ES2524355T3 - Procedimiento para la fabricación de nitrilos - Google Patents
Procedimiento para la fabricación de nitrilos Download PDFInfo
- Publication number
- ES2524355T3 ES2524355T3 ES11740745.2T ES11740745T ES2524355T3 ES 2524355 T3 ES2524355 T3 ES 2524355T3 ES 11740745 T ES11740745 T ES 11740745T ES 2524355 T3 ES2524355 T3 ES 2524355T3
- Authority
- ES
- Spain
- Prior art keywords
- liquid
- catalyst
- adiponitrile
- reaction zone
- stream
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000002825 nitriles Chemical class 0.000 title 1
- 239000007788 liquid Substances 0.000 abstract 19
- 238000000605 extraction Methods 0.000 abstract 13
- 239000003054 catalyst Substances 0.000 abstract 11
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract 9
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 8
- 239000002904 solvent Substances 0.000 abstract 7
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 abstract 4
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 abstract 4
- 238000009835 boiling Methods 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 239000003446 ligand Substances 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 238000007670 refining Methods 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
Classifications
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- 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
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/04—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton containing two cyano groups bound to the carbon skeleton
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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)
Abstract
Un procedimiento de producción de adiponitrilo, comprendiendo dicho procedimiento las etapas de: (a) hacer reaccionar en una primera zona de reacción una mezcla que comprende 1,3 - butadieno (BD) y cianuro de hidrógeno (HCN) en presencia de un primer catalizador que comprende Ni de valencia cero y un primer ligando que contiene fósforo para producir un producto de reacción que comprende 3 - pentenonitrilo (3PN) y 2 - metil - 3 - butenonitrilo (2M3BN); (b) isomerizar al menos una parte del 2M3BN de la etapa (a) en una segunda zona de reacción en presencia de un segundo catalizador que comprende Ni de valencia cero y un segundo ligando que contiene fósforo para producir un producto de reacción que comprende 3PN; y (c) hacer reaccionar en una tercera zona de reacción una mezcla que comprende 3PN de la etapa (b) y cianuro de hidrógeno (HCN) en presencia de un tercer catalizador que comprende Ni de valencia cero y un tercer ligando que contiene fósforo y en presencia de un promotor de ácido Lewis para producir un producto de reacción que comprende adiponitrilo, en el que el catalizador fluye a través de la primera, la segunda y la tercera zona de reacción junto a reactivos y productos, en el que el producto de la reacción de la etapa (a) comprende, además, dinitrilos que comprenden adiponitrilo (ADN) y metilglutaronitrilo (MGN), en el que, al menos, una parte del catalizador que fluye a través de la primera zona de reacción se recicla en la primera zona de reacción, y en el que el catalizador que fluye a través de la tercera zona de reacción se recicla en la tercera zona de reacción, en el que una parte de la corriente de reciclado del catalizador se pone en contacto con un primer disolvente de extracción en una primera etapa de extracción de líquido / líquido para producir una fase de disolvente y una fase de refinado, en el que se emplea una etapa de extracción de líquido / líquido separada para tratar el producto de la tercera zona de reacción de manera que dicho tercer catalizador no esté en contacto con dicho disolvente de extracción en dicha primera etapa de extracción de líquido / líquido, en el que la primera etapa de extracción de líquido / líquido comprende la introducción de una parte de la corriente de reciclado del catalizador, una primera corriente de disolvente de extracción y una corriente de reciclado de dinitrilo que comprende adiponitrilo (ADN) en una primera zona de extracción de líquido / líquido, en el que la primera etapa de extracción de líquido / líquido comprende además la separación de los líquidos en la primera zona de extracción de líquido / líquido en una primera fase de disolvente que comprende un primer disolvente de extracción y el catalizador y una primera fase de refinado que comprende adiponitrilo (ADN), metilglutaronitrilo (MGN), compuestos con un punto de ebullición mayor que el adiponitrilo (ADN) y compuestos con un punto de ebullición menor que el metilglutaronitrilo (MGN); en el que el catalizador de dicha primera fase de disolvente obtenido se recicla en la primera etapa de extracción de líquido / líquido en la primera, la segunda o ambas zonas de reacción, en el que dicha primera fase de refinado se destila en una o más etapas de destilación para separar adiponitrilo (ADN) y metilglutaronitrilo (MGN) de compuestos con un punto de ebullición mayor que el adiponitrilo (ADN) y compuestos con un punto de ebullición menor que el metilglutaronitrilo (MGN) para obtener una primera corriente de dinitrilo refinado, en el que dicha primera corriente de dinitrilo refinado se destila adicionalmente para retirar metilglutaronitrilo (MGN) de la primera corriente de dinitrilo refinado para obtener una segunda corriente de dinitrilo refinada rica en adiponitrilo, y en el que al menos una parte de dicha segunda corriente de dinitrilo refinado se recicla en la primera etapa de extracción de líquido / líquido.
Description
Claims (1)
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imagen1 imagen2 imagen3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36217510P | 2010-07-07 | 2010-07-07 | |
| US362175P | 2010-07-07 | ||
| PCT/US2011/040664 WO2012005915A1 (en) | 2010-07-07 | 2011-06-16 | Process for making nitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2524355T3 true ES2524355T3 (es) | 2014-12-05 |
Family
ID=44534788
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11729808.3T Active ES2542430T3 (es) | 2010-07-07 | 2011-06-16 | Proceso para hacer nitrilos |
| ES11740748.6T Active ES2522552T3 (es) | 2010-07-07 | 2011-06-16 | Proceso para producir nitrilos |
| ES11738858.7T Active ES2522845T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento de preparación de nitrilos |
| ES11729809.1T Active ES2449478T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento para preparar nitrilos |
| ES11740747.8T Active ES2533701T3 (es) | 2010-07-07 | 2011-06-16 | Proceso de preparación de nitrilos |
| ES11729810.9T Active ES2442927T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento de producción de nitrilos |
| ES11740746.0T Active ES2538658T3 (es) | 2010-07-07 | 2011-06-16 | Proceso para hacer nitrilos |
| ES11728474.5T Active ES2448957T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento de producción de nitrilos |
| ES11740745.2T Active ES2524355T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento para la fabricación de nitrilos |
Family Applications Before (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11729808.3T Active ES2542430T3 (es) | 2010-07-07 | 2011-06-16 | Proceso para hacer nitrilos |
| ES11740748.6T Active ES2522552T3 (es) | 2010-07-07 | 2011-06-16 | Proceso para producir nitrilos |
| ES11738858.7T Active ES2522845T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento de preparación de nitrilos |
| ES11729809.1T Active ES2449478T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento para preparar nitrilos |
| ES11740747.8T Active ES2533701T3 (es) | 2010-07-07 | 2011-06-16 | Proceso de preparación de nitrilos |
| ES11729810.9T Active ES2442927T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento de producción de nitrilos |
| ES11740746.0T Active ES2538658T3 (es) | 2010-07-07 | 2011-06-16 | Proceso para hacer nitrilos |
| ES11728474.5T Active ES2448957T3 (es) | 2010-07-07 | 2011-06-16 | Procedimiento de producción de nitrilos |
Country Status (8)
| Country | Link |
|---|---|
| US (9) | US9040733B2 (es) |
| EP (9) | EP2582661B1 (es) |
| JP (9) | JP5689960B2 (es) |
| KR (9) | KR20130041175A (es) |
| CN (9) | CN103080076B (es) |
| ES (9) | ES2542430T3 (es) |
| TW (9) | TWI417271B (es) |
| WO (9) | WO2012005917A1 (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2542430T3 (es) | 2010-07-07 | 2015-08-05 | Invista Technologies S.À.R.L. | Proceso para hacer nitrilos |
| US8642828B2 (en) * | 2012-01-03 | 2014-02-04 | Basf Se | Process for purifying a recycle stream from a 1,3-butadiene processing plant |
| 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 |
| 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 |
| CN103012197B (zh) * | 2012-12-18 | 2015-12-02 | 安徽省安庆市曙光化工股份有限公司 | 3-戊烯腈的制备方法和己二腈的制备方法 |
| US9676800B2 (en) | 2013-06-20 | 2017-06-13 | Invista North America S.A.R.L. | Extraction solvent control for reducing stable emulsions |
| US10759741B2 (en) | 2013-07-17 | 2020-09-01 | Invista North America S.A R.L. | Separating a solvent from a nickel catalyst by distillation |
| CN103694086B (zh) * | 2014-01-06 | 2015-09-16 | 重庆中平紫光科技发展有限公司 | 一种采用水解法分离回收含二腈萃余液中酚类的方法 |
| CN103739516B (zh) * | 2014-01-06 | 2016-04-27 | 重庆中平紫光科技发展有限公司 | 一种利用2-甲基-3-丁烯腈的异构化液合成己二腈的方法 |
| SI3102562T1 (en) * | 2014-02-07 | 2018-05-31 | Basf Se | Method for purification of adipodinitrile (ADN) |
| 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 |
| US9914700B2 (en) | 2014-06-27 | 2018-03-13 | Invista North America S.A R.L. | Enhanced extraction of impurities from mixture comprising nitriles |
| CN111995547B (zh) * | 2020-01-19 | 2021-07-09 | 浙江新和成股份有限公司 | 己二腈的制备方法和装置 |
| CN112794948B (zh) | 2020-12-31 | 2022-08-26 | 浙江大学 | 多孔聚合物及其制备方法、催化剂以及己二腈的制备方法 |
| CN113444018B (zh) * | 2021-06-25 | 2023-09-08 | 上海东庚化工技术有限公司 | 一种己二腈的生产方法 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
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| 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 |
| DE102004004673A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung von Butadien |
| DE102004004672A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| TW200535122A (en) | 2004-01-29 | 2005-11-01 | Basf Ag | Removal of nickel(0) complexes and phosphorus ligands from nitrile mixtures |
| DE102004004671A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von linearem Pentennitril |
| 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 |
| DE102004004684A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| 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 |
| DE102004004724A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Herstellung von 3-Pentennitril aus 1,3-Butadien |
| DE102004004721A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Trennung von Pentennitril-Isomeren |
| DE102004004720A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von 3-Pentennitril |
| DE102004004718A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| DE102004004716A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Isomerisierung von cis-2-Pentennitril zu 3-Pentennitril in einer Reaktivdestillation |
| DE102004004683A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Herstellung von Dinitrilen |
| DE102004004717A1 (de) | 2004-01-29 | 2005-08-18 | Basf Ag | Homogene Isomerisierung von cis-2-Pentennitril zu 3-Pentennitril |
| DE102004049339A1 (de) | 2004-10-08 | 2006-04-13 | Basf Ag | Verfahren zur Reinigung von phosphorhaltigen Chelat-Liganden |
| DE102004050935A1 (de) | 2004-10-18 | 2006-04-20 | Basf Ag | Extraktion von Nickel(0)-Komplexen aus Nitrilgemischen mit verminderter Mulmbildung |
| FR2878848B1 (fr) | 2004-12-07 | 2007-01-05 | Rhodia Chimie Sa | Procede de fabrication de composes dinitriles |
| EP1825914A1 (de) | 2006-02-22 | 2007-08-29 | Basf Aktiengesellschaft | Verbessertes Verfahren zur Herstellung von Nickel(0)-Phophorligand-Komplexen |
| KR20090006177A (ko) | 2006-04-07 | 2009-01-14 | 바스프 에스이 | 니트릴 혼합물로부터 니켈(0) 착물 및 인-함유 리간드의 분리 방법 |
| KR20090031941A (ko) | 2006-07-12 | 2009-03-30 | 바스프 에스이 | 할로겐을 함유하는 유기 인 화합물의 제조 방법 |
| WO2008017626A1 (de) * | 2006-08-08 | 2008-02-14 | Basf Se | Verfahren zur herstellung von 3-pentennitril durch hydrocyanierung von 1,3-butadien |
| CN101676261A (zh) * | 2008-09-19 | 2010-03-24 | 于网林 | 己二腈生产工艺 |
| KR20120104252A (ko) | 2009-12-18 | 2012-09-20 | 인비스타 테크놀러지스 에스.에이.알.엘. | 염기성 니켈 카르보네이트로부터 유도된 니켈 착체 및 니켈 금속 조성물 |
| CN102858734B (zh) | 2010-04-07 | 2014-11-05 | 巴斯夫欧洲公司 | 将顺-2-戊烯腈异构化成3-戊烯腈的方法 |
| ES2542430T3 (es) | 2010-07-07 | 2015-08-05 | Invista Technologies S.À.R.L. | Proceso para hacer nitrilos |
| EP2718013A2 (en) | 2011-06-10 | 2014-04-16 | Invista Technologies S.à.r.l. | Nickel calcination and reduction process including a fluidizing bed reactor |
| CN105148999B (zh) | 2011-06-10 | 2017-09-05 | 因温斯特技术公司 | 镍金属配体催化剂形成上的改进 |
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