrocyanation |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| US7015360B2 (en) * | 2003-03-28 | 2006-03-21 | Dow Global Technologies, Inc. | Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols |
| 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 |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| EP2154127A3 (en) | 2003-09-11 | 2010-10-13 | Invista Technologies S.à.r.l. | Conversion of hydrocyanated unsaturated carboxylic acid derivatives into amines |
| DE10350999A1 (de) * | 2003-10-30 | 2005-06-02 | Basf Ag | Katalysator, umfassend wenigstens einen Nickel(O)Komplex stabilisiert durch einen sterisch anspruchsvollen Chelatphosphinitphosphitliganden, sowie ein Verfahren zur Herstellung von Nitrilen |
| DE10351000A1 (de) * | 2003-10-30 | 2005-06-09 | Basf Ag | Verfahren zur Herstellung von Nickel(O)-Phosphorligand-Komplexen |
| DE10352757A1 (de) * | 2003-11-12 | 2005-06-16 | Studiengesellschaft Kohle Mbh | Chirale Di- und Triphosphite |
| DE102004004696A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von linearen Pentennitrilen |
| DE102004004720A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von 3-Pentennitril |
| US8119829B2 (en) * | 2004-09-08 | 2012-02-21 | Invista North America S.A.R.L. | Process of hydrocyanation of unsaturated carboxylic acid derivatives |
| DE102005015893A1 (de) * | 2005-04-06 | 2006-10-12 | Basf Ag | Verbessertes Verfahren zur Herstellung von Biphenolen aus Monophenolen |
| WO2007109005A2 (en) | 2006-03-17 | 2007-09-27 | Invista Technologies S.A R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7659422B2 (en) * | 2006-07-14 | 2010-02-09 | Invista North America S.A.R.L. | Hydrocyanation process with reduced yield losses |
| US7709673B2 (en) | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7709674B2 (en) | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
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| WO2009091771A2 (en) * | 2008-01-15 | 2009-07-23 | Invista Technologies S.A R.L | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| FR2926816B1 (fr) | 2008-01-25 | 2010-05-14 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
| FR2932477B1 (fr) | 2008-06-17 | 2013-01-18 | Rhodia Operations | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
| FR2937321B1 (fr) | 2008-10-21 | 2010-10-22 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
| FR2941455B1 (fr) | 2009-01-29 | 2011-02-11 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
| ES2542430T3 (es) | 2010-07-07 | 2015-08-05 | Invista Technologies S.À.R.L. | Proceso para hacer nitrilos |
| CN103080119B (zh) | 2010-09-07 | 2015-04-08 | 因温斯特技术公司 | 用于制备镍金属的镍组合物和镍配合物 |
| JP2014530221A (ja) | 2011-10-07 | 2014-11-17 | インヴィスタテクノロジーズ エスアエルエル | ニトリルの作製方法 |
| KR20150035479A (ko) | 2011-12-21 | 2015-04-06 | 인비스타 테크놀러지스 에스.에이 알.엘. | 안정한 에멀젼을 감소시키기 위한 추출 용매 제어 |
| EP2794047B1 (en) | 2011-12-21 | 2021-04-14 | INVISTA Textiles (U.K.) Limited | Extraction solvent control for reducing stable emulsions |
| US9133223B2 (en) | 2011-12-21 | 2015-09-15 | Invista North America S.A.R.L. | Extraction solvent control for reducing stable emulsions |
| JP2015512862A (ja) | 2011-12-21 | 2015-04-30 | インヴィスタ テクノロジーズ エスアエルエル | 安定なエマルジョンを減じるための抽出溶媒制御 |
| US9458185B2 (en) | 2012-02-10 | 2016-10-04 | The Regents Of The University Of California | First row metal-based catalysts for hydosilylation |
| KR20150021545A (ko) * | 2012-06-01 | 2015-03-02 | 인비스타 테크놀러지스 에스.에이 알.엘. | 안정한 리간드 혼합물 및 그의 제조 방법 |
| CN104662029A (zh) * | 2012-06-01 | 2015-05-27 | 因温斯特技术公司 | 稳定的氢氰化配体组合物 |
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| WO2014056736A1 (de) * | 2012-10-12 | 2014-04-17 | Evonik Degussa Gmbh | Gemisch von bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung |
| US10759741B2 (en) | 2013-07-17 | 2020-09-01 | Invista North America S.A R.L. | Separating a solvent from a nickel catalyst by distillation |
| ITMI20131612A1 (it) * | 2013-09-30 | 2015-03-31 | Maurizio Benaglia | Dioli bieteroaromatici e loro derivati. |
| US9914700B2 (en) | 2014-06-27 | 2018-03-13 | Invista North America S.A R.L. | Enhanced extraction of impurities from mixture comprising nitriles |
| CN107207406B (zh) | 2014-06-27 | 2019-12-03 | 英威达纺织（英国）有限公司 | 用增强的液-液萃取制造腈的整合方法 |
| CN108640854A (zh) * | 2018-04-28 | 2018-10-12 | 山东豪迈化工技术有限公司 | 一种己二腈的合成方法 |
| CN113912516B (zh) | 2021-10-15 | 2023-06-27 | 浙江新和成股份有限公司 | 一种多齿亚磷酸酯配体在催化合成己二腈中的应用 |
| WO2023228075A1 (en) | 2022-05-23 | 2023-11-30 | Inv Nylon Chemicals Americas, Llc | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| WO2023228077A1 (en) | 2022-05-23 | 2023-11-30 | Inv Nylon Chemicals Americas, Llc | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| CN119095862A (zh) | 2022-08-02 | 2024-12-06 | 英威达纺织（英国）有限公司 | 双齿亚磷酸酯配体、含有此类配体的催化组合物以及利用此类催化组合物的催化方法 |
| EP4511380B1 (en) | 2022-08-02 | 2025-11-05 | INVISTA Textiles (U.K.) Limited | Arsenic-containing ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| CN119095858A (zh) | 2022-08-02 | 2024-12-06 | 英威达纺织（英国）有限公司 | 双齿亚磷酸酯配体、含有此类配体的催化组合物以及利用此类催化组合物的催化方法 |
| WO2024028715A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Processes for producing nitriles and phosphorus-containing catalysts for use in such processes |
| US20260034540A1 (en) | 2022-08-02 | 2026-02-05 | Inv Nylon Chemicals Americas, Llc | Processes for producing nitriles and phosphorus-containing catalysts for use in such processes |
| WO2024028720A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| WO2024028718A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Bidfntate phosphite ligands. catalytic compositions containing such ligands. and catalytic processes utilizing such catalytic compositions |
| CN117797874B (zh) * | 2023-12-27 | 2026-01-30 | 上海蓝科石化环保科技股份有限公司 | 氢氰化催化剂、制备方法及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496215A (en) * | 1965-11-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins using selected nickel phosphite catalysts |
| US3536748A (en) * | 1965-11-23 | 1970-10-27 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles |
| US3496217A (en) * | 1967-05-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins |
| US3676481A (en) * | 1970-06-29 | 1972-07-11 | Du Pont | Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles in the presence of certain metal salt and/or tri(hydrocarbyl)boron promoters |
| JP3416956B2 (ja) * | 1991-06-11 | 2003-06-16 | 三菱化学株式会社 | ヒドロホルミル化法およびビスホスファイト化合物 |
| CA2177135C (en) * | 1993-11-23 | 2005-04-26 | Wilson Tam | Processes and catalyst compositions for hydrocyanation of monoolefins |
| US5512696A (en) * | 1995-07-21 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
| TW315370B (https=) * | 1994-10-07 | 1997-09-11 | Du Pont | |
| US5449807A (en) * | 1994-11-18 | 1995-09-12 | E. I. Du Pont De Nemours And Company | Catalyzed vapor phase hydrocyanation of diolefinic compounds |
| IN187044B (https=) * | 1995-01-27 | 2002-01-05 | Du Pont | |
| US5821378A (en) * | 1995-01-27 | 1998-10-13 | E. I. Du Pont De Nemours And Company | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
| US5710306A (en) * | 1996-03-15 | 1998-01-20 | Dsm N.V. | Process to prepare a multidentate phosphite compound |
| DE19717359B4 (de) * | 1996-04-30 | 2014-10-30 | Mitsubishi Chemical Corp. | Bisphosphitverbindungen und Verfahren zu deren Herstellung |
| JP3812046B2 (ja) * | 1996-04-30 | 2006-08-23 | 三菱化学株式会社 | ビスホスファイト化合物及びそれを用いるヒドロホルミル化方法 |
| JPH1045775A (ja) * | 1996-04-30 | 1998-02-17 | Mitsubishi Chem Corp | ビスホスファイト化合物の製造方法 |
| EP0839794A1 (en) * | 1996-11-04 | 1998-05-06 | Dsm N.V. | Process for the continuous preparation of an alkyl 5-formylvalerate compound |
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1998
- 1998-07-17 ZA ZA9806369A patent/ZA986369B/xx unknown
- 1998-07-23 JP JP51100799A patent/JP2002509550A/ja not_active Ceased
- 1998-07-23 CA CA002291443A patent/CA2291443A1/en not_active Abandoned
- 1998-07-23 KR KR1020007000945A patent/KR100545279B1/ko not_active Expired - Fee Related
- 1998-07-23 DE DE69808481T patent/DE69808481T2/de not_active Expired - Lifetime
- 1998-07-23 WO PCT/US1998/015198 patent/WO1999006357A1/en not_active Ceased
- 1998-07-23 ID IDW20000182A patent/ID23785A/id unknown
- 1998-07-23 CN CNB031368573A patent/CN1255415C/zh not_active Expired - Fee Related
- 1998-07-23 CN CN98807514A patent/CN1117728C/zh not_active Expired - Fee Related
- 1998-07-23 BR BRPI9810820-4A patent/BR9810820B1/pt not_active IP Right Cessation
- 1998-07-23 EP EP98936991A patent/EP1000021B1/en not_active Expired - Lifetime
- 1998-07-23 US US09/121,104 patent/US5981772A/en not_active Expired - Lifetime
- 1998-07-27 MY MYPI98003416A patent/MY125853A/en unknown
- 1998-08-01 TW TW087112450A patent/TW527339B/zh not_active IP Right Cessation
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1999
- 1999-08-12 US US09/373,492 patent/US6120700A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69808481T2 (de) | 2003-07-10 |
| DE69808481D1 (de) | 2002-11-07 |
| CA2291443A1 (en) | 1999-02-11 |
| BR9810820A (pt) | 2000-07-25 |
| EP1000021B1 (en) | 2002-10-02 |
| BR9810820B1 (pt) | 2010-06-01 |
| HK1029983A1 (en) | 2001-04-20 |
| CN1117728C (zh) | 2003-08-13 |
| WO1999006357A1 (en) | 1999-02-11 |
| MY125853A (en) | 2006-08-30 |
| EP1000021A1 (en) | 2000-05-17 |
| ID23785A (id) | 2000-05-11 |
| CN1265093A (zh) | 2000-08-30 |
| ZA986369B (en) | 2000-01-17 |
| KR100545279B1 (ko) | 2006-01-24 |
| US6120700A (en) | 2000-09-19 |
| KR20010022366A (ko) | 2001-03-15 |
| US5981772A (en) | 1999-11-09 |
| JP2002509550A (ja) | 2002-03-26 |
| TW527339B (en) | 2003-04-11 |
| CN1515576A (zh) | 2004-07-28 |
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