KR950011451A - 하이드리도 카르보닐트리스(트리오가노포스포러스)로듐의 제조방법 - Google Patents
하이드리도 카르보닐트리스(트리오가노포스포러스)로듐의 제조방법 Download PDFInfo
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- KR950011451A KR950011451A KR1019930022084A KR930022084A KR950011451A KR 950011451 A KR950011451 A KR 950011451A KR 1019930022084 A KR1019930022084 A KR 1019930022084A KR 930022084 A KR930022084 A KR 930022084A KR 950011451 A KR950011451 A KR 950011451A
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- Prior art keywords
- rhodium
- triorganophosphorus
- carbon monoxide
- distillation residue
- compound
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- 229910052703 rhodium Inorganic materials 0.000 title claims abstract 8
- 239000010948 rhodium Substances 0.000 title claims abstract 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims abstract 8
- 239000007983 Tris buffer Substances 0.000 title claims abstract 4
- -1 hydrido carbonyl Chemical group 0.000 title claims abstract 4
- 238000000034 method Methods 0.000 title claims 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract 7
- 238000006243 chemical reaction Methods 0.000 claims abstract 7
- 238000004821 distillation Methods 0.000 claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 239000003446 ligand Substances 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000007800 oxidant agent Substances 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 150000003283 rhodium Chemical class 0.000 claims abstract 2
- 150000003284 rhodium compounds Chemical class 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims abstract 2
- 230000002194 synthesizing effect Effects 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 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 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
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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
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
-
- 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
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
-
- 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
- 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
- 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
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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
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4053—Regeneration or reactivation of catalysts containing metals with recovery of phosphorous catalyst system constituents
-
- 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
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
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- 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
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- 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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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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- C07—ORGANIC CHEMISTRY
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- Materials Engineering (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract
하이드로포르밀화반응 증류잔류물에 함유되어 있는 로듐화합물을 출발물질로 하여 하이드리도카르보닐트리스(트리오가노포스포러스)로듐을 제조함에 있어서, 비활성화된 로듐촉매화합물 함유 증류잔류물을 산화제로 처리한 후 일산화탄소와 산소의 혼합기체존재하에서 로듐-카르보닐화합물로 전환시키고 이들 반응액으로부터 단리함이 없이 직접 수산기 함유화합물, 알칼리금속 하이드록사이드, 포름알데히드, 트리오가노포스포러스 리간드와 반응시키고 일산화탄소와 수소로 후처리함으로서 고수율로 하이드리도카르보닐트리스(트리오가노포스포러스) 로듐을 합성하는 유기단일상 반응임을 특징으로 하는 제조방법.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 하이드로포르밀화반응 증류잔류물에 함유되어있는 로듐화함물을 출발물질로하여 하이드리도카르보닐트리스(트리오가노포스포러스)로듐을 제조함에 있어서, 비활성화된 로듐촉매화합물함유 증류잔류물을 산화제로 처리한 후 일산화탄소와 산소의 혼합기 체존재하에서 로듐-카르보닐화합물로 전환시키고 이를 반응액으로부터 단리함이없이 직접 수산기 함유화합물, 알카리금속 하이드록사이드, 포름알데히드, 트리오가노포스포러스 리간드와 반응시키고 일산화탄소와 수소로 후처리함으로서 고수율로 하이드리도카르보닐트리스(트리오가노포스포러스)로듐을 합성하는 유기단일상 반응임을 특징으로 하는 제조방법.
- 제1항에 있어서, 산화제는 산소 또는 공기이며, 처리온도 및 압력이 60-120℃, 1-10기압임을 특징으로하는 제조방법.
- 제1항에 있어서, 증류잔류물중 로듐농도는 1500-30000ppm임을 특징으로하는 제조방법.
- 제1항에 있어서, 로듐-카르보닐화합물로 전환시 일산화탄소와 산소의 분압비를 5:1-30:1로하고 총압력을 10-100기압으로하여 반응시킴을 특징으로 하는 제조방법.
- 제2항에 있어서, 로듐-카르보닐화합물로 전환시의 반응은도는 80-120℃임을 특징으로 하는 제조방법.
- 제1항에 있어서, 수산기 함유화합물이 에탄올임을 특징으로하는 제조방법.
- 제6항에 있어서, 사용되는 수산기 함유화합물의 양이 사용되는 증류잔류물양의 1-10중량배임을 특징으로하는 제조방법.
- 제1항에 있어서, 알카리금속 하이드록사이드가 포타슘 하이드록사이드임을 특징으로 하는 제조방법.
- 제8항에 있어서, 알카리금속 하이드록사이드를 로듐몰수에 4-20몰배 사용함을 특징으로 하는 제조방법.
- 제1항에 있어서, 포름알데히드는 물이 거의 함유되지않은 메탄올 : 포름알데히드의 중량비가 5 : 1-1 : 1인 혼합물을 사용하고 증류잔류물의 0.1-10중량% 사용함을 특징으로 하는 제조방법.
- 제1항에 있어서, 트리오가노포스포러스 리간드는 트리페닐포스핀, 트리페닐포스파이트임을 특징으로 하는 제조방법.
- 제11항에 있어서, 사용되는 트리오가노포스포러스 리간드의 양은 로듐몰수에 4-20몰배 사용함을 특징으로하는 제조방법.
- 제1항에 있어서, 후처리시 일산화탄소처리후에 수소를 처리함을 특징으로 하는 제조방법.
- 제13항에 있어서, 일산화탄소처리시 온도 및 압력이 55-70℃, 1-100기압임을 특징으로 하는 제조방법.
- 제13항에 있어서, 수소처리시 온도 및 압력이 60-80℃, 1-100기압임을 특징으로 하는 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019930022084A KR0134494B1 (ko) | 1993-10-20 | 1993-10-20 | 하이드리도카르보닐트리스(트리오가노포스포러스)로듐의 제조방법 |
US08/245,659 US5414101A (en) | 1993-10-20 | 1994-05-18 | Preparation of hydridocarbonyl tris (triorganophosphorus) rhodium compounds |
DE69418418T DE69418418T2 (de) | 1993-10-20 | 1994-10-19 | Verfahren zur Herstellung einer Hydridocarbonyltris(triorganophosphor)-Rhodium-Verbindung |
EP94116502A EP0649851B1 (en) | 1993-10-20 | 1994-10-19 | Process for preparation of hydridocarbonyltris (triorganophosphorus) rhodium compound |
JP6254066A JP2588374B2 (ja) | 1993-10-20 | 1994-10-20 | ヒドリドカルボニルトリス(トリオガノホスホラス)ロジウム化合物の製造方法 |
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KR1019930022084A KR0134494B1 (ko) | 1993-10-20 | 1993-10-20 | 하이드리도카르보닐트리스(트리오가노포스포러스)로듐의 제조방법 |
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KR950011451A true KR950011451A (ko) | 1995-05-15 |
KR0134494B1 KR0134494B1 (ko) | 1998-04-20 |
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KR1019930022084A KR0134494B1 (ko) | 1993-10-20 | 1993-10-20 | 하이드리도카르보닐트리스(트리오가노포스포러스)로듐의 제조방법 |
Country Status (5)
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US (1) | US5414101A (ko) |
EP (1) | EP0649851B1 (ko) |
JP (1) | JP2588374B2 (ko) |
KR (1) | KR0134494B1 (ko) |
DE (1) | DE69418418T2 (ko) |
Cited By (1)
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CN112892603A (zh) * | 2019-12-03 | 2021-06-04 | 中国科学院大连化学物理研究所 | 一种用于氮甲酰化反应的固体多相催化剂及其制备和应用 |
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DE10048301A1 (de) * | 2000-09-29 | 2002-04-11 | Oxeno Olefinchemie Gmbh | Stabilisierung von Rhodiumkatalysatoren für die Hydroformylierung von Olefinen |
EP2136917B1 (en) | 2007-04-18 | 2011-08-17 | ExxonMobil Chemical Patents Inc. | Improvements in oxidative demetalling |
CN102382143B (zh) * | 2010-08-31 | 2014-05-28 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化均相络合催化剂的制备方法 |
CN102503985B (zh) * | 2011-10-25 | 2014-12-17 | 中国海洋石油总公司 | 一种三(三苯基膦)羰基氢铑的制备方法 |
EP3990176A1 (en) * | 2019-06-27 | 2022-05-04 | Dow Technology Investments LLC | Process to prepare solution from hydroformylation process for precious metal recovery |
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US446074A (en) * | 1891-02-10 | Attachment for metal-planers | ||
JPS5850234B2 (ja) * | 1980-10-23 | 1983-11-09 | 三菱化学株式会社 | 第8族貴金属固体錯体の取得方法 |
US4363764A (en) * | 1980-12-30 | 1982-12-14 | Union Carbide Corporation | Preparation of rhodium complex compounds |
US4446074A (en) * | 1981-12-24 | 1984-05-01 | Union Carbide Corporation | Preparation of rhodium complex compounds |
DE3822037A1 (de) * | 1988-06-30 | 1990-01-04 | Hoechst Ag | Verfahren zur abtrennung und wiedergewinnung von rhodium aus den produkten der oxosynthese |
-
1993
- 1993-10-20 KR KR1019930022084A patent/KR0134494B1/ko not_active IP Right Cessation
-
1994
- 1994-05-18 US US08/245,659 patent/US5414101A/en not_active Expired - Lifetime
- 1994-10-19 DE DE69418418T patent/DE69418418T2/de not_active Expired - Lifetime
- 1994-10-19 EP EP94116502A patent/EP0649851B1/en not_active Expired - Lifetime
- 1994-10-20 JP JP6254066A patent/JP2588374B2/ja not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112892603A (zh) * | 2019-12-03 | 2021-06-04 | 中国科学院大连化学物理研究所 | 一种用于氮甲酰化反应的固体多相催化剂及其制备和应用 |
CN112892603B (zh) * | 2019-12-03 | 2022-04-12 | 中国科学院大连化学物理研究所 | 一种用于氮甲酰化反应的固体多相催化剂及其制备和应用 |
Also Published As
Publication number | Publication date |
---|---|
EP0649851B1 (en) | 1999-05-12 |
JPH07252285A (ja) | 1995-10-03 |
DE69418418D1 (de) | 1999-06-17 |
DE69418418T2 (de) | 1999-09-16 |
US5414101A (en) | 1995-05-09 |
EP0649851A1 (en) | 1995-04-26 |
KR0134494B1 (ko) | 1998-04-20 |
JP2588374B2 (ja) | 1997-03-05 |
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