ES2216308T3 - Procedimiento para la obtencion de mezclas de mononitrilos monoolefinicos con 5 atomos de carbono mediante hidrocianado catalitico en presencia de un catalizador, que comprende al menos un complejo de metaloceno.fosforo(iii)-niquel(0). - Google Patents
Procedimiento para la obtencion de mezclas de mononitrilos monoolefinicos con 5 atomos de carbono mediante hidrocianado catalitico en presencia de un catalizador, que comprende al menos un complejo de metaloceno.fosforo(iii)-niquel(0).Info
- Publication number
- ES2216308T3 ES2216308T3 ES98945143T ES98945143T ES2216308T3 ES 2216308 T3 ES2216308 T3 ES 2216308T3 ES 98945143 T ES98945143 T ES 98945143T ES 98945143 T ES98945143 T ES 98945143T ES 2216308 T3 ES2216308 T3 ES 2216308T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- butadiene
- hydrocyanate
- carbon atoms
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000003054 catalyst Substances 0.000 title claims description 60
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims description 25
- 229910052759 nickel Inorganic materials 0.000 title claims description 14
- 230000003197 catalytic effect Effects 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 title description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title description 8
- 239000003446 ligand Substances 0.000 claims abstract description 49
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 28
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 28
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
- 239000011574 phosphorus Substances 0.000 claims abstract description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 90
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 90
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims description 39
- -1 dicyclohexylphosphino Chemical group 0.000 claims description 38
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
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- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 6
- 238000005669 hydrocyanation reaction Methods 0.000 claims description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 238000006317 isomerization reaction Methods 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
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- 150000002170 ethers Chemical class 0.000 claims description 3
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- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
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- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 150000001925 cycloalkenes Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
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- 208000012839 conversion disease Diseases 0.000 claims 1
- 150000002390 heteroarenes Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005538 phosphinite group Chemical group 0.000 claims 1
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- 239000000047 product Substances 0.000 description 10
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- PHJJWPXKTFKKPD-UHFFFAOYSA-N [Ni+3].[O-]P([O-])[O-] Chemical compound [Ni+3].[O-]P([O-])[O-] PHJJWPXKTFKKPD-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
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- 230000007704 transition Effects 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- JRTIUDXYIUKIIE-UHFFFAOYSA-N cycloocta-1,5-diene;nickel Chemical group [Ni].C1CC=CCCC=C1.C1CC=CCCC=C1 JRTIUDXYIUKIIE-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 231100000614 poison Toxicity 0.000 description 5
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- 239000002841 Lewis acid Substances 0.000 description 4
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- 229910052786 argon Inorganic materials 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 4
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- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 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
- 238000007493 shaping process Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (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 |
|---|---|---|---|
| DE19733682A DE19733682A1 (de) | 1997-08-04 | 1997-08-04 | Verfahren zur Herstellung von Gemischen monoolefinischer C¶5¶-Mononitrile durch katalytische Hydrocyanierung in Gegenwart eines katalysators, umfassend wenigstens einen Metallocenphosphor(III)-Nickel(0)-Komplex |
| DE19733682 | 1997-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2216308T3 true ES2216308T3 (es) | 2004-10-16 |
Family
ID=7837954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98945143T Expired - Lifetime ES2216308T3 (es) | 1997-08-04 | 1998-08-04 | Procedimiento para la obtencion de mezclas de mononitrilos monoolefinicos con 5 atomos de carbono mediante hidrocianado catalitico en presencia de un catalizador, que comprende al menos un complejo de metaloceno.fosforo(iii)-niquel(0). |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6169198B1 (enExample) |
| EP (1) | EP1003716B1 (enExample) |
| JP (1) | JP2001513528A (enExample) |
| KR (1) | KR20010022579A (enExample) |
| CN (1) | CN1266424A (enExample) |
| AR (1) | AR010428A1 (enExample) |
| AU (1) | AU9257098A (enExample) |
| BR (1) | BR9810978A (enExample) |
| CA (1) | CA2298585A1 (enExample) |
| DE (2) | DE19733682A1 (enExample) |
| ES (1) | ES2216308T3 (enExample) |
| ID (1) | ID24307A (enExample) |
| MY (1) | MY126401A (enExample) |
| RU (1) | RU2228329C2 (enExample) |
| TR (1) | TR200000327T2 (enExample) |
| TW (1) | TW466221B (enExample) |
| WO (1) | WO1999007671A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10033982A1 (de) * | 2000-07-13 | 2002-01-24 | Basf Ag | Verfahren zur Herstellung von Additionsprodukten ethylenisch ungesättigter Verbindungen |
| DE10136488A1 (de) * | 2001-07-27 | 2003-02-06 | Basf Ag | Ni(O) enthaltendes Katalysatorsystem |
| EP1344770A1 (en) * | 2002-03-12 | 2003-09-17 | E.I. du Pont de Nemours and Company | Process for the hydrocyanation of butadiene |
| FR2850966B1 (fr) * | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| DE102004004718A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| DE102004004671A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von linearem Pentennitril |
| DE102004004672A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| DE102004004673A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung von Butadien |
| JP4509125B2 (ja) | 2004-01-29 | 2010-07-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 直鎖のペンテンニトリルの製造方法 |
| DE102004004696A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von linearen Pentennitrilen |
| DE102004004721A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Trennung von Pentennitril-Isomeren |
| DE102004004682A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Adipodinitril durch Hydrocyanierung von 1,3-Butadien |
| DE102004004697A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Pentennitrilen aus n-Butan |
| MX2007008359A (es) | 2005-01-10 | 2007-09-06 | Cargill Inc | Vela y cera para vela que contiene productos de metatesis y similares a metatesis. |
| WO2007046799A1 (en) * | 2005-10-18 | 2007-04-26 | Invista Technologies S.A R.L. | Process of making 3-aminopentanenitrile |
| WO2007081987A2 (en) | 2006-01-10 | 2007-07-19 | Elevance Renewable Sciences, Inc. | Method of making hydrogenated metathesis products |
| WO2007103460A2 (en) * | 2006-03-07 | 2007-09-13 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
| AU2007223922B2 (en) | 2006-03-07 | 2013-05-02 | Wilmar Trading Pte Ltd | Compositions comprising metathesized unsaturated polyol esters |
| CA2644961A1 (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 |
| WO2008008440A2 (en) * | 2006-07-12 | 2008-01-17 | Elevance Renewable Sciences, Inc. | Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like |
| WO2008010961A2 (en) | 2006-07-13 | 2008-01-24 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis |
| US7919646B2 (en) * | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7880028B2 (en) | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| CN101558027B (zh) * | 2006-10-13 | 2013-10-16 | 埃莱文斯可更新科学公司 | 通过复分解反应制备α，ω-二羧酸烯烃衍生物的方法 |
| EP2076483A4 (en) * | 2006-10-13 | 2013-12-04 | Elevance Renewable Sciences | METHODS FOR PRODUCING ORGANIC COMPOUNDS BY METATHESIS AND HYDROCYANATION |
| US8501973B2 (en) * | 2006-10-13 | 2013-08-06 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
| US8906334B2 (en) | 2007-05-14 | 2014-12-09 | Invista North America S.A R.L. | High efficiency reactor and process |
| US8101790B2 (en) * | 2007-06-13 | 2012-01-24 | Invista North America S.A.R.L. | Process for improving adiponitrile quality |
| EP2229353B1 (en) * | 2008-01-15 | 2018-01-03 | INVISTA Textiles (U.K.) Limited | Hydrocyanation of pentenenitriles |
| US7977502B2 (en) * | 2008-01-15 | 2011-07-12 | Invista North America S.A R.L. | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| EP2257516A4 (en) * | 2008-03-19 | 2012-12-12 | Invista Tech Sarl | METHODS FOR PREPARING CYCLODODECATRIENE AND METHODS FOR PREPARING LAUROLACTONE |
| EP2334624B1 (en) | 2008-10-14 | 2014-10-01 | Invista Technologies S.à.r.l. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
| FR2937321B1 (fr) * | 2008-10-21 | 2010-10-22 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
| KR20120047251A (ko) | 2009-08-07 | 2012-05-11 | 인비스타 테크놀러지스 에스.에이.알.엘. | 디에스테르를 형성하기 위한 수소화 및 에스테르화 |
| EP2574191B1 (en) | 2010-07-07 | 2013-11-20 | Invista Technologies S.a r.l. | Process for making nitriles |
| WO2012033555A1 (en) | 2010-09-07 | 2012-03-15 | Invista Technologies S.A.R.L. | Nickel compositions for preparing nickel metal and nickel complexes |
| CN104640872A (zh) | 2012-06-01 | 2015-05-20 | 因温斯特技术公司 | 稳定的配体混合物及用于制备其的方法 |
| WO2013181092A1 (en) | 2012-06-01 | 2013-12-05 | Invista North America S.A.R.L. | Hydrolysis catalyst and process |
| CN108997167B (zh) * | 2018-08-09 | 2021-05-07 | 大连微凯化学有限公司 | 一种利用丁二烯氢氰化制备己二腈和甲基戊二腈的方法 |
| CN116120207B (zh) * | 2021-11-15 | 2025-06-06 | 中国科学院上海有机化学研究所 | 一种手性单齿膦配体催化丁二烯制备己二腈的方法 |
| CN114105817B (zh) * | 2021-12-10 | 2022-10-28 | 北京道思克矿山装备技术有限公司 | 1,3-丁二烯氢氰化连续制备己二腈的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4714773A (en) * | 1987-01-09 | 1987-12-22 | E. I. Du Pont De Nemours And Company | Hydrocyanation of butadiene |
| BE1008343A3 (nl) | 1994-05-06 | 1996-04-02 | Dsm Nv | Bidentaat fosfineligand |
-
1997
- 1997-08-04 DE DE19733682A patent/DE19733682A1/de not_active Withdrawn
-
1998
- 1998-07-31 AR ARP980103803A patent/AR010428A1/es unknown
- 1998-08-03 TW TW087112745A patent/TW466221B/zh not_active IP Right Cessation
- 1998-08-04 CN CN98807985A patent/CN1266424A/zh active Pending
- 1998-08-04 WO PCT/EP1998/004851 patent/WO1999007671A1/de not_active Ceased
- 1998-08-04 MY MYPI98003554A patent/MY126401A/en unknown
- 1998-08-04 AU AU92570/98A patent/AU9257098A/en not_active Abandoned
- 1998-08-04 US US09/463,820 patent/US6169198B1/en not_active Expired - Fee Related
- 1998-08-04 ES ES98945143T patent/ES2216308T3/es not_active Expired - Lifetime
- 1998-08-04 CA CA002298585A patent/CA2298585A1/en not_active Abandoned
- 1998-08-04 DE DE59810804T patent/DE59810804D1/de not_active Expired - Fee Related
- 1998-08-04 JP JP2000507207A patent/JP2001513528A/ja not_active Withdrawn
- 1998-08-04 RU RU2000106067/04A patent/RU2228329C2/ru not_active IP Right Cessation
- 1998-08-04 EP EP98945143A patent/EP1003716B1/de not_active Expired - Lifetime
- 1998-08-04 BR BR9810978-2A patent/BR9810978A/pt not_active IP Right Cessation
- 1998-08-04 ID IDW20000229A patent/ID24307A/id unknown
- 1998-08-04 KR KR1020007001170A patent/KR20010022579A/ko not_active Ceased
- 1998-08-04 TR TR2000/00327T patent/TR200000327T2/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010022579A (ko) | 2001-03-26 |
| CN1266424A (zh) | 2000-09-13 |
| ID24307A (id) | 2000-07-13 |
| AU9257098A (en) | 1999-03-01 |
| MY126401A (en) | 2006-09-29 |
| DE19733682A1 (de) | 1999-02-11 |
| EP1003716A1 (de) | 2000-05-31 |
| DE59810804D1 (de) | 2004-03-25 |
| BR9810978A (pt) | 2000-08-08 |
| WO1999007671A1 (de) | 1999-02-18 |
| TW466221B (en) | 2001-12-01 |
| AR010428A1 (es) | 2000-06-07 |
| EP1003716B1 (de) | 2004-02-18 |
| TR200000327T2 (tr) | 2000-11-21 |
| US6169198B1 (en) | 2001-01-02 |
| CA2298585A1 (en) | 1999-02-18 |
| RU2228329C2 (ru) | 2004-05-10 |
| JP2001513528A (ja) | 2001-09-04 |
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