KR940006983A - 하이드로포밀화 방법 - Google Patents

하이드로포밀화 방법 Download PDF

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KR940006983A
KR940006983A KR1019930020125A KR930020125A KR940006983A KR 940006983 A KR940006983 A KR 940006983A KR 1019930020125 A KR1019930020125 A KR 1019930020125A KR 930020125 A KR930020125 A KR 930020125A KR 940006983 A KR940006983 A KR 940006983A
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마이클 마허 존
에드워드 바빈 제임스
언스트빌리그
로버트 브라이언트 데이비드
와이 롱 타크
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카렌 엘. 존슨
유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션
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    • 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
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    • 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
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    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
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Abstract

부가수, 약산성 화합물 및 부가수와 약산성 화합물 둘다로 이루어진 그룹 중에서 선택된 촉매 활성 증강제의 존재하에서 수행함을 특징으로 하는 개선된 로듐-오가노 포스파이트 착물-촉매화된 하이드로포밀화 방법에 대해 기술하였다.

Description

하이드로포밀화 방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 올레핀계 불포화 화합물을, 비스포스파이트 리간드가 하기 일반식(Ⅰ)및 (Ⅱ)의 리간드로 이루어진 그룹중에서 선택된 리간드인 가용화된 로듐-비스포스파이트 착물 촉매의 존재하에 하이드로포밀화 반응매질중에 존재하는, 부가수, pka치가 약 1.0내지 약 12인 약산성 화합물 및 부가수와 pka치가 약 1.0내지 약 12인 약산성 화합물 둘다로 이루어진 그룹중에서 선택된 소량의 촉매 활성 증강제의 존재하에 일산화탄소 및 수소와 반응시킴을 특징으로 하는, 알데하이드를 제조하기 위한 연속식 하이드로포밀화 방법.
    상기식에서, X1및 X2는 각각 개별적으로 수소, 메틸, 에틸 및 n-프로필로 이루어진 그룹중에서 선택된 래디칼이고, Z1및 Z2는 각각 개별적으로 수소 또는 탄소수 1 내지 18의 치환체 래디칼이며, X는 각각 알킬렌, 알킬렌-옥시-알킬렌, 아릴렌 및 아릴렌-(Q)n-아릴렌〔여기서, 알킬렌 래디칼은 동일하거나 상이하며 각각 개별적으로 탄소수가 2내지 18이고, 아릴렌 래디칼은 동일하거나 상이하며 가각 개별적으로 탄소수가 6내지 18이고, Q는 각각 개별적으로 -CR5R6-2가 브릿지 그룹(여기서, R5및 R6래디칼은 각각 개별적으로 수소 또는 메틸 래디칼이다)이며, n은 각각 개별적으로 0또는 1이다〕으로 이루어진 그룹 중에서 선택된 2가 래디칼이다.
  2. 제1항에 있어서, 사용된 촉매 활성 증강제의 소량이 하이드로포밀화 반응 매질의 총중량을 기준으로 하여 약 0.05내지 약 20중량％ 범위일 수 있는 방법.
  3. 제2항에 있어서, 약산성 화합물이 2.2'-디하이드록시 비페닐인 방법.
  4. 제2항에 있어서, 상기한 임의의 약산성 화합물 부가제의 부재하에서 수행하는 방법.
  5. 제2항에 있어서, 사용된 비스포스파이트 리간드가 일반식(Ⅴ) 및 (Ⅵ)으로 이루어진 그룹중에서 선택된 리간드인 방법.
    상기식에서 Z1,Z2,R3및 R4는 각각 개별적으로 수소, 탄소수 1내지 8의 알킬 래디칼, 페닐, 벤질, 사이크로헥실, 및 1-메틸사이클로헥실, 하이드록시 및 탄소수 1내지 8의 알콕시 래디칼 중에서 선택된 래디칼이고, R1및 R2는 각각 개별적으로 탄소수 3내지 8의 측쇄 알킬 래디칼, 사이클로헥실 및 1-메틸사이클로헥실로 이루어진 그룹중에서 선택된 래디칼이며, X1,X2,Q 및 n은 제1항에서 정의한 바와 같다.
  6. 제2항에 있어서, 에폭사이드 화합물이 또한 하이드로포밀화 반응 매질중에 존재하는 방법.
  7. 제4항에 있어서, 비스포스파이트 리간드가 6,6'[[3,3', 5,5-테트라키스(1,1-디메틸에틸)1,1'-비페닐-2,2'-디일]비스(옥시)비스-디벤조[d,f][1,3,2]-디옥사포스페핀인 방법.
  8. 제4항에 있어서, 비스포스파이트 리간드가 6,6'[[3,3', 5,5-테트라키스(1,1-디메틸프로필)1,1'-비페닐-2,2'-디일]비스(옥시)비스-디벤조[d,f][1,3,2]-디옥사포스페핀인 방법.
  9. 제4항에 있어서, 비스포스파이트 리간드가 6,6'[[3,3', 비스(1,1-디메틸에틸)5,5'-디메톡시[1,1-비페닐]-2,2'-디일]비스(옥시)비스-디벤조[d,f][1,3,2]-디옥사포스페핀인 방법.
  10. 제4항에 있어서, 사용된 비스포스파이트 리간드가 일반식(Ⅴ) 및 (Ⅵ)으로 이루어진 그룹중에서 선택된 리간드인 방법.
    상기식에서 Z1,Z2,R3및 R4는 각각 개별적으로 수소, 탄소수 1내지 8의 알킬 래디칼, 페닐, 벤질, 사이클로헥실, 및 1-메틸사이클로헥실, 하이드록시 및 탄소수 1내지 8의 알콕시 래디칼 중에서 선택된 래디칼이고, R1및 R2는 각각 개별적으로 탄소수 3내지 8의 측쇄 알킬 래디칼, 사이클로헥실 및 1-메틸사이클로헥실로 이루어진 그룹중에서 선택된 래디칼이며, X1,X2,Q 및 n은 제1항에서 정의한 바와 같다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930020125A 1992-09-29 1993-09-28 하이드로포밀화 방법 KR100198688B1 (ko)

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US7/953,016 1992-09-29
US07/953,016 US5288918A (en) 1992-09-29 1992-09-29 Hydroformylation process

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KR100198688B1 KR100198688B1 (ko) 1999-06-15

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EP (1) EP0590613B1 (ko)
JP (1) JP2942693B2 (ko)
KR (1) KR100198688B1 (ko)
CN (1) CN1056364C (ko)
AU (1) AU4864393A (ko)
BR (1) BR9303934A (ko)
CA (1) CA2107192A1 (ko)
DE (1) DE69307240T2 (ko)
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MX (1) MX9305979A (ko)
PL (1) PL300521A1 (ko)
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SI (1) SI9300505A (ko)
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Families Citing this family (143)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9119955D0 (en) * 1991-09-18 1991-10-30 Imperial College Treatment of aqueous supplies containing organic material
CN1072980C (zh) 1994-04-14 2001-10-17 纳幕尔杜邦公司 用于单烯烃氢氰化的双配位亚磷酸酯和镍的催化剂复合物
US5756855A (en) * 1994-08-19 1998-05-26 Union Carbide Chemicals & Plastics Technology Corporation Stabilization of phosphite ligands in hydroformylation process
US5648553A (en) * 1994-12-09 1997-07-15 Mitsubishi Chemical Corporation Method for producing aldehydes
US5672766A (en) * 1994-12-12 1997-09-30 Mitsubishi Chemical Corporation Method for producing aldehydes
IN187044B (ko) * 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
US5648554A (en) * 1995-04-12 1997-07-15 Mitsubishi Chemical Corporation Method for producing aldehydes
KR970703805A (ko) * 1995-05-01 1997-08-09 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 막 분리방법(Membrane Separation)
JPH0977713A (ja) * 1995-09-19 1997-03-25 Mitsubishi Chem Corp アルデヒド類の製造方法
US5786517A (en) * 1995-12-06 1998-07-28 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5741942A (en) * 1996-11-26 1998-04-21 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
SK68698A3 (en) * 1995-12-06 1999-02-11 Union Carbide Chem Plastic Improved metal-ligand complex catalyzed processes
US5789625A (en) * 1995-12-06 1998-08-04 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5731472A (en) * 1995-12-06 1998-03-24 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5767321A (en) * 1995-12-06 1998-06-16 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5741944A (en) * 1995-12-06 1998-04-21 Union Carbide Chemicals & Plastics Technology Corporation Hydroformaylation processes
US5886235A (en) * 1995-12-06 1999-03-23 Union Carbide Chemicals & Plastics Technology Corporation. Metal-ligand complex catalyzed processes
EP0839787A1 (en) * 1996-11-04 1998-05-06 Dsm N.V. Process for the preparation of an aldehyde
US6153795A (en) * 1996-08-09 2000-11-28 Aag Industries, Inc. Ethyleneimine-containing resins, manufacture, and use for chemical separations
US6090950A (en) * 1996-08-23 2000-07-18 Zeeland Chemicals, Inc. Chiral hydride complexes
US6274773B1 (en) 1996-11-04 2001-08-14 Dsm Process for the continuous preparation of alkyl 5-formylvalerate compounds using homogeneous rhodium hydroformylation catalysts
EP0839794A1 (en) * 1996-11-04 1998-05-06 Dsm N.V. Process for the continuous preparation of an alkyl 5-formylvalerate compound
ZA9610314B (en) * 1996-11-26 1998-09-07 Union Carbide Chem Plastic Metal-ligand complex catalyzed processes
US5917095A (en) * 1996-11-26 1999-06-29 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US5874640A (en) * 1996-11-26 1999-02-23 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
US6127582A (en) * 1997-08-27 2000-10-03 Shell Oil Company Hydroformylation process
DE69802360T2 (de) * 1997-09-18 2002-10-17 Shell Internationale Research Maatschappij B.V., Den Haag/S'gravenhage Hydroformylierungsverfahren
JP3812095B2 (ja) 1997-10-28 2006-08-23 三菱化学株式会社 アルデヒド類の製造方法及びこれに用いるビスホスファイト
EP0943597B1 (en) * 1998-03-16 2003-06-04 Shell Internationale Researchmaatschappij B.V. Hydroformylation of olefin feeds containing dienes
US6156936A (en) * 1998-03-16 2000-12-05 Shell Oil Company Hydroformylation of olefin feeds containing dienes
US6229052B1 (en) * 1998-05-29 2001-05-08 E. I. Du Pont De Nemours And Company Hydroformylation of olefins using supported bis(phosphorus) ligands
US6090987A (en) * 1998-07-06 2000-07-18 Union Carbide Chemicals & Plastics Technology Corporation Metal-ligand complex catalyzed processes
KR100434589B1 (ko) * 1998-11-25 2004-09-08 현대석유화학 주식회사 하이드로포르밀레이션반응용촉매의배위자,이를포함하는촉매및이를이용한혼합올레핀의하이드로포르밀레이션방법
DE19940249A1 (de) * 1999-08-25 2001-03-01 Celanese Chem Europe Gmbh Verfahren zur Herstellung von Aldehyden
US6610891B1 (en) 1999-12-03 2003-08-26 Mitsubishi Chemical Corporation Method of producing aldehydes
EP1249441A1 (en) 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process
EP1249444A1 (en) * 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process for forming an aldehyde
EP1249438A1 (en) * 2001-04-13 2002-10-16 Dsm N.V. Continuous hydroformylation process for producing an aldehyde
US6693219B2 (en) 2001-06-02 2004-02-17 Eastman Chemical Company Epoxide stabilization of fluorophosphite-metal catalyst system in a hydroformylation process
US6831035B2 (en) 2002-01-22 2004-12-14 Eastman Kodak Company Stabilization of fluorophosphite-containing catalysts
DE10220801A1 (de) * 2002-05-10 2003-11-20 Oxeno Olefinchemie Gmbh Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste
US6664427B1 (en) * 2002-08-29 2003-12-16 E. I. Du Pont De Nemours And Company Process for preparing aldehyde compounds
RU2337090C2 (ru) * 2002-08-31 2008-10-27 Оксено Олефинхеми Гмбх Способ гидроформилирования олефиновых соединений в присутствии циклических эфиров угольной кислоты
ES2345770T3 (es) * 2003-01-16 2010-10-01 Teijin Fibers Limited Hilo compuesto por filamentos combinados de poliester que tienen diferentes coeficientes de contraccion.
CN1997616B (zh) * 2003-07-03 2011-01-19 陶氏技术投资有限责任公司 配体降解产物的最小化,或其向有用的膦配体的转化
GB0322247D0 (en) 2003-09-23 2003-10-22 Exxonmobil Chem Patents Inc Improvement in or relating to an isobutylene containing stream
GB0322246D0 (en) * 2003-09-23 2003-10-22 Exxonmobil Chem Patents Inc Improvement in or relating to isobutylene
CN1309728C (zh) * 2004-07-30 2007-04-11 中国科学院上海有机化学研究所 一类手性有机－无机高分子组装体催化剂、合成方法及用途
RU2388742C2 (ru) 2004-08-02 2010-05-10 Дау Текнолоджи Инвестментс Ллс. Стабилизация процесса гидроформилирования
JP2006306815A (ja) * 2005-04-28 2006-11-09 Mitsubishi Chemicals Corp アルデヒドの製造方法
WO2008115740A1 (en) * 2007-03-20 2008-09-25 Union Carbide Chemicals & Plastics Technology Llc Hydroformylation process with improved control over product isomers
US7674937B2 (en) * 2008-05-28 2010-03-09 Eastman Chemical Company Hydroformylation catalysts
US8507731B2 (en) * 2008-08-19 2013-08-13 Dow Technology Investments Llc Hydroformylation process using a symmetric bisphosphite ligand for improved control over product isomers
MX2011005103A (es) 2008-11-14 2011-08-04 Univ Kansas Complejos de catalizador de metal de transicion soportados en polimeros y metodos de uso.
WO2010117391A1 (en) 2009-03-31 2010-10-14 Dow Technology Investment Llc Hydroformylation process with a doubly open-ended bisphosphite ligand
US8586800B2 (en) * 2009-10-16 2013-11-19 Dow Technology Investments Llc Gas phase hydroformylation process
EP2516371B2 (en) † 2009-12-22 2022-08-17 Dow Technology Investments LLC Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure
KR101815328B1 (ko) 2009-12-22 2018-01-04 다우 테크놀로지 인베스트먼츠 엘엘씨. 합성가스 분압의 조절에 의한 혼합된 리간드 하이드로폼일화 공정에서의 노말:아이소 알데하이드 비의 조절 방법
US8598390B2 (en) 2009-12-22 2013-12-03 Dow Technology Investments Llc Controlling the normal:ISO aldehyde ratio in a mixed ligand hydroformylation process
JP5652052B2 (ja) * 2010-08-24 2015-01-14 三菱化学株式会社 アルデヒドの製造方法
JP2014502254A (ja) 2010-10-05 2014-01-30 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化の方法
RU2727149C2 (ru) * 2010-11-12 2020-07-21 Дау Текнолоджи Инвестментс Ллс Снижение загрязнения в процессах гидроформилирования посредством добавления воды
KR20130135286A (ko) 2010-12-23 2013-12-10 바스프 에스이 열가소성 엘라스토머 조성물 및 그의 제조 방법
US8513468B2 (en) 2010-12-30 2013-08-20 Eastman Chemical Company Process for removing degradation acids from hydroformylation reactions
SA112330271B1 (ar) * 2011-04-18 2015-02-09 داو تكنولوجى انفستمنتس ال ال سى تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء
CN102826974B (zh) * 2011-06-17 2015-11-25 中国石油化工股份有限公司 一种丙烯氢甲酰化反应制备丁醛的方法
EP2773649B1 (en) 2011-10-31 2017-07-12 Dow Technology Investments LLC Preventing solvent of crystallization in production of polyphosphite ligands
RU2606629C2 (ru) 2011-12-20 2017-01-10 Дау Текнолоджи Инвестментс Ллс Усовершенствованный способ гидроформилирования
MX363617B (es) 2011-12-30 2019-03-28 Basf Se Metodo para la purificacion de compuestos de difosfitos organicos.
RU2660899C2 (ru) 2011-12-30 2018-07-11 Басф Се Кристаллический сольват и несольватированные формы 6,6'-[[3,3',5,5'-тетракис(1,1-диметилэтил)-[1,1'-бифенил]-2,2'-диил]бис(окси)]бис-дибензо[d,f][1,3,2]-диоксафосфепина
MY185096A (en) 2012-03-07 2021-04-30 Basf Se Method for thermal integration in the hydrogenation and distillation of c3-c20 aldehydes
MY172695A (en) 2012-04-12 2019-12-10 Basf Se Method for replenishing the catalyst in continuous hydroformylation
US8889917B2 (en) 2012-04-12 2014-11-18 Basf Se Method of supplementing the catalyst in continuous hydroformylation
MY172419A (en) 2012-06-04 2019-11-25 Dow Technology Investments Llc Hydroformylation process
WO2013183796A1 (en) * 2012-06-04 2013-12-12 Lg Chem, Ltd. Hydroformylation method having improved catalyst stability in reaction
JP6339572B2 (ja) 2012-08-29 2018-06-06 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー 触媒製造方法
MX2015003905A (es) * 2012-09-25 2015-07-17 Dow Technology Investments Llc Proceso para estabilizar un ligando fosfito contra la degradacion.
DE102013219510A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Gemisch von Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung
WO2014056735A1 (de) 2012-10-12 2014-04-17 Evonik Degussa Gmbh Gemische konstitutionsisomerer bisphosphite
EP2740535A1 (en) 2012-12-04 2014-06-11 Dow Technology Investments LLC Bidentate ligands for hydroformylation of ethylene
JP6174711B2 (ja) * 2012-12-06 2017-08-02 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化方法
CN104045532B (zh) 2013-03-15 2018-05-25 陶氏技术投资有限责任公司 加氢甲酰化方法
CN104513143A (zh) 2013-09-26 2015-04-15 陶氏技术投资有限责任公司 加氢甲酰化方法
JP6382969B2 (ja) 2013-10-28 2018-08-29 ローム アンド ハース カンパニーRohm And Haas Company メタクロレインを分離するための方法
TWI654177B (zh) 2013-10-31 2019-03-21 德商巴斯夫歐洲公司 製備羧酸酯的方法及其作爲塑化劑的用途
EP3077453B1 (de) 2013-12-06 2018-03-28 Basf Se Weichmacher-zusammensetzung, die tetrahydrofuranderivate und 1,2-cyclohexandicarbonsäureester enthält
CN106103399B (zh) 2013-12-19 2019-07-09 陶氏技术投资有限责任公司 氢甲酰化方法
CN104725170B (zh) 2013-12-19 2019-08-23 陶氏技术投资有限责任公司 加氢甲酰化方法
ES2690081T3 (es) 2014-01-09 2018-11-19 Basf Se Composición plastificante que contiene derivados de furano y ésteres de ácido 1,2-ciclohexano dicarboxílico
RU2674698C1 (ru) 2014-03-31 2018-12-12 Дау Текнолоджи Инвестментс Ллк Способ гидроформилирования
RU2016145450A (ru) 2014-04-22 2018-05-22 Басф Се Способ получения сложных эфиров карбоновых кислот в присутствии ионной жидкости и кислотного катализатора этерификации и их применение в качестве пластификатора
DE102015207291A1 (de) 2014-04-24 2016-03-10 Basf Se Weichmacher-Zusammensetzung, die Furanderivate und 1,2-Cyclohexandicarbonsäureester enthält
WO2015175158A1 (en) 2014-05-14 2015-11-19 Dow Technology Investments Llc Stabilized organophosphorous compounds
TW201605945A (zh) 2014-07-08 2016-02-16 巴斯夫歐洲公司 包含二羧酸的酯及１，２－環己烷二羧酸的酯之模製化合物
TW201609628A (zh) 2014-07-08 2016-03-16 巴斯夫歐洲公司 包含脂族二羧酸二酯及對苯二甲酸二烷基酯之塑化劑組成物
TWI706979B (zh) 2014-08-19 2020-10-11 德商巴斯夫歐洲公司 包含聚合二羧酸酯的塑化劑組成物
TWI686444B (zh) 2014-09-04 2020-03-01 德商巴斯夫歐洲公司 包含聚合二羧酸酯的塑化劑組成物
TW201619119A (zh) 2014-10-09 2016-06-01 巴斯夫歐洲公司 包含飽和二羧酸之環烷基酯及１，２－環己烷二羧酸酯的塑化劑組成物
TW201619120A (zh) 2014-10-09 2016-06-01 巴斯夫歐洲公司 包含飽和二羧酸之環烷基酯及對苯二甲酯之塑化劑組成物
WO2016075070A1 (en) 2014-11-10 2016-05-19 Basf Se Ethylene-propylheptyl(meth-)acrylate copolymers
US10287417B2 (en) 2015-01-30 2019-05-14 Basf Se Plasticizer composition containing polymeric dicarboxylic acid esters and terephthalic acid dialkyl esters
CA2999998A1 (en) 2015-09-30 2017-04-06 Basf Se Plasticizer composition containing polymeric dicarboxylic acid esters and 1,2-cyclohexane dicarboxylic acid esters
EP3356459B1 (de) 2015-09-30 2019-11-13 Basf Se Weichmacher-zusammensetzung, die polymere dicarbonsäureester und dicarbonsäurediester enthält
CA2999933A1 (en) 2015-09-30 2017-04-06 Basf Se Plasticizer composition containing polymeric dicarboxylic acid esters and terephthalic acid dialkyl esters
KR20180081526A (ko) 2015-11-10 2018-07-16 다우 테크놀로지 인베스트먼츠 엘엘씨. 알데하이드를 생산하는 방법
CN105498855A (zh) * 2015-12-08 2016-04-20 中国海洋石油总公司 提高醚后c4羰基合成反应铑-双膦催化剂稳定性的方法
RU2729055C2 (ru) 2016-01-20 2020-08-04 Басф Се Пластифицирующая композиция, которая содержит алифатический сложный эфир дикарбоновой кислоты и сложный диэфир, выбранный из сложных эфиров 1,2-циклогександикарбоновой кислоты и сложных эфиров терефталевой кислоты
BR112018016320B1 (pt) 2016-02-11 2022-07-12 Dow Technology Investments Llc Processo para converter olefinas em álcoois, éteres ou combinações dos mesmos
CN107141204B (zh) 2016-03-01 2022-03-15 陶氏技术投资有限责任公司 氢甲酰化工艺
CA3018072A1 (en) 2016-03-18 2017-09-21 Dow Technology Investments Llc Hydroformylation process
PL3433309T3 (pl) 2016-03-23 2020-11-16 Basf Se Kompozycja polimerowa, zawierająca diester cykloalkilowo-alkilowy kwasu dikarboksylowego jako plastyfikator
WO2018024591A1 (de) 2016-08-01 2018-02-08 Basf Se Weichmacher-zusammensetzung
CA3032582A1 (en) 2016-08-01 2018-02-08 Basf Se Plasticizer composition
WO2018024597A1 (de) 2016-08-01 2018-02-08 Basf Se Weichmacher-zusammensetzung
TW201840362A (zh) 2016-11-08 2018-11-16 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
TWI758353B (zh) 2016-11-08 2022-03-21 美商陶氏科技投資有限公司 使去活化的氫甲醯化催化劑溶液再生的方法
TW201840363A (zh) 2016-11-08 2018-11-16 美商陶氏科技投資有限公司 處理氫甲醯化催化劑溶液之方法
EP3700882B1 (en) 2017-10-25 2022-10-26 Dow Technology Investments LLC Process to reduce heavies formation in a solution comprising aldehyde compounds formed during a hydroformylation process
JP7269238B2 (ja) 2017-11-13 2023-05-08 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化プロセスからロジウムを回収するためのプロセス
TWI793216B (zh) * 2017-12-07 2023-02-21 美商陶氏科技投資公司 氫甲醯化方法
WO2019185409A1 (de) 2018-03-29 2019-10-03 Basf Se Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung
CN112074347A (zh) 2018-05-30 2020-12-11 陶氏技术投资有限责任公司 在加氢甲酰化过程中减缓催化剂失活和/或减缓四膦配位体使用的方法
CN112055614A (zh) 2018-05-30 2020-12-08 陶氏技术投资有限责任公司 包括单膦、四膦配位体的组合的催化剂组合物和使用其的加氢甲酰化过程
KR20210015839A (ko) 2018-05-30 2021-02-10 다우 테크놀로지 인베스트먼츠 엘엘씨. 하이드로포밀화 공정의 제어 방법
KR20210098486A (ko) 2018-11-29 2021-08-10 다우 테크놀로지 인베스트먼츠 엘엘씨. 히드로포르밀화 공정
JPWO2020203950A1 (ko) * 2019-03-29 2020-10-08
EP3747860B1 (de) 2019-06-04 2023-07-26 Basf Se Neue weichmacher auf cyclohexanon-basis
US20220143590A1 (en) 2019-06-27 2022-05-12 Dow Technology Investments Llc Process to prepare solution from hydroformylation process for precious metal recovery
SE1930237A1 (en) 2019-07-05 2020-11-17 Perstorp Ab A use of epoxide in order to reduce the formation of heavy ends in a hydroformylation process
TW202126385A (zh) 2019-11-05 2021-07-16 美商陶氏科技投資有限公司 自氫甲醯化製程回收銠之方法
WO2021126421A1 (en) 2019-12-19 2021-06-24 Dow Technology Investments Llc Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms
KR20230120131A (ko) 2020-12-14 2023-08-16 다우 테크놀로지 인베스트먼츠 엘엘씨. 히드로포르밀화 공정에서 촉매 금속 책임량을 개선시키는 방법
JP2024513740A (ja) 2021-03-31 2024-03-27 ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー ヒドロホルミル化プロセス
CN113402367A (zh) * 2021-06-16 2021-09-17 上海华谊（集团）公司 连续氢甲酰化反应中调节正异比的方法
CN114027296A (zh) * 2021-11-10 2022-02-11 山东农业大学 用于防治松材线虫及其媒介昆虫的纳米农药制剂
CN118103532A (zh) 2021-11-11 2024-05-28 陶氏技术投资有限责任公司 用于从加氢甲酰化过程中回收铑的方法
CN118338965A (zh) 2021-12-16 2024-07-12 陶氏技术投资有限责任公司 包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法
WO2023114579A1 (en) 2021-12-16 2023-06-22 Dow Technology Investments Llc Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes
WO2024129290A1 (en) 2022-12-13 2024-06-20 Dow Technology Investments Llc Process to minimize polyphosphine usage by making use of degradation products
WO2024133359A1 (de) 2022-12-21 2024-06-27 Basf Se Weichmacher
WO2024133358A1 (de) 2022-12-21 2024-06-27 Basf Se Weichmacher-verbindung
WO2024153687A1 (de) 2023-01-19 2024-07-25 Basf Se Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH348284A (de) * 1956-11-30 1960-08-15 Geigy Ag J R Verfahren zur Stabilisierung von Estern von Säuren des drei- oder fünfwertigen Phosphors oder von solche Ester enthaltenden Gemischen
US3533298A (en) * 1968-08-28 1970-10-13 Gerber Scientific Instr Co Lead screw and nut mechanism
US4224255A (en) * 1978-06-15 1980-09-23 General Electric Company Process for the production of aldehydes and alcohols from olefinically unsaturated compounds by hydroformylation with suppression of olefin hydrogenation
ZA827645B (en) * 1981-11-12 1983-08-31 Union Carbide Corp Catalyst stabilizer
DE3368920D1 (en) * 1982-03-27 1987-02-12 Basf Ag Process for the preparation of olefines from methanol/dimethyl ether
DE3234701A1 (de) * 1982-09-18 1984-04-05 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur herstellung von aldehyden
GB8334359D0 (en) * 1983-12-23 1984-02-01 Davy Mckee Ltd Process
DE3413427A1 (de) * 1984-04-10 1985-10-17 Ruhrchemie Ag, 4200 Oberhausen Verfahren zur herstellung von aldehyden
US4650894A (en) * 1984-07-05 1987-03-17 Argus Chemical Corporation Tris-organophosphite compositions having improved hydrolytic stability
US4578523A (en) * 1985-05-29 1986-03-25 Ruhrchemie Aktiengesellschaft Process for the preparation of aldehydes
US4668651A (en) * 1985-09-05 1987-05-26 Union Carbide Corporation Transition metal complex catalyzed processes
BR8806809A (pt) * 1987-12-24 1989-08-29 Union Carbide Corp Processo de hidrocarbonilacao para a producao de um aldeido ou uma mistura de uma cetona e um aldeido;catalisador intermediario;processo para a producao de catalisador de complexo de rodio;e processo de hidroacilacao
US5210318A (en) * 1990-05-04 1993-05-11 Union Carbide Chemicals & Plastics Technology Corporation Catalysts and processes useful in producing 1,3-diols and/or 3-hydroxyldehydes
US5095061A (en) * 1990-07-13 1992-03-10 The Dow Chemical Company Process to reduce propenyl polyethers in hydroxyfunctional polyethers
TW213465B (ko) * 1991-06-11 1993-09-21 Mitsubishi Chemicals Co Ltd

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