CN1010011B - 改进的过渡金属络合物催化反应方法 - Google Patents
改进的过渡金属络合物催化反应方法Info
- Publication number
- CN1010011B CN1010011B CN87104311A CN87104311A CN1010011B CN 1010011 B CN1010011 B CN 1010011B CN 87104311 A CN87104311 A CN 87104311A CN 87104311 A CN87104311 A CN 87104311A CN 1010011 B CN1010011 B CN 1010011B
- Authority
- CN
- China
- Prior art keywords
- rhodium
- organic polymer
- phosphite
- inch
- catalyst
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 60
- 239000003054 catalyst Substances 0.000 title claims abstract description 57
- 229910052723 transition metal Inorganic materials 0.000 title description 2
- 150000003624 transition metals Chemical class 0.000 title description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 108
- 239000010948 rhodium Substances 0.000 claims abstract description 104
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 101
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 56
- 229920000620 organic polymer Polymers 0.000 claims abstract description 54
- 239000000654 additive Substances 0.000 claims abstract description 39
- 230000000996 additive effect Effects 0.000 claims abstract description 37
- 230000008569 process Effects 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 31
- 150000001299 aldehydes Chemical class 0.000 claims description 58
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 57
- 239000000047 product Substances 0.000 claims description 50
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 37
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- APVDIAOSUXFJNU-UHFFFAOYSA-N rhodium(3+) phosphite Chemical compound [Rh+3].[O-]P([O-])[O-] APVDIAOSUXFJNU-UHFFFAOYSA-N 0.000 claims description 27
- 238000004821 distillation Methods 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- -1 unsaturated allyl compound Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000012429 reaction media Substances 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 238000001556 precipitation Methods 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000005096 rolling process Methods 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 description 62
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 35
- 239000007789 gas Substances 0.000 description 28
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 23
- 125000000217 alkyl group Chemical group 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 150000001336 alkenes Chemical class 0.000 description 17
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 16
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 10
- 125000001118 alkylidene group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 229940117958 vinyl acetate Drugs 0.000 description 6
- 230000004913 activation Effects 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 150000004646 arylidenes Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000000536 complexating effect Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 5
- UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 3
- 239000006200 vaporizer Substances 0.000 description 3
- UVHQXWILFGUDTA-LNKPDPKZSA-N (z)-4-ethoxy-4-oxobut-2-enoic acid;methoxyethene Chemical compound COC=C.CCOC(=O)\C=C/C(O)=O UVHQXWILFGUDTA-LNKPDPKZSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000687955 Homo sapiens Phosphomevalonate kinase Proteins 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 102100024279 Phosphomevalonate kinase Human genes 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229950003988 decil Drugs 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000006259 organic additive Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 229920005735 poly(methyl vinyl ketone) Polymers 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HITROERJXNWVOI-SOFGYWHQSA-N (5e)-octa-1,5-diene Chemical compound CC\C=C\CCC=C HITROERJXNWVOI-SOFGYWHQSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- 101100433727 Caenorhabditis elegans got-1.2 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- NKQYVXQKXPHGCV-UHFFFAOYSA-N [Rh+4].[O-]P([O-])OP([O-])[O-] Chemical class [Rh+4].[O-]P([O-])OP([O-])[O-] NKQYVXQKXPHGCV-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004946 alkenylalkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 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
- IEKXSSZASGLISC-UHFFFAOYSA-N but-3-enyl acetate Chemical compound CC(=O)OCCC=C IEKXSSZASGLISC-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical class OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical group CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 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
- C07C45/49—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
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US865,061 | 1986-05-20 | ||
| US06/865,061 US4717775A (en) | 1984-12-28 | 1986-05-20 | Transition metal complex catalyzed reactions |
| US046,821 | 1987-05-11 | ||
| US07/046,821 US4774361A (en) | 1986-05-20 | 1987-05-11 | Transition metal complex catalyzed reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN87104311A CN87104311A (zh) | 1988-06-08 |
| CN1010011B true CN1010011B (zh) | 1990-10-17 |
Family
ID=26724327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87104311A Expired CN1010011B (zh) | 1986-05-11 | 1987-05-20 | 改进的过渡金属络合物催化反应方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4774361A (enExample) |
| EP (1) | EP0276231B1 (enExample) |
| JP (1) | JPS63503385A (enExample) |
| CN (1) | CN1010011B (enExample) |
| AU (1) | AU613312B2 (enExample) |
| CA (1) | CA1312094C (enExample) |
| DE (1) | DE3773890D1 (enExample) |
| ES (1) | ES2004935A6 (enExample) |
| IN (1) | IN169727B (enExample) |
| MX (1) | MX166107B (enExample) |
| NO (1) | NO166583C (enExample) |
| WO (1) | WO1987007261A2 (enExample) |
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835299A (en) * | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
| IT1237530B (it) * | 1989-12-12 | 1993-06-08 | Eniricerche Spa | Procedimento per la sintesi diretta di alcoli da olefine,ossidi di carbonio e idrogeno,promossa da un catalizzatore di rodio supportato |
| US5210318A (en) * | 1990-05-04 | 1993-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Catalysts and processes useful in producing 1,3-diols and/or 3-hydroxyldehydes |
| US5087763A (en) * | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| JP2946790B2 (ja) * | 1991-03-14 | 1999-09-06 | 三菱化学株式会社 | アルデヒド類の製造法 |
| US5360938A (en) * | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| GB9119955D0 (en) * | 1991-09-18 | 1991-10-30 | Imperial College | Treatment of aqueous supplies containing organic material |
| US5169981A (en) * | 1991-12-06 | 1992-12-08 | Union Carbide Chemicals & Plastics Technology Corporation | Synthesis of alpha-substituted alkadienes |
| US5243099A (en) * | 1991-12-06 | 1993-09-07 | Union Carbide Chemicals & Plastics Technology Corporation | Synthesis of alpha-substituted alkadienes |
| US5756855A (en) | 1994-08-19 | 1998-05-26 | Union Carbide Chemicals & Plastics Technology Corporation | Stabilization of phosphite ligands in hydroformylation process |
| US5672766A (en) * | 1994-12-12 | 1997-09-30 | Mitsubishi Chemical Corporation | Method for producing aldehydes |
| KR970703805A (ko) * | 1995-05-01 | 1997-08-09 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 | 막 분리방법(Membrane Separation) |
| US5739352A (en) * | 1995-10-19 | 1998-04-14 | United Carbide Chemicals & Plastics Technology Corporation | Process for preparing carboxylic acids |
| DE19605435A1 (de) * | 1996-02-14 | 1997-08-21 | Basf Ag | Verfahren zur Herstellung von Aldehyden durch Hydroformylierung mit einem Rhodiumkatalysator und Wiedergewinnung des Rhodiumkatalysators durch Extraktion |
| US6090987A (en) * | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| EP1312598B1 (en) * | 1998-12-10 | 2005-02-16 | Mitsubishi Chemical Corporation | Process for producing aldehyde |
| JP3921853B2 (ja) * | 1998-12-10 | 2007-05-30 | 三菱化学株式会社 | アルデヒド類及びアルコール類の製造方法 |
| GB9918229D0 (en) † | 1999-08-04 | 1999-10-06 | Ici Plc | Improvements relating to metal-compound catalysed processes |
| DE19954510A1 (de) | 1999-11-12 | 2001-05-17 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen |
| EP2453320B1 (en) | 2000-06-27 | 2016-06-29 | Dai Nippon Printing Co., Ltd. | Multilayer volume hologram, and label for multilayer volume hologram fabrication |
| EP1249441A1 (en) | 2001-04-13 | 2002-10-16 | Dsm N.V. | Continuous hydroformylation process |
| DE10220801A1 (de) * | 2002-05-10 | 2003-11-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste |
| US7193116B2 (en) | 2002-08-31 | 2007-03-20 | Oxeno Olefinchemie Gmbh | Method for producing aldehydes by means of hydroformylation of olefinically unsaturated compounds, said hydroformylation being catalyzed by unmodified metal complexes in the presence of cyclic carbonic acid esters |
| US7317130B2 (en) * | 2002-08-31 | 2008-01-08 | Oxeno Olefinchemie Gmbh | Method for the hydroformylation of olefinically unsaturated compounds, especially olefins, in the presence of cyclic carbonic acid esters |
| MXPA05007334A (es) * | 2003-01-16 | 2005-09-30 | Teijin Fibers Ltd | Hilos de filamentos combinados de poliester de contraccion diferente. |
| WO2005007602A1 (en) | 2003-07-03 | 2005-01-27 | Union Carbide Chemicals & Plastics Technology Corporation | Minimization of ligand degradation products, of reversion of same to useful phosphine ligands |
| DE10349343A1 (de) * | 2003-10-23 | 2005-06-02 | Basf Ag | Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden |
| JP4991538B2 (ja) | 2004-08-02 | 2012-08-01 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセスの安定化 |
| BRPI0808297B1 (pt) * | 2007-03-20 | 2017-02-07 | Dow Technology Investments Llc | processo de hidroformilação |
| WO2008123740A1 (en) * | 2007-04-09 | 2008-10-16 | Lg Chem, Ltd. | Catalyst composition including phosphite ligands and hydroformylation method using the same |
| EP2297077B1 (en) | 2008-07-03 | 2014-06-04 | Dow Technology Investments LLC | Process of controlling heavies in a recycle catalyst stream |
| AU2009313838B2 (en) | 2008-11-14 | 2015-02-05 | University Of Kansas | Polymer-supported transition metal catalyst complexes and methods of use |
| RU2541537C2 (ru) | 2009-03-31 | 2015-02-20 | Дау Текнолоджи Инвестментс Ллс | Способ гидроформилирования с помощью двойного открыто-концевого бисфосфитного лиганда |
| US7928267B1 (en) * | 2009-06-22 | 2011-04-19 | Eastman Chemical Company | Phosphite containing catalysts for hydroformylation processes |
| CN102574878A (zh) | 2009-10-16 | 2012-07-11 | 陶氏技术投资有限责任公司 | 气相加氢甲酰化方法 |
| US8664451B2 (en) | 2009-12-22 | 2014-03-04 | Dow Technology Investments Llc | Controlling the normal:ISO aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure |
| JP2013515058A (ja) | 2009-12-22 | 2013-05-02 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | シンガス分圧を制御することによる、混合配位子ヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
| EP2942343B1 (en) | 2009-12-22 | 2019-09-04 | Dow Technology Investments LLC | Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process |
| CN103153462B (zh) | 2010-10-05 | 2016-06-01 | 陶氏技术投资有限责任公司 | 加氢甲酰基化方法 |
| WO2012064586A1 (en) | 2010-11-12 | 2012-05-18 | Dow Technology Investments Llc | Mitigation of fouling in hydroformylation processes by water addition |
| SA112330271B1 (ar) | 2011-04-18 | 2015-02-09 | داو تكنولوجى انفستمنتس ال ال سى | تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء |
| SG10201607488XA (en) | 2012-03-07 | 2016-10-28 | Basf Se | Method for thermal integration in the hydrogenation and distillation of c3-c20 aldehydes |
| US8889917B2 (en) | 2012-04-12 | 2014-11-18 | Basf Se | Method of supplementing the catalyst in continuous hydroformylation |
| PL2836474T3 (pl) | 2012-04-12 | 2018-06-29 | Basf Se | Sposób uzupełniania katalizatora podczas ciągłego hydroformylowania |
| MY172419A (en) | 2012-06-04 | 2019-11-25 | Dow Technology Investments Llc | Hydroformylation process |
| BR112015003762B1 (pt) * | 2012-08-29 | 2021-04-13 | Dow Technology Investments Llc | Processo para a formação de um catalisador de hidroformilação |
| EP2900373B1 (en) | 2012-09-25 | 2019-04-17 | Dow Technology Investments LLC | Process for stabilizing a phosphite ligand against degradation |
| EP2740535A1 (en) | 2012-12-04 | 2014-06-11 | Dow Technology Investments LLC | Bidentate ligands for hydroformylation of ethylene |
| KR102098429B1 (ko) | 2012-12-06 | 2020-04-07 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 하이드로포밀화 방법 |
| CN104045532B (zh) | 2013-03-15 | 2018-05-25 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| CN104725170B (zh) | 2013-12-19 | 2019-08-23 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| BR112016013001B1 (pt) | 2013-12-19 | 2020-12-29 | Dow Technology Investments Llc | processo de hidroformilação |
| PL3126319T3 (pl) | 2014-03-31 | 2020-01-31 | Dow Technology Investments Llc | Proces hydroformylowania |
| WO2015175158A1 (en) | 2014-05-14 | 2015-11-19 | Dow Technology Investments Llc | Stabilized organophosphorous compounds |
| MY184826A (en) * | 2014-12-04 | 2021-04-24 | Dow Technology Investments Llc | Hydroformylation process |
| TWI709566B (zh) | 2015-09-30 | 2020-11-11 | 美商陶氏科技投資公司 | 用於製造有機磷化合物的方法 |
| TWI709568B (zh) | 2015-09-30 | 2020-11-11 | 美商陶氏科技投資公司 | 用於製造有機磷化合物的方法 |
| JP6908602B2 (ja) | 2015-11-10 | 2021-07-28 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | アルデヒドの生成プロセス |
| MX2018009690A (es) | 2016-02-11 | 2018-09-11 | Dow Technology Investments Llc | Procesos para convertir olefinas en alcoholes, eteres o combinaciones de los mismos. |
| EP3429984A1 (en) | 2016-03-18 | 2019-01-23 | Dow Technology Investments LLC | Hydroformylation process |
| TWI758353B (zh) | 2016-11-08 | 2022-03-21 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| TW201840363A (zh) | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 處理氫甲醯化催化劑溶液之方法 |
| TW201840362A (zh) | 2016-11-08 | 2018-11-16 | 美商陶氏科技投資有限公司 | 使去活化的氫甲醯化催化劑溶液再生的方法 |
| CN111212826B (zh) | 2017-10-25 | 2023-05-23 | 陶氏技术投资有限责任公司 | 减少在加氢甲酰化过程中形成的包含醛化合物的溶液中重物质形成的方法 |
| CN111278560B (zh) | 2017-11-13 | 2023-07-21 | 陶氏技术投资有限责任公司 | 从氢甲酰化方法回收铑的方法 |
| TWI793216B (zh) * | 2017-12-07 | 2023-02-21 | 美商陶氏科技投資公司 | 氫甲醯化方法 |
| EP3801899A1 (en) | 2018-05-30 | 2021-04-14 | Dow Technology Investments LLC | Methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in hydroformylation processes |
| US11344869B2 (en) | 2018-05-30 | 2022-05-31 | Dow Technology Investments Llc | Methods of controlling hydroformylation processes |
| CN112055614A (zh) | 2018-05-30 | 2020-12-08 | 陶氏技术投资有限责任公司 | 包括单膦、四膦配位体的组合的催化剂组合物和使用其的加氢甲酰化过程 |
| EP3887348B1 (en) * | 2018-11-29 | 2022-11-02 | Dow Technology Investments LLC | Hydroformylation process |
| JP7547397B2 (ja) * | 2019-06-27 | 2024-09-09 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 貴金属回収のためのヒドロホルミル化プロセスから溶液を調製するプロセス |
| TWI874467B (zh) | 2019-11-05 | 2025-03-01 | 美商陶氏科技投資有限公司 | 用於自ｃ６或更高碳數烯烴氫甲醯化製程之催化劑淨化流回收銠之方法 |
| WO2021126421A1 (en) | 2019-12-19 | 2021-06-24 | Dow Technology Investments Llc | Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms |
| CN114478214B (zh) * | 2020-10-23 | 2024-05-17 | 中国石油化工股份有限公司 | 一种氢甲酰化方法和一种氢甲酰化产物的分离方法 |
| CA3201268A1 (en) | 2020-12-14 | 2022-06-23 | Michael A. Brammer | Processes to improve catalytic metal accountability in hydroformylation processes |
| MX2024005136A (es) | 2021-11-11 | 2024-05-16 | Dow Technology Investments Llc | Procesos para recuperar rodio a partir de procesos de hidroformilacion. |
| US20240399349A1 (en) | 2021-12-16 | 2024-12-05 | Dow Technology Investments Llc | Transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes |
| EP4448170B1 (en) | 2021-12-16 | 2025-08-20 | Dow Technology Investments LLC | Compounds, transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes |
| CN120282943A (zh) | 2022-12-13 | 2025-07-08 | 陶氏技术投资有限责任公司 | 通过利用降解产物使多膦使用最小化的方法 |
| WO2024228768A1 (en) | 2023-05-04 | 2024-11-07 | Dow Technology Investments Llc | Hydroformylation process |
| GB202307175D0 (en) | 2023-05-15 | 2023-06-28 | Johnson Matthey Davy Technologies Ltd | Process for hydrogenating a substrate |
| CN121194957A (zh) | 2023-06-26 | 2025-12-23 | 陶氏技术投资有限责任公司 | 控制加氢甲酰化工艺的方法 |
| WO2025029369A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Process for improving rhodium/phosphite- based homogenous hydroformylation catalyst activity |
| WO2025029349A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Hydroformylation process |
| GB202404300D0 (en) | 2024-03-26 | 2024-05-08 | Johnson Matthey Davy Technologies Ltd | Process for the production of 2-alkylalkanol |
| CN121178080A (zh) * | 2025-11-21 | 2025-12-23 | 中海油天津化工研究设计院有限公司 | 一种高碳烯烃羰基合成制备高碳醛的生产系统及方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE156528C (enExample) * | ||||
| US4482748A (en) * | 1967-05-29 | 1984-11-13 | Celanese Corporation | Hydrocarbonylation |
| DE2145532C3 (de) * | 1971-09-11 | 1975-02-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Aufarbeitung von Hydroformylierungsgemischen |
| DE2326489A1 (de) * | 1973-05-24 | 1974-12-12 | Ernst Prof Dr Bayer | Verfahren zur katalyse unter verwendung von loeslichen metallverbindungen synthetischer polymerer |
| JPS5638576B2 (enExample) * | 1974-07-25 | 1981-09-08 | ||
| US4148830A (en) * | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| JPS6022688B2 (ja) * | 1976-12-29 | 1985-06-03 | 和光純薬工業株式会社 | アルデヒド化合物の蒸留方法 |
| DE2966350D1 (en) * | 1978-08-17 | 1983-12-01 | Heyl Chem Pharm | Polymeric hydrogenation catalysts, process for preparing these catalysts and their use for catalytic hydrogenations |
| US4235744A (en) * | 1978-10-30 | 1980-11-25 | Standard Oil Company (Ohio) | Carbonylation of olefinically unsaturated compounds |
| US4504684A (en) * | 1982-01-06 | 1985-03-12 | The Standard Oil Company | Metal coordination polymers as hydroformylation and hydrogenation catalysts |
| ATE28183T1 (de) * | 1982-06-11 | 1987-07-15 | Davy Mckee London | Hydroformylierungsverfahren. |
| US4528403A (en) * | 1982-10-21 | 1985-07-09 | Mitsubishi Chemical Industries Ltd. | Hydroformylation process for preparation of aldehydes and alcohols |
| US4528404A (en) * | 1983-03-16 | 1985-07-09 | Exxon Research And Engineering Co. | High temperature hydroformylation in the presence of triarylphosphine rhodium carbonyl hydride complex catalyst systems |
| GB8334359D0 (en) * | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
| US4599206A (en) * | 1984-02-17 | 1986-07-08 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4599456A (en) * | 1984-12-20 | 1986-07-08 | Phillips Petroleum Company | Novel aldehyde-phosphine compositions and uses therefor |
| US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| US4613701A (en) * | 1985-09-19 | 1986-09-23 | Celanese Corporation | Recovery of rhodium from hydroformylation reaction product |
-
1987
- 1987-05-11 US US07/046,821 patent/US4774361A/en not_active Expired - Lifetime
- 1987-05-19 DE DE8787903774T patent/DE3773890D1/de not_active Expired - Lifetime
- 1987-05-19 JP JP62503400A patent/JPS63503385A/ja active Granted
- 1987-05-19 EP EP87903774A patent/EP0276231B1/en not_active Expired - Lifetime
- 1987-05-19 WO PCT/US1987/001124 patent/WO1987007261A2/en not_active Ceased
- 1987-05-19 AU AU74898/87A patent/AU613312B2/en not_active Ceased
- 1987-05-20 CN CN87104311A patent/CN1010011B/zh not_active Expired
- 1987-05-20 MX MX006566A patent/MX166107B/es unknown
- 1987-05-20 CA CA000537549A patent/CA1312094C/en not_active Expired - Lifetime
- 1987-05-20 ES ES8701486A patent/ES2004935A6/es not_active Expired
- 1987-05-20 IN IN373/MAS/87A patent/IN169727B/en unknown
-
1988
- 1988-01-19 NO NO880207A patent/NO166583C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2004935A6 (es) | 1989-02-16 |
| AU7489887A (en) | 1987-12-22 |
| NO880207L (no) | 1988-01-19 |
| NO166583B (no) | 1991-05-06 |
| EP0276231A1 (en) | 1988-08-03 |
| JPH0548215B2 (enExample) | 1993-07-20 |
| IN169727B (enExample) | 1991-12-14 |
| CA1312094C (en) | 1992-12-29 |
| NO166583C (no) | 1991-08-14 |
| CN87104311A (zh) | 1988-06-08 |
| MX166107B (es) | 1992-12-21 |
| NO880207D0 (no) | 1988-01-19 |
| WO1987007261A3 (en) | 1988-04-07 |
| DE3773890D1 (de) | 1991-11-21 |
| US4774361A (en) | 1988-09-27 |
| JPS63503385A (ja) | 1988-12-08 |
| EP0276231B1 (en) | 1991-10-16 |
| AU613312B2 (en) | 1991-08-01 |
| WO1987007261A2 (en) | 1987-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1010011B (zh) | 改进的过渡金属络合物催化反应方法 | |
| CN1021202C (zh) | 过渡金属络合物的催化前体组合物 | |
| CN1237068C (zh) | 氢化硅烷化反应的催化剂 | |
| CN1020720C (zh) | 采用低挥发性/有机可溶性膦配位体的羰基化过程 | |
| CN1019396B (zh) | 纯化有机基亚磷酸三酯的方法 | |
| CN86106770A (zh) | 双-亚磷酸酯化合物 | |
| CN1021656C (zh) | 从非极性有机溶液中回收催化金属 | |
| CN1740183A (zh) | 氯亚磷酸酯的制备方法以及n,n－二烷基二芳基氨基亚磷酸酯的制备方法 | |
| CN1296469A (zh) | 改进的分离方法 | |
| CN1204131C (zh) | 制备α－亚甲基内酯的方法 | |
| CN1036248C (zh) | 一种从羰基合成产物的蒸馏残渣中回收铑的方法 | |
| CN87101178A (zh) | 用低挥发性膦配体进行醛化 | |
| CN1336940A (zh) | 可生物降解的和热敏的聚磷腈和它们的制备方法 | |
| CN1319102A (zh) | 制备n－(膦酰甲基)亚氨基二乙酸的连续方法 | |
| CN1025561C (zh) | 生产丙烯酸酯的方法 | |
| CN86101237A (zh) | 热稳定的烯类聚合物的制备方法 | |
| CN1130264C (zh) | 铑配合物溶液的制备方法和生产醛的方法 | |
| CN1046260C (zh) | 具备高伯羟基含量的二醇 | |
| CN1024656C (zh) | 磷酸钡催化的烷氧基化方法 | |
| CN1116199A (zh) | 碳酸酯的制备方法 | |
| CN1720218A (zh) | α－羟基羧酸酯的制造方法 | |
| CN1590360A (zh) | 制备（甲基）丙烯酸化合物的方法 | |
| CN86100221A (zh) | 氨基丙烯酸衍生物制备方法 | |
| CN1022318C (zh) | 生产1，2，4-苯三酸或1，2，4，5-苯四酸的方法 | |
| CN1112350C (zh) | β－羟基结构的季铵盐复合相转移催化剂及其制备 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C13 | Decision | ||
| GR02 | Examined patent application | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
| OR01 | Other related matters | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |