JP5039297B2 - 直鎖状のおよびβ−アルキル分岐した脂肪族カルボン酸の製造方法 - Google Patents
直鎖状のおよびβ−アルキル分岐した脂肪族カルボン酸の製造方法 Download PDFInfo
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- JP5039297B2 JP5039297B2 JP2005328995A JP2005328995A JP5039297B2 JP 5039297 B2 JP5039297 B2 JP 5039297B2 JP 2005328995 A JP2005328995 A JP 2005328995A JP 2005328995 A JP2005328995 A JP 2005328995A JP 5039297 B2 JP5039297 B2 JP 5039297B2
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- Prior art keywords
- aldehyde
- iron
- metal
- oxidation
- oxygen
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- 238000000034 method Methods 0.000 title claims description 50
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 64
- -1 alkyl carboxylic acid Chemical class 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 230000003647 oxidation Effects 0.000 claims abstract description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000001301 oxygen Substances 0.000 claims abstract description 32
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 32
- 239000007789 gas Substances 0.000 claims abstract description 14
- 230000001590 oxidative effect Effects 0.000 claims abstract description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 95
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
- 229910052742 iron Inorganic materials 0.000 claims description 17
- 150000001735 carboxylic acids Chemical class 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 150000002506 iron compounds Chemical class 0.000 claims 7
- 229910052751 metal Inorganic materials 0.000 abstract description 52
- 239000002184 metal Substances 0.000 abstract description 52
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 34
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 239000003513 alkali Substances 0.000 abstract description 7
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 abstract description 4
- 230000000737 periodic effect Effects 0.000 abstract description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 44
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 42
- 239000003054 catalyst Substances 0.000 description 38
- 229910052783 alkali metal Inorganic materials 0.000 description 36
- 150000001340 alkali metals Chemical class 0.000 description 33
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 25
- 239000002994 raw material Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 150000002739 metals Chemical class 0.000 description 14
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 13
- 238000007792 addition Methods 0.000 description 13
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 11
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000004364 calculation method Methods 0.000 description 10
- 229910052703 rhodium Inorganic materials 0.000 description 10
- 239000010948 rhodium Substances 0.000 description 10
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 10
- WTPYRCJDOZVZON-UHFFFAOYSA-N 3,5,5-Trimethylhexanal Chemical compound O=CCC(C)CC(C)(C)C WTPYRCJDOZVZON-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 150000002736 metal compounds Chemical class 0.000 description 8
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 6
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000007037 hydroformylation reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 6
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910052748 manganese Inorganic materials 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- OPCDHYPGIGFJGH-UHFFFAOYSA-M potassium;pentanoate Chemical compound [K+].CCCCC([O-])=O OPCDHYPGIGFJGH-UHFFFAOYSA-M 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 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
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- XWJWRUYIKNLZFO-UHFFFAOYSA-M potassium;7-methyloctanoate Chemical compound [K+].CC(C)CCCCCC([O-])=O XWJWRUYIKNLZFO-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 2
- GIGNTOMJQYNUNL-UHFFFAOYSA-N 4-methylhexanal Chemical compound CCC(C)CCC=O GIGNTOMJQYNUNL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002697 manganese compounds Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 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 2
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DQQOESGZHRAMSL-UHFFFAOYSA-N 2,5,5-trimethylhexanal Chemical compound O=CC(C)CCC(C)(C)C DQQOESGZHRAMSL-UHFFFAOYSA-N 0.000 description 1
- NSOOPPRQENEOLH-UHFFFAOYSA-N 3,4,5-trimethylhexanal Chemical compound CC(C)C(C)C(C)CC=O NSOOPPRQENEOLH-UHFFFAOYSA-N 0.000 description 1
- NHBINGOOBNESIC-UHFFFAOYSA-N 4,5,5-trimethylhexanal Chemical compound CC(C)(C)C(C)CCC=O NHBINGOOBNESIC-UHFFFAOYSA-N 0.000 description 1
- CBUWTGCATVNMJE-UHFFFAOYSA-N 6,6-dimethylheptanal Chemical compound CC(C)(C)CCCCC=O CBUWTGCATVNMJE-UHFFFAOYSA-N 0.000 description 1
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical compound CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- GHHJEMGOISKOBP-UHFFFAOYSA-L barium(2+);7-methyloctanoate Chemical compound [Ba+2].CC(C)CCCCCC([O-])=O.CC(C)CCCCCC([O-])=O GHHJEMGOISKOBP-UHFFFAOYSA-L 0.000 description 1
- OZOJSEUUJMZMCQ-UHFFFAOYSA-L barium(2+);pentanoate Chemical compound [Ba+2].CCCCC([O-])=O.CCCCC([O-])=O OZOJSEUUJMZMCQ-UHFFFAOYSA-L 0.000 description 1
- ZSPVALCQTXTOER-UHFFFAOYSA-N butanal;lead Chemical compound [Pb].CCCC=O ZSPVALCQTXTOER-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- KTYKLJLZEBJWRK-UHFFFAOYSA-L calcium;7-methyloctanoate Chemical compound [Ca+2].CC(C)CCCCCC([O-])=O.CC(C)CCCCCC([O-])=O KTYKLJLZEBJWRK-UHFFFAOYSA-L 0.000 description 1
- YZLMERHFSCVBKZ-UHFFFAOYSA-L calcium;pentanoate Chemical compound [Ca+2].CCCCC([O-])=O.CCCCC([O-])=O YZLMERHFSCVBKZ-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- ILOWUJWAQMHSRV-UHFFFAOYSA-N manganese;phthalic acid Chemical compound [Mn].OC(=O)C1=CC=CC=C1C(O)=O ILOWUJWAQMHSRV-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- TVLQCQIKBJXIQX-UHFFFAOYSA-M sodium;7-methyloctanoate Chemical compound [Na+].CC(C)CCCCCC([O-])=O TVLQCQIKBJXIQX-UHFFFAOYSA-M 0.000 description 1
- LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
- C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004055252.5 | 2004-11-16 | ||
| DE102004055252A DE102004055252A1 (de) | 2004-11-16 | 2004-11-16 | Verfahren zur Herstellung von aliphatischen geradkettigen und ß-alkylverzweigten Carbonsäuren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006143717A JP2006143717A (ja) | 2006-06-08 |
| JP2006143717A5 JP2006143717A5 (enExample) | 2008-12-11 |
| JP5039297B2 true JP5039297B2 (ja) | 2012-10-03 |
Family
ID=35839019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005328995A Expired - Fee Related JP5039297B2 (ja) | 2004-11-16 | 2005-11-14 | 直鎖状のおよびβ−アルキル分岐した脂肪族カルボン酸の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7138544B2 (enExample) |
| EP (1) | EP1657230B1 (enExample) |
| JP (1) | JP5039297B2 (enExample) |
| CN (1) | CN100567245C (enExample) |
| AT (1) | ATE426588T1 (enExample) |
| DE (2) | DE102004055252A1 (enExample) |
| PL (1) | PL1657230T3 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006022168B4 (de) * | 2006-05-12 | 2014-02-27 | Oxea Gmbh | Katalytisches Verfahren zur Herstellung von aliphatischen geradkettigen und ß-alkylverzweigten Carbonsäuren |
| DE102009014626A1 (de) * | 2009-03-24 | 2010-10-07 | Oxea Deutschland Gmbh | Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden durch Mikroreaktionstechnik |
| FR2983477B1 (fr) | 2011-12-01 | 2013-12-27 | Arkema France | Procede de coupure de chaines grasses insaturees |
| FR2983478B1 (fr) | 2011-12-01 | 2013-11-15 | Arkema France | Procede de preparation d'aminoacide comprenant une etape d'hydroformylation d'un nitrile gras insature |
| DE102011120587A1 (de) * | 2011-12-08 | 2013-06-13 | Oxea Gmbh | Verfahren zur Gewinnung von aliphatischen Monocarbonsäuren aus Destillationsrückständen |
| DE102012105878A1 (de) | 2012-07-02 | 2014-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Isopentanderivaten |
| DE102012014396B4 (de) * | 2012-07-13 | 2018-01-11 | Oxea Gmbh | Verfahren zur Herstellung eines Vinylestergemisches aus einem Gemisch stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
| DE102012013968A1 (de) * | 2012-07-13 | 2014-04-03 | Oxea Gmbh | Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| DE102012013969B4 (de) * | 2012-07-13 | 2017-09-14 | Oxea Gmbh | Verfahren zur Herstellung eines Gemisches stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
| DE102013113719A1 (de) | 2013-12-09 | 2015-06-11 | Oxea Gmbh | Verfahren zur Herstellung von Pentanderivaten und Derivaten α,β-ungesättigter Decenale |
| DE102013113724A1 (de) | 2013-12-09 | 2015-06-11 | Oxea Gmbh | Verfahren zur Herstellung von Pentanderivaten und Derivaten alpha, beta-ungesättigter Decenale aus Propylen |
| JP6361578B2 (ja) | 2015-05-22 | 2018-07-25 | トヨタ自動車株式会社 | 炭化水素の製造方法 |
| CN105753684B (zh) * | 2016-02-29 | 2018-07-31 | 苏州艾缇克药物化学有限公司 | 一种羟基特戊酸的制备方法 |
| ES2807998T3 (es) * | 2017-12-21 | 2021-02-25 | Evonik Operations Gmbh | Procedimiento para la hidroxicarbonilación de diisobuteno catalizada con Pd: proporción ligando/Pd |
| EP3502087B1 (de) * | 2017-12-21 | 2020-06-24 | Evonik Operations GmbH | Verfahren zur pd-katalysierten hydroxycarbonylierung von diisobuten: verhältnis essigsäure/diisobuten |
| EP3502081B1 (de) * | 2017-12-21 | 2020-07-01 | Evonik Operations GmbH | Verfahren zur pd-katalysierten hydroxycarbonylierung von diisobuten: verhältnis 3,5,5-trimethylhexansäure/h2o |
| ES2807544T3 (es) * | 2017-12-21 | 2021-02-23 | Evonik Operations Gmbh | Procedimiento para la hidroxicarbonilación de diisobuteno catalizada con Pd: proporción ácido sulfúrico/ligando |
| CN116178141B (zh) * | 2021-11-26 | 2025-11-18 | 中国石油化工股份有限公司 | 一种醇和醛氧化制酸的方法 |
| CN114149313B (zh) * | 2022-02-09 | 2022-04-15 | 山东亿科化学有限责任公司 | 一种制备异壬酸的方法 |
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| DE732720C (de) * | 1937-03-24 | 1943-03-10 | Wacker Chemie Gmbh | Verfahren zur Herstellung aliphatischer Carbonsaeuren |
| GB856962A (en) * | 1957-02-08 | 1960-12-21 | Ici Ltd | Improvements in and relating to an oxidation process for the preparation of saturated aliphatic mono-carboxylic acids |
| DE1618589A1 (de) * | 1967-04-01 | 1971-02-25 | Knapsack Ag | Verfahren zur Herstellung von Carbonsaeuren |
| JPS6055492B2 (ja) * | 1977-02-28 | 1985-12-05 | 三菱化学株式会社 | α−分岐脂肪族カルボン酸の製法 |
| JPS53105413A (en) * | 1977-02-28 | 1978-09-13 | Mitsubishi Chem Ind Ltd | Preparation of alpha-branched aliphatic carboxylic acid |
| JPS6055494B2 (ja) * | 1977-06-20 | 1985-12-05 | 三菱化学株式会社 | α−分岐脂肪族カルボン酸の製造方法 |
| JPS5517311A (en) * | 1978-07-21 | 1980-02-06 | Mitsubishi Chem Ind Ltd | Preparation of isobutyric acid |
| DE2931154C2 (de) * | 1979-08-01 | 1985-08-01 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von aliphatischen Carbonsäuren aus Aldehyden |
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| JPS58121239A (ja) * | 1982-01-11 | 1983-07-19 | Kuraray Co Ltd | カプリル酸の製造方法 |
| DE4333323A1 (de) * | 1993-09-30 | 1995-04-06 | Hoechst Ag | Gemische isomerer Pentansäuren, aus ihnen hergestellte Ester und deren Verwendung als Schmiermittel |
| MXPA02006387A (es) * | 1999-12-22 | 2002-11-29 | Celanese Int Corp | Procedimiento de oxidacion. |
| DE10010771C1 (de) * | 2000-03-04 | 2001-05-03 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden |
| DE10010769C1 (de) * | 2000-03-04 | 2001-10-31 | Celanese Chem Europe Gmbh | Nichtkatalytisches Verfahren zur Herstellung aliphatischer Carbonsäuren durch Oxidation in mindestens zwei Stufen von Aldehyden |
-
2004
- 2004-11-16 DE DE102004055252A patent/DE102004055252A1/de not_active Withdrawn
-
2005
- 2005-09-28 US US11/237,294 patent/US7138544B2/en not_active Expired - Lifetime
- 2005-11-04 PL PL05024054T patent/PL1657230T3/pl unknown
- 2005-11-04 DE DE502005006938T patent/DE502005006938D1/de not_active Expired - Lifetime
- 2005-11-04 EP EP05024054A patent/EP1657230B1/de not_active Expired - Lifetime
- 2005-11-04 AT AT05024054T patent/ATE426588T1/de not_active IP Right Cessation
- 2005-11-14 JP JP2005328995A patent/JP5039297B2/ja not_active Expired - Fee Related
- 2005-11-15 CN CNB2005101148261A patent/CN100567245C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN100567245C (zh) | 2009-12-09 |
| ATE426588T1 (de) | 2009-04-15 |
| US7138544B2 (en) | 2006-11-21 |
| CN1775724A (zh) | 2006-05-24 |
| DE502005006938D1 (de) | 2009-05-07 |
| EP1657230B1 (de) | 2009-03-25 |
| US20060106249A1 (en) | 2006-05-18 |
| JP2006143717A (ja) | 2006-06-08 |
| PL1657230T3 (pl) | 2009-06-30 |
| EP1657230A1 (de) | 2006-05-17 |
| DE102004055252A1 (de) | 2006-05-24 |
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