CA2077007C - Methode de preparation d'alcools - Google Patents

Methode de preparation d'alcools Download PDF

Info

Publication number: CA2077007C
Authority: CA; Canada
Prior art keywords: acid; hydrogenation; group; mmol; viii metal
Prior art date: 1991-08-30
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 - Fee Related

Application number

CA002077007A

Other languages

English (en)

Other versions

CA2077007A1 (fr

Inventor

Eit Drent

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

Priority date (The priority date 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 date listed.)

1991-08-30

Filing date

1992-08-27

Publication date

2003-02-11

1991-08-30 Priority claimed from GB919118603A external-priority patent/GB9118603D0/en

1992-08-27 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1993-03-01 Publication of CA2077007A1 publication Critical patent/CA2077007A1/fr

2003-02-11 Application granted granted Critical

2003-02-11 Publication of CA2077007C publication Critical patent/CA2077007C/fr

2012-08-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000001298 alcohols Chemical class 0.000 title description 11
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 26
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 25
150000001299 aldehydes Chemical class 0.000 claims abstract description 24
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 15
230000003197 catalytic effect Effects 0.000 claims abstract description 12
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 8
150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 7
239000007858 starting material Substances 0.000 claims abstract description 5
150000002736 metal compounds Chemical class 0.000 claims abstract description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
239000003054 catalyst Substances 0.000 claims description 18
229910052751 metal Inorganic materials 0.000 claims description 17
239000002184 metal Substances 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
150000002576 ketones Chemical class 0.000 claims description 12
229910052763 palladium Inorganic materials 0.000 claims description 11
150000001450 anions Chemical class 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
239000010948 rhodium Substances 0.000 claims description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
238000002955 isolation Methods 0.000 claims 1
239000001257 hydrogen Substances 0.000 description 18
229910052739 hydrogen Inorganic materials 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
-1 cationic hydride Chemical class 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 12
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
229910002091 carbon monoxide Inorganic materials 0.000 description 12
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 9
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 9
QRPNDOFSVHOGCK-UHFFFAOYSA-N 3-di(propan-2-yl)phosphanylpropyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)CCCP(C(C)C)C(C)C QRPNDOFSVHOGCK-UHFFFAOYSA-N 0.000 description 8
HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
239000002904 solvent Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000001030 gas--liquid chromatography Methods 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
150000003003 phosphines Chemical group 0.000 description 5
239000000047 product Substances 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
239000003446 ligand Substances 0.000 description 4
239000001294 propane Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
150000007513 acids Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XCJGLBWDZKLQCY-UHFFFAOYSA-N 2-methylpropane-2-sulfonic acid Chemical compound CC(C)(C)S(O)(=O)=O XCJGLBWDZKLQCY-UHFFFAOYSA-N 0.000 description 2
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
UDQOBFJTYHSIPJ-UHFFFAOYSA-N 3-diethylphosphanylpropyl(diethyl)phosphane Chemical compound CCP(CC)CCCP(CC)CC UDQOBFJTYHSIPJ-UHFFFAOYSA-N 0.000 description 2
GZDVNUHKYJNVNT-UHFFFAOYSA-N 3-dimethylphosphanylpropyl(dimethyl)phosphane Chemical compound CP(C)CCCP(C)C GZDVNUHKYJNVNT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
MYUQBFXQGIFTSC-UHFFFAOYSA-N dibutyl(3-dibutylphosphanylpropyl)phosphane Chemical compound CCCCP(CCCC)CCCP(CCCC)CCCC MYUQBFXQGIFTSC-UHFFFAOYSA-N 0.000 description 2
229940069096 dodecene Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000126 substance Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 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
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
RNDNSYIPLPAXAZ-UHFFFAOYSA-N 2-Phenyl-1-propanol Chemical compound OCC(C)C1=CC=CC=C1 RNDNSYIPLPAXAZ-UHFFFAOYSA-N 0.000 description 1
LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
HSXUNHYXJWDLDK-UHFFFAOYSA-N 2-hydroxypropane-1-sulfonic acid Chemical compound CC(O)CS(O)(=O)=O HSXUNHYXJWDLDK-UHFFFAOYSA-N 0.000 description 1
ZTUXPKBXKXWOPH-UHFFFAOYSA-N 3-dihexylphosphanylpropyl(dihexyl)phosphane Chemical compound CCCCCCP(CCCCCC)CCCP(CCCCCC)CCCCCC ZTUXPKBXKXWOPH-UHFFFAOYSA-N 0.000 description 1
BVPTWSGFFDWMIZ-UHFFFAOYSA-N 3-dipropylphosphanylpropyl(dipropyl)phosphane Chemical compound CCCP(CCC)CCCP(CCC)CCC BVPTWSGFFDWMIZ-UHFFFAOYSA-N 0.000 description 1
HRZSNESBRSONNG-UHFFFAOYSA-N 4-di(propan-2-yl)phosphanylbutyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)CCCCP(C(C)C)C(C)C HRZSNESBRSONNG-UHFFFAOYSA-N 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910004039 HBF4 Inorganic materials 0.000 description 1
229910004713 HPF6 Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001500 aryl chlorides Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
UDSXNEQFVVATEQ-UHFFFAOYSA-N butyl-[3-[butyl(ethyl)phosphanyl]propyl]-ethylphosphane Chemical compound CCCCP(CC)CCCP(CC)CCCC UDSXNEQFVVATEQ-UHFFFAOYSA-N 0.000 description 1
DYQVOBLANWJROQ-UHFFFAOYSA-N butyl-[3-[butyl(methyl)phosphanyl]propyl]-methylphosphane Chemical compound CCCCP(C)CCCP(C)CCCC DYQVOBLANWJROQ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000002993 cycloalkylene group Chemical group 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
VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
125000004978 cyclooctylene group Chemical group 0.000 description 1
BEISXQDCAHBFEI-UHFFFAOYSA-N di(butan-2-yl)-[3-di(butan-2-yl)phosphanylpropyl]phosphane Chemical compound CCC(C)P(C(C)CC)CCCP(C(C)CC)C(C)CC BEISXQDCAHBFEI-UHFFFAOYSA-N 0.000 description 1
KHQXDNILONPNNV-UHFFFAOYSA-N dibutyl(2-dibutylphosphanylethyl)phosphane Chemical compound CCCCP(CCCC)CCP(CCCC)CCCC KHQXDNILONPNNV-UHFFFAOYSA-N 0.000 description 1
PZSPGSBFRDDDDC-UHFFFAOYSA-N dibutyl-[2-[2-(2-dibutylphosphanylethoxy)ethoxy]ethyl]phosphane Chemical compound CCCCP(CCCC)CCOCCOCCP(CCCC)CCCC PZSPGSBFRDDDDC-UHFFFAOYSA-N 0.000 description 1
BOUYBUIVMHNXQB-UHFFFAOYSA-N dicyclohexyl(2-dicyclohexylphosphanylethyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)CCP(C1CCCCC1)C1CCCCC1 BOUYBUIVMHNXQB-UHFFFAOYSA-N 0.000 description 1
TWXWPPKDQOWNSX-UHFFFAOYSA-N dicyclohexylmethanone Chemical compound C1CCCCC1C(=O)C1CCCCC1 TWXWPPKDQOWNSX-UHFFFAOYSA-N 0.000 description 1
FJILYPCZXWVDMD-UHFFFAOYSA-N ditert-butyl(3-ditert-butylphosphanylpropyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CCCP(C(C)(C)C)C(C)(C)C FJILYPCZXWVDMD-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
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 1
239000008240 homogeneous mixture Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
ZODDGFAZWTZOSI-UHFFFAOYSA-N nitric acid;sulfuric acid Chemical compound O[N+]([O-])=O.OS(O)(=O)=O ZODDGFAZWTZOSI-UHFFFAOYSA-N 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
125000005156 substituted alkylene group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
239000001117 sulphuric acid Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003568 thioethers Chemical group 0.000 description 1
BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical class CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA002077007A 1991-08-30 1992-08-27 Methode de preparation d'alcools Expired - Fee Related CA2077007C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB919118603A GB9118603D0 (en)	1991-08-30	1991-08-30	Process for the preparation of alcohols
GB9118603.1		1991-08-30
EP92202087.0		1992-07-08
EP92202087A EP0529698B1 (fr)	1991-08-30	1992-07-08	Procédé pour la préparation d'alcools

Publications (2)

Publication Number	Publication Date
CA2077007A1 CA2077007A1 (fr)	1993-03-01
CA2077007C true CA2077007C (fr)	2003-02-11

Family

ID=26131545

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002077007A Expired - Fee Related CA2077007C (fr)	1991-08-30	1992-08-27	Methode de preparation d'alcools

Country Status (3)

Country	Link
JP (1)	JP3410120B2 (fr)
CN (1)	CN1042128C (fr)
CA (1)	CA2077007C (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1071731C (zh) *	1995-08-25	2001-09-26	纳幕尔杜邦公司	加氢甲酰化方法
JP3928315B2 (ja) *	1998-12-14	2007-06-13	三菱化学株式会社	アルデヒドの製造方法
JP5487537B2 (ja) *	2007-07-24	2014-05-07	三菱化学株式会社	アルコールの製造方法
US8680302B2 (en)	2008-12-11	2014-03-25	Takasago International Corporation	Method for producing alcohol compound
EP2374783A4 (fr)	2008-12-11	2012-08-01	Takasago Perfumery Co Ltd	Procédé de production d'un composé d'alcool
SI2805765T1 (sl) *	2009-03-17	2021-04-30	Johnson Matthey Public Limited Company	Postopek za hidrogeniranje ketonov v prisotnosti katalizatorjev Ru(II)
CN105001046A (zh) *	2015-07-09	2015-10-28	武汉工程大学	正壬醇的合成工艺
JP7192475B2 (ja) *	2018-12-18	2022-12-20	Jnc株式会社	不飽和カルボニル化合物からの飽和ホモエーテルの高効率な製造法

1992
- 1992-08-27 CA CA002077007A patent/CA2077007C/fr not_active Expired - Fee Related
- 1992-08-27 CN CN92109478A patent/CN1042128C/zh not_active Expired - Fee Related
- 1992-08-27 JP JP25043392A patent/JP3410120B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1069960A (zh)	1993-03-17
JP3410120B2 (ja)	2003-05-26
CN1042128C (zh)	1999-02-17
CA2077007A1 (fr)	1993-03-01
JPH05246916A (ja)	1993-09-24

Legal Events

Date	Code	Title	Description
1999-07-12	EEER	Examination request
2011-08-29	MKLA	Lapsed

Publication	Publication Date	Title
EP0529698B1 (fr)	1996-10-16	Procédé pour la préparation d'alcools
CA2297146C (fr)	2007-06-19	Hydrogenolyse du glycerol
CA2059233C (fr)	2003-02-04	Carbonylation d'olefines
CA1177845A (fr)	1984-11-13	Methode de carbonylation des olefines
AU623230B2 (en)	1992-05-07	Carbonylation catalyst system
JP3233670B2 (ja)	2001-11-26	オレフィンのカルボニル化方法
EP0499329B1 (fr)	1994-05-04	Système catalytique pour carbonylation
AU2001274046B2 (en)	2004-05-06	Bidentate ligands useful in catalyst system
WO1998042717A1 (fr)	1998-10-01	Diphosphines
CA2077007C (fr)	2003-02-11	Methode de preparation d'alcools
US4614816A (en)	1986-09-30	Preparation of carboxylic acids and esters thereof
US3917677A (en)	1975-11-04	Production of carboxylic acid esters by hydroesterification
US5227561A (en)	1993-07-13	Co-dimerization of vinyl aromatics with α-monoolefins
CA2099198A1 (fr)	1993-12-30	Obtention de derives alcanedioiques
US6114588A (en)	2000-09-05	Hydroformylation of alpha-alcohol-diolefins to dialcohols
EP0891321B1 (fr)	2001-08-16	Procede de carbonylation de composes insatures en acetylene
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JPH0641430B2 (ja)	1994-06-01	アルデヒド又はケトンとアルデヒドとの混合物の製造方法
US7098369B2 (en)	2006-08-29	Process for the production of primary alcohols
GB2265370A (en)	1993-09-29	Preparation of nitriles
MXPA00000707A (en)	2001-03-05	Hydrogenolysis of glycerol
WO2002018047A2 (fr)	2002-03-07	Catalyseur de carbonylation