SI9300506A - Process for stabilizing phosphite ligands - Google Patents

Process for stabilizing phosphite ligands Download PDF

Info

Publication number: SI9300506A
Authority: SI; Slovenia
Prior art keywords: group; ligand; epoxide; hydroformylation; reaction mixture
Prior art date: 1992-09-29

Application number

SI9300506A

Other languages

English (en)

Slovenian (sl)

Inventor

James Edward Babin

James Michael Maher

Ernst Billig

Original Assignee

Union Carbide Chem Plastic

Priority date (The priority date 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 date listed.)

1992-09-29

Filing date

1993-09-28

Publication date

1994-06-30

1993-09-28 Application filed by Union Carbide Chem Plastic filed Critical Union Carbide Chem Plastic

1994-06-30 Publication of SI9300506A publication Critical patent/SI9300506A/sl

Links

239000003446 ligand Substances 0.000 title claims abstract description 173
238000000034 method Methods 0.000 title claims abstract description 105
230000008569 process Effects 0.000 title claims abstract description 82
230000000087 stabilizing effect Effects 0.000 title claims abstract description 8
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title claims abstract 6
239000003054 catalyst Substances 0.000 claims abstract description 63
239000011541 reaction mixture Substances 0.000 claims abstract description 51
230000015556 catabolic process Effects 0.000 claims abstract description 33
238000006731 degradation reaction Methods 0.000 claims abstract description 30
229910052723 transition metal Inorganic materials 0.000 claims abstract description 13
150000003624 transition metals Chemical class 0.000 claims abstract description 13
238000007037 hydroformylation reaction Methods 0.000 claims description 102
238000006243 chemical reaction Methods 0.000 claims description 45
239000010948 rhodium Substances 0.000 claims description 43
229910052703 rhodium Inorganic materials 0.000 claims description 41
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
-1 substituent radical Chemical class 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 28
150000001336 alkenes Chemical class 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 22
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 22
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 21
229910002091 carbon monoxide Inorganic materials 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 20
239000004593 Epoxy Substances 0.000 claims description 18
125000004122 cyclic group Chemical group 0.000 claims description 16
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 15
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 8
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 8
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 7
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 7
125000000732 arylene group Chemical group 0.000 claims description 6
239000010941 cobalt Substances 0.000 claims description 5
229910017052 cobalt Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 4
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YITMLDIGEJSENC-UHFFFAOYSA-N Hexadecen Natural products CCCCCCCCCCCCCC=CC YITMLDIGEJSENC-UHFFFAOYSA-N 0.000 claims description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
OHNNZOOGWXZCPZ-UHFFFAOYSA-N exo-norbornene oxide Chemical compound C1CC2C3OC3C1C2 OHNNZOOGWXZCPZ-UHFFFAOYSA-N 0.000 claims description 3
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150000003254 radicals Chemical class 0.000 claims description 3
229910052707 ruthenium Inorganic materials 0.000 claims description 3
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 claims description 2
AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
150000002924 oxiranes Chemical class 0.000 claims 9
125000001183 hydrocarbyl group Chemical group 0.000 claims 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 claims 1
229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
150000002118 epoxides Chemical class 0.000 abstract description 62
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239000000243 solution Substances 0.000 description 69
150000001299 aldehydes Chemical class 0.000 description 54
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230000015572 biosynthetic process Effects 0.000 description 22
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235000011007 phosphoric acid Nutrition 0.000 description 12
238000012360 testing method Methods 0.000 description 12
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229910052698 phosphorus Inorganic materials 0.000 description 10
239000007858 starting material Substances 0.000 description 10
DNNUUTAVMJAIKT-UHFFFAOYSA-N 5-hydroxypentylphosphonic acid Chemical compound OCCCCCP(O)(O)=O DNNUUTAVMJAIKT-UHFFFAOYSA-N 0.000 description 9
239000000654 additive Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 9
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230000000996 additive effect Effects 0.000 description 8
150000003016 phosphoric acids Chemical class 0.000 description 8
APVDIAOSUXFJNU-UHFFFAOYSA-N rhodium(3+) phosphite Chemical class [Rh+3].[O-]P([O-])[O-] APVDIAOSUXFJNU-UHFFFAOYSA-N 0.000 description 8
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238000009835 boiling Methods 0.000 description 5
239000007857 degradation product Substances 0.000 description 5
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BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
YJLVKRVGSARISS-UHFFFAOYSA-N tris(2,6-dimethylphenyl) phosphite Chemical compound CC1=CC=CC(C)=C1OP(OC=1C(=CC=CC=1C)C)OC1=C(C)C=CC=C1C YJLVKRVGSARISS-UHFFFAOYSA-N 0.000 description 1
BRAZJWSWBBLGAH-UHFFFAOYSA-N tris(2-ethylphenyl) phosphite Chemical compound CCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CC)OC1=CC=CC=C1CC BRAZJWSWBBLGAH-UHFFFAOYSA-N 0.000 description 1
BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- 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
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
- 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
- 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
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/20—Olefin oligomerisation or telomerisation
- 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
- 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
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
- 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
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
- B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
- 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
- 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
- B01J2531/821—Ruthenium
- 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
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
- 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
- B01J31/22—Organic complexes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Inorganic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Adhesives Or Adhesive Processes (AREA)

SI9300506A 1992-09-29 1993-09-28 Process for stabilizing phosphite ligands SI9300506A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/953,015 US5364950A (en)	1992-09-29	1992-09-29	Process for stabilizing phosphite ligands in hydroformylation reaction mixtures

Publications (1)

Publication Number	Publication Date
SI9300506A true SI9300506A (en)	1994-06-30

Family

ID=25493465

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9300506A SI9300506A (en)	1992-09-29	1993-09-28	Process for stabilizing phosphite ligands

Country Status (16)

Country	Link
US (1)	US5364950A (de)
EP (1)	EP0590611B1 (de)
JP (1)	JP2707402B2 (de)
KR (1)	KR940007047A (de)
CN (1)	CN1092058A (de)
AU (1)	AU4864293A (de)
BR (1)	BR9303936A (de)
CA (1)	CA2107173A1 (de)
DE (1)	DE69315791T2 (de)
ES (1)	ES2110556T3 (de)
GR (1)	GR3026097T3 (de)
MX (1)	MX9305980A (de)
PL (1)	PL300523A1 (de)
RO (1)	RO111194B1 (de)
SI (1)	SI9300506A (de)
ZA (1)	ZA937193B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109535197A (zh) *	2018-12-19	2019-03-29	山东新和成维生素有限公司	一种稳定亚磷酸盐配体的方法及其应用

Families Citing this family (64)

* 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
BR9408151A (pt) *	1993-11-23	1997-08-05	Du Pont	Processos de hidrocianação de precursor de catalisador
US5756855A (en) *	1994-08-19	1998-05-26	Union Carbide Chemicals & Plastics Technology Corporation	Stabilization of phosphite ligands in hydroformylation process
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
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
US6090987A (en) *	1998-07-06	2000-07-18	Union Carbide Chemicals & Plastics Technology Corporation	Metal-ligand complex catalyzed processes
MY139272A (en)	1998-12-10	2009-09-30	Mitsubishi Chem Corp	Process for producing aldehyde
JP3928315B2 (ja) *	1998-12-14	2007-06-13	三菱化学株式会社	アルデヒドの製造方法
DE19954510A1 (de)	1999-11-12	2001-05-17	Oxeno Olefinchemie Gmbh	Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen
DE10206697A1 (de) *	2001-02-19	2002-08-29	Basf Ag	Hydroformylierungsverfahren
US6693219B2 (en)	2001-06-02	2004-02-17	Eastman Chemical Company	Epoxide stabilization of fluorophosphite-metal catalyst system in a hydroformylation process
KR20040050999A (ko) *	2002-12-11	2004-06-18	한국화학연구원	로듐포스파이트 착물 촉매 및 이의 제조방법 그리고 이를이용한 알데하이드의 선택적 제조 방법
CA2530739C (en)	2003-07-03	2012-09-25	Union Carbide Chemicals & Plastics Technology Corporation	Minimization of ligand degradation products, or reversion of same to useful phosphine ligands
GB0322246D0 (en) *	2003-09-23	2003-10-22	Exxonmobil Chem Patents Inc	Improvement in or relating to isobutylene
GB0322247D0 (en) *	2003-09-23	2003-10-22	Exxonmobil Chem Patents Inc	Improvement in or relating to an isobutylene containing stream
BRPI0513654A (pt)	2004-08-02	2008-05-13	Union Carbide Chem Plastic	processo de hidroformilação e aparelho para estabilizar um processo de hidroformilação
CN101657407B (zh) *	2007-03-20	2014-02-12	陶氏技术投资有限公司	改善对产物同分异构体的控制的加氢甲酰基化方法
WO2010003073A1 (en)	2008-07-03	2010-01-07	Dow Technology Investments Llc	Process of controlling heavies in a recycle catalyst stream
EP2414314B1 (de)	2009-03-31	2017-09-13	Dow Technology Investments LLC	Hydroformylierungsverfahren mit triphenylphosphin und doppelt offenendigem bisphosphitliganden
WO2011046781A1 (en)	2009-10-16	2011-04-21	Dow Technology Investments Llc	Gas phase hydroformylation process
WO2011087696A1 (en)	2009-12-22	2011-07-21	Dow Technology Investments Llc	Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure
WO2011087690A1 (en)	2009-12-22	2011-07-21	Dow Technology Investments Llc	Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process
MX365495B (es)	2009-12-22	2019-06-05	Dow Technology Investments Llc	Control de la proporcion de aldehido normal: iso en un proceso de hidroformilacion de ligando mixto al controlar la presion parcial del gas de sintesis.
WO2012047514A1 (en)	2010-10-05	2012-04-12	Dow Technology Investments Llc	Hydroformylation process
CN103402961B (zh)	2010-11-12	2016-03-16	陶氏技术投资有限公司	通过附加水减轻加氢甲酰化方法中的污染
KR101309918B1 (ko) *	2010-12-02	2013-09-17	주식회사 엘지화학	반응 중 촉매의 안정성이 개선된 하이드로포밀화 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
CA2851255C (en)	2011-10-07	2018-09-25	American Pacific Corporation	Bromofluorocarbon compositions
WO2013183796A1 (en) *	2012-06-04	2013-12-12	Lg Chem, Ltd.	Hydroformylation method having improved catalyst stability in reaction
CA2872823A1 (en)	2012-06-04	2013-12-12	Dow Technology Investments Llc	Hydroformylation process
BR112015003762B1 (pt)	2012-08-29	2021-04-13	Dow Technology Investments Llc	Processo para a formação de um catalisador de hidroformilação
KR102111182B1 (ko)	2012-09-25	2020-05-14	다우 테크놀로지 인베스트먼츠 엘엘씨.	포스파이트 리간드를 분해에 대해 안정화시키는 방법
DE102013219510A1 (de)	2012-10-12	2014-04-17	Evonik Degussa Gmbh	Gemisch von Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung
CN104854118B (zh)	2012-10-12	2016-12-14	赢创德固赛有限公司	各种不同的不对称双亚磷酸酯混合物及其作为催化剂混合物在加氢甲酰化中的用途
DE102013219512A1 (de)	2012-10-12	2014-04-17	Evonik Degussa Gmbh	Gemisch aus verschiedenen unsymmetrischen Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung
DE102013219508A1 (de)	2012-10-12	2014-04-17	Evonik Degussa Gmbh	Gemische konstitutionsisomerer Bisphosphite
DE102013219506A1 (de)	2012-10-12	2014-04-17	Evonik Degussa Gmbh	Unsymmetrisches Bisphosphit
WO2014088816A1 (en)	2012-12-06	2014-06-12	Dow Technology Investments Llc	Hydroformylation process
DE102012223572A1 (de)	2012-12-18	2014-06-18	Evonik Industries Ag	Steuerung der Viskosität von Reaktionslösungen in Hydroformylierungverfahren
DE102013214378A1 (de)	2013-07-23	2015-01-29	Evonik Industries Ag	Phosphoramiditderivate in der Hydroformylierung von olefinhaltigen Gemischen
EP3083542A1 (de)	2013-12-19	2016-10-26	Dow Technology Investments LLC	Hydroformylierungsverfahren
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
PL3126319T3 (pl)	2014-03-31	2020-01-31	Dow Technology Investments Llc	Proces hydroformylowania
CN106660915B (zh)	2014-05-14	2020-08-14	陶氏技术投资有限责任公司	稳定的有机磷化合物
MY184826A (en)	2014-12-04	2021-04-24	Dow Technology Investments Llc	Hydroformylation process
TWI709568B (zh)	2015-09-30	2020-11-11	美商陶氏科技投資公司	用於製造有機磷化合物的方法
TWI709566B (zh)	2015-09-30	2020-11-11	美商陶氏科技投資公司	用於製造有機磷化合物的方法
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
US9687837B1 (en)	2016-08-31	2017-06-27	Eastman Chemical Company	Stable hydroformylation catalyst for preparation of high N/Iso ratio aldehyde product
US9975833B2 (en)	2016-08-31	2018-05-22	Eastman Chemical Company	Efficient catalyst for the formation of polyaryl hydrocarbons suitable as precursors for polydentate organophosphorus catalyst ligands
WO2020263462A1 (en)	2019-06-27	2020-12-30	Dow Technology Investments Llc	Process to prepare solution from hydroformylation process for precious metal recovery
SE1930249A1 (en) *	2019-07-18	2020-11-17	Perstorp Ab	USE OF A METHOD FOR REDUCTION OF HEAVY END FORMATION AND CATALYST LOSS IN A HYDROFORMYLATION PROCESS COMPRISING A BIDENTATE PHOSPHITE LIGAND
WO2021006795A1 (en) *	2019-07-05	2021-01-14	Perstorp Ab	A method for reducing heavy end formation and catalyst loss in a hydroformylation process
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
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
CN114075244B (zh) *	2020-08-18	2024-06-04	中国石油化工股份有限公司	一种双齿亚磷酸酯及其纯化方法和应用
CN114433240A (zh) *	2020-11-02	2022-05-06	中国石油化工股份有限公司	一种利用高碳数烯烃生产高碳醛的方法
CN115246765B (zh) *	2021-04-26	2024-07-05	广东欧凯新材料有限公司	螺环二酚及其双亚膦酸酯制备方法和应用
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
WO2023086718A1 (en)	2021-11-11	2023-05-19	Dow Technology Investments Llc	Processes for recovering rhodium from 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

Family Cites Families (26)

* 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
BE606408A (de) *	1960-07-22
US3733361A (en) *	1966-08-23	1973-05-15	Gulf Research Development Co	Oxo process
US3499933A (en) *	1967-06-15	1970-03-10	Union Carbide Corp	Hydroformylation of cyclic olefins
US3553298A (en) *	1967-10-20	1971-01-05	Hooker Chemical Corp	Hydrolytic stabilized phosphite esters
US3644446A (en) *	1969-07-01	1972-02-22	Union Oil Co	Preparation of rhodium and iridium hydride carbonyl complexes
DE3372361D1 (en) *	1982-06-11	1987-08-13	Davy Mckee London	Hydroformylation process
EP0096987B1 (de) *	1982-06-11	1985-11-13	DAVY McKEE (LONDON) LIMITED	Hydroformylierungsverfahren
EP0096986B1 (de) *	1982-06-11	1987-04-22	DAVY McKEE (LONDON) LIMITED	Hydroformylierungsverfahren
CA1203047A (en) *	1982-12-08	1986-04-08	Hormoz Azizian	Polymer hydrogenation process
CA1220300A (en) *	1982-12-08	1987-04-07	Polysar Limited	Polymer hydrogenation process
GB8334359D0 (en) *	1983-12-23	1984-02-01	Davy Mckee Ltd	Process
US4599206A (en) *	1984-02-17	1986-07-08	Union Carbide Corporation	Transition metal complex catalyzed reactions
US4650894A (en) *	1984-07-05	1987-03-17	Argus Chemical Corporation	Tris-organophosphite compositions having improved hydrolytic stability
DE3567631D1 (en) *	1984-10-09	1989-02-23	Shell Int Research	Ethylene oligomerization process carried out in a diol-based solvent containing monohydric alcohol or water
US4737588A (en) *	1984-12-28	1988-04-12	Union Carbide Corporation	Transition metal complex catalyzed reactions
JPH0451057Y2 (de) *	1985-02-26	1992-12-02
US4668651A (en) *	1985-09-05	1987-05-26	Union Carbide Corporation	Transition metal complex catalyzed processes
US4714773A (en) *	1987-01-09	1987-12-22	E. I. Du Pont De Nemours And Company	Hydrocyanation of butadiene
US4810815A (en) *	1987-11-04	1989-03-07	E. I. Du Pont De Nemours And Company	Acceleration of diene hydrocyanation
US5059710A (en) *	1988-08-05	1991-10-22	Union Carbide Chemicals And Plastics Technology Corporation	Ionic phosphites and their use in homogeneous transition metal catalyzed processes
CA2000182C (en) *	1988-10-27	1999-04-06	Lynn H. Slaugh	Ethylene oligomerization process and catalyst
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
JPH0436355A (ja) *	1990-05-31	1992-02-06	Toray Dow Corning Silicone Co Ltd	シリコーンゴム組成物
DE4026406A1 (de) *	1990-08-21	1992-02-27	Basf Ag	Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden
US5103033A (en) *	1991-06-24	1992-04-07	Dow Corning Corporation	Process for preparation of β-cyanoalkylsilanes

1992
- 1992-09-29 US US07/953,015 patent/US5364950A/en not_active Expired - Lifetime
1993
- 1993-09-28 KR KR1019930020124A patent/KR940007047A/ko not_active Application Discontinuation
- 1993-09-28 BR BR9303936A patent/BR9303936A/pt not_active Application Discontinuation
- 1993-09-28 AU AU48642/93A patent/AU4864293A/en not_active Abandoned
- 1993-09-28 RO RO93-01282A patent/RO111194B1/ro unknown
- 1993-09-28 CA CA002107173A patent/CA2107173A1/en not_active Abandoned
- 1993-09-28 CN CN93114198A patent/CN1092058A/zh active Pending
- 1993-09-28 DE DE69315791T patent/DE69315791T2/de not_active Expired - Lifetime
- 1993-09-28 SI SI9300506A patent/SI9300506A/sl unknown
- 1993-09-28 PL PL93300523A patent/PL300523A1/xx unknown
- 1993-09-28 ES ES93115650T patent/ES2110556T3/es not_active Expired - Lifetime
- 1993-09-28 EP EP93115650A patent/EP0590611B1/de not_active Expired - Lifetime
- 1993-09-28 MX MX9305980A patent/MX9305980A/es unknown
- 1993-09-28 JP JP5263153A patent/JP2707402B2/ja not_active Expired - Lifetime
- 1993-09-28 ZA ZA937193A patent/ZA937193B/xx unknown
1998
- 1998-02-11 GR GR980400265T patent/GR3026097T3/el unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN109535197A (zh) *	2018-12-19	2019-03-29	山东新和成维生素有限公司	一种稳定亚磷酸盐配体的方法及其应用
CN109535197B (zh) *	2018-12-19	2020-04-21	山东新和成维生素有限公司	一种稳定亚磷酸盐配体的方法及其应用

Also Published As

Publication number	Publication date
JPH06199729A (ja)	1994-07-19
EP0590611B1 (de)	1997-12-17
BR9303936A (pt)	1994-06-14
MX9305980A (es)	1995-01-31
CA2107173A1 (en)	1994-03-30
KR940007047A (ko)	1994-04-26
PL300523A1 (en)	1994-04-05
EP0590611A1 (de)	1994-04-06
RO111194B1 (en)	1996-07-30
DE69315791T2 (de)	1998-05-28
ES2110556T3 (es)	1998-02-16
CN1092058A (zh)	1994-09-14
AU4864293A (en)	1994-04-14
GR3026097T3 (en)	1998-05-29
DE69315791D1 (de)	1998-01-29
ZA937193B (en)	1994-04-21
JP2707402B2 (ja)	1998-01-28
US5364950A (en)	1994-11-15

Publication	Publication Date	Title
SI9300506A (en)	1994-06-30	Process for stabilizing phosphite ligands
US5288918A (en)	1994-02-22	Hydroformylation process
AU579144B2 (en)	1988-11-17	Carboxylation process
EP0697391B1 (de)	1998-10-28	Stabilisierung von Phosphiteliganden in das Hydroformylierungsverfahren
JP5400627B2 (ja)	2014-01-29	生成物異性体の制御が改善されたヒドロホルミル化方法
US4717775A (en)	1988-01-05	Transition metal complex catalyzed reactions
AU720249B2 (en)	2000-05-25	Improved metal-ligand complex catalyzed processes
US8513469B2 (en)	2013-08-20	Hydroformylation process with doubly open-ended bisphosphite ligand
ES2719425T3 (es)	2019-07-10	Mitigación de incrustación en procedimientos de hidroformilación mediante adición de agua
RU2257370C2 (ru)	2005-07-27	Усовершенствованные способы выделения
US4789753A (en)	1988-12-06	Phosphite ligands
JPH0959200A (ja)	1997-03-04	ヒドロホルミル化方法におけるホスフィットリガンドの安定化
MXPA01000031A (en)	2002-02-26	Improved metal-ligand complex catalyzed processes