DE2639755C3 - Verfahren zur Herstellung von Aldehyden und/oder Alkoholen - Google Patents
Verfahren zur Herstellung von Aldehyden und/oder AlkoholenInfo
- Publication number
- DE2639755C3 DE2639755C3 DE2639755A DE2639755A DE2639755C3 DE 2639755 C3 DE2639755 C3 DE 2639755C3 DE 2639755 A DE2639755 A DE 2639755A DE 2639755 A DE2639755 A DE 2639755A DE 2639755 C3 DE2639755 C3 DE 2639755C3
- Authority
- DE
- Germany
- Prior art keywords
- phthalocyanine
- copper
- autoclave
- silver
- gold
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 28
- 150000001298 alcohols Chemical class 0.000 title claims description 14
- 150000001299 aldehydes Chemical class 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims description 32
- -1 oleic compound Chemical class 0.000 claims description 31
- 229910052737 gold Inorganic materials 0.000 claims description 27
- 239000010931 gold Substances 0.000 claims description 27
- 229910052709 silver Inorganic materials 0.000 claims description 27
- 239000004332 silver Substances 0.000 claims description 27
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 26
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 26
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 25
- 238000007037 hydroformylation reaction Methods 0.000 claims description 21
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 20
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003077 lignite Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052680 mordenite Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 22
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 19
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 17
- 229910052802 copper Inorganic materials 0.000 description 17
- 239000010949 copper Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000001336 alkenes Chemical class 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 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
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001030 gas--liquid chromatography Methods 0.000 description 5
- XJGIDGNLXAJIOA-UHFFFAOYSA-N 2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(36),2,4,6,8,10(40),11,13,15,17,19,21(38),22,24,26,28,30,32,34-nonadecaen-37-amine Chemical compound Nn1c2nc3nc(nc4[nH]c(nc5nc(nc1c1ccccc21)c1ccccc51)c1ccccc41)c1ccccc31 XJGIDGNLXAJIOA-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012263 liquid product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- XTDXBZMKUMZNMH-UHFFFAOYSA-N dec-1-en-3-one Chemical compound CCCCCCCC(=O)C=C XTDXBZMKUMZNMH-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- ABMKPZWSUTYTTF-UHFFFAOYSA-N dodec-1-en-6-one Chemical compound CCCCCCC(=O)CCCC=C ABMKPZWSUTYTTF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- GFLKFABQDSYXTM-UHFFFAOYSA-N oct-7-en-3-one Chemical compound CCC(=O)CCCC=C GFLKFABQDSYXTM-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- FAQAIHMZMAIJCR-BUHFOSPRSA-N (7e)-tetradeca-1,7-diene Chemical compound CCCCCC\C=C\CCCCC=C FAQAIHMZMAIJCR-BUHFOSPRSA-N 0.000 description 1
- 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 1
- VHVMXWZXFBOANQ-UHFFFAOYSA-N 1-Penten-3-ol Chemical compound CCC(O)C=C VHVMXWZXFBOANQ-UHFFFAOYSA-N 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- IFVMAGPISVKRAR-UHFFFAOYSA-N 1-ethylcyclohexene Chemical compound CCC1=CCCCC1 IFVMAGPISVKRAR-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 1
- TYKNILDYARKWKM-UHFFFAOYSA-N 1-oxoheptadecan-2-yl acetate Chemical compound CCCCCCCCCCCCCCCC(C=O)OC(C)=O TYKNILDYARKWKM-UHFFFAOYSA-N 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- MBVMMSONKHZAQF-UHFFFAOYSA-N 2-aminododecanal Chemical compound CCCCCCCCCCC(N)C=O MBVMMSONKHZAQF-UHFFFAOYSA-N 0.000 description 1
- TZZASJOLVVWFIE-UHFFFAOYSA-N 2-aminohexacosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(N)C=O TZZASJOLVVWFIE-UHFFFAOYSA-N 0.000 description 1
- BRHIPJKNONVTAB-UHFFFAOYSA-N 2-aminopentadecanal Chemical compound CCCCCCCCCCCCCC(N)C=O BRHIPJKNONVTAB-UHFFFAOYSA-N 0.000 description 1
- RQZBCUNQDJDCGV-UHFFFAOYSA-N 2-butylheptanal Chemical group CCCCCC(C=O)CCCC RQZBCUNQDJDCGV-UHFFFAOYSA-N 0.000 description 1
- LSYROLKFWITOGT-UHFFFAOYSA-N 2-ethoxyoct-1-ene Chemical compound CCCCCCC(=C)OCC LSYROLKFWITOGT-UHFFFAOYSA-N 0.000 description 1
- TXTDTCYVDJMLRP-UHFFFAOYSA-N 2-methoxybut-1-ene Chemical compound CCC(=C)OC TXTDTCYVDJMLRP-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- PCSMVMIDRQGTKB-UHFFFAOYSA-N 2-methylundecan-6-ol Chemical compound CCCCCC(O)CCCC(C)C PCSMVMIDRQGTKB-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- AMIMBVVTTZXHBC-UHFFFAOYSA-N 4-ethoxyheptadec-1-ene Chemical compound CCCCCCCCCCCCCC(CC=C)OCC AMIMBVVTTZXHBC-UHFFFAOYSA-N 0.000 description 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VCZXRQFWGHPRQB-UHFFFAOYSA-N CC(C)CC(C)(C)C.CC(C)CC(C)(C)C Chemical compound CC(C)CC(C)(C)C.CC(C)CC(C)(C)C VCZXRQFWGHPRQB-UHFFFAOYSA-N 0.000 description 1
- WZUSSAMSFSSFAI-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCCCCCCC(C(CCC=C)OCCC)OCCC Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(C(CCC=C)OCCC)OCCC WZUSSAMSFSSFAI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 229940000489 arsenate Drugs 0.000 description 1
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- UNYSKUBLZGJSLV-UHFFFAOYSA-L calcium;1,3,5,2,4,6$l^{2}-trioxadisilaluminane 2,4-dioxide;dihydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].[OH-].[Ca+2].O=[Si]1O[Al]O[Si](=O)O1.O=[Si]1O[Al]O[Si](=O)O1 UNYSKUBLZGJSLV-UHFFFAOYSA-L 0.000 description 1
- 229910052676 chabazite Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UCIYGNATMHQYCT-UHFFFAOYSA-N cyclodecene Chemical compound C1CCCCC=CCCC1 UCIYGNATMHQYCT-UHFFFAOYSA-N 0.000 description 1
- RCNFLHIGXJZJTB-UHFFFAOYSA-N cyclodecylmethanol Chemical compound OCC1CCCCCCCCC1 RCNFLHIGXJZJTB-UHFFFAOYSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- BMCQFFXPECPDPS-UHFFFAOYSA-N cycloheptylmethanol Chemical compound OCC1CCCCCC1 BMCQFFXPECPDPS-UHFFFAOYSA-N 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- BESIOWGPXPAVOS-UHFFFAOYSA-N cyclononene Chemical compound C1CCCC=CCCC1 BESIOWGPXPAVOS-UHFFFAOYSA-N 0.000 description 1
- KQTIRCUDIVJUNR-UHFFFAOYSA-N cyclononylmethanol Chemical compound OCC1CCCCCCCC1 KQTIRCUDIVJUNR-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- ZHPBLHYKDKSZCQ-UHFFFAOYSA-N cyclooctylmethanol Chemical compound OCC1CCCCCCC1 ZHPBLHYKDKSZCQ-UHFFFAOYSA-N 0.000 description 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 1
- VJOOMJDXFCBIQK-UHFFFAOYSA-N dec-1-en-1-amine Chemical compound CCCCCCCCC=CN VJOOMJDXFCBIQK-UHFFFAOYSA-N 0.000 description 1
- MWQWJUDADIEXCM-UHFFFAOYSA-N dec-1-en-4-ol Chemical compound CCCCCCC(O)CC=C MWQWJUDADIEXCM-UHFFFAOYSA-N 0.000 description 1
- CNCHKZTUPHZPHA-UHFFFAOYSA-N deca-1,5-diene Chemical compound CCCCC=CCCC=C CNCHKZTUPHZPHA-UHFFFAOYSA-N 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- HQQKMOJOCZFMSV-UHFFFAOYSA-N dilithium phthalocyanine Chemical compound [Li+].[Li+].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HQQKMOJOCZFMSV-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- AAOIESOYNOKGHR-UHFFFAOYSA-N docos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCC=CN AAOIESOYNOKGHR-UHFFFAOYSA-N 0.000 description 1
- OGNIRUSROLJRSJ-UHFFFAOYSA-N dodec-1-en-1-amine Chemical compound CCCCCCCCCCC=CN OGNIRUSROLJRSJ-UHFFFAOYSA-N 0.000 description 1
- 239000013051 drainage agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- SWQUXWQZEZROFF-UHFFFAOYSA-N henicos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCC=CN SWQUXWQZEZROFF-UHFFFAOYSA-N 0.000 description 1
- FMZFJPQPCLUKTN-UHFFFAOYSA-N henicos-1-enyl acetate Chemical compound CCCCCCCCCCCCCCCCCCCC=COC(C)=O FMZFJPQPCLUKTN-UHFFFAOYSA-N 0.000 description 1
- CTIVSZMFFGZVMI-UHFFFAOYSA-N hept-1-en-1-amine Chemical compound CCCCCC=CN CTIVSZMFFGZVMI-UHFFFAOYSA-N 0.000 description 1
- UXZDFWRRZQTZPT-UHFFFAOYSA-N heptacos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC=CN UXZDFWRRZQTZPT-UHFFFAOYSA-N 0.000 description 1
- XQOBMFQWXROKFJ-UHFFFAOYSA-N heptadec-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCC=CN XQOBMFQWXROKFJ-UHFFFAOYSA-N 0.000 description 1
- 150000002382 heptanals Chemical group 0.000 description 1
- RUDVQBCFUZDOTA-UHFFFAOYSA-N hex-1-en-1-amine Chemical compound CCCCC=CN RUDVQBCFUZDOTA-UHFFFAOYSA-N 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
- VSAVUXFZLGFWLL-UHFFFAOYSA-N hexacos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=CN VSAVUXFZLGFWLL-UHFFFAOYSA-N 0.000 description 1
- CKYMQVWGGFIENO-UHFFFAOYSA-N hexadec-1-en-5-one Chemical compound CCCCCCCCCCCC(=O)CCC=C CKYMQVWGGFIENO-UHFFFAOYSA-N 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical group CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052674 natrolite Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- NCZNMQDUMXZPLL-UHFFFAOYSA-N non-1-en-1-amine Chemical compound CCCCCCCC=CN NCZNMQDUMXZPLL-UHFFFAOYSA-N 0.000 description 1
- CAZYMTHQJINSGX-UHFFFAOYSA-N non-1-enyl acetate Chemical compound CCCCCCCC=COC(C)=O CAZYMTHQJINSGX-UHFFFAOYSA-N 0.000 description 1
- BZHOOBZQGCMVAP-UHFFFAOYSA-N nonacos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC=CN BZHOOBZQGCMVAP-UHFFFAOYSA-N 0.000 description 1
- ZBECGVPJBLUNQT-UHFFFAOYSA-N nonadec-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCC=CN ZBECGVPJBLUNQT-UHFFFAOYSA-N 0.000 description 1
- WYVKDMFLDYWJTE-UHFFFAOYSA-N oct-1-en-1-amine Chemical compound CCCCCCC=CN WYVKDMFLDYWJTE-UHFFFAOYSA-N 0.000 description 1
- WAGPKLWZLHYVFU-UHFFFAOYSA-N octacos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC=CN WAGPKLWZLHYVFU-UHFFFAOYSA-N 0.000 description 1
- WGNKXCMZCXHUHX-UHFFFAOYSA-N octadec-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCC=CN WGNKXCMZCXHUHX-UHFFFAOYSA-N 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- WKMKTIVRRLOHAJ-UHFFFAOYSA-N oxygen(2-);thallium(1+) Chemical compound [O-2].[Tl+].[Tl+] WKMKTIVRRLOHAJ-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- FSEKYSAWZRQAPN-UHFFFAOYSA-N pent-1-en-1-amine Chemical compound CCCC=CN FSEKYSAWZRQAPN-UHFFFAOYSA-N 0.000 description 1
- GMCCOMANYJMMCH-UHFFFAOYSA-N pentacos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC=CN GMCCOMANYJMMCH-UHFFFAOYSA-N 0.000 description 1
- MRZLYZFWARBILB-UHFFFAOYSA-N pentacos-1-en-11-one Chemical compound CCCCCCCCCCCCCCC(=O)CCCCCCCCC=C MRZLYZFWARBILB-UHFFFAOYSA-N 0.000 description 1
- MRDGVIIORJFCOZ-UHFFFAOYSA-N pentacos-1-en-7-ol Chemical compound CCCCCCCCCCCCCCCCCCC(O)CCCCC=C MRDGVIIORJFCOZ-UHFFFAOYSA-N 0.000 description 1
- KDEOBTMOGRXBDR-UHFFFAOYSA-N pentacosa-1,6-diene Chemical compound CCCCCCCCCCCCCCCCCCC=CCCCC=C KDEOBTMOGRXBDR-UHFFFAOYSA-N 0.000 description 1
- HAGKFWXVDSAFHB-UHFFFAOYSA-N pentacosanal Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=O HAGKFWXVDSAFHB-UHFFFAOYSA-N 0.000 description 1
- CEKMJGNDDUMKRF-UHFFFAOYSA-N pentadec-1-en-5-one Chemical compound CCCCCCCCCCC(=O)CCC=C CEKMJGNDDUMKRF-UHFFFAOYSA-N 0.000 description 1
- PJLHTVIBELQURV-UHFFFAOYSA-N pentadecene Natural products CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- JACPFCQFVIAGDN-UHFFFAOYSA-M sipc iv Chemical compound [OH-].[Si+4].CN(C)CCC[Si](C)(C)[O-].C=1C=CC=C(C(N=C2[N-]C(C3=CC=CC=C32)=N2)=N3)C=1C3=CC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 JACPFCQFVIAGDN-UHFFFAOYSA-M 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- XVKIUEYBWYEGSO-UHFFFAOYSA-N tetracos-1-en-8-ol Chemical compound CCCCCCCCCCCCCCCCC(O)CCCCCC=C XVKIUEYBWYEGSO-UHFFFAOYSA-N 0.000 description 1
- RZYFONVAFJSMQJ-UHFFFAOYSA-N tetradec-1-en-1-amine Chemical compound CCCCCCCCCCCCC=CN RZYFONVAFJSMQJ-UHFFFAOYSA-N 0.000 description 1
- UECPLNNAVLEZGO-UHFFFAOYSA-N tetradec-1-enyl acetate Chemical compound CCCCCCCCCCCCC=COC(C)=O UECPLNNAVLEZGO-UHFFFAOYSA-N 0.000 description 1
- 229910003438 thallium oxide Inorganic materials 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- HLZWBGYAYPSZSZ-UHFFFAOYSA-N triacont-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC=CN HLZWBGYAYPSZSZ-UHFFFAOYSA-N 0.000 description 1
- RTARBPFSQAUEIS-UHFFFAOYSA-N triaconta-1,5-diene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC=CCCC=C RTARBPFSQAUEIS-UHFFFAOYSA-N 0.000 description 1
- HHOXCJRIVIUSOC-UHFFFAOYSA-N tricos-1-en-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCC=CN HHOXCJRIVIUSOC-UHFFFAOYSA-N 0.000 description 1
- LUQBNMYIWSJINE-UHFFFAOYSA-N tridec-1-en-5-one Chemical compound CCCCCCCCC(=O)CCC=C LUQBNMYIWSJINE-UHFFFAOYSA-N 0.000 description 1
- ZMKXDWIJLNQLPW-UHFFFAOYSA-N undec-1-en-1-amine Chemical compound CCCCCCCCCC=CN ZMKXDWIJLNQLPW-UHFFFAOYSA-N 0.000 description 1
- NCDKMTFVFSSJEX-UHFFFAOYSA-N undec-1-en-4-ol Chemical compound CCCCCCCC(O)CC=C NCDKMTFVFSSJEX-UHFFFAOYSA-N 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical group CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/611,471 US4039585A (en) | 1975-09-08 | 1975-09-08 | Hydroformylation process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2639755A1 DE2639755A1 (de) | 1977-03-10 |
| DE2639755B2 DE2639755B2 (de) | 1979-02-01 |
| DE2639755C3 true DE2639755C3 (de) | 1979-10-04 |
Family
ID=24449159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2639755A Expired DE2639755C3 (de) | 1975-09-08 | 1976-09-03 | Verfahren zur Herstellung von Aldehyden und/oder Alkoholen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4039585A (enExample) |
| JP (1) | JPS5262210A (enExample) |
| AU (1) | AU502428B2 (enExample) |
| CA (1) | CA1068724A (enExample) |
| DE (1) | DE2639755C3 (enExample) |
| FR (1) | FR2322841A1 (enExample) |
| GB (1) | GB1554305A (enExample) |
| IT (1) | IT1065127B (enExample) |
| ZA (1) | ZA764658B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4246177A (en) * | 1979-06-21 | 1981-01-20 | Phillips Petroleum Company | Preparation of dihydropyrans |
| US4749810A (en) * | 1980-11-14 | 1988-06-07 | The Standard Oil Company | Strong acid hydrocarboxylation of propylene to isobutyric acid using metal phthalocyanines as co-catalysts |
| US4417973A (en) * | 1982-09-07 | 1983-11-29 | Mobil Oil Corporation | Upgrading olefinic stocks via sequential hydroformylation/hydrogenation |
| BR9405545A (pt) * | 1993-08-09 | 1999-05-25 | Firmenich & Cie | Processo para perfumar e lavar texteis e para prolongar o efeito de difusão do odor caracteristico de um alcool e um aldeido odorante detergente ou amaciante textil composto e composição perfumante |
| JP4552294B2 (ja) * | 2000-08-31 | 2010-09-29 | ソニー株式会社 | コンテンツ配信システム、コンテンツ配信方法、および情報処理装置、並びにプログラム提供媒体 |
| MXPA05005682A (es) * | 2002-11-28 | 2005-07-26 | Ciba Sc Holding Ag | Composicion de resina fotosensible que comprende un colorante libre de halogeno. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526742A (en) * | 1945-12-20 | 1950-10-24 | Du Pont | Ketones from secondary alcohols, olefinic compounds, and carbon monoxide |
| US2648694A (en) * | 1950-09-16 | 1953-08-11 | Standard Oil Dev Co | Higher fatty acid synthesis from oxo bottoms |
| US2945050A (en) * | 1957-05-21 | 1960-07-12 | Gulf Research Development Co | Oxidation process |
| GB1326012A (en) * | 1969-07-14 | 1973-08-08 | Johnson Matthey Co Ltd | Catalyst compositions |
-
1975
- 1975-09-08 US US05/611,471 patent/US4039585A/en not_active Expired - Lifetime
-
1976
- 1976-08-03 ZA ZA764658A patent/ZA764658B/xx unknown
- 1976-08-06 AU AU16631/76A patent/AU502428B2/en not_active Expired
- 1976-08-23 CA CA259,623A patent/CA1068724A/en not_active Expired
- 1976-08-25 FR FR7625727A patent/FR2322841A1/fr active Granted
- 1976-09-03 DE DE2639755A patent/DE2639755C3/de not_active Expired
- 1976-09-07 GB GB36973/76A patent/GB1554305A/en not_active Expired
- 1976-09-07 IT IT26934/76A patent/IT1065127B/it active
- 1976-09-07 JP JP51107170A patent/JPS5262210A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1065127B (it) | 1985-02-25 |
| AU502428B2 (en) | 1979-07-26 |
| CA1068724A (en) | 1979-12-25 |
| JPS5522454B2 (enExample) | 1980-06-17 |
| JPS5262210A (en) | 1977-05-23 |
| AU1663176A (en) | 1978-02-09 |
| FR2322841B1 (enExample) | 1978-05-05 |
| GB1554305A (en) | 1979-10-17 |
| ZA764658B (en) | 1977-07-27 |
| US4039585A (en) | 1977-08-02 |
| DE2639755B2 (de) | 1979-02-01 |
| DE2639755A1 (de) | 1977-03-10 |
| FR2322841A1 (fr) | 1977-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |