JP6151743B2 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP6151743B2 JP6151743B2 JP2015136747A JP2015136747A JP6151743B2 JP 6151743 B2 JP6151743 B2 JP 6151743B2 JP 2015136747 A JP2015136747 A JP 2015136747A JP 2015136747 A JP2015136747 A JP 2015136747A JP 6151743 B2 JP6151743 B2 JP 6151743B2
- Authority
- JP
- Japan
- Prior art keywords
- ligand
- partial pressure
- catalyst
- group
- hydroformylation
- 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.)
- Active
Links
- 239000003446 ligand Substances 0.000 title claims description 111
- 238000000034 method Methods 0.000 title claims description 89
- 230000008569 process Effects 0.000 title claims description 62
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 55
- 230000036961 partial effect Effects 0.000 title claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 55
- 239000010948 rhodium Substances 0.000 claims description 42
- 150000001336 alkenes Chemical class 0.000 claims description 32
- 229910052703 rhodium Inorganic materials 0.000 claims description 31
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 30
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 28
- 230000015572 biosynthetic process Effects 0.000 claims description 26
- 238000003786 synthesis reaction Methods 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052723 transition metal Inorganic materials 0.000 claims description 20
- 150000001299 aldehydes Chemical class 0.000 claims description 19
- 150000003624 transition metals Chemical class 0.000 claims description 19
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 16
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 230000007423 decrease Effects 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 2
- RMLOZYVMENRVSS-UHFFFAOYSA-N formaldehyde;rhodium Chemical compound [Rh].O=C RMLOZYVMENRVSS-UHFFFAOYSA-N 0.000 claims description 2
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 43
- 229910002091 carbon monoxide Inorganic materials 0.000 description 43
- 239000007789 gas Substances 0.000 description 34
- 125000003118 aryl group Chemical group 0.000 description 31
- 229910052739 hydrogen Inorganic materials 0.000 description 31
- 239000001257 hydrogen Substances 0.000 description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- -1 propylene Chemical class 0.000 description 22
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- 125000000732 arylene group Chemical group 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229920000388 Polyphosphate Polymers 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- 150000001767 cationic compounds Chemical class 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 125000002993 cycloalkylene group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002892 organic cations Chemical class 0.000 description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000008300 phosphoramidites Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 239000001205 polyphosphate Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 0 CC*(C)(O*OCO*=CC(C)C)ONC Chemical compound CC*(C)(O*OCO*=CC(C)C)ONC 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Chemical group 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 125000005499 phosphonyl group Chemical group 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 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 2
- GRYAOKJSWOPBLD-UHFFFAOYSA-N (2,6-ditert-butyl-4-methoxyphenyl) dihydrogen phosphite Chemical compound COc1cc(c(OP(O)O)c(c1)C(C)(C)C)C(C)(C)C GRYAOKJSWOPBLD-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- DTCCTIQRPGSLPT-ONEGZZNKSA-N (E)-2-pentenal Chemical compound CC\C=C\C=O DTCCTIQRPGSLPT-ONEGZZNKSA-N 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QQHQTCGEZWTSEJ-UHFFFAOYSA-N 1-ethenyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C=C)C=C1 QQHQTCGEZWTSEJ-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- JRBDENXMNZQUIP-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylbutane-1,4-diol Chemical compound OCC(C)(CO)CCO JRBDENXMNZQUIP-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- JSDZSLGMRRSAHD-UHFFFAOYSA-N 3-methylbutan-2-ylcyclopropane Chemical compound CC(C)C(C)C1CC1 JSDZSLGMRRSAHD-UHFFFAOYSA-N 0.000 description 1
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- RMZIOVJHUJAAEY-UHFFFAOYSA-N Allyl butyrate Chemical compound CCCC(=O)OCC=C RMZIOVJHUJAAEY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FNDXFUBHPXBGMD-UHFFFAOYSA-N OP(O)O.OP(O)(O)=O Chemical compound OP(O)O.OP(O)(O)=O FNDXFUBHPXBGMD-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 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
- DTCCTIQRPGSLPT-UHFFFAOYSA-N beta-Aethyl-acrolein Natural products CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- IEKXSSZASGLISC-UHFFFAOYSA-N but-3-enyl acetate Chemical compound CC(=O)OCCC=C IEKXSSZASGLISC-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- UOGFCIYBLKSQHL-UHFFFAOYSA-N hex-5-en-3-ol Chemical compound CCC(O)CC=C UOGFCIYBLKSQHL-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 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
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- UZGCMRVEDHLBGY-UHFFFAOYSA-N oct-1-en-4-ol Chemical compound CCCCC(O)CC=C UZGCMRVEDHLBGY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005120 petroleum cracking Methods 0.000 description 1
- 238000005504 petroleum refining Methods 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
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004886 process control 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
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000004230 steam cracking Methods 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
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005650 substituted phenylene group Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000004711 α-olefin Substances 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
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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)
- 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)
- Catalysts (AREA)
Description
のものが含まれる。aが2又はそれ以上の値を有するとき、それぞれのR1基は、同じか又は異なっていてよく、bが1又はそれ以上の値を有するとき、それぞれのR2基は、同じか又は異なってよい。
のもののようなビスホスファイトが含まれる。好ましくはXはアルキレン、アリーレン、アリーレン−アルキレン−アリーレン及びビスアリーレンから選択された二価の炭化水素基を表し、R1はアリーレン、アリーレン−アルキレン−アリーレン及びビスアリーレンから選択された二価の炭化水素基を表し、それぞれのR2基は一価のアリール基を表す。このような式(II)〜(IV)のオルガノポリホスファイト配位子は、例えば米国特許第4,668,651号、同第4,748,261号、同第4,769,498号、同第4,774,361号、同第4,885,401号、同第5,113,022号、同第5,179,055号、同第5,202,297号、同第5,235,113号、同第5,254,741号、同第5,264,616号、同第5,312,996号及び同第5,364,950号中に開示されている。
のものである。最も好ましくは、Xは、二価のアリール−(CH2)y−(Q)m−(CH2)y−アリール基(式中、それぞれのyは、個々に、0又は1の値を有し、mは0又は1の値を有し、Qは−O−、−S−又は−C(R3)2−(式中、それぞれのR3は、同じか又は異なり、水素又はC1−10アルキル基、好ましくはメチル基を表す)である)を表す。更に好ましくは、式(V)〜(VII)の前記定義されたAr、X、R1及びR2基のそれぞれのアリール基は、6〜18個の炭素原子を含有することができ、この基は同じか又は異なっていてよく、一方、Xの好ましいアルキレン基は、2〜18個の炭素原子を含有することができる。更に、好ましくは、前記の式の二価のAr基及びXの二価のアリール基は、フェニレン基(ここで、−(CH2)y−(Q)m−(CH2)y−によって表される橋架け単位は、フェニレン基をそれらのリン原子に接続している、式の酸素原子に対してオルトである位置で、このフェニレン基に結合されている)である。このようなフェニレン基上に存在しているとき、任意の置換基は、好ましくは与えられた置換フェニレン基をそのリン原子に結合している酸素原子に関して、フェニレン基のパラ及び/又はオルト位で結合されている。
のものが含まれる。このようなオルガノモノホスファイトは、例えば米国特許第4,567,306号中に、更に詳細に記載されている。
のものが含まれる。
のものである。このようなジオルガノモノホスファイトは、例えば米国特許第4,599,206号、同第4,717,775号及び同第4,835,299号中に更に詳細に記載されている。
のものが含まれてよい。例示的トリオルガノモノホスファイトには、例えばトリアルキルホスファイト、ジアルキルアリールホスファイト、アルキルジアリールホスファイト及びトリアリールホスファイト、例えばトリフェニルホスファイト、トリス(2,6−トリイソプロピル)ホスファイト、トリス(2,6−ジ−tert−ブチル−4−メトキシフェニル)ホスファイト並びに更に好ましいトリス(2,4−ジ−tert−ブチルフェニル)ホスファイトが含まれる。官能基が、遷移金属と著しく相互作用しないか又は他の方法でヒドロホルミル化を妨害しない限り、一価の炭化水素基単位自体が官能化されていてよい。代表的な官能基には、アルキル又はアリール基、エーテル、ニトリル、アミド、エステル、−N(R11)2、−Si(R12)3、ホスフェートなど(式中、R11及びR12は、前記に定義された通りである)が含まれる。このようなトリオルガノモノホスファイトは米国特許第3,527,809号及び同第5,277,532号中に更に詳細に記載されている。
合成ガス分圧における変化による、N:I生成物比の制御
合成ガス分圧に対する異なる応答を有する、配位子1、かさ高のオルガノモノホスファイト及び配位子2、オルガノポリホスファイトを、ロジウムと組合せ、可変性選択率触媒系として評価する。
態様1.ノルマル(N)アルデヒド及びイソ(I)アルデヒドを、或るN:I比で製造するヒドロホルミル化プロセスの制御方法であって、前記プロセスが、オレフィン性不飽和化合物を、合成ガス並びに遷移金属並びにオルガノポリホスファイト及びオルガノモノホスファイト配位子を含んでなる触媒と接触させることを含んでなり、前記接触が合成ガス分圧を含むヒドロホルミル化条件で実施され、前記方法が、合成ガス分圧を上昇させてN:I比を減少させるか又は合成ガス分圧を低下させてN:I比を増加させることを含んでなる方法。
態様2.前記オレフィン性不飽和化合物が合計3〜10個の炭素原子を有するオレフィンである態様1に記載の方法。
態様3.前記オレフィン性不飽和化合物がブテン−1、ブテン−2、イソブチレン、ブタン及び任意的にブタジエンを含むC4ラフィネートI又はC4ラフィネートII異性体混合物である態様1に記載の方法。
態様4.前記オレフィン性不飽和化合物がプロピレンである態様1に記載の方法。
態様5.前記シンガスが、10:1〜1:10のH2:COモル比で、一酸化炭素及び水素を含む態様1に記載の方法。
態様6.前記触媒が(1)ロジウムカルボニルハイドライド、(2)安定化触媒錯体のロジウム金属成分に対して1:1モル基準以下の濃度で触媒系に与えられるビスホスファイト配位子及び(3)安定化触媒錯体のロジウム金属成分に対して過剰モル量で与えられる一座ホスファイト配位子の安定化錯体を含む態様1に記載の方法。
態様7.前記触媒が、1モルのロジウム源対5〜100モルの一座ホスファイト配位子の比で混合し、ヒドロホルミル化反応の開始後に、0.1モル〜1モル未満のビスホスファイト配位子を添加することによって、製造される態様1に記載の方法。
態様8.前記一座ホスファイト配位子が式:
態様9.ヒドロホルミル化条件が、−25℃よりも高く200℃よりも低い反応温度並びに1psia(6.8kPa)〜10,000psia(68.9MPa)の、オレフィン反応剤、一酸化炭素、水素及び任意の不活性軽質物を含む全気体圧力を含む態様1に記載の方法。
態様10.前記ヒドロホルミル化プロセスを連続方式で実施する態様1に記載の方法。
態様11.ノルマル(N)アルデヒド及びイソ(I)アルデヒドを、或るN:I比で製造するヒドロホルミル化プロセスの改良された制御プロセスであって、前記プロセスが、オレフィン性不飽和化合物を、合成ガス並びに遷移金属並びにオルガノポリホスファイト及びオルガノモノホスファイト配位子を含んでなる触媒と接触させることを含んでなり、前記接触を、ヒドロホルミル化条件で運転される反応ゾーン内で実施し、前記改良が、新しいシンガス分圧目標を確立した後に、前記合成ガスを反応ゾーンに一定速度で供給することを含んでなるプロセス。
Claims (6)
- ノルマル(N)アルデヒド及びイソ(I)アルデヒドを、或るN:I比で製造するヒドロホルミル化プロセスの制御方法であって、前記プロセスが、オレフィン性不飽和化合物を、合成ガス並びに遷移金属並びにオルガノポリホスファイト及びオルガノモノホスファイト配位子を含んでなる触媒と、接触させることを含んでなり、前記接触がヒドロホルミル化条件で実施され、前記方法が、新たな合成ガス分圧目標を確立した後に、前記合成ガスを反応ゾーンに一定速度で供給することを含み、当該供給によって、合成ガス分圧を上昇させてN:I比を減少させるか又は合成ガス分圧を低下させてN:I比を増加させることを含んでなるヒドロホルミル化プロセスの制御方法。
- 前記オレフィン性不飽和化合物がイソブチレン及びノルマルブテンを含むC4ラフィネートI異性体混合物又は1−ブテン、2−ブテン、イソブチレン及びブタンを含むC4ラフィネートII異性体混合物である請求項1に記載の方法。
- 前記触媒が(1)ロジウムカルボニルハイドライド、(2)安定化触媒錯体のロジウム金属成分に対して1:1モル基準以下の濃度で触媒系に与えられるビスホスファイト配位子及び(3)安定化触媒錯体のロジウム金属成分に対して過剰モル量で与えられるモノホスファイト配位子の安定化錯体を含む請求項1に記載の方法。
- 前記ヒドロホルミル化プロセスを連続方式で実施する請求項1に記載の方法。
- 前記プロセスを、合成ガス分圧及びオレフィン反応剤圧を含む全気体圧力6.9kPa〜13,800kPaで実施する請求項1に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28911509P | 2009-12-22 | 2009-12-22 | |
US61/289,115 | 2009-12-22 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012546037A Division JP2013515058A (ja) | 2009-12-22 | 2010-12-15 | 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 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015180694A JP2015180694A (ja) | 2015-10-15 |
JP6151743B2 true JP6151743B2 (ja) | 2017-06-21 |
Family
ID=43662205
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012546037A Withdrawn JP2013515058A (ja) | 2009-12-22 | 2010-12-15 | 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 |
JP2015136747A Active JP6151743B2 (ja) | 2009-12-22 | 2015-07-08 | 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 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012546037A Withdrawn JP2013515058A (ja) | 2009-12-22 | 2010-12-15 | 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 |
Country Status (14)
Country | Link |
---|---|
US (1) | US8598389B2 (ja) |
EP (2) | EP2722325B2 (ja) |
JP (2) | JP2013515058A (ja) |
KR (2) | KR101918054B1 (ja) |
CN (1) | CN102753511B (ja) |
CA (1) | CA2784943C (ja) |
ES (1) | ES2446722T5 (ja) |
MX (1) | MX365495B (ja) |
MY (1) | MY159684A (ja) |
PL (2) | PL2722325T5 (ja) |
RU (1) | RU2546110C2 (ja) |
TW (1) | TWI516470B (ja) |
WO (1) | WO2011087688A1 (ja) |
ZA (1) | ZA201204577B (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2942343B1 (en) | 2009-12-22 | 2019-09-04 | Dow Technology Investments LLC | Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process |
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 |
WO2011087696A1 (en) † | 2009-12-22 | 2011-07-21 | Dow Technology Investments Llc | Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure |
CN102826967B (zh) * | 2011-06-17 | 2015-07-22 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应制备醛的方法 |
CN104662029A (zh) * | 2012-06-01 | 2015-05-27 | 因温斯特技术公司 | 稳定的氢氰化配体组合物 |
JP2015523344A (ja) * | 2012-06-01 | 2015-08-13 | インヴィスタ テクノロジーズ エスアエルエル | 加水分解触媒およびプロセス |
MY181661A (en) * | 2012-08-29 | 2020-12-31 | Dow Technology Investments Llc | Catalyst preparation process |
CN106256893A (zh) * | 2015-06-18 | 2016-12-28 | 中国石油化工股份有限公司 | 一种喷气燃料的制备方法 |
CN108698962B (zh) * | 2016-02-11 | 2022-02-25 | 陶氏技术投资有限责任公司 | 将烯烃转化成醇、醚或其组合的方法 |
KR102073732B1 (ko) | 2016-07-08 | 2020-02-05 | 주식회사 엘지화학 | 하이드로포밀화 촉매, 이를 포함하는 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
KR102610473B1 (ko) * | 2018-10-16 | 2023-12-05 | 주식회사 엘지화학 | 알데히드의 제조방법 |
US11976017B2 (en) | 2019-12-19 | 2024-05-07 | Dow Technology Investments Llc | Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms |
CN114931961B (zh) * | 2022-06-10 | 2024-02-27 | 万华化学集团股份有限公司 | 一种氢甲酰化催化剂及其应用 |
Family Cites Families (56)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3415906A (en) | 1964-05-29 | 1968-12-10 | Hooker Chemical Corp | Phosphite phospholane and phosphorinane compounds |
US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
US4247486A (en) | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
US4169861A (en) | 1977-08-19 | 1979-10-02 | Celanese Corporation | Hydroformylation process |
DE2965158D1 (en) * | 1979-03-21 | 1983-05-11 | Davy Mckee London | Hydroformylation process |
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 |
US5110990A (en) | 1984-03-30 | 1992-05-05 | Union Carbide Chemicals & Plastics Technology Corporation | Process for recovery of phosphorus ligand from vaporized aldehyde |
US4567302A (en) | 1984-07-20 | 1986-01-28 | Angus Chemical | Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof |
US4737588A (en) | 1984-12-28 | 1988-04-12 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
US4885401A (en) | 1985-09-05 | 1989-12-05 | Union Carbide Corporation | Bis-phosphite compounds |
US4668651A (en) | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
US4748261A (en) | 1985-09-05 | 1988-05-31 | Union Carbide Corporation | Bis-phosphite compounds |
US4774361A (en) | 1986-05-20 | 1988-09-27 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
RU2005713C1 (ru) * | 1987-01-06 | 1994-01-15 | Юнион Карбид Корпорейшн | Способ получения альдегидов c4-c5 |
US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
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 |
US4873213A (en) | 1988-08-12 | 1989-10-10 | Puckette Thomas A | Low pressure rhodium catalyzed hydroformylation of olefins |
US5114473A (en) | 1988-08-25 | 1992-05-19 | Union Carbide Chemicals And Plastics Technology Corporation | Transition metal recovery |
US5277532A (en) | 1989-07-31 | 1994-01-11 | Cefin S.P.A. | Mechanical acceleration device in can welding machines |
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 |
DE4026406A1 (de) † | 1990-08-21 | 1992-02-27 | Basf Ag | Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden |
US5179055A (en) | 1990-09-24 | 1993-01-12 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
US5102505A (en) | 1990-11-09 | 1992-04-07 | Union Carbide Chemicals & Plastics Technology Corporation | Mixed aldehyde product separation by distillation |
TW213465B (ja) | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
DE4204808A1 (de) | 1992-02-18 | 1993-08-19 | Basf Ag | Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern |
US5312996A (en) | 1992-06-29 | 1994-05-17 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process for producing 1,6-hexanedials |
JP3379550B2 (ja) * | 1992-09-25 | 2003-02-24 | 三菱化学株式会社 | ヒドロホルミル化反応の制御方法 |
US5364950A (en) | 1992-09-29 | 1994-11-15 | Union Carbide Chimicals & Plastics Technology Corporation | Process for stabilizing phosphite ligands in hydroformylation reaction mixtures |
US5288918A (en) | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
US5410091A (en) † | 1994-06-02 | 1995-04-25 | Quimica Oxal C.A. | Rhodium catalyzed oxo process in tubular reactor |
US5744650A (en) † | 1995-12-06 | 1998-04-28 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-Ligand complex catalyzed processes |
EP0839787A1 (en) | 1996-11-04 | 1998-05-06 | Dsm N.V. | Process for the preparation of an aldehyde |
US5874640A (en) | 1996-11-26 | 1999-02-23 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
US5892119A (en) | 1996-11-26 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
US6090987A (en) | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
DE19954510A1 (de) † | 1999-11-12 | 2001-05-17 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Ligandenmischungen |
US6294700B1 (en) | 2000-03-15 | 2001-09-25 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
KR20060096433A (ko) | 2003-10-21 | 2006-09-11 | 바스프 악티엔게젤샤프트 | 알데히드의 연속식 제조 방법 |
KR100547587B1 (ko) | 2004-06-12 | 2006-01-31 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
KR100596365B1 (ko) † | 2004-06-12 | 2006-07-03 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
ZA200701001B (en) * | 2004-08-02 | 2008-05-28 | Union Carbide Chem Plastic | Stabilization of a hydroformylation process |
DE102004055832A1 (de) † | 2004-11-19 | 2006-06-01 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
US7615546B2 (en) † | 2005-08-19 | 2009-11-10 | Bioderm Research | Topical delivery system for phytosterols |
EP1960409B2 (en) † | 2005-12-15 | 2023-08-02 | The Penn State Research Foundation | Tetraphosphorus ligands for catalytic hydroformylation and related reactions |
US7586010B2 (en) | 2006-12-21 | 2009-09-08 | Eastman Chemical Company | Phosphonite-containing catalysts for hydroformylation processes |
MY146608A (en) * | 2007-03-20 | 2012-09-14 | Dow Technology Investments Llc | Hydroformylation process with improved control over product isomers |
US7906688B2 (en) * | 2007-04-05 | 2011-03-15 | Dow Global Technologies Inc. | Calixarene bisphosphite ligand for use in hydroformylation processes |
CN101293818B (zh) | 2007-04-28 | 2010-07-07 | 中国石油化工股份有限公司 | 混合丁烯氢甲酰化的两段反应方法 |
CN101565353B (zh) | 2008-04-25 | 2013-01-02 | 中国石油化工股份有限公司 | 一种2-丙基庚醇的制备方法 |
US7674937B2 (en) † | 2008-05-28 | 2010-03-09 | Eastman Chemical Company | Hydroformylation catalysts |
EP2328857B1 (en) † | 2008-08-19 | 2016-03-23 | Dow Technology Investments LLC | Hydroformylation process using a symmetric bisphosphite ligand for improved control over product isomers |
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 |
-
2010
- 2010-12-15 JP JP2012546037A patent/JP2013515058A/ja not_active Withdrawn
- 2010-12-15 CN CN201080063170.4A patent/CN102753511B/zh active Active
- 2010-12-15 MX MX2012007453A patent/MX365495B/es active IP Right Grant
- 2010-12-15 EP EP13194944.8A patent/EP2722325B2/en not_active Not-in-force
- 2010-12-15 PL PL13194944T patent/PL2722325T5/pl unknown
- 2010-12-15 ES ES10795580T patent/ES2446722T5/es active Active
- 2010-12-15 WO PCT/US2010/060471 patent/WO2011087688A1/en active Application Filing
- 2010-12-15 EP EP10795580.9A patent/EP2516372B2/en active Active
- 2010-12-15 US US13/516,484 patent/US8598389B2/en active Active
- 2010-12-15 KR KR1020177037443A patent/KR101918054B1/ko active IP Right Grant
- 2010-12-15 CA CA2784943A patent/CA2784943C/en active Active
- 2010-12-15 KR KR1020127019021A patent/KR101815328B1/ko active IP Right Grant
- 2010-12-15 PL PL10795580T patent/PL2516372T5/pl unknown
- 2010-12-15 RU RU2012131275/04A patent/RU2546110C2/ru active
- 2010-12-15 MY MYPI2012002856A patent/MY159684A/en unknown
- 2010-12-21 TW TW099144931A patent/TWI516470B/zh active
-
2012
- 2012-06-20 ZA ZA2012/04577A patent/ZA201204577B/en unknown
-
2015
- 2015-07-08 JP JP2015136747A patent/JP6151743B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2015180694A (ja) | 2015-10-15 |
EP2516372B1 (en) | 2014-01-22 |
WO2011087688A1 (en) | 2011-07-21 |
MY159684A (en) | 2017-01-13 |
JP2013515058A (ja) | 2013-05-02 |
CA2784943A1 (en) | 2011-07-21 |
EP2722325A1 (en) | 2014-04-23 |
PL2516372T5 (pl) | 2020-08-10 |
EP2516372A1 (en) | 2012-10-31 |
US20120253081A1 (en) | 2012-10-04 |
EP2722325B2 (en) | 2019-01-16 |
KR101815328B1 (ko) | 2018-01-04 |
CN102753511A (zh) | 2012-10-24 |
KR101918054B1 (ko) | 2018-11-13 |
TWI516470B (zh) | 2016-01-11 |
PL2722325T3 (pl) | 2015-12-31 |
MX365495B (es) | 2019-06-05 |
ES2446722T5 (es) | 2020-03-20 |
KR20120095474A (ko) | 2012-08-28 |
PL2722325T5 (pl) | 2019-07-31 |
CA2784943C (en) | 2016-09-06 |
ZA201204577B (en) | 2013-08-28 |
RU2546110C2 (ru) | 2015-04-10 |
ES2446722T3 (es) | 2014-03-10 |
US8598389B2 (en) | 2013-12-03 |
MX2012007453A (es) | 2012-11-23 |
PL2516372T3 (pl) | 2014-07-31 |
RU2012131275A (ru) | 2014-01-27 |
TW201129537A (en) | 2011-09-01 |
EP2722325B1 (en) | 2015-08-05 |
KR20180004304A (ko) | 2018-01-10 |
CN102753511B (zh) | 2014-11-19 |
EP2516372B2 (en) | 2019-08-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6151743B2 (ja) | 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 | |
JP5912084B2 (ja) | オレフィン分圧の制御による、混合リガンド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 | |
EP2516373B1 (en) | Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process | |
JP5400627B2 (ja) | 生成物異性体の制御が改善されたヒドロホルミル化方法 | |
RU2541537C2 (ru) | Способ гидроформилирования с помощью двойного открыто-концевого бисфосфитного лиганда | |
RU2598386C2 (ru) | Способы хранения катализаторов на основе фосфорорганических лигандов с переходными металлами |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150710 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20150710 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160229 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160315 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160530 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A132 Effective date: 20160920 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161110 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170425 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170525 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6151743 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |