SE462528B - Katalytiskt foerfarande foer hydroformulering av olefiner i tvaafassystem - Google Patents
Katalytiskt foerfarande foer hydroformulering av olefiner i tvaafassystemInfo
- Publication number
- SE462528B SE462528B SE8104987A SE8104987A SE462528B SE 462528 B SE462528 B SE 462528B SE 8104987 A SE8104987 A SE 8104987A SE 8104987 A SE8104987 A SE 8104987A SE 462528 B SE462528 B SE 462528B
- Authority
- SE
- Sweden
- Prior art keywords
- process according
- platinum group
- group metal
- organic phase
- aqueous phase
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 33
- 230000003197 catalytic effect Effects 0.000 title claims description 9
- 239000012074 organic phase Substances 0.000 claims description 39
- 239000003153 chemical reaction reagent Substances 0.000 claims description 34
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 28
- 239000008346 aqueous phase Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 17
- 239000010948 rhodium Substances 0.000 claims description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 13
- 229910052703 rhodium Inorganic materials 0.000 claims description 13
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- -1 nitro, amino Chemical group 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 12
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 12
- 238000007037 hydroformylation reaction Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical class CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910000510 noble metal Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
- UURSXESKOOOTOV-MDZDMXLPSA-N (e)-dec-5-ene Chemical compound CCCC\C=C\CCCC UURSXESKOOOTOV-MDZDMXLPSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 2
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PIYDVAYKYBWPPY-UHFFFAOYSA-N heptadecanal Chemical class CCCCCCCCCCCCCCCCC=O PIYDVAYKYBWPPY-UHFFFAOYSA-N 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HWKANZROSA-N (E)-Hept-2-ene Chemical compound CCCC\C=C\C OTTZHAVKAVGASB-HWKANZROSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical group C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 101150041213 FES1 gene Proteins 0.000 description 1
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical group [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 208000014342 histiocytosis-lymphadenopathy plus syndrome Diseases 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical group 0.000 description 1
Classifications
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G55/00—Compounds of ruthenium, rhodium, palladium, osmium, iridium, or platinum
- C01G55/001—Preparation involving a liquid-liquid extraction, an adsorption or an ion-exchange
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
- C22B3/38—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds containing phosphorus
- C22B3/381—Phosphines, e.g. compounds with the formula PRnH3-n, with n = 0-3
-
- 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
- B01J2531/821—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
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- 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
- B01J2531/828—Platinum
-
- 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
- B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
- B01J2531/96—Water
-
- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/10—Non-coordinating groups comprising only oxygen beside carbon or hydrogen
- B01J2540/12—Carboxylic acid groups
-
- 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
- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
- B01J2540/30—Non-coordinating groups comprising sulfur
- B01J2540/32—Sulfonic acid groups or their salts
-
- 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
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Metallurgy (AREA)
- Biochemistry (AREA)
- Mechanical Engineering (AREA)
- Geology (AREA)
- Geochemistry & Mineralogy (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Environmental & Geological Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8028521 | 1980-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8104987L SE8104987L (sv) | 1982-03-05 |
| SE462528B true SE462528B (sv) | 1990-07-09 |
Family
ID=10515832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8104987A SE462528B (sv) | 1980-09-04 | 1981-08-24 | Katalytiskt foerfarande foer hydroformulering av olefiner i tvaafassystem |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4399312A (zh) |
| JP (1) | JPS57114545A (zh) |
| BE (1) | BE890210A (zh) |
| CA (1) | CA1211467A (zh) |
| DE (1) | DE3135127A1 (zh) |
| FR (1) | FR2489308B1 (zh) |
| GB (1) | GB2085874B (zh) |
| NL (1) | NL8103989A (zh) |
| SE (1) | SE462528B (zh) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3341035A1 (de) * | 1983-11-12 | 1985-05-23 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3347406A1 (de) * | 1983-12-29 | 1985-07-11 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur abtrennung und wiedergewinnung von rhodium aus den produkten der oxosynthese |
| DE3412335A1 (de) * | 1984-04-03 | 1985-10-10 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| US5091350A (en) * | 1984-03-26 | 1992-02-25 | Hoechst Aktiengesellschaft | Process for hydroformylation with rhodium catalysts and the separation of rhodium therefrom |
| DE3411034A1 (de) * | 1984-03-26 | 1985-09-26 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur rueckgewinnung von rhodium aus reaktionsprodukten der oxosynthese |
| US4731485A (en) * | 1984-04-03 | 1988-03-15 | Ruhrchemie Aktiengesellschaft | Process for hydroformylation with rhodium catalysts and the separation of rhodium therefrom |
| DE3415968A1 (de) * | 1984-04-28 | 1985-10-31 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| DE3420491A1 (de) * | 1984-06-01 | 1985-12-05 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von aldehyden |
| ATE34166T1 (de) * | 1984-08-30 | 1988-05-15 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden. |
| FR2571725B1 (fr) * | 1984-10-16 | 1987-09-18 | Rhone Poulenc Chim Base | Complexes rhodies, dinucleaires et hydrosolubles et leur utilisation comme catalyseur d'hydroformylation |
| DE3447030A1 (de) * | 1984-12-22 | 1986-07-03 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur herstellung von 8- und 9-formyl-tricyclo (5,2,1,0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decen-8 |
| DE3534314A1 (de) * | 1985-09-26 | 1987-04-02 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| DE3546123A1 (de) * | 1985-12-24 | 1987-06-25 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| DE3760813D1 (en) * | 1986-01-30 | 1989-11-23 | Ciba Geigy Ag | Polymeric compositions containing a dissolved dibenzal acetone palladium complex |
| US4716250A (en) * | 1986-07-10 | 1987-12-29 | Union Carbide Corporation | Hydroformylation using low volatile/organic soluble phosphine ligands |
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| DE3726128A1 (de) * | 1987-08-06 | 1989-02-16 | Ruhrchemie Ag | Verfahren zur herstellung von aldehyden |
| CA1327365C (en) * | 1988-06-29 | 1994-03-01 | Stephen R. Stobart | Process for catalytic hydroformylation |
| US5180854A (en) * | 1988-07-14 | 1993-01-19 | Union Carbide Chemicals & Plastics Technology Corporation | Process for catalyst aldehyde product separation |
| US5113022A (en) * | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| 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 |
| US4935550A (en) * | 1988-08-12 | 1990-06-19 | Union Carbide Chemicals And Plastics Company Inc. | Catalytic metal recovery from non-polar organic solutions |
| IT1229512B (it) * | 1989-01-27 | 1991-09-03 | Eniricerche Spa | Procedimento per la idroformilazione catalitica di.olefine |
| FR2652514A1 (fr) * | 1989-06-22 | 1991-04-05 | Rhone Poulenc Sante | Nouveau catalyseur a base de palladium et son emploi. |
| IT1237530B (it) * | 1989-12-12 | 1993-06-08 | Eniricerche Spa | Procedimento per la sintesi diretta di alcoli da olefine,ossidi di carbonio e idrogeno,promossa da un catalizzatore di rodio supportato |
| FR2671078A1 (fr) * | 1990-12-31 | 1992-07-03 | Rhone Poulenc Chimie | Reactif et procede d'hydrocarbonylation triphasique. |
| US5288818A (en) * | 1991-08-20 | 1994-02-22 | Exxon Chemical Patents Inc. | Method for separating a water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| US5215667A (en) * | 1991-08-20 | 1993-06-01 | Exxon Chemical Patents Inc. | Method for separating water soluble noble metal catalyst from a noble metal catalyzed hydroformylation reaction |
| DE4135050A1 (de) * | 1991-10-24 | 1993-04-29 | Hoechst Ag | Verfahren zur reaktivierung wasserloeslicher hydroformylierungskatalysatoren |
| DE4242723A1 (de) * | 1992-12-17 | 1994-06-23 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden |
| US5300617A (en) * | 1993-01-21 | 1994-04-05 | Exxon Chemical Patents Inc. | Potassium para-diphenyl phosphino benzene sulfonate ligand |
| US5395979A (en) * | 1993-02-25 | 1995-03-07 | Exxon Chemical Patents Inc. | Method for separating catalyst from a hydroformylation reaction product using alkylated ligands |
| US5736480A (en) * | 1994-02-22 | 1998-04-07 | California Institute Of Technology | Supported phase chiral sulfonated BINAP catalyst solubilized in alcohol and method of asymmetric hydrogenation |
| US5935892A (en) * | 1994-02-22 | 1999-08-10 | California Institute Of Technology | Supported phase catalyst |
| ES2094092B1 (es) * | 1994-09-14 | 1997-08-01 | Univ Barcelona Autonoma | Ligados para la formacion de catalizadores ambifilicos y metodo para su obtencion. |
| FR2729385B1 (fr) * | 1995-01-17 | 1997-04-04 | Centre Nat Rech Scient | Procede d'hydroformylation d'une olefine en milieu biphasique |
| FR2743010B1 (fr) * | 1995-12-29 | 1998-02-20 | Rhone Poulenc Fibres | Procede de preparation par hydrogenation de catalyseurs a base de metal de transition et de phosphine |
| DE19700804C1 (de) * | 1997-01-13 | 1998-08-06 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung olefinischer Verbindungen mit 6 bis 16 Kohlenstoffatomen in Anwesenheit einer Rhodium und sulfonierte Triarylphosphine als Katalysator enthaltenden wäßrigen Phase |
| DE19700805C1 (de) * | 1997-01-13 | 1998-08-06 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung olefinischer Verbindungen mit 3 bis 5 Kohlenstoffatomen in Anwesenheit einer Rhodium und sulfonierte Triarylphosphine als Katalysator enthhaltenden wäßrigen Phase |
| DE19742305A1 (de) | 1997-09-25 | 1999-04-01 | Hoechst Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung in Gegenwart von Kronenether |
| DE19822968A1 (de) | 1998-05-25 | 1999-12-02 | Rwe Dea Ag | Verfahren zur katalytischen Hydroformylierung von Olefinen |
| DE102005019237B4 (de) | 2005-04-26 | 2008-11-20 | Oxea Deutschland Gmbh | Verfahren zur Hydroformylierung von substituierten Allylbenzolen |
| CN104045532B (zh) | 2013-03-15 | 2018-05-25 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| DE102014002103B4 (de) | 2014-02-15 | 2020-10-22 | Oxea Gmbh | Verfahren zur Regenerierung gebrauchter Hydroformylierungskatalysatoren |
| CN112739678A (zh) * | 2018-09-17 | 2021-04-30 | 埃克森美孚化学专利公司 | 用于生产含氧化合物的转移加氢甲酰化 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB708441A (en) * | 1951-05-23 | 1954-05-05 | Standard Oil Dev Co | Synthesis of oxygenated organic compounds |
| US3855307A (en) * | 1967-02-20 | 1974-12-17 | Monsanto Co | Catalysis |
| US3937742A (en) * | 1970-03-06 | 1976-02-10 | Atlantic Richfield Company | Hydroformylation process using catalyst comprising platinum group metal on support having separate alumina phase |
| US3981925A (en) * | 1972-05-08 | 1976-09-21 | Texaco Inc. | Selective hydroformylation process using homogeneous catalysts |
| US4248802A (en) * | 1975-06-20 | 1981-02-03 | Rhone-Poulenc Industries | Catalytic hydroformylation of olefins |
| US4306085A (en) * | 1979-07-05 | 1981-12-15 | Shell Oil Company | Hydroformylation process using resin-ligand-metal catalyst |
-
1981
- 1981-08-21 GB GB8125581A patent/GB2085874B/en not_active Expired
- 1981-08-24 SE SE8104987A patent/SE462528B/sv not_active IP Right Cessation
- 1981-08-27 NL NL8103989A patent/NL8103989A/nl not_active Application Discontinuation
- 1981-08-27 US US06/297,083 patent/US4399312A/en not_active Expired - Lifetime
- 1981-09-03 BE BE0/205863A patent/BE890210A/fr not_active IP Right Cessation
- 1981-09-03 FR FR8116751A patent/FR2489308B1/fr not_active Expired
- 1981-09-04 JP JP56138662A patent/JPS57114545A/ja active Granted
- 1981-09-04 CA CA000385314A patent/CA1211467A/en not_active Expired
- 1981-09-04 DE DE19813135127 patent/DE3135127A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE890210A (fr) | 1982-03-03 |
| SE8104987L (sv) | 1982-03-05 |
| JPS57114545A (en) | 1982-07-16 |
| DE3135127A1 (de) | 1982-08-12 |
| JPS6332342B2 (zh) | 1988-06-29 |
| GB2085874B (en) | 1984-08-08 |
| DE3135127C2 (zh) | 1990-08-23 |
| GB2085874A (en) | 1982-05-06 |
| CA1211467A (en) | 1986-09-16 |
| NL8103989A (nl) | 1982-04-01 |
| FR2489308A1 (fr) | 1982-03-05 |
| US4399312A (en) | 1983-08-16 |
| FR2489308B1 (fr) | 1986-11-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE462528B (sv) | Katalytiskt foerfarande foer hydroformulering av olefiner i tvaafassystem | |
| EP0714385B1 (en) | Hydroformylation process | |
| KR0148012B1 (ko) | 신규한 포스핀으로 구성되는 촉매시스템 및 이를 이용한 아세틸렌형 또는 올레핀형 불포화화합물의 카르보닐화방법 | |
| EP0862546B1 (en) | Hydroformylation process | |
| EP0073961A1 (en) | Hydroformylation process using a rhodium complex catalyst with biphosphine monoxide ligands | |
| CA1243687A (en) | Process for preparing aldehydes | |
| CA1268776A (en) | Rhodium catalysts and methods of preparation and use thereof | |
| JP4210800B2 (ja) | オレフィン化合物のヒドロホルミル化方法 | |
| EP0982314B1 (de) | Valeraldehyd und Verfahren zu seiner Herstellung | |
| US4069273A (en) | Dimerization of linear alpha-olefins | |
| DE69915669T2 (de) | Hydroformylierungsverfahren unter verwendung eines chlorphosphit-metall katalysatorsystems | |
| DE60317533T2 (de) | Verfahren zur hydroformylierung von ethylenisch ungesättigten verbindungen mittels einer zweizähnigen diphosphin-zusammensetzung mit einer verbrückenden gruppe enthaltend sp2-hybridisierte und an die phosphoratome gebundene kohlenstoffatome | |
| EP0924182B1 (de) | Verfahren zur Herstellung von Aldehyden | |
| US5488174A (en) | Hydroformylation process | |
| EP0107430B1 (en) | Method for the preparation of alcohols and aldehydes by reacting olefins with carbon monoxide and hydrogen | |
| US5103065A (en) | Transition metal complexes as catalysts for hydrogenation hydroformylation and cyclotrimerization | |
| DE10243446B4 (de) | Verfahren zur Herstellung von Aldehyden | |
| JP2000159707A (ja) | ジエンを含有するオレフィン供給原料のヒドロホルミル化 | |
| KR100908990B1 (ko) | 알데히드의 제조방법 | |
| JP3410120B2 (ja) | アルコールの製造方法 | |
| DE69807148T2 (de) | Verfahren zur Hydroformylierung von Olefininen | |
| EP0900776B1 (en) | Hydroformylation process | |
| EP1017492B1 (de) | Verfahren zur herstellung von aldehyden durch hydroformulierung | |
| US6452055B1 (en) | Method for the catalytic hydroformylation of olefins in a microemulsion | |
| US5498801A (en) | Process for the catalytic hydroformylation of alkenes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8104987-6 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8104987-6 Format of ref document f/p: F |