KR830007136A - 로듐 복합 하이드로포르밀화 반응촉매를 재활성화 시키는 방법 - Google Patents
로듐 복합 하이드로포르밀화 반응촉매를 재활성화 시키는 방법 Download PDFInfo
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- KR830007136A KR830007136A KR1019810003535A KR810003535A KR830007136A KR 830007136 A KR830007136 A KR 830007136A KR 1019810003535 A KR1019810003535 A KR 1019810003535A KR 810003535 A KR810003535 A KR 810003535A KR 830007136 A KR830007136 A KR 830007136A
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- Prior art keywords
- hydroformylation
- medium
- phosphine
- weight
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- 238000007037 hydroformylation reaction Methods 0.000 title claims 23
- 229910052703 rhodium Inorganic materials 0.000 title claims 4
- 239000010948 rhodium Substances 0.000 title claims 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims 4
- 239000003054 catalyst Substances 0.000 title claims 2
- 230000007420 reactivation Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims 17
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000003003 phosphines Chemical class 0.000 claims 7
- 239000012429 reaction media Substances 0.000 claims 7
- 150000001299 aldehydes Chemical class 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000006227 byproduct Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical group C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 claims 4
- 230000003647 oxidation Effects 0.000 claims 4
- 238000007254 oxidation reaction Methods 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- 238000009835 boiling Methods 0.000 claims 2
- 230000006698 induction Effects 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- -1 olefin compound Chemical class 0.000 claims 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 claims 1
- GNFABDZKXNKQKN-UHFFFAOYSA-N tris(prop-2-enyl)phosphane Chemical compound C=CCP(CC=C)CC=C GNFABDZKXNKQKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004711 α-olefin Substances 0.000 claims 1
Classifications
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- 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
- B01J31/40—Regeneration or reactivation
-
- 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
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- 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
- B01J31/20—Carbonyls
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/12—Treating with free oxygen-containing gas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
-
- 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
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
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- 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
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
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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
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 반응 용기내에서 진행되고 있는 하이드로포르밀화 반응을 중지시킨후, 비-하이드로포르밀화 조건하에서, 약 5내지 약 60중량%의 알데히드 생성물, 약 10 내지 약 70중량%의 고비점 알데히드 농축 부산물, 유리 금속으로 계산하여 상기 반응 매질내에서 약 25피피엠 내지 1200피피엠의 로듐 농도를 제공해줄 수 있는 충분한 량의 부분적으로 비활성된 가용성 로듐 복합 하이드로 포르밀화 반응촉매, 약 0.1 내지 약 5중량%의 하기 구조식(I)의 유리 알킬치환 포스핀 부산물 및 약 5 내지 약 25중량%의 유리 트리알릴 포스핀 리간드를 필수적으로 구성하고 있는 이들의 화합물로부터 유도된 모든 하이드로 포르밀화 반응매질 또는 적당한 부의 이의 매질과 약 20℃ 내지 약 80℃의 온도에서 충분한 량의 산소 또는 장시간 동안 가스를 함유하는 산소를 처리시켜 최소한 약 25중량%의 알킬치환 포스핀을 이의 알킬 치환 산화 포스핀으로 전환시키며, 약 50중량% 이하의 트리아릴 포스핀 리간드를 이의 산화 트리아릴 포스핀으로 전환시킴을 특징으로 하여 알킬 치환 초스핀 부산물을 이에 상응하는 산화 포스핀으로 전환시키며, 반응 용기내의 하이드로포르밀화 반응 매질의 존재하에서 올레핀 화합물, 일산화 탄소 및 수소와 반응되어 알데히드 생성물을 제조하는 연속적인 하이드로 포르밀화 반응에 사용되므로써 부분적으로 사활성이 되는 하이드로포르밀화 반응 매질내의 로듐 복합 하이드로포르밀화 촉매의 활성은 증진시키는 방법.상기 식에서R은 알킬기이고,R'은 알킬기 또는 아랄기이고,R"은 아랄기이고상기 또는 중량%는 상기 유도된 하이드로 포르밀화 반응매청를 기준으로 한 것임.
- 제1항에 있어서, 처리된 상기 유도 하이드로포르밀화 매질이 약 10 내지 약 30중량%의 알데히드 생성물을 함유하는 상기 방법.
- 제1항에 있어서 처리된 상기 유도 하이드로 포르밀화 매질이 약 25 내지 약 60중량%의 고비점 알데히드 농축 부산물을 함유하는 상기 방법.
- 제1항에 있어서 올레핀 화합물이 탄소수 2 내지 20을 함유하는 α-올레핀인 상기 방법.
- 제1항에 있어서 상기 유도 하이드로포르밀화 반응매질이 약 0.2 내지 약 2.5중량%의 유리 알킬 치환 포스핀을 함유하는 상기 방법.
- 제5항에 있어서 유리 알킬 치환포스핀이 프로필디페닐 포스핀인 상기 방법.
- 제1항에 있어서 상기 유도 하이드로포르밀화 매질이 약 8 내지 약 15중량%의 유리 트리아릴포스핀을 함유하는 상기 방법.
- 제7항에 있어서 트리아릴 포스핀이 트릴페닐포스핀인 상기 방법.
- 제1항에 있어서 유도된 하이드로포르밀화 매질의 산화 처리를 25 내지 60℃의 온도에서 행하는 상기 방법.
- 제1항에 있어서 최소한 50중량%의 상기 알킬 치환 포스핀을 이의 알킬치환 산화 포스핀으로 전환 시키며, 약 25중량% 이하의 상기 트리아릴포스핀을 이의 산화 트리아릴포스핀으로 전환시키는 상기 방법.
- 제1항에 있어서, 유도된 하이드로포르밀화 매질의 산화처리를 상기 매체를 유도시키는 하이드로 포르밀화 방법의 똑같은 반응용기에서 행하는 상기 방법.
- 제1항에 있어서 공기 또는 공기-질소 혼합물이 상기 유도된 하이드로 포르밀화 매질을 산화처리시키기 위해 산소의 공급원으로 사용되는 상기 방법.
- 제1항에 있어서 처리될 상기 유도 하이드로 포르밀화 매질이 약 10 내지 30중량%의 부틸 알데히드 생성물, 유리알킬 치환 포스핀이 프로필 디페닐포시핀이고, 유리트리아릴포스핀이 트리페닐 포스핀이고, 유도 하이드로 포르밀화 매질의 산화처리를 약 25 내지 약 60℃의 온도에서 행하며 적어도 50중량%의 상기 프로필 디페닐 포스핀이 산화 프로필 디페닐포스핀으로 전화되며, 25중량% 이하의 상기 트리페닐포스핀이 산화 트리페닐 포스핀으로 전환됨을 특징으로 하는 상기 방법.
- 제13항에 있어서 유도된 하이드로 포르밀화 매질의 산화처리를 상기 매질이 유도된 하이드로포르밀화 방법의 똑같은 반응용기 내에서 행하는 상기 방법.
- 제14항에 있어서 공기 또는 공기-질소 혼합물이 상기 유도된 하이드로 포르밀화 반응매질의 산화 처리시키기 위해 산소의 공급원으로 사용되는 상기 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US190280 | 1980-09-24 | ||
| US06/190,280 US4605780A (en) | 1980-09-24 | 1980-09-24 | Reactivation of rhodium complex hydroformylation catalysts |
| US190.280 | 1980-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007136A true KR830007136A (ko) | 1983-10-14 |
| KR880000058B1 KR880000058B1 (ko) | 1988-02-22 |
Family
ID=22700690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810003535A KR880000058B1 (ko) | 1980-09-24 | 1981-09-22 | 로듐 착화합물 하이드로포르밀화 반응촉매를 재활성화 시키는 방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4605780A (ko) |
| EP (1) | EP0049781B1 (ko) |
| JP (1) | JPS607941B2 (ko) |
| KR (1) | KR880000058B1 (ko) |
| AT (1) | ATE6992T1 (ko) |
| BR (1) | BR8105868A (ko) |
| CA (1) | CA1187100A (ko) |
| DE (1) | DE3163094D1 (ko) |
| ES (1) | ES505725A0 (ko) |
| MX (1) | MX158918A (ko) |
| PL (1) | PL131753B1 (ko) |
| SU (1) | SU1757458A3 (ko) |
| YU (1) | YU43040B (ko) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5976034A (ja) * | 1982-10-21 | 1984-04-28 | Mitsubishi Chem Ind Ltd | ヒドロホルミル化法 |
| US4861918A (en) * | 1988-08-12 | 1989-08-29 | Union Carbide Corporation | Reactivation of hydroformylation catalysts |
| US4929767A (en) * | 1988-08-12 | 1990-05-29 | Union Carbide Chemicals And Plastics Company Inc. | Treatment of rhodium catalysts |
| US5099047A (en) * | 1989-11-17 | 1992-03-24 | Mitsubishi Kasei Corporation | Method for recovering a group viii metal solid complex and hydroformylation method |
| DE4135050A1 (de) * | 1991-10-24 | 1993-04-29 | Hoechst Ag | Verfahren zur reaktivierung wasserloeslicher hydroformylierungskatalysatoren |
| US5237106A (en) * | 1992-01-24 | 1993-08-17 | Union Carbide Chemicals & Plastics Technology Corporation | Reactivation of hydroformylation catalysts |
| US5290743A (en) * | 1993-03-22 | 1994-03-01 | Arco Chemical Technology L.P. | Process for regenerating a deactivated rhodium hydroformylation catalyst system |
| CZ283697A3 (cs) * | 1996-09-11 | 1998-04-15 | Mitsubishi Chemical Corporation | Způsob přípravy roztoku komplexu rhodia a jeho použití |
| 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 |
| CN104248994B (zh) * | 2013-06-25 | 2018-03-20 | 中国石油化工股份有限公司 | 羰基化铑膦催化剂的活性恢复方法 |
| CN103570514B (zh) * | 2013-10-07 | 2015-11-18 | 青岛科技大学 | 一种均相催化-两相分离烯烃氢甲酰化的方法 |
| CN108349863B (zh) | 2015-11-10 | 2021-07-27 | 陶氏技术投资有限责任公司 | 用于生产醛的方法 |
| 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 |
| 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 |
| 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 |
| EP3712126B1 (en) | 2017-11-15 | 2023-08-23 | Mitsubishi Chemical Corporation | Method for producing aldehyde and method for producing alcohol |
| 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 |
| CN113351249B (zh) * | 2021-04-29 | 2023-02-03 | 四川大学 | 一种催化内烯烃氢甲酰化制醛的催化体系 |
| WO2023095907A1 (ja) * | 2021-11-29 | 2023-06-01 | 三菱ケミカル株式会社 | アルデヒドの製造方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US3555098A (en) * | 1967-12-13 | 1971-01-12 | Union Oil Co | Hydroformylation |
| US3547964A (en) * | 1968-07-24 | 1970-12-15 | Union Oil Co | Group viii noble metal catalyst recovery |
| JPS5123212A (en) * | 1974-08-17 | 1976-02-24 | Mitsubishi Chem Ind | Arudehidono seizohoho |
| US4148830A (en) * | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| US4221743A (en) * | 1976-07-07 | 1980-09-09 | Union Carbide Corporation | Hydroformylation process |
| AT356639B (de) * | 1977-01-20 | 1980-05-12 | Stamicarbon | Verfahren zur katalytischen umsetzung ole- finisch ungesaettigter verbindungen mit wasser- stoff und kohlenmonoxid |
| US4135911A (en) * | 1977-07-28 | 1979-01-23 | E. I. Du Pont De Nemours And Company | Rhodium recovery from hydroformylation still heel with triaryl phosphite ligand |
| FR2428021A1 (fr) * | 1978-06-05 | 1980-01-04 | Kuraray Co | Hydroformylation de composes olefiniques |
| EP0007768A3 (en) * | 1978-07-27 | 1980-02-20 | DAVY McKEE (LONDON) LIMITED | Hydroformylation of alpha-olefinic compounds |
| US4196096A (en) * | 1979-02-12 | 1980-04-01 | Eastman Kodak Company | Process for regeneration of rhodium hydroformylation catalysts |
| US4283304A (en) * | 1979-05-21 | 1981-08-11 | Union Carbide Corporation | Process for removing triorganophosphine from a liquid composition |
| US4260828A (en) * | 1980-04-16 | 1981-04-07 | Union Carbide Corporation | Hydroformylation process |
-
1980
- 1980-09-24 US US06/190,280 patent/US4605780A/en not_active Expired - Lifetime
-
1981
- 1981-08-14 CA CA000383918A patent/CA1187100A/en not_active Expired
- 1981-09-15 BR BR8105868A patent/BR8105868A/pt unknown
- 1981-09-18 AT AT81107434T patent/ATE6992T1/de active
- 1981-09-18 DE DE8181107434T patent/DE3163094D1/de not_active Expired
- 1981-09-18 EP EP81107434A patent/EP0049781B1/en not_active Expired
- 1981-09-22 KR KR1019810003535A patent/KR880000058B1/ko active
- 1981-09-22 JP JP56148906A patent/JPS607941B2/ja not_active Expired
- 1981-09-23 SU SU813336900A patent/SU1757458A3/ru active
- 1981-09-23 YU YU2280/81A patent/YU43040B/xx unknown
- 1981-09-23 ES ES505725A patent/ES505725A0/es active Granted
- 1981-09-23 MX MX189273A patent/MX158918A/es unknown
- 1981-09-23 PL PL1981233146A patent/PL131753B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU228081A (en) | 1984-08-31 |
| PL233146A1 (ko) | 1982-05-24 |
| JPS607941B2 (ja) | 1985-02-28 |
| EP0049781B1 (en) | 1984-04-11 |
| KR880000058B1 (ko) | 1988-02-22 |
| BR8105868A (pt) | 1982-06-08 |
| SU1757458A3 (ru) | 1992-08-23 |
| MX158918A (es) | 1989-03-30 |
| ES8207189A1 (es) | 1982-08-16 |
| US4605780A (en) | 1986-08-12 |
| PL131753B1 (en) | 1984-12-31 |
| YU43040B (en) | 1989-02-28 |
| JPS5787845A (en) | 1982-06-01 |
| DE3163094D1 (en) | 1984-05-17 |
| ES505725A0 (es) | 1982-08-16 |
| CA1187100A (en) | 1985-05-14 |
| ATE6992T1 (de) | 1984-04-15 |
| EP0049781A1 (en) | 1982-04-21 |
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