UA78982C2 - Method for producing toluol derivatives - Google Patents

Method for producing toluol derivatives Download PDF

Info

Publication number: UA78982C2
Authority: UA; Ukraine
Prior art keywords: differs; hydrogenation; formula; catalyst; components
Prior art date: 2002-01-24

Application number

UA20040806960A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Basf Ag

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.)

2002-01-24

Filing date

2003-01-20

Publication date

2007-05-10

2003-01-20 Application filed by Basf Ag filed Critical Basf Ag

2007-05-10 Publication of UA78982C2 publication Critical patent/UA78982C2/uk

Links

150000003613 toluenes Chemical class 0.000 title claims abstract description 12
238000004519 manufacturing process Methods 0.000 title abstract description 3
239000003054 catalyst Substances 0.000 claims abstract description 47
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
150000003935 benzaldehydes Chemical class 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 28
238000000034 method Methods 0.000 claims description 21
229910052751 metal Inorganic materials 0.000 claims description 16
239000002184 metal Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 11
239000007789 gas Substances 0.000 claims description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
150000004679 hydroxides Chemical class 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
150000002739 metals Chemical class 0.000 claims description 6
229910052703 rhodium Inorganic materials 0.000 claims description 6
239000010948 rhodium Substances 0.000 claims description 6
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
235000019445 benzyl alcohol Nutrition 0.000 claims description 5
150000003938 benzyl alcohols Chemical class 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
229910052750 molybdenum Inorganic materials 0.000 claims description 5
239000011733 molybdenum Substances 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
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 claims description 4
229910052697 platinum Inorganic materials 0.000 claims description 4
229910052702 rhenium Inorganic materials 0.000 claims description 4
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 4
229910052710 silicon Inorganic materials 0.000 claims description 4
239000010703 silicon Substances 0.000 claims description 4
229910052709 silver Inorganic materials 0.000 claims description 4
239000004332 silver Substances 0.000 claims description 4
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
229910052721 tungsten Inorganic materials 0.000 claims description 4
239000010937 tungsten Substances 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
229910052726 zirconium Inorganic materials 0.000 claims description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
150000004996 alkyl benzenes Chemical class 0.000 claims description 3
229910052787 antimony Inorganic materials 0.000 claims description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
229910052785 arsenic Inorganic materials 0.000 claims description 3
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
229910052797 bismuth Inorganic materials 0.000 claims description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
229910052761 rare earth metal Inorganic materials 0.000 claims description 3
150000002910 rare earth metals Chemical class 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
239000011135 tin Substances 0.000 claims description 3
239000000155 melt Substances 0.000 claims description 2
KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 claims 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
229910000000 metal hydroxide Inorganic materials 0.000 claims 1
229910044991 metal oxide Inorganic materials 0.000 claims 1
150000004706 metal oxides Chemical class 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
229910052719 titanium Inorganic materials 0.000 claims 1
239000010936 titanium Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 abstract description 6
229910052736 halogen Inorganic materials 0.000 abstract description 4
150000002367 halogens Chemical group 0.000 abstract description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 10
150000001299 aldehydes Chemical group 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
150000002823 nitrates Chemical class 0.000 description 5
239000002243 precursor Substances 0.000 description 5
CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
230000004913 activation Effects 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000126 substance Substances 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001242 acetic acid derivatives Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
-1 p-methoxybenzyl alcohols Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
QPHLRCUCFDXGLY-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methanol Chemical compound COC1=CC(CO)=CC(OC)=C1OC QPHLRCUCFDXGLY-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
150000001983 dialkylethers Chemical class 0.000 description 2
230000005611 electricity Effects 0.000 description 2
150000004675 formic acid derivatives Chemical class 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000011734 sodium Substances 0.000 description 2
YPZQHCLBLRWNMJ-LPEHRKFASA-N (2R)-2-[(2S,5S)-5-methyl-5-vinyltetrahydrofuran-2-yl]propanal Chemical class O=C[C@H](C)[C@@H]1CC[C@@](C)(C=C)O1 YPZQHCLBLRWNMJ-LPEHRKFASA-N 0.000 description 1
ZFBNNSOJNZBLLS-UHFFFAOYSA-N 2,6-Dimethoxy-4-methylphenol Chemical compound COC1=CC(C)=CC(OC)=C1O ZFBNNSOJNZBLLS-UHFFFAOYSA-N 0.000 description 1
YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 description 1
MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001000161 Mago Species 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
238000001354 calcination Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
150000001934 cyclohexanes Chemical class 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
230000006324 decarbonylation Effects 0.000 description 1
238000006606 decarbonylation reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 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
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 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
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000012041 precatalyst Substances 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/885—Molybdenum and copper
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8898—Manganese, technetium or rhenium containing also molybdenum
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/72—Copper
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/75—Cobalt
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UA20040806960A 2002-01-24 2003-01-20 Method for producing toluol derivatives UA78982C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10202837		2002-01-24
PCT/EP2003/000488 WO2003062174A1 (de)	2002-01-24	2003-01-20	Verfahren zur herstellung von toluolderivaten

Publications (1)

Publication Number	Publication Date
UA78982C2 true UA78982C2 (en)	2007-05-10

Family

ID=27588050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040806960A UA78982C2 (en)	2002-01-24	2003-01-20	Method for producing toluol derivatives

Country Status (14)

Country	Link
US (1)	US7230141B2 (pl)
EP (1)	EP1470094A1 (pl)
JP (1)	JP2005515248A (pl)
KR (1)	KR20040077781A (pl)
CN (1)	CN1257870C (pl)
AR (1)	AR038314A1 (pl)
BR (1)	BR0306939A (pl)
CA (1)	CA2473936A1 (pl)
EA (1)	EA007065B1 (pl)
MX (1)	MXPA04006744A (pl)
PL (1)	PL372164A1 (pl)
UA (1)	UA78982C2 (pl)
WO (1)	WO2003062174A1 (pl)
ZA (1)	ZA200406665B (pl)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101531574B (zh) *	2009-04-14	2012-07-25	大连理工大学	一种制备3,4,5-三甲氧基甲苯的方法
EP2635544B1 (de) *	2010-11-02	2014-12-17	Basf Se	Verfahren zur herstellung eines phenylcyclohexans
CN102746100A (zh) *	2011-04-20	2012-10-24	中国石油化工股份有限公司	制备异丙苯的方法
KR101930087B1 (ko)	2011-07-26	2018-12-18	에스케이이노베이션 주식회사	방향족 카르복시산 및/또는 방향족 카르복시산 알킬 에스테르 제조 공정에서 발생하는 부산물로부터 방향족 탄화수소 제조방법
WO2014062757A1 (en) *	2012-10-17	2014-04-24	Archer Daniels Midland Company	Improved hydrogenolysis catalysts and uses thereof
US9205412B2 (en)	2013-03-01	2015-12-08	Clariant Corporation	Catalyst for polyol hydrogenolysis
RU2625656C1 (ru) *	2016-02-17	2017-07-18	Общество с ограниченной ответственностью "Научно-производственное объединение "НИИПАВ" (ООО НПО "НИИПАВ")	Способ получения алкилдиметиламинов

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR678954A (fr) *	1928-11-19	1930-04-07	Expl Des Matieres Organiques S	Procédé pour la transformation des crésols en benzène et méthylbenzène en présence d'un catalyseur de réduction ou d'hydrogénation, avec ou sans addition de gazhydrogène
DE904529C (de) *	1942-08-07	1954-02-18	Bayer Ag	Verwendung eines Nickel, Chromoxyd und Aluminiumoxyd enthaltenden Hydrierungskatalysators
US2682562A (en) *	1951-05-10	1954-06-29	Us Interior	Reduction of aromatic carbinols
EP0053884A1 (en) *	1980-11-27	1982-06-16	Johnson Matthey Public Limited Company	Three dimensional interstitial catalyst supports, its manufacture and use
DE4300297C2 (de)	1993-01-08	1998-01-29	Degussa	Verfahren zur selektiven katalytischen Hydrierung der Carbonylgruppe von 4-Carboxylbenzaldehyd

2003
- 2003-01-20 WO PCT/EP2003/000488 patent/WO2003062174A1/de not_active Ceased
- 2003-01-20 CN CNB038027135A patent/CN1257870C/zh not_active Expired - Fee Related
- 2003-01-20 UA UA20040806960A patent/UA78982C2/uk unknown
- 2003-01-20 CA CA002473936A patent/CA2473936A1/en not_active Abandoned
- 2003-01-20 US US10/500,718 patent/US7230141B2/en not_active Expired - Fee Related
- 2003-01-20 KR KR10-2004-7011404A patent/KR20040077781A/ko not_active Withdrawn
- 2003-01-20 PL PL03372164A patent/PL372164A1/pl unknown
- 2003-01-20 BR BR0306939-7A patent/BR0306939A/pt not_active IP Right Cessation
- 2003-01-20 JP JP2003562059A patent/JP2005515248A/ja not_active Withdrawn
- 2003-01-20 EP EP03701527A patent/EP1470094A1/de not_active Withdrawn
- 2003-01-20 EA EA200400876A patent/EA007065B1/ru not_active IP Right Cessation
- 2003-01-20 MX MXPA04006744A patent/MXPA04006744A/es not_active Application Discontinuation
- 2003-01-23 AR ARP030100204A patent/AR038314A1/es not_active Application Discontinuation
2004
- 2004-08-23 ZA ZA200406665A patent/ZA200406665B/xx unknown

Also Published As

Publication number	Publication date
JP2005515248A (ja)	2005-05-26
CA2473936A1 (en)	2003-07-31
EA200400876A1 (ru)	2004-12-30
US7230141B2 (en)	2007-06-12
ZA200406665B (en)	2006-06-28
PL372164A1 (pl)	2005-07-11
BR0306939A (pt)	2004-12-14
CN1257870C (zh)	2006-05-31
KR20040077781A (ko)	2004-09-06
EA007065B1 (ru)	2006-06-30
WO2003062174A1 (de)	2003-07-31
MXPA04006744A (es)	2005-06-08
CN1622926A (zh)	2005-06-01
EP1470094A1 (de)	2004-10-27
US20050032627A1 (en)	2005-02-10
AR038314A1 (es)	2005-01-12

Publication	Publication Date	Title
RU2347612C2 (ru)	2009-02-27	Катализатор производства акрилонитрила
WO2001062701A1 (en)	2001-08-30	Process for preparation of formate esters or methanol and catalyst therefor
CN103769162B (zh)	2016-03-30	一种用于不饱和醇氧化的负载型复合金属催化剂及其制备方法
JPWO2013073704A1 (ja)	2015-04-02	アルカンジオールの製造方法
ES2363571T3 (es)	2011-08-09	Proceso para preparar un compuesto aromático alquilado.
KR20110032929A (ko)	2011-03-30	에탄올로부터 아세트알데하이드를 합성하기 위한 탈수소화 반응용 혼합금속 산화물 촉매 및 이의 제조방법
JP2017218404A (ja)	2017-12-14	３，４−ジヒドロ−２ｈ−ピランの製造方法
TW201639629A (zh)	2016-11-16	用於製備鄰苯基苯酚之觸媒組成物及用該觸媒組成物製備鄰苯基苯酚之方法
EA007065B1 (ru)	2006-06-30	Способ получения производных толуола
CN104230635A (zh)	2014-12-24	苯乙酮加氢制乙苯的方法
JP2005515248A6 (ja)	2005-08-04	トルオール誘導体の製造方法
Reddy et al.	2000	Vapour phase synthesis of quinoline from aniline and glycerol over mixed oxide catalysts
EP0130068A2 (en)	1985-01-02	A process for producing formaldehyde
US5654489A (en)	1997-08-05	Process for producing alicyclic diketone compounds
WO2019208281A1 (ja)	2019-10-31	インデンの製造方法
US5026922A (en)	1991-06-25	Process for preparing glycol aldehyde
EP0452695B1 (en)	1994-08-03	Production of a catalyst and its use for producing phenol
EP2673244A1 (en)	2013-12-18	Process for the oxidation of mesitol
JP4990125B2 (ja)	2012-08-01	ギ酸エステル及びメタノールの製造方法、メタノール製造用触媒、並びに当該触媒の製造方法
JPH10109949A (ja)	1998-04-28	α−フェニルエチルアルコールの製造方法
PL94416B1 (pl)	1977-08-31	Sposob wytwarzania cyklopropylometylo-n-alkiloamin
JPH07103064B2 (ja)	1995-11-08	３−アルキルブテン−１−ア−ルの製法
JP4412451B2 (ja)	2010-02-10	ラクトンの製造方法
JP2000327596A (ja)	2000-11-28	ジイソプロピルベンゼンの脱水素方法
JP2010006737A (ja)	2010-01-14	アルキル化芳香族化合物の製造方法およびフェノールの製造方法