HU204489B - Hydroformilating process with utilizing transition metal catalyst and hydroformilating catalyst precurzor composition - Google Patents
Hydroformilating process with utilizing transition metal catalyst and hydroformilating catalyst precurzor composition Download PDFInfo
- Publication number
- HU204489B HU204489B HU863820A HU382086A HU204489B HU 204489 B HU204489 B HU 204489B HU 863820 A HU863820 A HU 863820A HU 382086 A HU382086 A HU 382086A HU 204489 B HU204489 B HU 204489B
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- HU
- Hungary
- Prior art keywords
- polyphosphite
- ligand
- formula
- transition metal
- group
- Prior art date
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- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- UOGFCIYBLKSQHL-UHFFFAOYSA-N hex-5-en-3-ol Chemical compound CCC(O)CC=C UOGFCIYBLKSQHL-UHFFFAOYSA-N 0.000 description 1
- RTKJOHNRJGFJQF-UHFFFAOYSA-N hex-5-enamide Chemical compound NC(=O)CCCC=C RTKJOHNRJGFJQF-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012685 metal catalyst precursor Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 125000005461 organic phosphorous group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- KJBRZWADVLEUIE-UHFFFAOYSA-N propyl oct-7-enoate Chemical compound CCCOC(=O)CCCCCC=C KJBRZWADVLEUIE-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- B01J31/22—Organic complexes
-
- 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
- B01J2531/02—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
- B01J2531/822—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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/772,859 US4668651A (en) | 1985-09-05 | 1985-09-05 | Transition metal complex catalyzed processes |
Publications (2)
Publication Number | Publication Date |
---|---|
HUT46642A HUT46642A (en) | 1988-11-28 |
HU204489B true HU204489B (en) | 1992-01-28 |
Family
ID=25096469
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU863820A HU204489B (en) | 1985-09-05 | 1986-09-04 | Hydroformilating process with utilizing transition metal catalyst and hydroformilating catalyst precurzor composition |
Country Status (22)
Families Citing this family (251)
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US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
US4885401A (en) * | 1985-09-05 | 1989-12-05 | Union Carbide Corporation | Bis-phosphite compounds |
US4774361A (en) * | 1986-05-20 | 1988-09-27 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
US4835299A (en) * | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
JPH0819028B2 (ja) * | 1987-07-22 | 1996-02-28 | 株式会社クラレ | ヒドロホルミル化方法 |
FR2629367B1 (fr) * | 1988-03-30 | 1990-11-23 | Norsolor Sa | Systeme catalytique, son procede de preparation et son application a la fabrication d'aldehydes |
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 |
US5113022A (en) * | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
US5001274A (en) * | 1989-06-23 | 1991-03-19 | Union Carbide Chemicals And Plastics Company Inc. | Hydroformylation process |
US5135901A (en) * | 1989-06-29 | 1992-08-04 | Eastman Chemical Company | A catalyst composition comprising rhodium, ruthenium,and a promoter |
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 |
DE4026406A1 (de) * | 1990-08-21 | 1992-02-27 | Basf Ag | Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden |
WO1992004118A1 (en) * | 1990-08-31 | 1992-03-19 | The Governors Of The University Of Alberta | Carbonylation of methanol using a novel transition metal catalyst precursor |
US5179055A (en) * | 1990-09-24 | 1993-01-12 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
US5260491A (en) * | 1990-09-24 | 1993-11-09 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
US5087763A (en) * | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
JP2946790B2 (ja) * | 1991-03-14 | 1999-09-06 | 三菱化学株式会社 | アルデヒド類の製造法 |
TW213465B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
US5360938A (en) * | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
GB9119955D0 (en) * | 1991-09-18 | 1991-10-30 | Imperial College | Treatment of aqueous supplies containing organic material |
DE4204808A1 (de) * | 1992-02-18 | 1993-08-19 | Basf Ag | Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern |
US5292785A (en) * | 1992-05-05 | 1994-03-08 | Ciba-Geigy Corporation | Bis-phosphite stabilized compositions |
US5334791A (en) * | 1992-05-22 | 1994-08-02 | Ligands Inc. | Hydrogenation process with transition metal catalysts derived from bifunctional phosphorus-nitrogen ligands |
US5312996A (en) * | 1992-06-29 | 1994-05-17 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process for producing 1,6-hexanedials |
US5364950A (en) * | 1992-09-29 | 1994-11-15 | Union Carbide Chimicals & Plastics Technology Corporation | Process for stabilizing phosphite ligands in hydroformylation reaction mixtures |
US5288918A (en) * | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
US5322633A (en) * | 1992-11-16 | 1994-06-21 | Albemarle Corporation | Preparation of branched chain carboxylic esters |
CN1082946C (zh) * | 1993-11-23 | 2002-04-17 | 纳幕尔杜邦公司 | 用于单烯烃氢氰化的方法和催化剂组合物 |
US5512695A (en) * | 1994-04-14 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins |
BR9507460A (pt) | 1994-04-14 | 1997-09-02 | Du Pont | Processo para hidrocianação e composição 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 |
DE4431528A1 (de) * | 1994-09-03 | 1996-03-07 | Basf Ag | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
TW315370B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1994-10-07 | 1997-09-11 | Du Pont | |
US5512696A (en) * | 1995-07-21 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
CN1174545A (zh) * | 1994-11-25 | 1998-02-25 | Dsm有限公司 | 醛的制备方法 |
US5672766A (en) * | 1994-12-12 | 1997-09-30 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
US5663403A (en) * | 1995-01-24 | 1997-09-02 | Mitsubishi Chemical Corporation | Bisphosphite compound and method for producing aldehydes |
IN187044B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 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 |
JP3766990B2 (ja) * | 1995-10-02 | 2006-04-19 | 住友化学株式会社 | 亜リン酸エステル類、その製造方法及びその用途 |
US5741942A (en) * | 1996-11-26 | 1998-04-21 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
US5789625A (en) * | 1995-12-06 | 1998-08-04 | 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 |
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US5763680A (en) * | 1995-12-06 | 1998-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed process |
US5654455A (en) * | 1995-12-21 | 1997-08-05 | Ciba-Geigy Corporation | Tris-phosphite ligands and their use in transitioin metal catalyzed processes |
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US5874641A (en) * | 1996-03-15 | 1999-02-23 | Dsm N.V. | Process to prepare a terminal aldehyde |
US5710306A (en) * | 1996-03-15 | 1998-01-20 | Dsm N.V. | Process to prepare a multidentate phosphite compound |
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US5821389A (en) * | 1996-04-24 | 1998-10-13 | Union Carbide Chemicals & Technology Corporation | Processes for producing hydroxyaldehydes |
US5886237A (en) * | 1996-04-24 | 1999-03-23 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing alkenals and alkenols |
US5892127A (en) * | 1996-04-24 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing 1,6-hexanedials and derivatives |
US5817883A (en) * | 1996-04-24 | 1998-10-06 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing hydroxyaldehydes |
DE19631521A1 (de) * | 1996-08-03 | 1998-02-05 | Basf Ag | Verfahren zur Herstellung von 6-Aminocapronitril |
US6274773B1 (en) | 1996-11-04 | 2001-08-14 | Dsm | Process for the continuous preparation of alkyl 5-formylvalerate compounds using homogeneous rhodium hydroformylation catalysts |
US5710344A (en) * | 1996-11-08 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Process to prepare a linear aldehyde |
US5874640A (en) * | 1996-11-26 | 1999-02-23 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
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US5925754A (en) * | 1997-04-15 | 1999-07-20 | Union Carbide Chemicals & Plastics Technology Corporation | Epsilon caprolactam compositions |
US6031120A (en) * | 1997-07-29 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Selective synthesis of organodiphosphite compounds |
MY120454A (en) | 1997-07-29 | 2005-10-31 | Du Pont | Improved process of preparation of linear aldehydes |
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- 1986-09-04 NO NO863546A patent/NO167652C/no unknown
- 1986-09-04 CN CN86106811A patent/CN1007348B/zh not_active Expired
- 1986-09-04 PL PL1986261286A patent/PL152601B1/pl unknown
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- 1986-09-04 JP JP61206937A patent/JPS62116535A/ja active Granted
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- 1986-09-04 HU HU863820A patent/HU204489B/hu not_active IP Right Cessation
- 1986-09-04 KR KR1019860007409A patent/KR910009181B1/ko not_active Expired
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- 1986-09-04 AR AR86305146A patent/AR242182A1/es active
- 1986-09-04 AT AT86112257T patent/ATE76054T1/de not_active IP Right Cessation
- 1986-09-04 IN IN713/MAS/86A patent/IN168034B/en unknown
- 1986-09-04 CS CS866430A patent/CS8606430A3/cs not_active IP Right Cessation
- 1986-09-04 EP EP86112257A patent/EP0214622B1/en not_active Expired - Lifetime
- 1986-09-04 DE DE8686112257T patent/DE3685276D1/de not_active Expired - Lifetime
- 1986-09-04 ZA ZA866728A patent/ZA866728B/xx unknown
- 1986-09-04 DK DK423486A patent/DK423486A/da unknown
- 1986-09-05 AU AU62373/86A patent/AU597593B2/en not_active Ceased
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