DE1543471C - - Google Patents
Info
- Publication number
- DE1543471C DE1543471C DE19661543471 DE1543471A DE1543471C DE 1543471 C DE1543471 C DE 1543471C DE 19661543471 DE19661543471 DE 19661543471 DE 1543471 A DE1543471 A DE 1543471A DE 1543471 C DE1543471 C DE 1543471C
- Authority
- DE
- Germany
- Prior art keywords
- phosphine
- cobalt
- catalyst
- alcohols
- carbon atoms
- 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 82
- 239000003054 catalyst Substances 0.000 claims description 69
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 41
- 150000001336 alkenes Chemical class 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 150000001298 alcohols Chemical class 0.000 claims description 34
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 33
- -1 9-eicosyl-9-phosphabicyclo [4,2,1] -nona-2,4,7-triene Chemical compound 0.000 claims description 31
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910017052 cobalt Inorganic materials 0.000 claims description 26
- 239000010941 cobalt Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 22
- 150000001299 aldehydes Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 4
- NAVAJJFSYTYZGQ-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCCCC)P1CCCCC1 Chemical compound C(CCCCCCCCCCCCCCCCCCC)P1CCCCC1 NAVAJJFSYTYZGQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- IVRDHSXWBGOMKG-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-phenylphosphinane Chemical group CC1(C)CCCC(C)(C)P1C1=CC=CC=C1 IVRDHSXWBGOMKG-UHFFFAOYSA-N 0.000 claims 1
- DKPWQXOONAEKGH-UHFFFAOYSA-N 2-cyclononyl-1-icosylphosphonane Chemical compound CCCCCCCCCCCCCCCCCCCCP1CCCCCCCC1C1CCCCCCCC1 DKPWQXOONAEKGH-UHFFFAOYSA-N 0.000 claims 1
- VMJOBMHRAPELBO-UHFFFAOYSA-N 9-phenyl-9-phosphabicyclo[4.2.1]nona-2,4,7-triene Chemical compound C1=CC2C=CC=CC1P2C1=CC=CC=C1 VMJOBMHRAPELBO-UHFFFAOYSA-N 0.000 claims 1
- XRJSDVKYPIBRLD-UHFFFAOYSA-N CC(CC(C)(C)C)=CP1CCCCC1 Chemical compound CC(CC(C)(C)C)=CP1CCCCC1 XRJSDVKYPIBRLD-UHFFFAOYSA-N 0.000 claims 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 42
- 239000003446 ligand Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 27
- 229940069096 dodecene Drugs 0.000 description 22
- 238000007037 hydroformylation reaction Methods 0.000 description 22
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 description 18
- 150000003003 phosphines Chemical class 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 150000001868 cobalt Chemical class 0.000 description 5
- 150000003138 primary alcohols Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000000743 hydrocarbylene group Chemical group 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 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 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- HWVKIRQMNIWOLT-UHFFFAOYSA-L cobalt(2+);octanoate Chemical compound [Co+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HWVKIRQMNIWOLT-UHFFFAOYSA-L 0.000 description 2
- IUZCCOPYZPLYBX-UHFFFAOYSA-N cobalt;phosphane Chemical compound P.[Co] IUZCCOPYZPLYBX-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical group C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000004962 sulfoxyl group Chemical group 0.000 description 2
- GRAKJTASWCEOQI-UHFFFAOYSA-N tridodecylphosphane Chemical compound CCCCCCCCCCCCP(CCCCCCCCCCCC)CCCCCCCCCCCC GRAKJTASWCEOQI-UHFFFAOYSA-N 0.000 description 2
- OGQVROWWFUXRST-FNORWQNLSA-N (3e)-hepta-1,3-diene Chemical compound CCC\C=C\C=C OGQVROWWFUXRST-FNORWQNLSA-N 0.000 description 1
- SICXXVCLNRYNCC-UHFFFAOYSA-N 1,2,3,4-tetrahydroisophosphinoline Chemical compound C1=CC=C2CPCCC2=C1 SICXXVCLNRYNCC-UHFFFAOYSA-N 0.000 description 1
- LWHXMYTXHFOYHA-UHFFFAOYSA-N 1,2,3,4-tetrahydrophosphinoline Chemical compound C1=CC=C2CCCPC2=C1 LWHXMYTXHFOYHA-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- PFILEFCRRKEBFA-UHFFFAOYSA-N 1-phenylphosphinane Chemical compound C1CCCCP1C1=CC=CC=C1 PFILEFCRRKEBFA-UHFFFAOYSA-N 0.000 description 1
- OVNKJCJEHZIBLX-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-phenylphosphinan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)P1C1=CC=CC=C1 OVNKJCJEHZIBLX-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- FFDNRFMIOVQZMT-UHFFFAOYSA-N 3-chloropropanal Chemical compound ClCCC=O FFDNRFMIOVQZMT-UHFFFAOYSA-N 0.000 description 1
- GTBKYDODFYFMIA-UHFFFAOYSA-N 4,4-dimethyl-1-phenylphosphinane Chemical compound C1CC(C)(C)CCP1C1=CC=CC=C1 GTBKYDODFYFMIA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VSEJNLHFNZPKAJ-UHFFFAOYSA-N P1(=CC=CC=CCCC1)C1=CC=CC=CCCC1 Chemical class P1(=CC=CC=CCCC1)C1=CC=CC=CCCC1 VSEJNLHFNZPKAJ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- OIQOECYRLBNNBQ-UHFFFAOYSA-N carbon monoxide;cobalt Chemical compound [Co].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] OIQOECYRLBNNBQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical class [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 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
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- BAFUCSUXLLWRRF-UHFFFAOYSA-N dodecan-1-ol;pentadecan-1-ol;tetradecan-1-ol;tridecan-1-ol Chemical compound CCCCCCCCCCCCO.CCCCCCCCCCCCCO.CCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCO BAFUCSUXLLWRRF-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 125000001802 myricyl 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])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
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ALQHHUFONRFGMF-UHFFFAOYSA-N phosphinan-2-one Chemical compound O=C1CCCCP1 ALQHHUFONRFGMF-UHFFFAOYSA-N 0.000 description 1
- GVFQLFXNYFKVCA-UHFFFAOYSA-N phosphinan-4-one Chemical compound O=C1CCPCC1 GVFQLFXNYFKVCA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011555 saturated liquid Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44370365A | 1965-03-29 | 1965-03-29 | |
| US44370365 | 1965-03-29 | ||
| US46857465A | 1965-06-30 | 1965-06-30 | |
| US46857365A | 1965-06-30 | 1965-06-30 | |
| US46857565A | 1965-06-30 | 1965-06-30 | |
| US468572A US3400163A (en) | 1965-06-30 | 1965-06-30 | Bicyclic heterocyclic sec- and tert-phosphines |
| US46857565 | 1965-06-30 | ||
| US46857465 | 1965-06-30 | ||
| US46857365 | 1965-06-30 | ||
| US46857265 | 1965-06-30 | ||
| US49355565A | 1965-10-06 | 1965-10-06 | |
| US49355565 | 1965-10-06 | ||
| DES0102826 | 1966-03-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1543471A1 DE1543471A1 (de) | 1969-08-21 |
| DE1543471C true DE1543471C (enrdf_load_stackoverflow) | 1973-05-30 |
Family
ID=27559997
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661667286 Granted DE1667286B2 (de) | 1965-03-29 | 1966-03-28 | Verfahren zur herstellung von loesungen von kobalt und phosphor enthaltenden komplexkatalysatoren |
| DE19661543471 Granted DE1543471A1 (de) | 1965-03-29 | 1966-03-28 | Verfahren zur Herstellung von Aldehyden und/oder Alkoholen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661667286 Granted DE1667286B2 (de) | 1965-03-29 | 1966-03-28 | Verfahren zur herstellung von loesungen von kobalt und phosphor enthaltenden komplexkatalysatoren |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US3420898A (enrdf_load_stackoverflow) |
| BE (1) | BE678614A (enrdf_load_stackoverflow) |
| DE (2) | DE1667286B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1109787A (enrdf_load_stackoverflow) |
| NL (1) | NL145534B (enrdf_load_stackoverflow) |
| SE (2) | SE345254B (enrdf_load_stackoverflow) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502730A (en) * | 1965-03-29 | 1970-03-24 | Shell Oil Co | Heterocyclic phosphine oxides |
| GB1127965A (en) * | 1965-11-26 | 1968-09-25 | Shell Int Research | Ditertiary phosphines and application thereof as catalyst components for alcohol production |
| DE1768391C2 (de) * | 1968-05-09 | 1979-03-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Aldehyden und Alkoholen nach der Oxosynthese |
| US3665947A (en) * | 1970-01-05 | 1972-05-30 | Bendix Corp | Fluidic sensing circuit and pressure regulator |
| US3859369A (en) * | 1971-07-26 | 1975-01-07 | Du Pont | Process for the production of 2-methyl-1,4-butanediol |
| US4005112A (en) * | 1973-11-30 | 1977-01-25 | General Electric Company | Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid |
| US4005113A (en) * | 1973-12-03 | 1977-01-25 | General Electric Company | Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid |
| EP0024761A1 (en) * | 1979-08-29 | 1981-03-11 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of alcohols or aldehydes, alcohols or aldehydes prepared by this process and stabilized compositions suitable for use in the said process |
| US5112519A (en) * | 1989-06-05 | 1992-05-12 | Mobil Oil Corporation | Process for production of biodegradable surfactants and compositions thereof |
| GB9119955D0 (en) * | 1991-09-18 | 1991-10-30 | Imperial College | Treatment of aqueous supplies containing organic material |
| KR970703805A (ko) * | 1995-05-01 | 1997-08-09 | 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀러지 코포레이션 | 막 분리방법(Membrane Separation) |
| US6756411B2 (en) * | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
| US6150322A (en) * | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US5849960A (en) * | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US5780694A (en) | 1996-11-26 | 1998-07-14 | Shell Oil Company | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| CA2419271C (en) * | 2000-08-14 | 2010-01-19 | Sasol Technology (Proprietary) Limited | Production of oxygenated products |
| US6747165B2 (en) | 2001-02-15 | 2004-06-08 | Shell Oil Company | Process for preparing (branched-alkyl) arylsulfonates and a (branched-alkyl) arylsulfonate composition |
| US6765106B2 (en) | 2001-02-15 | 2004-07-20 | Shell Oil Company | Process for preparing a branched olefin, a method of using the branched olefin for making a surfactant, and a surfactant |
| MY128880A (en) * | 2001-06-12 | 2007-02-28 | Shell Int Research | Process for the preparation of a highly liear alcohol composition |
| JP2005519973A (ja) | 2001-11-14 | 2005-07-07 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | ヒドロホルミル化方法 |
| DE10163347A1 (de) * | 2001-12-21 | 2003-07-10 | Basf Ag | Verfahren zur Hydroformylierung in Gegenwart eines polymeren Liganden mit Phosphacyclohexan-Strukturelementen |
| WO2003068719A2 (en) * | 2002-02-13 | 2003-08-21 | Sasol Technology (Proprietary) Limited | Production of oxygenated products |
| AU2003218441A1 (en) * | 2002-03-29 | 2003-10-13 | Exxonmobil Chemical Patents, Inc. | A process for preparing an olefinic hydrocarbon mixture |
| WO2003082781A1 (en) * | 2002-03-29 | 2003-10-09 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization process |
| ATE407106T1 (de) * | 2002-07-05 | 2008-09-15 | Sasol Technology Uk Ltd | Phosphor enthaltende ligande für metathese katalysatoren |
| CA2510469A1 (en) * | 2002-12-19 | 2004-07-08 | Shell Internationale Research Maatschappij B.V. | Hydroformylation process in the presence of a sulfur-containing additive |
| US20040176655A1 (en) * | 2003-02-05 | 2004-09-09 | Ayoub Paul Marie | Methods of preparing branched alkyl aromatic hydrocarbons |
| US7335802B2 (en) * | 2003-10-15 | 2008-02-26 | Shell Oil Company | Methods of preparing branched aliphatic alcohols |
| US7329783B2 (en) * | 2005-06-30 | 2008-02-12 | Shell Oil Company | Hydroformylation process |
| US20080021179A1 (en) * | 2006-06-30 | 2008-01-24 | Mul Wilhelmus P | Catalytic chemical reaction process |
| US7858787B2 (en) * | 2006-09-22 | 2010-12-28 | Shell Oil Company | Process for producing olefins |
| GB2458051B (en) * | 2006-12-21 | 2011-06-29 | Shell Int Research | Hydroformylation process |
| WO2008142143A1 (en) * | 2007-05-23 | 2008-11-27 | Shell Internationale Research Maatschappij B.V. | Hydroformylation process |
| GB2461479B (en) * | 2007-05-23 | 2011-08-24 | Shell Int Research | Hydroformylation process |
| US7767862B2 (en) * | 2008-08-11 | 2010-08-03 | Shell Oil Company | Ligand, catalyst and process for hydroformylation |
| US7994369B2 (en) | 2008-09-22 | 2011-08-09 | The Procter & Gamble Company | Specific polybranched polyaldehydes, polyalcohols, and surfactants, and consumer products based thereon |
| US8232431B2 (en) * | 2008-09-22 | 2012-07-31 | The Procter & Gamble Company | Specific branched surfactants and consumer products |
| US8383869B2 (en) * | 2009-09-01 | 2013-02-26 | Shell Oil Company | Olefin oligomer composition |
| WO2012072594A1 (en) | 2010-11-30 | 2012-06-07 | Shell Internationale Research Maatschappij B.V. | Ligand, catalyst and process for hydroformylation |
| WO2012091880A2 (en) | 2010-12-29 | 2012-07-05 | Shell Oil Company | Method and composition for enhanced hydrocarbons recovery from a formation containing a crude oil |
| US9150492B2 (en) | 2011-06-01 | 2015-10-06 | Shell Oil Company | Nonyl alcohols with a low degree of branching and their derivatives |
| US9012694B2 (en) | 2011-12-27 | 2015-04-21 | Shell Oil Company | Process for the production of alcohols |
| WO2013098196A1 (en) | 2011-12-27 | 2013-07-04 | Shell Internationale Research Maatschappij B.V. | Process for the production of alcohols |
| WO2013144735A1 (en) | 2012-03-26 | 2013-10-03 | Sasol Technology (Proprietary) Limited | Conversion of a mixture of c2 - and c3 -olefins to butanol |
| WO2013181083A1 (en) | 2012-05-29 | 2013-12-05 | Shell Oil Company | A laundry detergent composition and method of making thereof |
| US20160016860A1 (en) * | 2013-03-14 | 2016-01-21 | Dublin City University | Methods for phosphine oxide reduction in catalytic wittig reactions |
| US9828565B2 (en) | 2015-12-22 | 2017-11-28 | Shell Oil Company | Alcohol composition and derivatives thereof |
| US9828573B2 (en) | 2015-12-22 | 2017-11-28 | Shell Oil Company | Alcohol composition and derivatives thereof |
| US20180201875A1 (en) | 2017-01-13 | 2018-07-19 | The Procter & Gamble Company | Compositions comprising branched sulfonated surfactants |
| EP3424895A1 (de) | 2017-07-06 | 2019-01-09 | Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen | Verfahren zur herstellung eines treibstoffes für verbrennungsmotoren |
| CN114426469B (zh) * | 2020-09-28 | 2024-07-09 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化制备醇和醛的方法 |
| JP7696501B2 (ja) | 2022-04-27 | 2025-06-20 | クラサスケミカル株式会社 | アルコールの製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2564130A (en) * | 1948-07-24 | 1951-08-14 | Du Pont | One-step butyl alcohol process |
| NL146830C (enrdf_load_stackoverflow) * | 1960-07-22 | |||
| US3239569A (en) * | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
| US3310576A (en) * | 1963-02-05 | 1967-03-21 | Exxon Research Engineering Co | Hydroformylation catalyst and process relating thereto |
-
1965
- 1965-06-30 US US468573A patent/US3420898A/en not_active Expired - Lifetime
- 1965-10-06 US US493555A patent/US3440291A/en not_active Expired - Lifetime
-
1966
- 1966-03-28 SE SE4084/66A patent/SE345254B/xx unknown
- 1966-03-28 GB GB13556/66A patent/GB1109787A/en not_active Expired
- 1966-03-28 SE SE01919/70A patent/SE356692B/xx unknown
- 1966-03-28 DE DE19661667286 patent/DE1667286B2/de active Granted
- 1966-03-28 DE DE19661543471 patent/DE1543471A1/de active Granted
- 1966-03-29 BE BE678614D patent/BE678614A/xx not_active IP Right Cessation
- 1966-03-29 NL NL666604094A patent/NL145534B/xx not_active IP Right Cessation
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