DE19754848C2 - Verfahren zur Herstellung von Alkoholen - Google Patents
Verfahren zur Herstellung von AlkoholenInfo
- Publication number
- DE19754848C2 DE19754848C2 DE19754848A DE19754848A DE19754848C2 DE 19754848 C2 DE19754848 C2 DE 19754848C2 DE 19754848 A DE19754848 A DE 19754848A DE 19754848 A DE19754848 A DE 19754848A DE 19754848 C2 DE19754848 C2 DE 19754848C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- aldehydes
- catalyst
- aldehyde
- weight
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 61
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 49
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007858 starting material Substances 0.000 claims abstract description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 59
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 39
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052759 nickel Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- -1 hexyl - Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- PYLMCYQHBRSDND-UHFFFAOYSA-N 2-ethyl-2-hexenal Chemical compound CCCC=C(CC)C=O PYLMCYQHBRSDND-UHFFFAOYSA-N 0.000 claims description 6
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 5
- 239000012876 carrier material Substances 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- BATOPAZDIZEVQF-MQQKCMAXSA-N (E,E)-2,4-hexadienal Chemical compound C\C=C\C=C\C=O BATOPAZDIZEVQF-MQQKCMAXSA-N 0.000 claims description 2
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N caprinaldehyde Natural products CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000005755 formation reaction Methods 0.000 description 17
- 239000006227 byproduct Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- 239000011148 porous material Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
- 229910000480 nickel oxide Inorganic materials 0.000 description 2
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
- 229910001948 sodium oxide Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 description 1
- JGEGJYXHCFUMJF-UHFFFAOYSA-N 4-methylpentanal Chemical compound CC(C)CCC=O JGEGJYXHCFUMJF-UHFFFAOYSA-N 0.000 description 1
- YKGBNAGNNUEZQC-UHFFFAOYSA-N 6-methyl-n,n-bis(6-methylheptyl)heptan-1-amine Chemical compound CC(C)CCCCCN(CCCCCC(C)C)CCCCCC(C)C YKGBNAGNNUEZQC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 239000005700 Putrescine Substances 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000006423 Tishchenko reaction Methods 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000002459 porosimetry Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19754848A DE19754848C2 (de) | 1997-12-10 | 1997-12-10 | Verfahren zur Herstellung von Alkoholen |
| IDP981543A ID21417A (id) | 1997-12-10 | 1998-11-26 | Proses pembuatan alkohol |
| ES98122544T ES2178095T3 (es) | 1997-12-10 | 1998-12-01 | Procedimiento para la fabricacion de alcoholes. |
| EP98122544A EP0922687B1 (de) | 1997-12-10 | 1998-12-01 | Verfahren zur Herstellung von Alkoholen |
| DK98122544T DK0922687T3 (da) | 1997-12-10 | 1998-12-01 | Fremgangsmåde til fremstilling af alkoholer |
| DE59804718T DE59804718D1 (de) | 1997-12-10 | 1998-12-01 | Verfahren zur Herstellung von Alkoholen |
| AT98122544T ATE220390T1 (de) | 1997-12-10 | 1998-12-01 | Verfahren zur herstellung von alkoholen |
| PT98122544T PT922687E (pt) | 1997-12-10 | 1998-12-01 | Processo para a preparacao de alcoois |
| US09/204,597 US6096931A (en) | 1997-12-10 | 1998-12-03 | Process for preparing alcohols |
| JP34912198A JP4121647B2 (ja) | 1997-12-10 | 1998-12-08 | アルコールの製造方法 |
| ZA9811224A ZA9811224B (en) | 1997-12-10 | 1998-12-08 | Process for preparing alcohols |
| CA002255242A CA2255242A1 (en) | 1997-12-10 | 1998-12-08 | Process for preparing alcohols |
| MXPA/A/1998/010399A MXPA98010399A (en) | 1997-12-10 | 1998-12-08 | Procedure for preparing alcohol |
| TW087120393A TW470739B (en) | 1997-12-10 | 1998-12-09 | Process for preparing alcohols |
| AU97003/98A AU9700398A (en) | 1997-12-10 | 1998-12-09 | Process for preparing alcohols |
| KR1019980053841A KR100659913B1 (ko) | 1997-12-10 | 1998-12-09 | 알콜의제조방법 |
| BR9805254-3A BR9805254A (pt) | 1997-12-10 | 1998-12-09 | Processo para preparação de álcoois. |
| PL98330179A PL330179A1 (en) | 1997-12-10 | 1998-12-09 | Method of obtaining alcohols |
| CN98123286A CN1113049C (zh) | 1997-12-10 | 1998-12-10 | 制备醇的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19754848A DE19754848C2 (de) | 1997-12-10 | 1997-12-10 | Verfahren zur Herstellung von Alkoholen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE19754848A1 DE19754848A1 (de) | 1999-06-17 |
| DE19754848C2 true DE19754848C2 (de) | 2003-06-18 |
Family
ID=7851425
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19754848A Expired - Fee Related DE19754848C2 (de) | 1997-12-10 | 1997-12-10 | Verfahren zur Herstellung von Alkoholen |
| DE59804718T Expired - Lifetime DE59804718D1 (de) | 1997-12-10 | 1998-12-01 | Verfahren zur Herstellung von Alkoholen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59804718T Expired - Lifetime DE59804718D1 (de) | 1997-12-10 | 1998-12-01 | Verfahren zur Herstellung von Alkoholen |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6096931A (enExample) |
| EP (1) | EP0922687B1 (enExample) |
| JP (1) | JP4121647B2 (enExample) |
| KR (1) | KR100659913B1 (enExample) |
| CN (1) | CN1113049C (enExample) |
| AT (1) | ATE220390T1 (enExample) |
| AU (1) | AU9700398A (enExample) |
| BR (1) | BR9805254A (enExample) |
| CA (1) | CA2255242A1 (enExample) |
| DE (2) | DE19754848C2 (enExample) |
| DK (1) | DK0922687T3 (enExample) |
| ES (1) | ES2178095T3 (enExample) |
| ID (1) | ID21417A (enExample) |
| PL (1) | PL330179A1 (enExample) |
| PT (1) | PT922687E (enExample) |
| TW (1) | TW470739B (enExample) |
| ZA (1) | ZA9811224B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10150556A1 (de) * | 2001-10-15 | 2003-04-17 | Basf Ag | Verfahren zur katalytischen Hydrierung |
| BR0317023A (pt) | 2002-12-04 | 2005-10-25 | Mitsubishi Chem Corp | Processo para produção de álcool |
| WO2004050592A1 (ja) * | 2002-12-04 | 2004-06-17 | Mitsubishi Chemical Corporation | アルコールの製造方法 |
| JP5101495B2 (ja) * | 2006-04-28 | 2012-12-19 | 株式会社クラレ | ３−メチル−１，５−ペンタンジオールの製造方法 |
| US9056824B2 (en) | 2013-01-31 | 2015-06-16 | Eastman Chemical Company | Preparation of hydroxy aldehydes |
| US8710278B1 (en) | 2013-01-31 | 2014-04-29 | Eastman Chemical Company | Process for producing polyols |
| CN106470965B (zh) * | 2014-06-30 | 2019-07-26 | 托普索公司 | 从糖制备乙二醇的方法 |
| CN106179373A (zh) * | 2015-05-07 | 2016-12-07 | 中国石油化工股份有限公司 | 一种用于癸烯醛液相加氢制异癸醇的催化剂及其制备方法 |
| CA3010750C (en) * | 2016-01-07 | 2023-12-12 | Haldor Topsoe A/S | Process for the preparation of ethylene glycol from sugars |
| CN117242047A (zh) | 2021-05-25 | 2023-12-15 | 陶氏技术投资有限责任公司 | 用于醛的气相加氢的方法 |
| CN114618491A (zh) * | 2022-04-06 | 2022-06-14 | 北京石油化工学院 | 铜基催化剂的制备方法及铜基催化剂催化加氢制备烷醇的方法 |
| DE112023003671T5 (de) * | 2022-09-29 | 2025-06-18 | Jgc Catalysts And Chemicals Ltd. | Aldehyd-hydrierungskatalysator und produktionverfahren dafür |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4134497A1 (de) * | 1991-10-18 | 1993-04-22 | Basf Ag | Verfahren zur herstellung von 4-halogenbenzylalkoholen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1276618B (de) * | 1965-11-26 | 1968-09-05 | Huels Chemische Werke Ag | Verfahren zur Herstellung von gesaettigten aliphatischen Alkoholen |
| DE3932332A1 (de) * | 1989-09-28 | 1991-04-11 | Hoechst Ag | Verfahren zur herstellung von alkoholen (einstufig) |
-
1997
- 1997-12-10 DE DE19754848A patent/DE19754848C2/de not_active Expired - Fee Related
-
1998
- 1998-11-26 ID IDP981543A patent/ID21417A/id unknown
- 1998-12-01 DE DE59804718T patent/DE59804718D1/de not_active Expired - Lifetime
- 1998-12-01 EP EP98122544A patent/EP0922687B1/de not_active Expired - Lifetime
- 1998-12-01 AT AT98122544T patent/ATE220390T1/de not_active IP Right Cessation
- 1998-12-01 ES ES98122544T patent/ES2178095T3/es not_active Expired - Lifetime
- 1998-12-01 PT PT98122544T patent/PT922687E/pt unknown
- 1998-12-01 DK DK98122544T patent/DK0922687T3/da active
- 1998-12-03 US US09/204,597 patent/US6096931A/en not_active Expired - Lifetime
- 1998-12-08 CA CA002255242A patent/CA2255242A1/en not_active Abandoned
- 1998-12-08 JP JP34912198A patent/JP4121647B2/ja not_active Expired - Fee Related
- 1998-12-08 ZA ZA9811224A patent/ZA9811224B/xx unknown
- 1998-12-09 TW TW087120393A patent/TW470739B/zh not_active IP Right Cessation
- 1998-12-09 PL PL98330179A patent/PL330179A1/xx unknown
- 1998-12-09 AU AU97003/98A patent/AU9700398A/en not_active Abandoned
- 1998-12-09 KR KR1019980053841A patent/KR100659913B1/ko not_active Expired - Fee Related
- 1998-12-09 BR BR9805254-3A patent/BR9805254A/pt not_active IP Right Cessation
- 1998-12-10 CN CN98123286A patent/CN1113049C/zh not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4134497A1 (de) * | 1991-10-18 | 1993-04-22 | Basf Ag | Verfahren zur herstellung von 4-halogenbenzylalkoholen |
Non-Patent Citations (1)
| Title |
|---|
| Patents Abstracts of Japan C-393, 23.12.1986, Vol. 10, No. 383=JP 61-1 72 838 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PT922687E (pt) | 2002-11-29 |
| ATE220390T1 (de) | 2002-07-15 |
| ES2178095T3 (es) | 2002-12-16 |
| AU9700398A (en) | 1999-07-01 |
| TW470739B (en) | 2002-01-01 |
| DK0922687T3 (da) | 2002-10-14 |
| PL330179A1 (en) | 1999-06-21 |
| JPH11236341A (ja) | 1999-08-31 |
| DE59804718D1 (de) | 2002-08-14 |
| BR9805254A (pt) | 2000-02-01 |
| MX203582B (enExample) | 2001-08-07 |
| ZA9811224B (en) | 1999-06-09 |
| MX9810399A (enExample) | 1999-06-30 |
| ID21417A (id) | 1999-06-10 |
| CA2255242A1 (en) | 1999-06-10 |
| CN1221723A (zh) | 1999-07-07 |
| EP0922687B1 (de) | 2002-07-10 |
| JP4121647B2 (ja) | 2008-07-23 |
| KR19990062909A (ko) | 1999-07-26 |
| EP0922687A1 (de) | 1999-06-16 |
| DE19754848A1 (de) | 1999-06-17 |
| KR100659913B1 (ko) | 2007-05-14 |
| CN1113049C (zh) | 2003-07-02 |
| US6096931A (en) | 2000-08-01 |
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