CN1019110B - 过渡金属络合物催化反应 - Google Patents
过渡金属络合物催化反应Info
- Publication number
- CN1019110B CN1019110B CN85104683A CN85104683A CN1019110B CN 1019110 B CN1019110 B CN 1019110B CN 85104683 A CN85104683 A CN 85104683A CN 85104683 A CN85104683 A CN 85104683A CN 1019110 B CN1019110 B CN 1019110B
- Authority
- CN
- China
- Prior art keywords
- rhodium
- hydroformylation
- alkyl
- reaction
- ligand
- 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
- 238000006243 chemical reaction Methods 0.000 title claims description 137
- 150000003624 transition metals Chemical class 0.000 title description 37
- 229910052723 transition metal Inorganic materials 0.000 title description 33
- 239000003446 ligand Substances 0.000 claims abstract description 321
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 237
- 238000000034 method Methods 0.000 claims abstract description 234
- 230000008569 process Effects 0.000 claims abstract description 158
- 239000003054 catalyst Substances 0.000 claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000010948 rhodium Substances 0.000 claims description 194
- 229910052703 rhodium Inorganic materials 0.000 claims description 183
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 177
- -1 Alpha-Naphthyl Chemical group 0.000 claims description 120
- 150000001336 alkenes Chemical class 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 63
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 44
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 43
- 239000007788 liquid Substances 0.000 claims description 41
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 239000012429 reaction media Substances 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 31
- 229920005989 resin Polymers 0.000 claims description 31
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 239000003957 anion exchange resin Substances 0.000 claims description 25
- 150000001721 carbon Chemical group 0.000 claims description 23
- 230000000536 complexating effect Effects 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000004711 α-olefin Substances 0.000 claims description 15
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 9
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 238000005349 anion exchange Methods 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910003450 rhodium oxide Inorganic materials 0.000 claims 1
- 238000005810 carbonylation reaction Methods 0.000 abstract description 37
- 230000003197 catalytic effect Effects 0.000 abstract description 30
- 230000006315 carbonylation Effects 0.000 abstract description 20
- 229910052751 metal Inorganic materials 0.000 abstract description 20
- 239000002184 metal Substances 0.000 abstract description 20
- 150000002739 metals Chemical class 0.000 abstract description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 226
- 150000001299 aldehydes Chemical class 0.000 description 156
- 239000000047 product Substances 0.000 description 80
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 74
- 239000007789 gas Substances 0.000 description 59
- 239000012452 mother liquor Substances 0.000 description 56
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 43
- 239000002904 solvent Substances 0.000 description 42
- 238000006555 catalytic reaction Methods 0.000 description 40
- 239000007791 liquid phase Substances 0.000 description 40
- 229910052698 phosphorus Inorganic materials 0.000 description 39
- 239000000243 solution Substances 0.000 description 38
- 239000006227 byproduct Substances 0.000 description 32
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 32
- 239000011574 phosphorus Substances 0.000 description 32
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 29
- 230000000694 effects Effects 0.000 description 27
- 238000002474 experimental method Methods 0.000 description 26
- 239000002994 raw material Substances 0.000 description 26
- 230000007704 transition Effects 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- 239000011521 glass Substances 0.000 description 24
- LGNMAJBHLWLBKR-UHFFFAOYSA-N CCBBB.[Rh] Chemical compound CCBBB.[Rh] LGNMAJBHLWLBKR-UHFFFAOYSA-N 0.000 description 23
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 23
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 21
- 125000005461 organic phosphorous group Chemical group 0.000 description 20
- 238000010926 purge Methods 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 230000000875 corresponding effect Effects 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 230000008901 benefit Effects 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 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 10
- 238000004679 31P NMR spectroscopy Methods 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 239000006200 vaporizer Substances 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 238000006170 formylation reaction Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 150000003009 phosphonic acids Chemical class 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 238000007789 sealing Methods 0.000 description 8
- 239000013638 trimer Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000004437 phosphorous atom Chemical group 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 230000002411 adverse Effects 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000022244 formylation Effects 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- JQOXUBZNPNBWRU-UHFFFAOYSA-N [Rh].C(=O)(NC(=O)OCC)NC(=O)OCC Chemical compound [Rh].C(=O)(NC(=O)OCC)NC(=O)OCC JQOXUBZNPNBWRU-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 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 5
- 150000002500 ions Chemical class 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 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 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000003003 phosphines Chemical class 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- 238000006317 isomerization reaction Methods 0.000 description 4
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000013110 organic ligand Substances 0.000 description 4
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- 238000003825 pressing Methods 0.000 description 4
- 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 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
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- 102100038239 Protein Churchill Human genes 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
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- 229910017052 cobalt Inorganic materials 0.000 description 3
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 3
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
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- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 239000003643 water by type Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN85104683A CN1019110B (zh) | 1984-02-17 | 1985-06-19 | 过渡金属络合物催化反应 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58135284A | 1984-02-17 | 1984-02-17 | |
| CN85104683A CN1019110B (zh) | 1984-02-17 | 1985-06-19 | 过渡金属络合物催化反应 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85104683A CN85104683A (zh) | 1986-12-24 |
| CN1019110B true CN1019110B (zh) | 1992-11-18 |
Family
ID=24324862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85104683A Expired CN1019110B (zh) | 1984-02-17 | 1985-06-19 | 过渡金属络合物催化反应 |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN1019110B (https=) |
| IN (1) | IN164243B (https=) |
| SU (1) | SU1516007A3 (https=) |
| ZA (1) | ZA851189B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102826974B (zh) * | 2011-06-17 | 2015-11-25 | 中国石油化工股份有限公司 | 一种丙烯氢甲酰化反应制备丁醛的方法 |
| MY184826A (en) * | 2014-12-04 | 2021-04-24 | Dow Technology Investments Llc | Hydroformylation process |
-
1985
- 1985-02-15 ZA ZA851189A patent/ZA851189B/xx unknown
- 1985-02-16 IN IN133/MAS/85A patent/IN164243B/en unknown
- 1985-06-19 CN CN85104683A patent/CN1019110B/zh not_active Expired
- 1985-10-16 SU SU853973222A patent/SU1516007A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA851189B (en) | 1985-09-25 |
| CN85104683A (zh) | 1986-12-24 |
| SU1516007A3 (ru) | 1989-10-15 |
| IN164243B (https=) | 1989-02-04 |
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