DE19733682A1 - Verfahren zur Herstellung von Gemischen monoolefinischer C¶5¶-Mononitrile durch katalytische Hydrocyanierung in Gegenwart eines katalysators, umfassend wenigstens einen Metallocenphosphor(III)-Nickel(0)-Komplex - Google Patents
Verfahren zur Herstellung von Gemischen monoolefinischer C¶5¶-Mononitrile durch katalytische Hydrocyanierung in Gegenwart eines katalysators, umfassend wenigstens einen Metallocenphosphor(III)-Nickel(0)-KomplexInfo
- Publication number
- DE19733682A1 DE19733682A1 DE19733682A DE19733682A DE19733682A1 DE 19733682 A1 DE19733682 A1 DE 19733682A1 DE 19733682 A DE19733682 A DE 19733682A DE 19733682 A DE19733682 A DE 19733682A DE 19733682 A1 DE19733682 A1 DE 19733682A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrocyanation
- butadiene
- hydrogen
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 239000003054 catalyst Substances 0.000 title claims abstract description 50
- 238000005669 hydrocyanation reaction Methods 0.000 title claims abstract description 41
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 41
- 238000002360 preparation method Methods 0.000 title claims description 19
- VOKXPKSMYJLAIW-UHFFFAOYSA-N nickel;phosphane Chemical compound P.[Ni] VOKXPKSMYJLAIW-UHFFFAOYSA-N 0.000 title abstract description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 88
- 239000003446 ligand Substances 0.000 claims abstract description 44
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 28
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 28
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 76
- -1 Co Chemical class 0.000 claims description 43
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- 238000006243 chemical reaction Methods 0.000 claims description 30
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims description 26
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
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- 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 5
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- 208000012839 conversion disease Diseases 0.000 claims 1
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- JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical group [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229940073644 nickel Drugs 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 4
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- 238000004817 gas chromatography Methods 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
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- 150000001247 metal acetylides Chemical class 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002815 nickel Chemical class 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
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- UVKXJAUUKPDDNW-UHFFFAOYSA-N pent-3-enenitrile Chemical compound CC=CCC#N UVKXJAUUKPDDNW-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
- 239000012071 phase Substances 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012552 review 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
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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)
Priority Applications (18)
| 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 |
| ARP980103803A AR010428A1 (es) | 1997-08-04 | 1998-07-31 | Metodo para preparar mezclas de mononitrilos c5 monoolefinicos con enlaces no conjugados c=c y c=n por cianhidracion catalitica de 1,3-butadieno o unamezcla de hidrocarburos que contienen 1,3-butadieno, metodo para preparar adiponitrilos a partir de dichas mezclas de mononitrilos y uso de catalizado |
| TW087112745A TW466221B (en) | 1997-08-04 | 1998-08-03 | The preparation of mixtures of monoolefinic C5 mononitriles by catalytic hydrocyanation in the presence of a catalyst comprising at least one metallocene-phosphorus (III)-nickel(0) complex |
| BR9810978-2A BR9810978A (pt) | 1997-08-04 | 1998-08-04 | Processos para preparar misturas de mononitrilas e para preparar adiponitrila, e, uso de catalisadores |
| EP98945143A EP1003716B1 (de) | 1997-08-04 | 1998-08-04 | Verfahren zur herstellung von gemischen monoolefinischer c 5-mononitrile durch katalytische hydrocyanierung in gebenwart eines katalysators, umfassend wenigstens einen metallocenphosphor (iii)-nickel(0)-komplex |
| KR1020007001170A KR20010022579A (ko) | 1997-08-04 | 1998-08-04 | 1종 이상의 메탈로센 인 (ｉｉｉ)-니켈 -(0) 착물을 함유하는 촉매 존재하의 촉매적 히드로시안화에 의한 모노올레핀계 ｃ5-모노니트릴 혼합물의 제조 방법 |
| AU92570/98A AU9257098A (en) | 1997-08-04 | 1998-08-04 | Method for producing mixtures of monoolefinic c5-mononitriles by catalytic hydrocyanation in the presence of a catalyst containing at least one metallocene phosphor (iii)-nickel-(0) complex |
| PCT/EP1998/004851 WO1999007671A1 (de) | 1997-08-04 | 1998-08-04 | Verfahren zur herstellung von gemischen monoolefinischer c5-mononitrile durch katalytische hydrocyanierung in gebenwart eines katalysators, umfassend wenigstens einen metallocenphosphor (iii)-nickel(0)-komplex |
| ES98945143T 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). |
| TR2000/00327T TR200000327T2 (tr) | 1997-08-04 | 1998-08-04 | Katalitik hidrosiyanizasyon yoluyla, mono-olefinik C5-Mononitril karışımların üretilmesi |
| JP2000507207A JP2001513528A (ja) | 1997-08-04 | 1998-08-04 | モノオレフィン性ｃ５モノニトリルの混合物を、少なくとも１個のメタロセン−燐（ｉｉｉ）−ニッケル（０）錯体を含有する触媒の存在下に、接触的ヒドロシアン化により製造する方法 |
| RU2000106067/04A RU2228329C2 (ru) | 1997-08-04 | 1998-08-04 | Способ получения смесей моноолефиновых мононитрилов |
| CN98807985A CN1266424A (zh) | 1997-08-04 | 1998-08-04 | 在含至少一种金属茂一磷(ⅲ)一镍(o)配合物的催化剂存在下催化氢氰化反应制备烯c5单腈混合物的方法 |
| IDW20000229A ID24307A (id) | 1997-08-04 | 1998-08-04 | Pembuatan campuran monoolefin c5 mononitril dengan cara hidrosinasi katalitik dengan adanya katalis yang terdiri dari sedikitnya satu metalosena-fosforus (iii)-nikel (0) kompleks |
| US09/463,820 US6169198B1 (en) | 1997-08-04 | 1998-08-04 | Method for producing mixtures of monoolefinic C5-mononitriles by catalytic hydrocyanation |
| DE59810804T DE59810804D1 (de) | 1997-08-04 | 1998-08-04 | Verfahren zur herstellung von gemischen monoolefinischer c 5-mononitrile durch katalytische hydrocyanierung in gebenwart eines katalysators, umfassend wenigstens einen metallocenphosphor (iii)-nickel(0)-komplex |
| MYPI98003554A MY126401A (en) | 1997-08-04 | 1998-08-04 | Method for producing mixtures of monoolefinic c5-mononitriles by catalytic hydrocyanation |
| CA002298585A CA2298585A1 (en) | 1997-08-04 | 1998-08-04 | Method for producing mixtures of monoolefinic c5-mononitriles by catalytic hydrocyanation in the presence of a catalyst containing at least one metallocene phosphor (iii)-nickel-(0) complex |
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19733682A1 true DE19733682A1 (de) | 1999-02-11 |
Family
ID=7837954
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19733682A Withdrawn 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 |
| DE59810804T Expired - Fee Related DE59810804D1 (de) | 1997-08-04 | 1998-08-04 | Verfahren zur herstellung von gemischen monoolefinischer c 5-mononitrile durch katalytische hydrocyanierung in gebenwart eines katalysators, umfassend wenigstens einen metallocenphosphor (iii)-nickel(0)-komplex |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59810804T Expired - Fee Related DE59810804D1 (de) | 1997-08-04 | 1998-08-04 | Verfahren zur herstellung von gemischen monoolefinischer c 5-mononitrile durch katalytische hydrocyanierung in gebenwart eines katalysators, umfassend wenigstens einen metallocenphosphor (iii)-nickel(0)-komplex |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6169198B1 (https=) |
| EP (1) | EP1003716B1 (https=) |
| JP (1) | JP2001513528A (https=) |
| KR (1) | KR20010022579A (https=) |
| CN (1) | CN1266424A (https=) |
| AR (1) | AR010428A1 (https=) |
| AU (1) | AU9257098A (https=) |
| BR (1) | BR9810978A (https=) |
| CA (1) | CA2298585A1 (https=) |
| DE (2) | DE19733682A1 (https=) |
| ES (1) | ES2216308T3 (https=) |
| ID (1) | ID24307A (https=) |
| MY (1) | MY126401A (https=) |
| RU (1) | RU2228329C2 (https=) |
| TR (1) | TR200000327T2 (https=) |
| TW (1) | TW466221B (https=) |
| WO (1) | WO1999007671A1 (https=) |
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 |
| DE102004004697A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Pentennitrilen aus n-Butan |
| WO2005073174A1 (de) * | 2004-01-29 | 2005-08-11 | Basf Aktiengesellschaft | Verfahren zur herstellung von linearem pentennitril |
| DE102004004696A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von linearen Pentennitrilen |
| DE102004004718A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| DE102004004682A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Adipodinitril durch Hydrocyanierung von 1,3-Butadien |
| DE102004004671A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von linearem Pentennitril |
| DE102004004721A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Trennung von Pentennitril-Isomeren |
| 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 |
| CA2592786C (en) | 2005-01-10 | 2013-11-19 | Cargill, Incorporated | Candle and candle wax containing metathesis and metathesis-like products |
| US7973174B2 (en) | 2005-10-18 | 2011-07-05 | Invista North America 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 |
| BRPI0708675B1 (pt) | 2006-03-07 | 2017-04-04 | Elevance Renewable Sciences | composições compreendendo poliol ésteres insaturados que sofreram metátese e artigos para cuidados pessoais compreendendo as referidas composições |
| US8888908B2 (en) * | 2006-03-07 | 2014-11-18 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
| 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 |
| 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 |
| US7880028B2 (en) | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| EP2076484B1 (en) | 2006-10-13 | 2020-01-08 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
| WO2008048520A2 (en) * | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
| DK2121546T3 (en) * | 2006-10-13 | 2018-03-12 | Elevance Renewable Sciences | Process for preparing omega-dicarboxylic acid olefin derivative by metathesis |
| CN101687658B (zh) | 2007-05-14 | 2013-07-24 | 因温斯特技术公司 | 高效反应器和方法 |
| WO2008157218A1 (en) | 2007-06-13 | 2008-12-24 | Invista Technologies S.A.R.L. | Process for improving adiponitrile quality |
| 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 |
| WO2009091790A1 (en) * | 2008-01-15 | 2009-07-23 | Invista Technologies S.A.R.L. | Hydrocyanation of pentenenitriles |
| 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 |
| CN102471218B (zh) * | 2009-08-07 | 2014-11-05 | 因温斯特技术公司 | 用于形成二酯的氢化并酯化 |
| WO2012005918A1 (en) | 2010-07-07 | 2012-01-12 | Invista Technologies S.A.R.L. | Process for making nitriles |
| EP2614070B1 (en) | 2010-09-07 | 2017-07-26 | Invista Technologies S.à r.l. | Nickel compositions for preparing nickel metal and nickel complexes |
| KR20150021545A (ko) | 2012-06-01 | 2015-03-02 | 인비스타 테크놀러지스 에스.에이 알.엘. | 안정한 리간드 혼합물 및 그의 제조 방법 |
| CN104619711B (zh) | 2012-06-01 | 2018-02-13 | 英威达纺织（英国）有限公司 | 水解催化剂及方法 |
| 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 EP EP98945143A patent/EP1003716B1/de not_active Expired - Lifetime
- 1998-08-04 CA CA002298585A patent/CA2298585A1/en not_active Abandoned
- 1998-08-04 KR KR1020007001170A patent/KR20010022579A/ko not_active Ceased
- 1998-08-04 AU AU92570/98A patent/AU9257098A/en not_active Abandoned
- 1998-08-04 MY MYPI98003554A patent/MY126401A/en unknown
- 1998-08-04 ES ES98945143T patent/ES2216308T3/es not_active Expired - Lifetime
- 1998-08-04 JP JP2000507207A patent/JP2001513528A/ja not_active Withdrawn
- 1998-08-04 BR BR9810978-2A patent/BR9810978A/pt not_active IP Right Cessation
- 1998-08-04 WO PCT/EP1998/004851 patent/WO1999007671A1/de not_active Ceased
- 1998-08-04 RU RU2000106067/04A patent/RU2228329C2/ru not_active IP Right Cessation
- 1998-08-04 DE DE59810804T patent/DE59810804D1/de not_active Expired - Fee Related
- 1998-08-04 TR TR2000/00327T patent/TR200000327T2/xx unknown
- 1998-08-04 ID IDW20000229A patent/ID24307A/id unknown
- 1998-08-04 US US09/463,820 patent/US6169198B1/en not_active Expired - Fee Related
- 1998-08-04 CN CN98807985A patent/CN1266424A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| TR200000327T2 (tr) | 2000-11-21 |
| EP1003716B1 (de) | 2004-02-18 |
| AR010428A1 (es) | 2000-06-07 |
| EP1003716A1 (de) | 2000-05-31 |
| BR9810978A (pt) | 2000-08-08 |
| AU9257098A (en) | 1999-03-01 |
| KR20010022579A (ko) | 2001-03-26 |
| JP2001513528A (ja) | 2001-09-04 |
| MY126401A (en) | 2006-09-29 |
| CN1266424A (zh) | 2000-09-13 |
| CA2298585A1 (en) | 1999-02-18 |
| TW466221B (en) | 2001-12-01 |
| US6169198B1 (en) | 2001-01-02 |
| DE59810804D1 (de) | 2004-03-25 |
| RU2228329C2 (ru) | 2004-05-10 |
| WO1999007671A1 (de) | 1999-02-18 |
| ID24307A (id) | 2000-07-13 |
| ES2216308T3 (es) | 2004-10-16 |
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