KR830007711A - 할로카보닐 비스(트리올가노 폿포러스)로듐 화합물 및 하이드리도-카보닐 트리스(트리올가노 포스포러스)로듐 화합물의 제조방법 - Google Patents
할로카보닐 비스(트리올가노 폿포러스)로듐 화합물 및 하이드리도-카보닐 트리스(트리올가노 포스포러스)로듐 화합물의 제조방법 Download PDFInfo
- Publication number
- KR830007711A KR830007711A KR1019810005294A KR810005294A KR830007711A KR 830007711 A KR830007711 A KR 830007711A KR 1019810005294 A KR1019810005294 A KR 1019810005294A KR 810005294 A KR810005294 A KR 810005294A KR 830007711 A KR830007711 A KR 830007711A
- Authority
- KR
- South Korea
- Prior art keywords
- rhodium
- triorganophosphorus
- ligand
- rhodium compound
- bis
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 5
- 150000003284 rhodium compounds Chemical class 0.000 title claims 5
- -1 hydrido-carbonyl Chemical group 0.000 title claims 4
- 239000007983 Tris buffer Substances 0.000 title claims 3
- 125000004997 halocarbonyl group Chemical group 0.000 title claims 2
- 238000000034 method Methods 0.000 claims 16
- 239000003446 ligand Substances 0.000 claims 9
- 239000012141 concentrate Substances 0.000 claims 8
- 229910052703 rhodium Inorganic materials 0.000 claims 8
- 239000010948 rhodium Substances 0.000 claims 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 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 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 238000007037 hydroformylation reaction Methods 0.000 claims 4
- 239000012429 reaction media Substances 0.000 claims 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- YWHYLYDGWQNMND-UHFFFAOYSA-N [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(Cl)(C=1C=CC=CC=1)C(=O)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Rh].C=1C=CC=CC=1P(C=1C=CC=CC=1)(Cl)(C=1C=CC=CC=1)C(=O)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YWHYLYDGWQNMND-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 239000011521 glass Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000004678 hydrides Chemical class 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 2
- 150000004681 metal hydrides Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 238000006053 organic reaction Methods 0.000 claims 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 claims 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 229910003450 rhodium oxide Inorganic materials 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- 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
- B01J31/16—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
- B01J31/40—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
- B01J31/40—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
- 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
-
- 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
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (20)
- 주로 (a) 로디움콤플렉스 농축물, (b) 할로겐이온 방출물, (c) 일산화탄소 또는 일산화탄소 방출물과 (d) 유리트리오르가노 포스포러스 리간드를 주성분으로 하는 거의 비수용성, 균일 유기반응 용액을 약 20℃ 내지 약 200℃ 온도에서 반응시키며/이때 로디움콤플렉스 농축물이 약 0.1 내지 약 30중량%의 1차사용 하이드로포밀화 반응매질을 주성분으로 하고/또 1차사용 하이드로포밀화 반응매질중에 존재하는 촉매의 로디움 값을 대부분 유지한채로 이 매질중에 존재하는 유리 트리오르가노 포스포러스 리간드의 비점보다 낮은 비점을 갖는 비교적 고비점의 알데히드 축합부생물의 50중량% 이상 이 매질중에 존재하는 유리 트리오르가노 포스포러스 리간드의 50중량% 이상을 매질로부터 제거할 수 있도록 부분적으로 비활성 가용성 로디움 콤플렉스 하이드로포밀화 촉매, 알데히드 생성물, 비교적 고비점의 알데히드 축합부생물과 유리 트리오르가노 포스포러스 리간드를 함유하는 1차 하이드로 포밀화 반응매질을 농축시켜 로디움 콤플렉스 농축물을 제조하는 단계로 구성되는 유기단일상의 할로카보닐-비스(트리오르가노포스포러스)로디움 화합물의 제조방법.
- 제1항에 있어서 로디움콤플렉스 농축물이 약 1 내지 10중량%의 1차사용 하이드로포밀화 반응매질을 주성분으로 하는 제조방법.
- 제2항에 있어서 적어도 농축물에 존재하는 잔유유리 트리오르가노 포스포러스 리간드를 상응하는 트리오르가노 포스포러스 옥사이드로 변환시키는데 충분한 산화작용을 할 수 있게끔, 농축물을 산화시키는 제조방법.
- 제3항에 있어서 산화작용을 약 90 내지 약 175℃ 온도에서 진행시키는 제조방법.
- 제4항에 있어서 산화제가 공기인 제조방법.
- 제4항에 있어서 할로겐이온 방출물이 할로겐화 수소산인 제조방법.
- 제6항에 있어서 산이 염산인 제조방법.
- 제4항에 있어서 일산화탄소 가스가 사용된 제조방법.
- 제4항에 있어서 일산화탄소 방출물이 사용된 제조방법.
- 제9항에 있어서 일산화탄소 방출물이 아미드이고, 또 반응온도 범위가 약 130℃ 내지 약 190℃인 제조방법.
- 제10항에 있어서 아미드가 N,N-디메틸포름아미드인 제조방법.
- 제4항에 있어서 유리 트리오르가노 포스포러스 리간드가 트리페닐 포스핀인 제조방법.
- 제4항에 있어서 침전된 클로로카보닐 비스)트리오르가노포스핀)로디움의 현탁액을 주로 (a) 산화로디움 콤플렉스 농축물 (b) 염산 (c) N,N-디메틸포름아미드 및 (d) 유리 트리페닐포스핀 리간드로 구성되는 거의 비수용성 균일 반응용액을 약130℃ 내지 약 190℃ 온도에서 환류시켜 제조하는 방법.
- 제13항에 있어서 산화제가 공기인)제조방법.
- 제14항에 있어서 클로로카보닐 비스(트리페닐포스핀)로디움 화합물이 현탁액에서 분리 회수하는 제조방법.
- 제1항에 있어서 기술한 바에 따라 제조된 할로카보닐 비스(트리오르가노 포스포러스)로디움 화합물을 그 생성 혼합물로부터 분리하지 않은 상태의 약 20℃ 내지 약 100℃ 온도에서 금속 수소화물 환원제 및 유리 트리오르가노 포스포러스 리간드와 하이드리도카보닐-트리스(트리오르가노 포스포러스) 로디움 화합물을 형성하기에 충분한 시간동안 반응시킴을 특징으로 하여 하이드리도카보닐-트리스(트리오르가노포스포러스)로디움 화합물을 제조하는 방법.
- 제16항에 있어서 금속수소화물이 보로하이드라이드이고 또 유리 트리오르가노 포스포러스 리간드가 트리페닐포스핀인 제조방법.
- 제13항에 기술한 방법에 따라 제조된 클로로카보닐 비스(트리페닐포스핀) 로디움 화합물을 그 생성 혼합물로부터 분리하지 않은 상태의 약 20℃ 내지 약 100℃ 온도에서 금속 보로하이드라이드 환원제 및 유리 트리리페닐포스핀과 하이드리도카보닐트리스-(트리페닐포스핀) 로디움 화합물을 형성하기에 충분한 시간동안 반응시킴을 특징으로 하여 하이드리도카보닐트리스-(트리페닐포스핀)로디움을 제조하는 방법.
- 제18항에 있어서, 금속보호 하이드라이드가 나트륨보호하이드라이드이고 또 환원반응이 3개 내지 5개 탄소원자를 함유하는 지방족 알콜 존재하에서 진행되는 제조방법.
- 제19항에 있어서 로디움 콤플렉스 농축물을 산화하는데 사용되는 산화제가 공기이고, 지방족알콜이 에탄올 또는 이소프로판올이며 나트륨 보로하이드라이드의 용매 용액을 사용하는 제조방법.참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/221,502 US4363764A (en) | 1980-12-30 | 1980-12-30 | Preparation of rhodium complex compounds |
| US221502 | 1980-12-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830007711A true KR830007711A (ko) | 1983-11-04 |
| KR860001612B1 KR860001612B1 (ko) | 1986-10-14 |
Family
ID=22828092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810005294A KR860001612B1 (ko) | 1980-12-30 | 1981-12-29 | 할로카보닐비스(트리유기인)로듐 화합물 및 하이드리도-카보닐트리스(트리유기인)로듐 화합물의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4363764A (ko) |
| EP (1) | EP0055487B1 (ko) |
| JP (2) | JPS57167998A (ko) |
| KR (1) | KR860001612B1 (ko) |
| AT (1) | ATE9701T1 (ko) |
| BR (1) | BR8108413A (ko) |
| CA (1) | CA1174243A (ko) |
| DE (1) | DE3166529D1 (ko) |
| ES (2) | ES508413A0 (ko) |
| MX (1) | MX163334A (ko) |
| PL (2) | PL135114B1 (ko) |
| YU (2) | YU43059B (ko) |
| ZA (1) | ZA818634B (ko) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446074A (en) * | 1981-12-24 | 1984-05-01 | Union Carbide Corporation | Preparation of rhodium complex compounds |
| US4595753A (en) * | 1982-05-03 | 1986-06-17 | Exxon Research And Engineering Co. | Heterocycle-substituted alkyl diaryl phosphine rhodium caronyl hydride complex hydroformylation catalyst compositions |
| US4668809A (en) * | 1982-05-03 | 1987-05-26 | Exxon Research And Engineering | Transition metal complex catalysts |
| JPS6127994A (ja) * | 1984-07-16 | 1986-02-07 | Agency Of Ind Science & Technol | ロジウム化合物の製造法 |
| US4673753A (en) * | 1986-02-03 | 1987-06-16 | Minnesota Mining And Manufacturing Company | Rhodium oxymetallate catalysts |
| US4788308A (en) * | 1986-02-03 | 1988-11-29 | Minnesota Mining And Manufacturing Company | Rhodium oxymetallate catalysts |
| KR0134494B1 (ko) * | 1993-10-20 | 1998-04-20 | 성재갑 | 하이드리도카르보닐트리스(트리오가노포스포러스)로듐의 제조방법 |
| UA27055C2 (uk) * | 1993-12-14 | 2000-02-28 | Центр Ембріональних Тканин "Емселл" | Лікарський препарат імуhозаміhhої дії hа осhові клітиhhої суспеhзії та спосіб лікуваhhя сиhдрому hабутого імуhодефіциту (віл-іhфекції) з використаhhям цього препарату |
| US5520722A (en) * | 1995-01-18 | 1996-05-28 | Exxon Research And Engineering Company | Multiunsaturates removal process |
| US5516965A (en) * | 1995-01-18 | 1996-05-14 | Exxon Research And Engineering Company | Unsaturates recovery and recycle process |
| US5675041A (en) * | 1995-01-18 | 1997-10-07 | Exxon Research & Engineering Company | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide, hydrogen, ethylene, and acetylene |
| DE102004028183B4 (de) * | 2003-06-10 | 2008-04-30 | Bayer Schering Pharma Aktiengesellschaft | Verfahren zum Regenerieren der Katalysatorverbindungen Rh(PX3)3(Y) |
| 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 |
| WO2016005282A1 (de) | 2014-07-11 | 2016-01-14 | Umicore Ag & Co. Kg | Verfahren zur herstellung von hydridocarbonyltris(triphenylphosphin)rhodium(i) |
| WO2020049622A1 (ja) | 2018-09-03 | 2020-03-12 | 日本電気株式会社 | 情報処理装置、分析システム、分析方法及び分析プログラムが格納された非一時的なコンピュータ可読媒体 |
| JP7350674B2 (ja) | 2020-02-26 | 2023-09-26 | 株式会社東芝 | 情報処理装置、情報処理方法、およびプログラム |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3560539A (en) * | 1968-08-21 | 1971-02-02 | Union Oil Co | Selective catalyst recovery |
| US3857895A (en) * | 1969-05-12 | 1974-12-31 | Union Oil Co | Recovery of catalyst complexes |
| US3644446A (en) * | 1969-07-01 | 1972-02-22 | Union Oil Co | Preparation of rhodium and iridium hydride carbonyl complexes |
| US3859359A (en) * | 1970-04-27 | 1975-01-07 | Ethyl Corp | Compound and method |
| US3641076A (en) * | 1970-08-24 | 1972-02-08 | Union Oil Co | Catalyst recovery |
| JPS5136799B2 (ko) * | 1971-10-06 | 1976-10-12 | ||
| IT1007026B (it) * | 1974-01-23 | 1976-10-30 | Montedison Spa | Procedimento per il ricupero di sistemi catalitici da grezzi di idroformilazione |
| DE2448005C2 (de) * | 1974-10-09 | 1983-10-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Regenerierung von Rhodium oder Iridium enthaltenden Katalysatoren aus Destillationsrückständen von Hydroformylierungsgemischen |
| DE2614799C2 (de) * | 1976-04-06 | 1986-02-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen |
| JPS5594390A (en) * | 1979-01-08 | 1980-07-17 | Toyo Soda Mfg Co Ltd | Preparation of catalyst |
| US4196096A (en) * | 1979-02-12 | 1980-04-01 | Eastman Kodak Company | Process for regeneration of rhodium hydroformylation catalysts |
| NO156742C (no) * | 1979-03-28 | 1987-11-18 | Union Carbide Corp | Fremgangsmaate for fremstilling av et hydroformyleringsmedium, og fremgangsmaate for fremstilling av aldehyder. |
-
1980
- 1980-12-30 US US06/221,502 patent/US4363764A/en not_active Expired - Lifetime
-
1981
- 1981-12-11 ZA ZA818634A patent/ZA818634B/xx unknown
- 1981-12-11 CA CA000392136A patent/CA1174243A/en not_active Expired
- 1981-12-16 MX MX190705A patent/MX163334A/es unknown
- 1981-12-28 JP JP56210073A patent/JPS57167998A/ja active Granted
- 1981-12-28 BR BR8108413A patent/BR8108413A/pt unknown
- 1981-12-29 PL PL1981243688A patent/PL135114B1/pl unknown
- 1981-12-29 DE DE8181110826T patent/DE3166529D1/de not_active Expired
- 1981-12-29 ES ES508413A patent/ES508413A0/es active Granted
- 1981-12-29 PL PL1981234494A patent/PL134893B1/pl unknown
- 1981-12-29 KR KR1019810005294A patent/KR860001612B1/ko active
- 1981-12-29 EP EP81110826A patent/EP0055487B1/en not_active Expired
- 1981-12-29 AT AT81110826T patent/ATE9701T1/de not_active IP Right Cessation
- 1981-12-29 YU YU3133/81A patent/YU43059B/xx unknown
-
1983
- 1983-01-07 ES ES518851A patent/ES518851A0/es active Granted
- 1983-06-08 YU YU01274/83A patent/YU127483A/xx unknown
-
1987
- 1987-03-05 JP JP62048994A patent/JPS62265294A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6338036B2 (ko) | 1988-07-28 |
| ES8401980A1 (es) | 1984-02-01 |
| PL234494A1 (ko) | 1982-09-13 |
| DE3166529D1 (en) | 1984-11-08 |
| US4363764A (en) | 1982-12-14 |
| CA1174243A (en) | 1984-09-11 |
| JPS62265294A (ja) | 1987-11-18 |
| EP0055487A1 (en) | 1982-07-07 |
| YU127483A (en) | 1983-12-31 |
| ZA818634B (en) | 1982-10-27 |
| YU313381A (en) | 1983-10-31 |
| EP0055487B1 (en) | 1984-10-03 |
| PL134893B1 (en) | 1985-09-30 |
| MX163334A (es) | 1992-04-22 |
| PL135114B1 (en) | 1985-09-30 |
| YU43059B (en) | 1989-02-28 |
| ES8304583A1 (es) | 1983-04-01 |
| ATE9701T1 (de) | 1984-10-15 |
| ES508413A0 (es) | 1983-04-01 |
| KR860001612B1 (ko) | 1986-10-14 |
| BR8108413A (pt) | 1982-10-13 |
| ES518851A0 (es) | 1984-02-01 |
| JPH0120160B2 (ko) | 1989-04-14 |
| JPS57167998A (en) | 1982-10-16 |
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