CN1224413A - 末端醛的制备方法 - Google Patents
末端醛的制备方法 Download PDFInfo
- Publication number
- CN1224413A CN1224413A CN97194561A CN97194561A CN1224413A CN 1224413 A CN1224413 A CN 1224413A CN 97194561 A CN97194561 A CN 97194561A CN 97194561 A CN97194561 A CN 97194561A CN 1224413 A CN1224413 A CN 1224413A
- Authority
- CN
- China
- Prior art keywords
- ligand
- alkyl
- aryl
- rhodium
- group
- Prior art date
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- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 230000008569 process Effects 0.000 title claims abstract description 19
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 title abstract 2
- 239000003446 ligand Substances 0.000 claims abstract description 116
- 239000010948 rhodium Substances 0.000 claims abstract description 51
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 35
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 35
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 32
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 14
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 11
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 carbonyl aryloxy Chemical group 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- 150000001336 alkenes Chemical class 0.000 claims description 26
- 150000004702 methyl esters Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims description 11
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- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims description 9
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical group C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims 1
- UMLQAWUDAFCGGS-HWKANZROSA-N ethyl (e)-pent-3-enoate Chemical compound CCOC(=O)C\C=C\C UMLQAWUDAFCGGS-HWKANZROSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 10
- 125000001424 substituent group Chemical group 0.000 abstract description 5
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- 150000001299 aldehydes Chemical group 0.000 description 30
- 239000000047 product Substances 0.000 description 22
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- 238000002474 experimental method Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 5
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- 230000000694 effects Effects 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 229940070710 valerate Drugs 0.000 description 5
- HITROERJXNWVOI-SOFGYWHQSA-N (5e)-octa-1,5-diene Chemical compound CC\C=C\CCC=C HITROERJXNWVOI-SOFGYWHQSA-N 0.000 description 4
- 238000004679 31P NMR spectroscopy Methods 0.000 description 4
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 239000006227 byproduct Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
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- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OBTVATRSWTWNGS-UHFFFAOYSA-N acetyl 2-oxopropanoate Chemical group CC(=O)OC(=O)C(C)=O OBTVATRSWTWNGS-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- UNRQTHVKJQUDDF-UHFFFAOYSA-M acetylpyruvate Chemical compound CC(=O)CC(=O)C([O-])=O UNRQTHVKJQUDDF-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
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- 238000013459 approach Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000006251 butylcarbonyl group Chemical group 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
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- 229960003280 cupric chloride Drugs 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- SJYROXINNJQCSO-UHFFFAOYSA-N cyclohexyl pent-3-enoate Chemical compound CC=CCC(=O)OC1CCCCC1 SJYROXINNJQCSO-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 150000002628 limonene derivativess Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical class CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical class CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N n-alpha-hexadecene Natural products CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- LIINGNMKNRSOGW-UHFFFAOYSA-N oct-7-enal Chemical compound C=CCCCCCC=O LIINGNMKNRSOGW-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- UPZFGZWGGFFLRT-UHFFFAOYSA-N oxolane;phenoxybenzene Chemical compound C1CCOC1.C=1C=CC=CC=1OC1=CC=CC=C1 UPZFGZWGGFFLRT-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- UIUWNILCHFBLEQ-UHFFFAOYSA-N pent-3-enoic acid Chemical class CC=CCC(O)=O UIUWNILCHFBLEQ-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing 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
- 239000012429 reaction media 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
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003942 tert-butylamines Chemical class 0.000 description 1
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical class CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZQDPJFUHLCOCRG-AATRIKPKSA-N trans-3-hexene Chemical compound CC\C=C\CC ZQDPJFUHLCOCRG-AATRIKPKSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
实施例 | 配位体 | R1 | R2 | Conv | Redn | Sel | Lin |
6 | 3 | CO2i-Pr | CO2i-Pr | 53 | 4 | 85 | 94 |
7 | 4 | CH3 | CH3 | 36 | 5 | 75 | 93 |
8 | 5 | C2H5 | C2H5 | 36 | 5 | 75 | 92 |
9 | 6 | C2H5 | H | 23 | 4 | 74 | 88 |
比较试验10 | H | H | 70 | 9 | 66 | 82 |
实施例 | 配位体 | R1 | R2 | Conv | Redn | Sel | Lin |
11 | 8 | CO2Et | CO2Et | 99 | 11 | 64 | 77 |
12 | 9 | SiPh3 | SiPh3 | 73 | 23 | 64 | 97 |
13 | 10 | CO2i-Pr | CO2i-Pr | 91 | 8 | 63 | 78 |
14 | 11 | CO2Me | CO2Me | 98 | 9 | 61 | 72 |
实施例 | 配位体 | Conv | Redn | Sel | Lin |
15a | 12 | 82.2 | 6.7 | 55.0 | 70.0 |
15b | 13 | 16.0 | 2.0 | 51.7 | 69.3 |
实施例 | 配位体 | 作用物 | Conv.to转化成醛(1) | Lin. |
16 | 1 | 己烯-1 | 73.4 | 98.7 |
17 | 1 | 己烯-2 | 50.4 | 97.3 |
比较试验17a | C | 己烯-2 | 10.3 | 95.8 |
实施例 | 配位体 | Conv | Redn* | Sel** | Lin |
18 | 1 | 85.2 | 21.0 | 42.7 | 54.4 |
19 | 14 | 37.4 | 16.3 | 44.6 | 55.6 |
实施例 | 配位体 | Conv | 戊醛 | 3-戊醛 | 二醛 |
20 | 8 | 76.7 | 2.8 | 45.2 | 7.1 |
21 | 10 | 66.7 | 2.1 | 29.2 | 5.0 |
实施例 | 配位体 | L/Rh1 | 时间(hrs) | Conv(%) | Sel(%) | Redn(%) | Lin(%) |
22 | 15 | 3.1 | 7 | 81.8 | 84.6 | 3.9 | 94.9 |
23 | 16 | 3.1 | 6 | 77.1 | 72.9 | 2.6 | 79.6 |
24 | 17 | 2.2 | 8 | 84.2 | 79.2 | 4.0 | 93.2 |
25 | 18 | 2.9 | 6 | 87.3 | 81.2 | 4.7 | 92.3 |
26 | 19 | 2.2 | 21 | 69.5 | 82.0 | 3.6 | 94.6 |
27 | 7 | 2.2 | 18.5 | 84.0 | 81.0 | 4.4 | 94.5 |
实施例 | 配位体号 | Conv. | Sel. | Lin. |
29 | 20 | 73.0 | 84.9 | 96.0 |
30 | 21 | 53.1 | 84.5 | 93.6 |
31 | 22 | 88.1 | 83.4 | 95.8 |
32 | 23 | 88.0 | 83.4 | 94.5 |
33 | 24 | 91.5 | 83.3 | 93.6 |
34 | 25 | 94.8 | 83.2 | 97.9 |
35 | 26 | 97.5 | 82.2 | 97.4 |
36 | 27 | 53.4 | 80.8 | 91.3 |
37 | 28 | 56.3 | 80.1 | 89.8 |
实施例 | 配位体号 | Conv. | Sel. | Lin. |
38 | 15 | 99 | 65.6 | 78.1 |
39* | 15 | 59 | 67.3 | 87.9 |
40 | 25 | 99 | 73.7 | 83.8 |
41** | 25 | 94 | 69.7 | 79.6 |
42 | 26 | 99 | 72.1 | 85.8 |
43** | 26 | 91 | 73.9 | 82.6 |
44 | 20 | 82 | 53.1 | 64.3 |
Claims (22)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61672196A | 1996-03-15 | 1996-03-15 | |
US08/616,721 | 1996-03-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1224413A true CN1224413A (zh) | 1999-07-28 |
CN1131850C CN1131850C (zh) | 2003-12-24 |
Family
ID=24470694
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN97194561A Expired - Fee Related CN1131850C (zh) | 1996-03-15 | 1997-03-07 | 末端醛的制备方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US6018081A (zh) |
EP (1) | EP0888274B1 (zh) |
JP (1) | JP2000506525A (zh) |
KR (1) | KR100570852B1 (zh) |
CN (1) | CN1131850C (zh) |
AU (1) | AU2045197A (zh) |
CA (1) | CA2249026A1 (zh) |
DE (1) | DE69703035T2 (zh) |
ES (1) | ES2152085T3 (zh) |
ID (1) | ID16457A (zh) |
MY (1) | MY117848A (zh) |
TW (1) | TW343195B (zh) |
WO (1) | WO1997033854A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100345635C (zh) * | 2001-11-26 | 2007-10-31 | 因维斯塔技术有限公司 | 聚合物型含磷组合物以及它们在氢氰化、不饱和腈的异构化和加氢甲酰基化反应中的用途 |
CN104024215A (zh) * | 2011-12-01 | 2014-09-03 | 阿肯马法国公司 | 包括不饱和脂肪腈的加氢甲酰化步骤的氨基酸制备方法 |
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US5710344A (en) * | 1996-11-08 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Process to prepare a linear aldehyde |
MY120454A (en) * | 1997-07-29 | 2005-10-31 | Du Pont | Improved process of preparation of linear aldehydes |
US6121184A (en) * | 1997-07-29 | 2000-09-19 | E. I. Du Pont De Nemours And Company | Supported bis(phosphorus) ligands |
US6229052B1 (en) | 1998-05-29 | 2001-05-08 | E. I. Du Pont De Nemours And Company | Hydroformylation of olefins using supported bis(phosphorus) ligands |
DE19838742A1 (de) | 1998-08-26 | 2000-03-02 | Celanese Chem Europe Gmbh | Valeraldehyd und Verfahren zu seiner Herstellung |
US6380421B1 (en) | 1999-09-20 | 2002-04-30 | E. I. Du Pont De Nemours And Company | Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions |
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 |
MY127358A (en) | 2000-03-14 | 2006-11-30 | Shell Int Research | Process for the carbonylation of ethylenically unsaturated compounds |
US6743911B2 (en) * | 2000-03-14 | 2004-06-01 | Shell Oil Company | Process for the carbonylation of pentenenitrile |
EP1332124A1 (en) * | 2000-09-27 | 2003-08-06 | Dsm N.V. | Process for the carbonylation of a conjugated diene |
EP1223155A1 (en) * | 2001-01-15 | 2002-07-17 | Dsm N.V. | Process for the preparation of a caprolactam precursor from butadiene |
EP1249445A1 (en) * | 2001-04-13 | 2002-10-16 | Dsm N.V. | Continuous process for producing an aldehyde |
EP1251122A1 (en) * | 2001-04-17 | 2002-10-23 | Dsm N.V. | Process for the preparation of epsilon-Caprolactam |
DE60304034T2 (de) * | 2002-03-11 | 2006-10-12 | Union Carbide Chemicals & Plastics Technology Corp., Danbury | Bisphosphit-ligande für carbonylierungsverfahren |
DE10349343A1 (de) | 2003-10-23 | 2005-06-02 | Basf Ag | Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden |
US8513469B2 (en) * | 2009-03-31 | 2013-08-20 | Dow Technology Investments Llc | Hydroformylation process with doubly open-ended bisphosphite ligand |
SG175182A1 (en) * | 2009-04-21 | 2011-11-28 | Invista Tech Sarl | Highly selective process for producing organodiphosphites |
WO2014163506A1 (en) | 2013-04-05 | 2014-10-09 | Universiteit Leiden | Process to prepare epsilon-caprolactam |
CN103665037B (zh) * | 2013-12-06 | 2016-04-20 | 惠州市莱佛士制药技术有限公司 | 一种2,2′-双[(3,5-二甲苯基)磷]联萘的制备方法 |
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US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
US5059710A (en) * | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
US5113022A (en) * | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
DE3937610A1 (de) * | 1989-11-11 | 1991-05-16 | Hoechst Ag | Verfahren zur gewinnung von phosphorigsaeure-bis-(2,4-di-tert.-butyl-phenyl)ester-halogeniden |
TW213465B (zh) * | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
TW315370B (zh) * | 1994-10-07 | 1997-09-11 | Du Pont |
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1996
- 1996-07-18 TW TW085108836A patent/TW343195B/zh not_active IP Right Cessation
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1997
- 1997-03-07 WO PCT/NL1997/000114 patent/WO1997033854A1/en not_active Application Discontinuation
- 1997-03-07 CA CA002249026A patent/CA2249026A1/en not_active Abandoned
- 1997-03-07 ES ES97908575T patent/ES2152085T3/es not_active Expired - Lifetime
- 1997-03-07 JP JP9532461A patent/JP2000506525A/ja active Pending
- 1997-03-07 CN CN97194561A patent/CN1131850C/zh not_active Expired - Fee Related
- 1997-03-07 KR KR1019980707364A patent/KR100570852B1/ko not_active IP Right Cessation
- 1997-03-07 DE DE69703035T patent/DE69703035T2/de not_active Expired - Lifetime
- 1997-03-07 EP EP97908575A patent/EP0888274B1/en not_active Expired - Lifetime
- 1997-03-07 AU AU20451/97A patent/AU2045197A/en not_active Abandoned
- 1997-03-14 ID IDP970830A patent/ID16457A/id unknown
- 1997-03-14 MY MYPI97001075A patent/MY117848A/en unknown
- 1997-04-28 US US08/843,130 patent/US6018081A/en not_active Expired - Fee Related
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100345635C (zh) * | 2001-11-26 | 2007-10-31 | 因维斯塔技术有限公司 | 聚合物型含磷组合物以及它们在氢氰化、不饱和腈的异构化和加氢甲酰基化反应中的用途 |
CN104024215A (zh) * | 2011-12-01 | 2014-09-03 | 阿肯马法国公司 | 包括不饱和脂肪腈的加氢甲酰化步骤的氨基酸制备方法 |
Also Published As
Publication number | Publication date |
---|---|
ES2152085T3 (es) | 2001-01-16 |
KR19990087823A (ko) | 1999-12-27 |
TW343195B (en) | 1998-10-21 |
KR100570852B1 (ko) | 2006-07-25 |
DE69703035T2 (de) | 2001-04-12 |
AU2045197A (en) | 1997-10-01 |
CA2249026A1 (en) | 1997-09-18 |
EP0888274A1 (en) | 1999-01-07 |
MY117848A (en) | 2004-08-30 |
US6018081A (en) | 2000-01-25 |
JP2000506525A (ja) | 2000-05-30 |
WO1997033854A1 (en) | 1997-09-18 |
DE69703035D1 (de) | 2000-10-12 |
CN1131850C (zh) | 2003-12-24 |
ID16457A (id) | 1997-10-02 |
EP0888274B1 (en) | 2000-09-06 |
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