FI88916C - Hydroformyleringsfoerfarande foer framstaellning av aldehyder samt prekursorkomposition foer den vid foerfarande utnyttjade rodiumkomplexkatalysatorn - Google Patents
Hydroformyleringsfoerfarande foer framstaellning av aldehyder samt prekursorkomposition foer den vid foerfarande utnyttjade rodiumkomplexkatalysatorn Download PDFInfo
- Publication number
- FI88916C FI88916C FI863570A FI863570A FI88916C FI 88916 C FI88916 C FI 88916C FI 863570 A FI863570 A FI 863570A FI 863570 A FI863570 A FI 863570A FI 88916 C FI88916 C FI 88916C
- Authority
- FI
- Finland
- Prior art keywords
- rhodium
- polyphosphite
- ligand
- radical
- group
- Prior art date
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- 101100148710 Clarkia breweri SAMT gene Proteins 0.000 title 1
- 239000003446 ligand Substances 0.000 claims description 186
- -1 arylene radical Chemical class 0.000 claims description 119
- 238000007037 hydroformylation reaction Methods 0.000 claims description 107
- 239000010948 rhodium Substances 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 98
- 229910052703 rhodium Inorganic materials 0.000 claims description 95
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 91
- 230000008569 process Effects 0.000 claims description 77
- 239000003054 catalyst Substances 0.000 claims description 75
- 150000001299 aldehydes Chemical class 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 52
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 36
- 150000003254 radicals Chemical class 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 29
- 239000012018 catalyst precursor Substances 0.000 claims description 26
- 239000002243 precursor Substances 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 150000001336 alkenes Chemical class 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000007858 starting material Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 239000007789 gas Substances 0.000 claims description 21
- 239000012429 reaction media Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims description 13
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004958 1,4-naphthylene group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
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- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000005499 phosphonyl group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- APVDIAOSUXFJNU-UHFFFAOYSA-N rhodium(3+) phosphite Chemical compound [Rh+3].[O-]P([O-])[O-] APVDIAOSUXFJNU-UHFFFAOYSA-N 0.000 claims 1
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
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- 238000010924 continuous production Methods 0.000 description 6
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 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 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
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- 150000001450 anions Chemical class 0.000 description 4
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- 238000011065 in-situ storage Methods 0.000 description 4
- 125000004957 naphthylene group Chemical group 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
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- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- 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
- 238000009826 distribution Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000705 flame atomic absorption spectrometry Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- RMLOZYVMENRVSS-UHFFFAOYSA-N formaldehyde;rhodium Chemical compound [Rh].O=C RMLOZYVMENRVSS-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- VNVQLDDPGAWSSB-UHFFFAOYSA-H iridium(3+);trisulfate Chemical compound [Ir+3].[Ir+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VNVQLDDPGAWSSB-UHFFFAOYSA-H 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 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
- 238000006263 metalation reaction Methods 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 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
- 125000004433 nitrogen atom Chemical group N* 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
- UZGCMRVEDHLBGY-UHFFFAOYSA-N oct-1-en-4-ol Chemical compound CCCCC(O)CC=C UZGCMRVEDHLBGY-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000000962 organic group Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 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
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 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
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77285985 | 1985-09-05 | ||
| US06/772,859 US4668651A (en) | 1985-09-05 | 1985-09-05 | Transition metal complex catalyzed processes |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI863570A0 FI863570A0 (fi) | 1986-09-04 |
| FI863570L FI863570L (fi) | 1987-03-06 |
| FI88916B FI88916B (fi) | 1993-04-15 |
| FI88916C true FI88916C (fi) | 1993-07-26 |
Family
ID=25096469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI863570A FI88916C (fi) | 1985-09-05 | 1986-09-04 | Hydroformyleringsfoerfarande foer framstaellning av aldehyder samt prekursorkomposition foer den vid foerfarande utnyttjade rodiumkomplexkatalysatorn |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4668651A (OSRAM) |
| EP (1) | EP0214622B1 (OSRAM) |
| JP (1) | JPS62116535A (OSRAM) |
| KR (1) | KR910009181B1 (OSRAM) |
| CN (2) | CN1007348B (OSRAM) |
| AR (1) | AR242182A1 (OSRAM) |
| AT (1) | ATE76054T1 (OSRAM) |
| AU (1) | AU597593B2 (OSRAM) |
| BR (1) | BR8604261A (OSRAM) |
| CA (1) | CA1281704C (OSRAM) |
| CS (2) | CS8606430A3 (OSRAM) |
| DE (1) | DE3685276D1 (OSRAM) |
| DK (1) | DK423486A (OSRAM) |
| ES (1) | ES2001416A6 (OSRAM) |
| FI (1) | FI88916C (OSRAM) |
| HU (1) | HU204489B (OSRAM) |
| IN (1) | IN168034B (OSRAM) |
| MX (1) | MX164384B (OSRAM) |
| NO (1) | NO167652C (OSRAM) |
| PL (1) | PL152601B1 (OSRAM) |
| YU (1) | YU46024B (OSRAM) |
| ZA (1) | ZA866728B (OSRAM) |
Families Citing this family (252)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4885401A (en) * | 1985-09-05 | 1989-12-05 | Union Carbide Corporation | Bis-phosphite compounds |
| US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| 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 |
| EP0545997B1 (en) * | 1990-08-31 | 1995-11-02 | 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 (OSRAM) * | 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 |
| US5288918A (en) * | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| US5364950A (en) * | 1992-09-29 | 1994-11-15 | Union Carbide Chimicals & Plastics Technology Corporation | Process for stabilizing phosphite ligands in hydroformylation reaction mixtures |
| US5322633A (en) * | 1992-11-16 | 1994-06-21 | Albemarle Corporation | Preparation of branched chain carboxylic esters |
| ATE169902T1 (de) * | 1993-11-23 | 1998-09-15 | Du Pont | Verfahren und katalysator-zusammensetzungen für die anlagerung von cyanwassenstoff an monoolefine |
| 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 |
| EP0755302B1 (en) | 1994-04-14 | 2000-10-04 | E.I. Du Pont De Nemours And Company | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins |
| 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 |
| 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 |
| TW315370B (OSRAM) * | 1994-10-07 | 1997-09-11 | Du Pont | |
| WO1996016923A1 (en) * | 1994-11-25 | 1996-06-06 | Dsm N.V. | Process for the preparation of an aldehyde |
| 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 |
| 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 |
| IN187044B (OSRAM) * | 1995-01-27 | 2002-01-05 | Du Pont | |
| 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 |
| US5789625A (en) * | 1995-12-06 | 1998-08-04 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5763671A (en) * | 1995-12-06 | 1998-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation processes |
| US5741942A (en) * | 1996-11-26 | 1998-04-21 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| AU1147897A (en) * | 1995-12-06 | 1997-06-27 | Union Carbide Chemicals & Plastics Technology Corporation | Improved metal-ligand complex catalyzed processes |
| US5767321A (en) † | 1995-12-06 | 1998-06-16 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5654455A (en) * | 1995-12-21 | 1997-08-05 | Ciba-Geigy Corporation | Tris-phosphite ligands and their use in transitioin metal catalyzed processes |
| US5710306A (en) * | 1996-03-15 | 1998-01-20 | Dsm N.V. | Process to prepare a multidentate phosphite compound |
| US5874641A (en) * | 1996-03-15 | 1999-02-23 | Dsm N.V. | Process to prepare a terminal aldehyde |
| TW343195B (en) * | 1996-03-15 | 1998-10-21 | Dsm Nv | Process to prepare a terminal aldehyde |
| EP0839787A1 (en) † | 1996-11-04 | 1998-05-06 | Dsm N.V. | Process for the preparation of an aldehyde |
| US5892127A (en) * | 1996-04-24 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing 1,6-hexanedials and derivatives |
| US5886237A (en) * | 1996-04-24 | 1999-03-23 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing alkenals and alkenols |
| US5821389A (en) * | 1996-04-24 | 1998-10-13 | Union Carbide Chemicals & Technology Corporation | Processes for producing hydroxyaldehydes |
| 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 |
| US5917095A (en) * | 1996-11-26 | 1999-06-29 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5892119A (en) * | 1996-11-26 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5874640A (en) * | 1996-11-26 | 1999-02-23 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| 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 |
| EP0895811A1 (en) | 1997-08-08 | 1999-02-10 | Dsm N.V. | Process to separate a group 8-10 metal/phosphite ligand complex from an organic liquid |
| 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 |
| US5962744A (en) * | 1998-03-27 | 1999-10-05 | The Research Foundation Of State University Of New York | Process for hydrocarbonylations in supercritical carbon dioxide |
| WO2000002656A2 (en) | 1998-07-10 | 2000-01-20 | Manzer Leo E | Supported dendrimer catalyst and its use in hydroformylation or carbon-carbon bond formation |
| CN1163463C (zh) | 1998-12-10 | 2004-08-25 | 三菱化学株式会社 | 醛的制备方法 |
| US6307107B1 (en) | 1999-09-20 | 2001-10-23 | E.I. Du Pont De Nemours And Company | Hydroformylation of acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes |
| US6420611B1 (en) * | 1999-09-20 | 2002-07-16 | E. I. Du Pont De Nemours And Company | Composition comprising polymeric phosphite |
| US6509555B1 (en) * | 1999-11-03 | 2003-01-21 | Nexicor Llc | Hand held induction tool |
| DE19954510A1 (de) | 1999-11-12 | 2001-05-17 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen |
| US6610891B1 (en) | 1999-12-03 | 2003-08-26 | Mitsubishi Chemical Corporation | Method of producing aldehydes |
| EP1172143A1 (en) * | 2000-07-14 | 2002-01-16 | Dsm N.V. | Process for the recovery of rhodium |
| DE10038037A1 (de) * | 2000-08-02 | 2002-04-18 | Basf Ag | Zur Herstellung von Nitrilen geeigneter Katalysator und Verfahren zur Herstellung von Nitrilen |
| US6350819B1 (en) | 2000-10-27 | 2002-02-26 | Union Carbide Chemicals & Plastics Technology Corporation | Dendritic macromolecules for metal-ligand catalyzed processes |
| DE10053272A1 (de) * | 2000-10-27 | 2002-05-08 | Oxeno Olefinchemie Gmbh | Neue Bisphosphitverbindungen und deren Metallkomplexe |
| US6437192B1 (en) | 2000-11-17 | 2002-08-20 | E. I. Du Pont De Nmeours And Company | Hydroformylation of conjugated dienes to alkenals using phosphonite ligands |
| US6362354B1 (en) | 2000-11-17 | 2002-03-26 | E. I. Du Pont De Nemours And Company | Phosphonite ligands, catalyst compositions and hydroformylation process utilizing same |
| DE10058383A1 (de) * | 2000-11-24 | 2002-05-29 | Oxeno Olefinchemie Gmbh | Neue Phosphininverbindungen und deren Metallkomplexe |
| US7012098B2 (en) * | 2001-03-23 | 2006-03-14 | Pharmacia Corporation | Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers |
| EP1249441A1 (en) | 2001-04-13 | 2002-10-16 | Dsm N.V. | Continuous hydroformylation process |
| EP1249438A1 (en) * | 2001-04-13 | 2002-10-16 | Dsm N.V. | Continuous hydroformylation process for producing an aldehyde |
| DE10140083A1 (de) * | 2001-08-16 | 2003-02-27 | Oxeno Olefinchemie Gmbh | Neue Phosphitverbindungen und deren Metallkomplexe |
| DE10140086A1 (de) * | 2001-08-16 | 2003-02-27 | Oxeno Olefinchemie Gmbh | Neue Phosphitverbindungen und neue Phosphitmetallkomplexe |
| US6660876B2 (en) | 2001-11-26 | 2003-12-09 | E. I. Du Pont De Nemours And Company | Phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions |
| MY138064A (en) * | 2002-01-24 | 2009-04-30 | Basf Ag | Method for the separation of acids from chemical reaction mixtures by means of ionic fluids |
| DE10220801A1 (de) * | 2002-05-10 | 2003-11-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste |
| US20040127569A1 (en) * | 2002-08-02 | 2004-07-01 | Manning Pamela T. | Methods for treatment and prevention of gastrointestinal conditions |
| US6664427B1 (en) | 2002-08-29 | 2003-12-16 | E. I. Du Pont De Nemours And Company | Process for preparing aldehyde compounds |
| JP2004091363A (ja) * | 2002-08-30 | 2004-03-25 | Sumitomo Chem Co Ltd | 亜リン酸エステル類、その製造法及びその用途 |
| EP1532094A1 (de) * | 2002-08-31 | 2005-05-25 | Oxeno Olefinchemie GmbH | Verfahren zur hydroformylierung von olefinisch ungesättigten verbindungen, insbesondere olefinen in gegenwart cyclischer kohlensäureester |
| ES2345770T3 (es) * | 2003-01-16 | 2010-10-01 | Teijin Fibers Limited | Hilo compuesto por filamentos combinados de poliester que tienen diferentes coeficientes de contraccion. |
| US7015360B2 (en) * | 2003-03-28 | 2006-03-21 | Dow Global Technologies, Inc. | Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols |
| CN101654462B (zh) | 2003-07-03 | 2013-05-29 | 陶氏技术投资有限责任公司 | 配体降解产物的最小化,或其向有用的膦配体的转化 |
| US20050203082A1 (en) * | 2003-08-13 | 2005-09-15 | Hsu Chung Y. | Combination therapy with inhibitors of inducible nitric oxide synthase and alkylating agents |
| GB0322247D0 (en) | 2003-09-23 | 2003-10-22 | Exxonmobil Chem Patents Inc | Improvement in or relating to an isobutylene containing stream |
| GB0322246D0 (en) * | 2003-09-23 | 2003-10-22 | Exxonmobil Chem Patents Inc | Improvement in or relating to isobutylene |
| JP2007509093A (ja) * | 2003-10-21 | 2007-04-12 | ビーエーエスエフ アクチェンゲゼルシャフト | アルデヒドの連続的な製造方法 |
| DE10349343A1 (de) | 2003-10-23 | 2005-06-02 | Basf Ag | Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden |
| DE10352757A1 (de) * | 2003-11-12 | 2005-06-16 | Studiengesellschaft Kohle Mbh | Chirale Di- und Triphosphite |
| DE10360771A1 (de) * | 2003-12-23 | 2005-07-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von dreiwertigen Organophosphor-Verbindungen |
| US20080027218A1 (en) * | 2004-04-29 | 2008-01-31 | Daugs Edward D | Hydroformylation Process for Pharmaceutical Intermediate |
| KR100596365B1 (ko) * | 2004-06-12 | 2006-07-03 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| KR100547587B1 (ko) * | 2004-06-12 | 2006-01-31 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| PL209549B1 (pl) | 2004-08-02 | 2011-09-30 | Dow Technology Investments Llc | Sposób hydroformylowania |
| KR100744477B1 (ko) | 2004-09-15 | 2007-08-01 | 주식회사 엘지화학 | 인 화합물을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| DE102004059293A1 (de) | 2004-12-09 | 2006-06-14 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydroformylierung von Olefinen |
| US7674499B2 (en) * | 2004-12-15 | 2010-03-09 | E.I. Du Pont De Nemours And Company | Durable coating compositions containing novel aspartic amine compounds |
| WO2007078859A2 (en) * | 2005-12-15 | 2007-07-12 | The Penn State Research Foundation | Tetraphosphorus ligands for catalytic hydroformylation and related reactions |
| US7671231B2 (en) * | 2006-01-18 | 2010-03-02 | Lloyd Michael C | Process for making amino acids |
| US7365234B2 (en) | 2006-03-17 | 2008-04-29 | University Of Kansas | Tuning product selectivity in catalytic hydroformylation reactions with carbon dioxide expanded liquids |
| KR101381015B1 (ko) | 2006-04-04 | 2014-04-04 | 가부시키가이샤 구라레 | 비스포스파이트 및 제 8 ∼ 10 족 금속 화합물을 사용한 알데히드의 제조 방법, 그리고 그 비스포스파이트 |
| KR101495929B1 (ko) | 2006-11-30 | 2015-02-25 | 바스프 에스이 | 올레핀의 하이드로포르밀화 방법 |
| DE102006058682A1 (de) | 2006-12-13 | 2008-06-19 | Evonik Oxeno Gmbh | Bisphosphitliganden für die übergangsmetallkatalysierte Hydroformylierung |
| US7586010B2 (en) * | 2006-12-21 | 2009-09-08 | Eastman Chemical Company | Phosphonite-containing catalysts for hydroformylation processes |
| RU2458906C2 (ru) * | 2007-03-20 | 2012-08-20 | Дау Текнолоджи Инвестментс Ллс | Способ гидроформилирования с усовершенствованным контролем над изомерами продуктов |
| US7943801B2 (en) * | 2007-04-09 | 2011-05-17 | Lg Chem, Ltd. | Catalyst composition including phosphite ligands and hydroformylation method using the same |
| DE102007023514A1 (de) | 2007-05-18 | 2008-11-20 | Evonik Oxeno Gmbh | Stabile Katalysatorvorstufe von Rh-Komplexkatalysatoren |
| US7872157B2 (en) * | 2007-12-26 | 2011-01-18 | Eastman Chemical Company | Phosphonite containing catalysts for hydroformylation processes |
| US7872156B2 (en) * | 2007-12-26 | 2011-01-18 | Eastman Chemical Company | Fluorophosphite containing catalysts for hydroformylation processes |
| CN101981042B (zh) * | 2008-03-28 | 2014-02-19 | 联合碳化化学品及塑料技术公司 | 用于单氯代亚磷酸酯合成的淤浆方法 |
| JP5576357B2 (ja) * | 2008-03-28 | 2014-08-20 | ダウ グローバル テクノロジーズ エルエルシー | ホスホロモノクロリダイト合成のための等温プロセス |
| US8097749B2 (en) * | 2008-03-28 | 2012-01-17 | Union Carbide Chemical and Plastics Technology Technology | Isothermal process for phosphoromonochloridite synthesis |
| DE102008002188A1 (de) | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Abtrennung von 1-Buten aus C4-haltigen Kohlenwasserstoffströmen durch Hydroformylierung |
| DE102008002187A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von C5-Aldehydgemischen mit hohem n-Pentanalanteil |
| US8404903B2 (en) | 2008-07-03 | 2013-03-26 | Dow Technology Investments, Llc | Process of controlling heavies in a recycle catalyst stream |
| US8507731B2 (en) * | 2008-08-19 | 2013-08-13 | Dow Technology Investments Llc | Hydroformylation process using a symmetric bisphosphite ligand for improved control over product isomers |
| EP2346887B1 (en) * | 2008-10-08 | 2013-12-25 | Dow Technology Investments LLC | Slurry process for synthesis of bisphosphites |
| DE102008043582A1 (de) | 2008-11-07 | 2010-05-12 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 6-Chlorodibenzo(d,f) (1,3,2)-dioxaphosphepin |
| DE102008043584A1 (de) | 2008-11-07 | 2010-05-12 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von 6-Chlorodibenzo(d,f) (1,3,2)-dioxaphosphepin |
| US8921486B2 (en) | 2008-11-14 | 2014-12-30 | University Of Kansas | Polymer-supported transition metal catalyst complexes and methods of use |
| FR2940801B1 (fr) * | 2009-01-06 | 2012-08-17 | Arkema France | Procede de fabrication d'un methacrylate de methyle derive de la biomasse |
| DE102009001225A1 (de) | 2009-02-27 | 2010-09-02 | Evonik Oxeno Gmbh | Verfahren zur Anreicherung eines Homogenkatalysators aus einem Prozessstrom |
| JP5603407B2 (ja) | 2009-03-31 | 2014-10-08 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 二重オープンエンド型ビスホスファイトリガンドによるヒドロホルミル化方法 |
| US7928267B1 (en) | 2009-06-22 | 2011-04-19 | Eastman Chemical Company | Phosphite containing catalysts for hydroformylation processes |
| DE102009029050A1 (de) | 2009-08-31 | 2011-03-03 | Evonik Oxeno Gmbh | Organophosphorverbindungen basierend auf Tetraphenol(TP)-substituierten Strukturen |
| US8586800B2 (en) | 2009-10-16 | 2013-11-19 | Dow Technology Investments Llc | Gas phase hydroformylation process |
| WO2011059855A1 (en) * | 2009-11-11 | 2011-05-19 | Dow Global Technologies Llc. | Reductive hydroformylation of an alkylene to an alkanol |
| WO2011087690A1 (en) | 2009-12-22 | 2011-07-21 | Dow Technology Investments Llc | Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process |
| PL2516372T5 (pl) | 2009-12-22 | 2020-08-10 | Dow Technology Investments Llc | Regulowanie stosunku aldehyd normalny : izoaldehyd w procesie hydroformowania z mieszanymi ligandami przez regulowanie ciśnienia cząsteczkowego gazu syntezowego |
| US8664451B2 (en) | 2009-12-22 | 2014-03-04 | Dow Technology Investments Llc | Controlling the normal:ISO aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure |
| JP2014502254A (ja) | 2010-10-05 | 2014-01-30 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化の方法 |
| ES2719425T3 (es) | 2010-11-12 | 2019-07-10 | Dow Technology Investments Llc | Mitigación de incrustación en procedimientos de hidroformilación mediante adición de agua |
| DE102011002640B4 (de) | 2011-01-13 | 2021-10-07 | Evonik Operations Gmbh | Verfahren zur Aufreinigung von Biphephos |
| DE102011002639A1 (de) * | 2011-01-13 | 2012-07-19 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Biphephos |
| WO2012116977A1 (en) | 2011-02-28 | 2012-09-07 | Dsm Ip Assets B.V. | PROCESS FOR THE PREPARATION OF 3-METHYLENE-γ-BUTYROLACTONE |
| SA112330271B1 (ar) | 2011-04-18 | 2015-02-09 | داو تكنولوجى انفستمنتس ال ال سى | تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء |
| EP2751122B1 (en) | 2011-09-30 | 2018-10-24 | Dow Technology Investments LLC | Purification process |
| CN104093729B (zh) | 2011-10-31 | 2016-09-07 | 陶氏技术投资有限责任公司 | 防止多亚磷酸酯配体生产中的溶剂结晶 |
| DE102011085883A1 (de) | 2011-11-08 | 2013-05-08 | Evonik Oxeno Gmbh | Neue Organophosphorverbindungen auf Basis von Anthracentriol |
| IN2014CN04467A (OSRAM) | 2011-12-20 | 2015-09-04 | Dow Technology Investments Llc | |
| US9108988B2 (en) | 2011-12-30 | 2015-08-18 | Basf Se | Method of purifying organic diphosphite compounds |
| MX363617B (es) | 2011-12-30 | 2019-03-28 | Basf Se | Metodo para la purificacion de compuestos de difosfitos organicos. |
| MX342865B (es) | 2011-12-30 | 2016-10-17 | Basf Se | Metodo para la produccion de 6 - clorodibenzo [d, f] [1, 3, 2] dioxafosfepina. |
| RU2660899C2 (ru) | 2011-12-30 | 2018-07-11 | Басф Се | Кристаллический сольват и несольватированные формы 6,6'-[[3,3',5,5'-тетракис(1,1-диметилэтил)-[1,1'-бифенил]-2,2'-диил]бис(окси)]бис-дибензо[d,f][1,3,2]-диоксафосфепина |
| US8841474B2 (en) | 2011-12-30 | 2014-09-23 | Basf Se | Process for preparing 6-chlorodibenzo[D,F][1,3,2]dioxaphosphepin |
| US8796481B2 (en) | 2011-12-30 | 2014-08-05 | Basf Se | Crystalline solvate and non-solvated forms of 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′biphenyl]-2,2′-diyl]bis(oxy)]bis-dibenzo [d,f] [1,3,2]-dioxaphosphepine |
| WO2013131936A1 (de) | 2012-03-07 | 2013-09-12 | Basf Se | Verfahren zur wärmeintegration bei der hydrierung und destillation von c3-c20-aldehyden |
| SG10201608258PA (en) | 2012-04-12 | 2016-11-29 | Basf Se | Method for replenishing the catalyst in continuous hydroformylation |
| US8889917B2 (en) | 2012-04-12 | 2014-11-18 | Basf Se | Method of supplementing the catalyst in continuous hydroformylation |
| CN104379258B (zh) | 2012-06-04 | 2017-05-03 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| CN103814006B (zh) | 2012-06-04 | 2015-08-12 | Lg化学株式会社 | 在反应中具有改善的催化剂稳定性的氢甲酰化方法 |
| DE102012105878A1 (de) | 2012-07-02 | 2014-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Isopentanderivaten |
| KR102131204B1 (ko) | 2012-08-29 | 2020-07-07 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 촉매 제조 방법 |
| CN104955568B (zh) | 2012-09-25 | 2017-05-03 | 陶氏技术投资有限责任公司 | 用于稳定亚磷酸酯配体抵抗降解的方法 |
| DE102013219508A1 (de) | 2012-10-12 | 2014-04-17 | Evonik Degussa Gmbh | Gemische konstitutionsisomerer Bisphosphite |
| DE102013219512A1 (de) | 2012-10-12 | 2014-04-17 | Evonik Degussa Gmbh | Gemisch aus verschiedenen unsymmetrischen Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung |
| DE102013219506A1 (de) | 2012-10-12 | 2014-04-17 | Evonik Degussa Gmbh | Unsymmetrisches Bisphosphit |
| DE102013219510A1 (de) | 2012-10-12 | 2014-04-17 | Evonik Degussa Gmbh | Gemisch von Bisphosphiten und dessen Verwendung als Katalysatorgemisch in der Hydroformylierung |
| US9272973B2 (en) * | 2012-10-12 | 2016-03-01 | Evonik Industries Ag | Stable long-term method for producing C5-aldehydes |
| EP2740535A1 (en) | 2012-12-04 | 2014-06-11 | Dow Technology Investments LLC | Bidentate ligands for hydroformylation of ethylene |
| CN104837800B (zh) | 2012-12-06 | 2017-08-29 | 陶氏技术投资有限责任公司 | 氢甲酰化方法 |
| 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 |
| CN104248860A (zh) | 2013-06-27 | 2014-12-31 | 陶氏技术投资有限责任公司 | 热管理方法 |
| DE102013214378A1 (de) | 2013-07-23 | 2015-01-29 | Evonik Industries Ag | Phosphoramiditderivate in der Hydroformylierung von olefinhaltigen Gemischen |
| DE102013217166A1 (de) * | 2013-08-28 | 2015-03-05 | Evonik Industries Ag | Verfahren zur Hydroformylierung von ungesättigten Verbindungen durch SILP-Katalyse |
| DE102013217174A1 (de) | 2013-08-28 | 2015-03-05 | Evonik Industries Ag | Zusammensetzung und deren Verwendung in Verfahren zur Hydroformylierung von ungesättigten Verbindungen |
| CN104513143A (zh) | 2013-09-26 | 2015-04-15 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| CN103509055B (zh) * | 2013-10-10 | 2016-08-17 | 中国海洋石油总公司 | 一种双亚磷酸三(3，3’-二叔丁基-5，5’-二甲氧基-2，2’-联苯酚)酯的微波合成方法 |
| 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 |
| US9688598B2 (en) | 2013-12-19 | 2017-06-27 | Dow Technology Investments Llc | Hydroformylation process |
| DE102014202499A1 (de) | 2014-02-12 | 2015-08-13 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 6,6'-((3,3'-di-tert-butyl-5,5'-dimethoxy-[1,1'-biphenyl]-2,2'-diyl)bis(oxy))bis(2,4,8,10-tetramethyldibenzo[d,f][1,3,2]dioxaphosphepin |
| JP6560248B2 (ja) | 2014-03-31 | 2019-08-14 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセス |
| JP6694396B2 (ja) | 2014-05-14 | 2020-05-13 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 安定化された有機リン化合物 |
| DE102014209534A1 (de) * | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Neue Monophosphitliganden mit einer Carbonat-Gruppe |
| MY184826A (en) | 2014-12-04 | 2021-04-24 | Dow Technology Investments Llc | Hydroformylation process |
| EP3029045B1 (de) * | 2014-12-04 | 2018-06-13 | Evonik Degussa GmbH | Bisphosphite die eine 2,3 -Biphenol-Einheit als Zentral-Baustein aufweisen |
| DE102015207870A1 (de) * | 2015-04-29 | 2016-11-03 | Evonik Degussa Gmbh | Neue Monophosphitverbindungen mit einer Sulfonatgruppe |
| RU2735683C2 (ru) | 2015-06-19 | 2020-11-05 | Дау Текнолоджи Инвестментс Ллк | Кристаллический лиганд 6,6'-[[3,3',5,5'-тетракис(1,1-диметилэтил)-[1,1'-бифенил]-2,2'-диил]бис(окси)]бисдибензо[d,f][1,3,2]-диоксафосфепин |
| 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 |
| 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 |
| MX389162B (es) | 2015-11-10 | 2025-03-20 | Dow Technology Investments Llc | Proceso para producir aldehidos. |
| WO2017139543A1 (en) | 2016-02-11 | 2017-08-17 | Dow Technology Investments Llc | Processes for converting olefins to alcohols, ethers, or combinations thereof |
| JP6889179B2 (ja) | 2016-03-18 | 2021-06-18 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセス |
| CN106008184B (zh) * | 2016-05-30 | 2018-04-20 | 大庆高新利华环保科技有限公司 | 异丁烯制备3‑甲基丁醛的方法 |
| CN105801625B (zh) * | 2016-05-30 | 2017-08-25 | 郑州大学 | 双齿亚磷酸酯配体的制备方法及其在Buchwald‑Hartwig反应中的应用 |
| PL3318569T3 (pl) | 2016-11-08 | 2020-03-31 | Evonik Degussa Gmbh | Bisfosfoniany z jednostkami 2,4-tert.-butylofenylu i ich zastosowanie jako ligandów w hydroformylowaniu |
| TWI758353B (zh) | 2016-11-08 | 2022-03-21 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| TW201840362A (zh) | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| EP3318570B1 (de) | 2016-11-08 | 2019-08-07 | Evonik Degussa GmbH | Phosphorigsäure-p,p'-[5,5',6,6'-tetramethyl-3,3'-bis(1-methylethyl)[1,1'-biphenyl]-2,2'-diyl] p,p,p',p'-tetrakis(2,4-dimethylphenyl)-ester in der hydroformylierung |
| TW201840363A (zh) | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 處理氫甲醯化催化劑溶液之方法 |
| TWI788364B (zh) | 2017-06-23 | 2023-01-01 | 美商陶氏科技投資有限公司 | 氫甲醯化反應製程 |
| US11214533B2 (en) | 2017-06-28 | 2022-01-04 | Dow Global Technologies Llc | Readily biodegradable alkoxylate mixtures |
| CN108303385B (zh) * | 2017-10-21 | 2021-12-24 | 聊城鲁西多元醇新材料科技有限公司 | 一种测定双膦配体铑催化剂中铑含量的方法 |
| US10981851B2 (en) | 2017-10-25 | 2021-04-20 | Dow Technology Investments Llc | Hydroformylation process |
| US11033890B2 (en) | 2017-11-13 | 2021-06-15 | Dow Technology Investments Llc | Processes for recovery of rhodium from a hydroformylation process |
| TWI793216B (zh) | 2017-12-07 | 2023-02-21 | 美商陶氏科技投資公司 | 氫甲醯化方法 |
| KR20250057144A (ko) | 2018-05-30 | 2025-04-28 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포밀화 공정에서 촉매의 탈활성화를 느리게 하고/하거나 테트라포스핀 리간드 사용을 느리게 하는 방법 |
| KR102756407B1 (ko) | 2018-05-30 | 2025-01-20 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포밀화 공정의 제어 방법 |
| MY207749A (en) | 2018-05-30 | 2025-03-16 | Dow Technology Investments Llc | Catalyst composition comprising the combination of a monophopsphine, a tetraphosphine ligand and a hydroformylation process using it |
| CA3120660A1 (en) | 2018-11-29 | 2020-06-04 | Dow Technology Investments Llc | Hydroformylation process |
| CN111320656A (zh) * | 2018-12-17 | 2020-06-23 | 中国石油化工股份有限公司 | 膦配体化合物及其制备方法、催化剂组合物及其应用和醋酸乙烯酯氢甲酰化的方法 |
| EP3990176B1 (en) | 2019-06-27 | 2024-11-06 | Dow Technology Investments LLC | Process to prepare solution from hydroformylation process for precious metal recovery |
| TWI874467B (zh) | 2019-11-05 | 2025-03-01 | 美商陶氏科技投資有限公司 | 用於自ｃ６或更高碳數烯烴氫甲醯化製程之催化劑淨化流回收銠之方法 |
| CN114929660A (zh) | 2019-12-19 | 2022-08-19 | 陶氏技术投资有限责任公司 | 用于制备异戊二烯和包含至少六个碳原子的单烯烃的方法 |
| EP4192807A1 (en) | 2020-08-04 | 2023-06-14 | Eastman Chemical Company | Propionic acid process |
| US20230242711A1 (en) * | 2020-10-13 | 2023-08-03 | Dow Silicones Corporation | Preparation of organosilicon compounds with aldehyde functionality |
| US20230406801A1 (en) | 2020-12-14 | 2023-12-21 | Dow Technology Investments Llc | Processes to improve catalytic metal accountability in hydroformylation processes |
| WO2022139989A1 (en) | 2020-12-22 | 2022-06-30 | Dow Technology Investments Llc | Hydroformylation reaction processes |
| GB202102673D0 (en) | 2021-02-25 | 2021-04-14 | Johnson Matthey Davy Technologies Ltd | Process |
| JP7785093B2 (ja) | 2021-03-31 | 2025-12-12 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセス |
| CN115385960B (zh) * | 2021-05-24 | 2025-11-14 | 广东欧凯新材料有限公司 | 一种大位阻氧杂螺环化合物的制备方法和应用 |
| US12195489B2 (en) | 2021-04-26 | 2025-01-14 | Guangdong Oxo Chem Ltd. | Spiro-bisphosphorous compound, and preparation and application thereof |
| WO2023060155A1 (en) | 2021-10-06 | 2023-04-13 | Dow Global Technologies Llc | Preparation of propylimine-functional organosilicon compounds and primary aminopropyl-functional organosilicon compounds |
| KR20240074835A (ko) | 2021-10-06 | 2024-05-28 | 다우 글로벌 테크놀로지스 엘엘씨 | 아미노-작용성 유기규소 화합물의 제조 |
| CN118019747A (zh) | 2021-10-06 | 2024-05-10 | 陶氏环球技术有限责任公司 | 丙基亚胺官能化有机硅化合物和伯氨基丙基官能化有机硅化合物的制备 |
| MX2024005136A (es) | 2021-11-11 | 2024-05-16 | Dow Technology Investments Llc | Procesos para recuperar rodio a partir de procesos de hidroformilacion. |
| US20250122229A1 (en) | 2021-11-22 | 2025-04-17 | Dow Silicones Corporation | Preparation of organosilicon compounds with carbinol functionality |
| CN114716306B (zh) * | 2021-11-30 | 2024-01-30 | 国家能源集团宁夏煤业有限责任公司 | 费托产物氢甲酰化的方法 |
| JP2024545069A (ja) | 2021-12-16 | 2024-12-05 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | そのような化合物を含む遷移金属錯体ヒドロホルミル化触媒前駆体組成物、及びヒドロホルミル化プロセス |
| CN118317834A (zh) | 2021-12-16 | 2024-07-09 | 陶氏技术投资有限责任公司 | 化合物、包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 |
| EP4198001B1 (de) * | 2021-12-17 | 2024-05-22 | Evonik Oxeno GmbH & Co. KG | Pt-biphenyl-iod-komplex und pt-biphenyl-brom-komplex |
| JP2025509182A (ja) | 2022-03-21 | 2025-04-11 | ダウ グローバル テクノロジーズ エルエルシー | カルボキシ官能性を有する有機ケイ素化合物の調製 |
| EP4508109A1 (en) | 2022-04-13 | 2025-02-19 | Dow Silicones Corporation | Composition, urethane prepolymer, and related methods and uses |
| KR20250003710A (ko) | 2022-04-13 | 2025-01-07 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리에테르-작용성 유기규소 화합물의 제조 |
| KR20250003711A (ko) | 2022-04-13 | 2025-01-07 | 다우 글로벌 테크놀로지스 엘엘씨 | 실리콘 ― 비닐에스테르 관능성 화합물 및 이의 제조 방법 및 퍼스널 케어 조성물에서의 용도 |
| EP4508054A1 (en) | 2022-04-13 | 2025-02-19 | Dow Global Technologies LLC | Preparation of organosilicon compounds with vinylester functionality |
| CN120152789A (zh) | 2022-11-18 | 2025-06-13 | 陶氏环球技术有限责任公司 | 非均相催化剂 |
| WO2024123510A1 (en) | 2022-12-06 | 2024-06-13 | Dow Technology Investments Llc | Process of controlling heavies in a recycle catalyst stream |
| WO2024129290A1 (en) | 2022-12-13 | 2024-06-20 | Dow Technology Investments Llc | Process to minimize polyphosphine usage by making use of degradation products |
| WO2024200242A2 (en) | 2023-03-30 | 2024-10-03 | Universitat De Barcelona | Supramolecular hydroformylation catalyst |
| KR20260004447A (ko) | 2023-05-04 | 2026-01-08 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포르밀화 공정 |
| GB202307175D0 (en) | 2023-05-15 | 2023-06-28 | Johnson Matthey Davy Technologies Ltd | Process for hydrogenating a substrate |
| CN121194957A (zh) | 2023-06-26 | 2025-12-23 | 陶氏技术投资有限责任公司 | 控制加氢甲酰化工艺的方法 |
| CN116854632A (zh) * | 2023-07-07 | 2023-10-10 | 深圳职业技术学院 | 一种大位阻杂原子化合物的合成方法及其应用 |
| WO2025029349A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Hydroformylation process |
| WO2025193446A1 (en) | 2024-03-12 | 2025-09-18 | Dow Technology Investments Llc | Heterogeneous catalysts |
| GB202404300D0 (en) | 2024-03-26 | 2024-05-08 | Johnson Matthey Davy Technologies Ltd | Process for the production of 2-alkylalkanol |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290379A (en) * | 1961-09-01 | 1966-12-06 | Diamond Alkali Co | Selective hydroformylation of olefinic compounds |
| US3187062A (en) * | 1962-06-14 | 1965-06-01 | Columbian Carbon | Cycloolefin production |
| US3448158A (en) * | 1966-01-28 | 1969-06-03 | Shell Oil Co | Hydroformylation of olefins |
| US3499933A (en) * | 1967-06-15 | 1970-03-10 | Union Carbide Corp | Hydroformylation of cyclic olefins |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| JPS4726762Y1 (OSRAM) * | 1968-09-19 | 1972-08-17 | ||
| US3644446A (en) * | 1969-07-01 | 1972-02-22 | Union Oil Co | Preparation of rhodium and iridium hydride carbonyl complexes |
| US3910980A (en) * | 1973-02-28 | 1975-10-07 | Sagami Chem Res | Process for preparing monosilanes from polysilanes |
| US4148830A (en) * | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| US4094855A (en) * | 1976-07-30 | 1978-06-13 | Ciba-Geigy Corporation | Hindered phenyl phosphites |
| US4143028A (en) * | 1977-12-05 | 1979-03-06 | Ciba-Geigy Corporation | Alkylated 1,1'-biphenyl-2,2'-diyl phosphonites and stabilized compositions |
| US4196117A (en) * | 1978-01-03 | 1980-04-01 | Ciba-Geigy Corporation | Alkylated 1,1'-biphenyl-2,2'-diyl phosphites and stabilized compositions |
| US4351759A (en) * | 1978-01-03 | 1982-09-28 | Ciba-Geigy Corporation | Alkylated 2,2'-biphenylene phosphites and stabilized compositions |
| US4288391A (en) * | 1978-01-03 | 1981-09-08 | Ciba-Geigy Corporation | Alkylated 2,2'-biphenylene phosphites |
| DE2837027A1 (de) * | 1978-08-24 | 1980-03-06 | Bayer Ag | Neue phosphorigsaeureester und ihre verwendung zur stabilisierung von polyamiden |
| JPS5699246A (en) * | 1980-01-10 | 1981-08-10 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
| US4318845A (en) * | 1980-11-24 | 1982-03-09 | Ciba-Geigy Corporation | Alkanolamine esters of 1,1'-biphenyl-2,2'-diyl-and alkylidene-1,1'-biphenyl-2,2'-diyl-cyclic phosphites |
| US4374219A (en) * | 1980-11-24 | 1983-02-15 | Ciba-Geigy Corporation | Alkanolamine ester of 1,1-biphenyl-2,2-diyl-and alkylidene-1,1-biphenyl-2,2-diyl-cyclic phosphites |
| US4491675A (en) * | 1981-08-17 | 1985-01-01 | Union Carbide Corporation | Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands |
| US4522933A (en) * | 1981-08-17 | 1985-06-11 | Union Carbide Corporation | Hydroformylation catalyst containing bisphosphine monooxide ligands |
| US4400548A (en) * | 1981-08-17 | 1983-08-23 | Union Carbide Corporation | Hydroformylation process using bisphosphine monooxide ligands |
| US4593011A (en) * | 1981-08-17 | 1986-06-03 | Union Carbide Corporation | Hydroformylation process using triarylphosphine and bisphosphine monooxide ligands |
| ATE26696T1 (de) * | 1982-06-11 | 1987-05-15 | Davy Mckee London | Hydroformylierungsverfahren. |
| DE3372361D1 (en) * | 1982-06-11 | 1987-08-13 | Davy Mckee London | Hydroformylation 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 |
| US4737588A (en) * | 1984-12-28 | 1988-04-12 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
-
1985
- 1985-09-05 US US06/772,859 patent/US4668651A/en not_active Expired - Lifetime
-
1986
- 1986-08-26 CA CA000516846A patent/CA1281704C/en not_active Expired - Lifetime
- 1986-09-04 DK DK423486A patent/DK423486A/da unknown
- 1986-09-04 CN CN86106811A patent/CN1007348B/zh not_active Expired
- 1986-09-04 MX MX3654A patent/MX164384B/es unknown
- 1986-09-04 BR BR8604261A patent/BR8604261A/pt not_active IP Right Cessation
- 1986-09-04 AT AT86112257T patent/ATE76054T1/de not_active IP Right Cessation
- 1986-09-04 JP JP61206937A patent/JPS62116535A/ja active Granted
- 1986-09-04 NO NO863546A patent/NO167652C/no unknown
- 1986-09-04 PL PL1986261286A patent/PL152601B1/pl unknown
- 1986-09-04 ES ES8601617A patent/ES2001416A6/es not_active Expired
- 1986-09-04 ZA ZA866728A patent/ZA866728B/xx unknown
- 1986-09-04 FI FI863570A patent/FI88916C/fi not_active IP Right Cessation
- 1986-09-04 CS CS866430A patent/CS8606430A3/cs not_active IP Right Cessation
- 1986-09-04 YU YU155086A patent/YU46024B/sh unknown
- 1986-09-04 IN IN713/MAS/86A patent/IN168034B/en unknown
- 1986-09-04 AR AR86305146A patent/AR242182A1/es active
- 1986-09-04 KR KR1019860007409A patent/KR910009181B1/ko not_active Expired
- 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 HU HU863820A patent/HU204489B/hu not_active IP Right Cessation
- 1986-09-04 CS CS887490A patent/CS8807490A3/cs not_active IP Right Cessation
- 1986-09-05 AU AU62373/86A patent/AU597593B2/en not_active Ceased
-
1987
- 1987-02-09 US US07/012,329 patent/US4769498A/en not_active Expired - Lifetime
-
1989
- 1989-09-19 CN CN89107465A patent/CN1021202C/zh not_active Expired - Lifetime
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