CA2091765C - Recovery of high-boiling aldehydes from rhodium-catalyzed hydroformylation processes - Google Patents
Recovery of high-boiling aldehydes from rhodium-catalyzed hydroformylation processesInfo
- Publication number
- CA2091765C CA2091765C CA002091765A CA2091765A CA2091765C CA 2091765 C CA2091765 C CA 2091765C CA 002091765 A CA002091765 A CA 002091765A CA 2091765 A CA2091765 A CA 2091765A CA 2091765 C CA2091765 C CA 2091765C
- Authority
- CA
- Canada
- Prior art keywords
- hydroformylation
- aldehyde
- water
- carbon atoms
- solution
- 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.)
- Expired - Fee Related
Links
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 330
- 238000009835 boiling Methods 0.000 title claims abstract description 67
- 238000011084 recovery Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 89
- 150000001299 aldehydes Chemical class 0.000 title claims description 55
- 230000008569 process Effects 0.000 title claims description 54
- 238000000605 extraction Methods 0.000 claims abstract description 203
- 239000002904 solvent Substances 0.000 claims abstract description 135
- 239000010948 rhodium Substances 0.000 claims abstract description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 123
- 239000003054 catalyst Substances 0.000 claims abstract description 118
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 115
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 100
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 97
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 150000001336 alkenes Chemical class 0.000 claims abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 192
- 239000012071 phase Substances 0.000 claims description 131
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- -1 formylethyl Chemical group 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000007791 liquid phase Substances 0.000 claims description 10
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- HHXKXIHLMHPLTD-UHFFFAOYSA-N 4-(2-oxoethyl)bicyclo[2.2.1]heptane-3-carbaldehyde Chemical compound C1CC2CC(C=O)C1(CC=O)C2 HHXKXIHLMHPLTD-UHFFFAOYSA-N 0.000 claims description 2
- VWIHTPCNDUFBTK-UHFFFAOYSA-N cyclododecane-1,5,9-tricarbaldehyde Chemical compound O=CC1CCCC(C=O)CCCC(C=O)CCC1 VWIHTPCNDUFBTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- WLUYPGQZOFXAFA-UHFFFAOYSA-N 3-(5,5-dimethyl-1,3-dioxan-2-yl)propanal Chemical compound CC1(C)COC(CCC=O)OC1 WLUYPGQZOFXAFA-UHFFFAOYSA-N 0.000 claims 1
- GDZKHVVMMVRJKY-UHFFFAOYSA-N 4-(3-oxopropyl)cyclohexane-1-carbaldehyde Chemical compound O=CCCC1CCC(C=O)CC1 GDZKHVVMMVRJKY-UHFFFAOYSA-N 0.000 claims 1
- NEBVYRMLDPEQIC-UHFFFAOYSA-N 4-formyl-1-methoxycarbonylcyclohexane-1-carboxylic acid Chemical compound COC(=O)C1(C(O)=O)CCC(C=O)CC1 NEBVYRMLDPEQIC-UHFFFAOYSA-N 0.000 claims 1
- XGCHYASVGZWRIX-UHFFFAOYSA-N 4-formylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C=O)CC1 XGCHYASVGZWRIX-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- QWKLKVRIQGSSKF-UHFFFAOYSA-N cyclohexane-1,4-dicarbaldehyde Chemical compound O=CC1CCC(C=O)CC1 QWKLKVRIQGSSKF-UHFFFAOYSA-N 0.000 claims 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexane-carboxaldehyde Natural products O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 219
- 239000000243 solution Substances 0.000 description 199
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- 239000007789 gas Substances 0.000 description 42
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 36
- 229910052799 carbon Inorganic materials 0.000 description 32
- 239000011734 sodium Substances 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 24
- SZKMTZNASRXXCE-UHFFFAOYSA-N [2-[2-(diphenylphosphanylmethyl)phenyl]phenyl]methyl-diphenylphosphane Chemical compound C=1C=CC=C(C=2C(=CC=CC=2)CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 SZKMTZNASRXXCE-UHFFFAOYSA-N 0.000 description 22
- 238000005192 partition Methods 0.000 description 21
- 239000001257 hydrogen Substances 0.000 description 19
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 18
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 16
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 238000005191 phase separation Methods 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 4
- BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000006286 aqueous extract Substances 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
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- 125000000524 functional group Chemical group 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 4
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- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical group [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
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- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
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- 238000001514 detection method Methods 0.000 description 2
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- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
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- IGGUWVNICWZJQU-UHFFFAOYSA-N cyclooctanecarbaldehyde Chemical compound O=CC1CCCCCCC1 IGGUWVNICWZJQU-UHFFFAOYSA-N 0.000 description 1
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- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000004457 myocytus nodalis Anatomy 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
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- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| US07/732,898 | 1991-07-19 | ||
| US07/732,898 US5138101A (en) | 1991-07-19 | 1991-07-19 | Recovery of high-boiling aldehydes from rhodium-catalyzed hydroformylation processes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2091765A1 CA2091765A1 (en) | 1993-01-20 |
| CA2091765C true CA2091765C (en) | 1996-10-08 |
Family
ID=24945382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002091765A Expired - Fee Related CA2091765C (en) | 1991-07-19 | 1992-07-17 | Recovery of high-boiling aldehydes from rhodium-catalyzed hydroformylation processes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5138101A (OSRAM) |
| EP (1) | EP0553322B1 (OSRAM) |
| JP (1) | JP3323497B2 (OSRAM) |
| AT (1) | ATE138634T1 (OSRAM) |
| CA (1) | CA2091765C (OSRAM) |
| DE (1) | DE69211116T2 (OSRAM) |
| TW (1) | TW231288B (OSRAM) |
| WO (1) | WO1993002024A2 (OSRAM) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5648554A (en) * | 1995-04-12 | 1997-07-15 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
| MY120454A (en) * | 1997-07-29 | 2005-10-31 | Du Pont | Improved process of preparation of linear aldehydes |
| US5952530A (en) * | 1998-02-02 | 1999-09-14 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US5932772A (en) * | 1998-02-02 | 1999-08-03 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US5945549A (en) * | 1999-01-22 | 1999-08-31 | Eastman Chemical Company | Production of aqueous solutions of mixtures of formyltertrahydrofuran and hydrates thereof |
| JP4573003B2 (ja) * | 1999-07-02 | 2010-11-04 | 三菱瓦斯化学株式会社 | トリシクロデカンジメタノール及び／又はペンタシクロペンタデカンジメタノールの製造法 |
| JP4573002B2 (ja) * | 1999-07-02 | 2010-11-04 | 三菱瓦斯化学株式会社 | トリシクロデカンジカルバルデヒド及び／又はペンタシクロペンタデカンジカルバルデヒドの製造法 |
| JP4608713B2 (ja) * | 1999-12-13 | 2011-01-12 | 三菱瓦斯化学株式会社 | 反応生成液からのアルデヒドの回収法 |
| EP1065194B2 (en) * | 1999-07-02 | 2007-03-28 | Mitsubishi Gas Chemical Company, Inc. | Production of tricyclodecane dicarbaldehyde, pentacyclopentadecane dicarbaldehyde and corresponding dimethanols |
| US6252121B1 (en) * | 1999-07-27 | 2001-06-26 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US6310260B1 (en) | 2000-03-15 | 2001-10-30 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6307108B1 (en) | 2000-03-15 | 2001-10-23 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US6303829B1 (en) | 2000-03-15 | 2001-10-16 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6294700B1 (en) | 2000-03-15 | 2001-09-25 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6303830B1 (en) * | 2000-03-15 | 2001-10-16 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US6307109B1 (en) | 2000-03-15 | 2001-10-23 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6307110B1 (en) | 2000-03-15 | 2001-10-23 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6350819B1 (en) | 2000-10-27 | 2002-02-26 | Union Carbide Chemicals & Plastics Technology Corporation | Dendritic macromolecules for metal-ligand catalyzed processes |
| US7189579B2 (en) * | 2002-02-22 | 2007-03-13 | Gas Technology Institute | Zero headspace extractor and method for determining partitioning and contaminant release rates of volatile and semi-volatile compounds |
| CA2496838A1 (en) * | 2002-08-31 | 2004-03-11 | Oxeno Olefinchemie Gmbh | Process for the hydroformylation of olefinically unsaturated compounds, in particular olefins, in the presence of cyclic carbonic esters |
| DE10357718A1 (de) | 2003-12-09 | 2005-07-21 | Basf Ag | Verfahren zur Herstellung von Tricyclodecandialdehyd |
| MY147009A (en) * | 2006-05-15 | 2012-10-15 | Dow Global Technologies Inc | Hydroformylation process and product separation with improved recovery of rhodium |
| US8304583B2 (en) † | 2007-09-07 | 2012-11-06 | Dow Global Technologies Llc | Hydrogenation of aliphatic dialdehydes to aliphatic diols |
| TWI361181B (en) | 2007-12-31 | 2012-04-01 | Ind Tech Res Inst | A hydroformylation process |
| CN101497561B (zh) * | 2008-01-29 | 2015-03-18 | 财团法人工业技术研究院 | 氢甲酰化制程 |
| WO2009114466A1 (en) * | 2008-03-12 | 2009-09-17 | Dow Global Technologies Inc. | Ethylenically unsaturated monomers comprising aliphatic and aromatic moieties |
| US20110098380A1 (en) * | 2008-03-12 | 2011-04-28 | Dow Global Technologies Inc. | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
| SG178808A1 (en) * | 2008-03-12 | 2012-03-29 | Dow Global Technologies Inc | Aromatic polycyanate compounds and process for the production thereof |
| US20110040030A1 (en) * | 2008-05-14 | 2011-02-17 | Basf Se | Use of a cyclohexane diol mixture for manufacturing polymers |
| TWI361182B (en) | 2008-09-16 | 2012-04-01 | Ind Tech Res Inst | A hydroformylation process |
| CN103038205A (zh) * | 2010-04-29 | 2013-04-10 | 陶氏环球技术有限责任公司 | 聚环戊二烯多酚的乙烯基苄基醚 |
| KR20130073905A (ko) * | 2010-04-29 | 2013-07-03 | 다우 글로벌 테크놀로지스 엘엘씨 | 에폭시 폴리시클로펜타디엔 화합물 |
| JP5908891B2 (ja) * | 2010-04-29 | 2016-04-26 | ブルー キューブ アイピー エルエルシー | ポリシクロペンタジエンポリフェノールおよびポリシアネートポリシクロペンタジエンポリフェノール化合物 |
| JP5652052B2 (ja) * | 2010-08-24 | 2015-01-14 | 三菱化学株式会社 | アルデヒドの製造方法 |
| AU2012224721A1 (en) * | 2011-03-08 | 2013-10-03 | Basf Se | Method for producing primary amines by means of homogeneously-catalysed alcohol amination |
| BR112014018132B1 (pt) | 2012-02-24 | 2019-12-24 | Dow Global Technologies Llc | compostos, método para fabricar composto, composição de resina curável e composições curadas |
| WO2015053704A1 (en) * | 2013-10-11 | 2015-04-16 | Invico Metanol Ab | Process for removal of sulphur from raw methanol |
| EP3388413A1 (de) * | 2017-04-11 | 2018-10-17 | Evonik Degussa GmbH | Verfahren zur hydroformylierung von cyclooctadien unter einsatz von 2-(anthracen-9-yloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaphospholan |
| KR102712499B1 (ko) * | 2018-06-15 | 2024-10-02 | 에스케이케미칼 주식회사 | 3(4),8(9)-비스포밀트리사이클로[5.2.1.0^2,6]데칸의 제조방법 |
| US10538472B1 (en) * | 2019-02-14 | 2020-01-21 | Dairen Chemical Corporation | Extraction process for high-boiling aldehyde product separation and catalyst recovery |
| WO2021188940A1 (en) * | 2020-03-19 | 2021-09-23 | North Carolina State University | Aldehyde generation via alkene hydroformylation |
| JP7729055B2 (ja) * | 2021-03-23 | 2025-08-26 | 三菱ケミカル株式会社 | トリシクロデカンジメタノールの製造方法 |
| US11801504B2 (en) | 2021-12-30 | 2023-10-31 | Industrial Technology Research Institute | Hydrophilic phosphorus ligand and method for separation and recovery of catalyst |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1093346B (de) * | 1958-10-22 | 1960-11-24 | Basf Ag | Verfahren zur Reinigung von rohen Oxo-Reaktionsprodukten unter Rueckgewinnung des Katalysators |
| US3896047A (en) * | 1973-06-06 | 1975-07-22 | Gen Electric | Process for recycling a cobalt hydroformylation catalyst |
| US4678857A (en) * | 1986-03-31 | 1987-07-07 | Texaco Inc. | Process for separation of product resulting from hydroformylation |
| US4845306A (en) * | 1987-04-24 | 1989-07-04 | Eastman Kodak Company | Catalyst material recovery or concentration process |
| JPH01238751A (ja) * | 1988-03-17 | 1989-09-22 | Asahi Sangyo Kk | 減速装置 |
| CA1328281C (en) * | 1988-07-14 | 1994-04-05 | Anthony George Abatjoglou | Process for catalyst aldehyde product separation |
-
1991
- 1991-07-19 US US07/732,898 patent/US5138101A/en not_active Expired - Lifetime
-
1992
- 1992-05-26 TW TW081104112A patent/TW231288B/zh active
- 1992-07-17 AT AT92916343T patent/ATE138634T1/de not_active IP Right Cessation
- 1992-07-17 WO PCT/US1992/006027 patent/WO1993002024A2/en not_active Ceased
- 1992-07-17 EP EP92916343A patent/EP0553322B1/en not_active Expired - Lifetime
- 1992-07-17 JP JP50300293A patent/JP3323497B2/ja not_active Expired - Fee Related
- 1992-07-17 CA CA002091765A patent/CA2091765C/en not_active Expired - Fee Related
- 1992-07-17 DE DE69211116T patent/DE69211116T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69211116D1 (de) | 1996-07-04 |
| JPH06501958A (ja) | 1994-03-03 |
| ATE138634T1 (de) | 1996-06-15 |
| CA2091765A1 (en) | 1993-01-20 |
| DE69211116T2 (de) | 1996-10-02 |
| JP3323497B2 (ja) | 2002-09-09 |
| EP0553322A1 (en) | 1993-08-04 |
| WO1993002024A3 (en) | 1993-04-01 |
| US5138101A (en) | 1992-08-11 |
| EP0553322B1 (en) | 1996-05-29 |
| TW231288B (OSRAM) | 1994-10-01 |
| WO1993002024A2 (en) | 1993-02-04 |
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