JPH06211722A - アルデヒドの製造方法 - Google Patents
アルデヒドの製造方法Info
- Publication number
- JPH06211722A JPH06211722A JP5229952A JP22995293A JPH06211722A JP H06211722 A JPH06211722 A JP H06211722A JP 5229952 A JP5229952 A JP 5229952A JP 22995293 A JP22995293 A JP 22995293A JP H06211722 A JPH06211722 A JP H06211722A
- Authority
- JP
- Japan
- Prior art keywords
- rhodium
- hydroformylation
- sulfonated
- complexing agent
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 3
- 239000010948 rhodium Substances 0.000 claims abstract description 124
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 122
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 120
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 113
- 239000008139 complexing agent Substances 0.000 claims abstract description 61
- 239000003054 catalyst Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 54
- 150000001336 alkenes Chemical class 0.000 claims abstract description 23
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000284 extract Substances 0.000 claims abstract description 7
- 150000003222 pyridines Chemical class 0.000 claims abstract description 7
- 150000003248 quinolines Chemical class 0.000 claims abstract description 7
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical class C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012429 reaction media Substances 0.000 claims abstract description 5
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims abstract description 4
- 230000008569 process Effects 0.000 claims description 33
- 239000008346 aqueous phase Substances 0.000 claims description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 9
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- 150000001299 aldehydes Chemical class 0.000 abstract description 18
- 150000005045 1,10-phenanthrolines Chemical class 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 38
- 239000012074 organic phase Substances 0.000 description 21
- 238000000605 extraction Methods 0.000 description 15
- 239000003446 ligand Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- -1 polyisobutene Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000006277 sulfonation reaction Methods 0.000 description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 8
- 229920002367 Polyisobutene Polymers 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 150000007942 carboxylates Chemical group 0.000 description 6
- 230000000536 complexating effect Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 150000003284 rhodium compounds Chemical class 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000009918 complex formation Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- BKHBKOXMXKWMDZ-UHFFFAOYSA-N 1,10-phenanthroline-2-sulfonic acid Chemical compound C1=CN=C2C3=NC(S(=O)(=O)O)=CC=C3C=CC2=C1 BKHBKOXMXKWMDZ-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- UEBRTEPMBUWFED-UHFFFAOYSA-N 2-quinolin-2-ylquinoline-3-sulfonic acid Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3S(=O)(=O)O)=CC=C21 UEBRTEPMBUWFED-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003283 rhodium Chemical class 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- MTAHTDBOMUECCQ-UHFFFAOYSA-N 1,10-phenanthroline-2-carboxylic acid Chemical compound C1=CN=C2C3=NC(C(=O)O)=CC=C3C=CC2=C1 MTAHTDBOMUECCQ-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- MTNKRTXSIXNCAP-UHFFFAOYSA-N 1-(4-butoxyphenyl)-n-[4-[2-[4-[(4-butoxyphenyl)methylideneamino]phenyl]ethyl]phenyl]methanimine Chemical compound C1=CC(OCCCC)=CC=C1C=NC(C=C1)=CC=C1CCC1=CC=C(N=CC=2C=CC(OCCCC)=CC=2)C=C1 MTNKRTXSIXNCAP-UHFFFAOYSA-N 0.000 description 1
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- FXPLCAKVOYHAJA-UHFFFAOYSA-N 2-(4-carboxypyridin-2-yl)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(C=2N=CC=C(C=2)C(O)=O)=C1 FXPLCAKVOYHAJA-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- MSCQJTWEONCASP-UHFFFAOYSA-N 2-pyridin-2-yl-1H-pyridine-2-carboxylic acid Chemical compound N1=C(C=CC=C1)C1(NC=CC=C1)C(=O)O MSCQJTWEONCASP-UHFFFAOYSA-N 0.000 description 1
- UNWZJTKOAMQGFH-UHFFFAOYSA-N 2-pyridin-2-ylpyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1C1=CC=CC=N1 UNWZJTKOAMQGFH-UHFFFAOYSA-N 0.000 description 1
- RGIIAYDCZSXHGL-UHFFFAOYSA-N 2-pyridin-4-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCC1=CC=NC=C1 RGIIAYDCZSXHGL-UHFFFAOYSA-N 0.000 description 1
- KRWOIPAWRWTEQE-UHFFFAOYSA-N 2-quinolin-2-ylquinoline-3-carboxylic acid Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3C(=O)O)=CC=C21 KRWOIPAWRWTEQE-UHFFFAOYSA-N 0.000 description 1
- YLRBBYWLBNWYGZ-UHFFFAOYSA-N 4,5-diazafluorene Chemical compound C1=CC=C2CC3=CC=CN=C3C2=N1 YLRBBYWLBNWYGZ-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- KVQMUHHSWICEIH-UHFFFAOYSA-N 6-(5-carboxypyridin-2-yl)pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=N1 KVQMUHHSWICEIH-UHFFFAOYSA-N 0.000 description 1
- IGVQQWPYILJSIP-UHFFFAOYSA-N 6-pyridin-2-ylpyridine-3-sulfonic acid Chemical compound N1=CC(S(=O)(=O)O)=CC=C1C1=CC=CC=N1 IGVQQWPYILJSIP-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XGTQBLCVBIESKZ-UHFFFAOYSA-N O.O.O.O.O.O.O.O.O.O.O.O.S(=O)(=O)(O)C1=CC=C(C=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.S(=O)(=O)(O)C1=CC=C(C=C1)C1=C2NC(=C1)C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2 XGTQBLCVBIESKZ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- CNXSPTPPLUUKDE-UHFFFAOYSA-K [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O.C1CCC=CC=CC1 Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O.C1CCC=CC=CC1 CNXSPTPPLUUKDE-UHFFFAOYSA-K 0.000 description 1
- NTTNIIASQJDANE-UHFFFAOYSA-K [Rh+3].[Cl-].N.[Cl-].[Cl-] Chemical compound [Rh+3].[Cl-].N.[Cl-].[Cl-] NTTNIIASQJDANE-UHFFFAOYSA-K 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 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
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- BVQAWSJMUYMNQN-UHFFFAOYSA-N dipyridophenazine Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CN=C3C2=N1 BVQAWSJMUYMNQN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- IYRGXJIJGHOCFS-UHFFFAOYSA-N neocuproine Chemical compound C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 IYRGXJIJGHOCFS-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003444 phase transfer catalyst Substances 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
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ZKIHLVYBGPFUAD-UHFFFAOYSA-N quinoline-2-sulfonic acid Chemical class C1=CC=CC2=NC(S(=O)(=O)O)=CC=C21 ZKIHLVYBGPFUAD-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- ITDJKCJYYAQMRO-UHFFFAOYSA-L rhodium(2+);diacetate Chemical compound [Rh+2].CC([O-])=O.CC([O-])=O ITDJKCJYYAQMRO-UHFFFAOYSA-L 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
- PJRGNVSDUQPLCM-UHFFFAOYSA-H rhodium(3+);trisulfite Chemical compound [Rh+3].[Rh+3].[O-]S([O-])=O.[O-]S([O-])=O.[O-]S([O-])=O PJRGNVSDUQPLCM-UHFFFAOYSA-H 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- BPNZDJSIOYWYDE-UHFFFAOYSA-M sodium 1,10-phenanthroline-2-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)c1ccc2ccc3cccnc3c2n1 BPNZDJSIOYWYDE-UHFFFAOYSA-M 0.000 description 1
- FLOBDFYQBYCFTI-UHFFFAOYSA-M sodium;6-pyridin-2-ylpyridine-3-sulfonate Chemical compound [Na+].N1=CC(S(=O)(=O)[O-])=CC=C1C1=CC=CC=N1 FLOBDFYQBYCFTI-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- B01J31/16—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
- B01J31/18—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
- B01J31/1805—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 nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- 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
-
- 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
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
- B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4230871A DE4230871A1 (de) | 1992-09-16 | 1992-09-16 | Verfahren zur Herstellung von Aldehyden |
| DE4230871.2 | 1993-05-14 | ||
| DE4316180.4 | 1993-05-14 | ||
| DE4316180A DE4316180A1 (de) | 1992-09-16 | 1993-05-14 | Verfahren zur Herstellung von Aldehyden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06211722A true JPH06211722A (ja) | 1994-08-02 |
Family
ID=25918557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5229952A Withdrawn JPH06211722A (ja) | 1992-09-16 | 1993-09-16 | アルデヒドの製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5387719A (enExample) |
| EP (1) | EP0588225B1 (enExample) |
| JP (1) | JPH06211722A (enExample) |
| DE (2) | DE4316180A1 (enExample) |
| ES (1) | ES2102567T3 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4344064C1 (de) * | 1993-12-23 | 1995-06-01 | Hoechst Ag | Verfahren zur Herstellung von in alpha-Stellung durch einen Alkylrest substituierten Aldehyden |
| DE4408950A1 (de) * | 1994-03-16 | 1995-09-21 | Basf Ag | Verfahren zur Herstellung von Alkoholen und/oder Aldehyden |
| DE4427428A1 (de) * | 1994-08-03 | 1996-02-29 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE4440801A1 (de) * | 1994-11-17 | 1996-05-23 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| DE19603201A1 (de) * | 1996-01-30 | 1997-07-31 | Basf Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung von Olefinen |
| CA2204676A1 (en) * | 1996-05-15 | 1997-11-15 | Helmut Bahrmann | Process for preparing aldehydes |
| DE19801437A1 (de) | 1998-01-16 | 1999-07-22 | Basf Ag | Verfahren zur Herstellung von Aldehyden |
| JP4414653B2 (ja) * | 2001-04-30 | 2010-02-10 | チバ ホールディング インコーポレーテッド | 酸化触媒としての金属錯体化合物及びその使用 |
| CN116920958B (zh) * | 2022-04-08 | 2026-03-24 | 中国石油天然气股份有限公司 | 铑膦络合催化剂在线再生的方法、烯烃氢甲酰化反应系统、方法 |
| CN118894992B (zh) * | 2024-07-12 | 2026-03-31 | 四川大学 | 一种含氮配体超分子聚合物催化剂及其制备方法和应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1532460A (fr) * | 1967-05-26 | 1968-07-12 | Melle Usines Sa | Procédé d'oxydation d'aldéhydes aliphatiques inférieures |
| GB1296435A (enExample) * | 1970-02-16 | 1972-11-15 | ||
| US3920754A (en) * | 1970-09-11 | 1975-11-18 | Celanese Corp | Hydroformylation process |
| DE2045416C3 (de) * | 1970-09-15 | 1979-10-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Elution von Rhodium, das als Rhodiumcarbonylat auf einem basischen Ionenaustauscher gebunden ist |
| DE2404855C3 (de) * | 1974-02-01 | 1981-01-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Verhinderung von Emulsionsbildung bei der Aufbereitung von Butyraldehyden und Kobalt enthaltenden Reaktionsgemischen |
| US3984478A (en) * | 1975-05-27 | 1976-10-05 | Universal Oil Products Company | Hydroformylation process |
| DE2604545C3 (de) * | 1976-02-06 | 1978-08-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Alkylcarbonsäuren |
| DE2614799C2 (de) * | 1976-04-06 | 1986-02-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Regenerierung von Rhodium enthaltenden Katalysatoren durch Behandeln von rhodiumhaltigen Destillationsrückständen von Hydroformylierungsgemischen |
| US4221743A (en) * | 1976-07-07 | 1980-09-09 | Union Carbide Corporation | Hydroformylation process |
| GB1566716A (en) * | 1977-03-15 | 1980-05-08 | Gen Electric Co Ltd | Laser resonators and their manufacture |
| US4225458A (en) * | 1979-01-30 | 1980-09-30 | Exxon Research & Engineering Co. | Process for the continuous manufacture and separation of oxo catalysts |
| US4292196A (en) * | 1979-12-10 | 1981-09-29 | Uop Inc. | Catalyst recovery |
| US4298499A (en) * | 1980-07-14 | 1981-11-03 | Uop Inc. | Recovery of catalysts |
| US4400547A (en) * | 1981-04-10 | 1983-08-23 | Eastman Kodak Company | Hydroformylation process utilizing an unmodified rhodium catalyst and the stabilization and regeneration thereof |
| US4388476A (en) * | 1981-05-01 | 1983-06-14 | Eastman Kodak Company | Hydroformylation process with rhodium catalyst and oxygen stabilization thereof |
| US4528403A (en) * | 1982-10-21 | 1985-07-09 | Mitsubishi Chemical Industries Ltd. | Hydroformylation process for preparation of aldehydes and alcohols |
-
1993
- 1993-05-14 DE DE4316180A patent/DE4316180A1/de not_active Withdrawn
- 1993-09-08 EP EP93114394A patent/EP0588225B1/de not_active Expired - Lifetime
- 1993-09-08 DE DE59306778T patent/DE59306778D1/de not_active Expired - Lifetime
- 1993-09-08 ES ES93114394T patent/ES2102567T3/es not_active Expired - Lifetime
- 1993-09-14 US US08/120,427 patent/US5387719A/en not_active Expired - Fee Related
- 1993-09-16 JP JP5229952A patent/JPH06211722A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE4316180A1 (de) | 1994-11-17 |
| EP0588225B1 (de) | 1997-06-18 |
| US5387719A (en) | 1995-02-07 |
| EP0588225A3 (enExample) | 1994-04-27 |
| ES2102567T3 (es) | 1997-08-01 |
| DE59306778D1 (de) | 1997-07-24 |
| EP0588225A2 (de) | 1994-03-23 |
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Legal Events
| Date | Code | Title | Description |
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| A300 | Application deemed to be withdrawn because no request for examination was validly filed |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20001128 |