DE2010534A1 - Verfahren zur Herstellung von aromatischen Aldehyden und den entsprechenden Alkoholen - Google Patents
Verfahren zur Herstellung von aromatischen Aldehyden und den entsprechenden AlkoholenInfo
- Publication number
- DE2010534A1 DE2010534A1 DE19702010534 DE2010534A DE2010534A1 DE 2010534 A1 DE2010534 A1 DE 2010534A1 DE 19702010534 DE19702010534 DE 19702010534 DE 2010534 A DE2010534 A DE 2010534A DE 2010534 A1 DE2010534 A1 DE 2010534A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroperoxide
- metal
- catalyst
- salt
- oxidation
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 18
- 150000003934 aromatic aldehydes Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001298 alcohols Chemical class 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 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 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000005502 peroxidation Methods 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 28
- 230000003647 oxidation Effects 0.000 description 27
- 238000007254 oxidation reaction Methods 0.000 description 27
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 26
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 14
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 13
- 235000019445 benzyl alcohol Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- YVJRCWCFDJYONJ-UHFFFAOYSA-N hydroperoxymethylbenzene Chemical compound OOCC1=CC=CC=C1 YVJRCWCFDJYONJ-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000002432 hydroperoxides Chemical class 0.000 description 4
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 229940048086 sodium pyrophosphate Drugs 0.000 description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- VCEHMDXCOGIOJJ-UHFFFAOYSA-N 1-(hydroperoxymethyl)-4-methylbenzene Chemical compound CC1=CC=C(COO)C=C1 VCEHMDXCOGIOJJ-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- NQKOZSGQMDFMHY-UHFFFAOYSA-N 1-(hydroperoxymethyl)-4-methoxybenzene Chemical compound COC1=CC=C(COO)C=C1 NQKOZSGQMDFMHY-UHFFFAOYSA-N 0.000 description 1
- CGAOBAKQFDGVIX-UHFFFAOYSA-N 4-(hydroperoxymethyl)benzonitrile Chemical compound C(#N)C1=CC=C(COO)C=C1 CGAOBAKQFDGVIX-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000282941 Rangifer tarandus Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- -1 benzene compound Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 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
- 238000009835 boiling Methods 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002315 glycerophosphates Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6906063A FR2036148A5 (en) | 1969-03-05 | 1969-03-05 | Mixtures of aromatic aldehydes and corres- - ponding alcohols |
| FR7001234A FR2076413A6 (enrdf_load_stackoverflow) | 1970-01-14 | 1970-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2010534A1 true DE2010534A1 (de) | 1970-09-10 |
Family
ID=26214882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702010534 Withdrawn DE2010534A1 (de) | 1969-03-05 | 1970-03-05 | Verfahren zur Herstellung von aromatischen Aldehyden und den entsprechenden Alkoholen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4820538B1 (enrdf_load_stackoverflow) |
| BE (1) | BE746845A (enrdf_load_stackoverflow) |
| BR (1) | BR7017210D0 (enrdf_load_stackoverflow) |
| CH (1) | CH507178A (enrdf_load_stackoverflow) |
| DE (1) | DE2010534A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1244456A (enrdf_load_stackoverflow) |
| NL (1) | NL153513B (enrdf_load_stackoverflow) |
| SU (1) | SU438175A3 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0084417A1 (en) * | 1982-01-07 | 1983-07-27 | Sumitomo Chemical Company, Limited | Production of aromatic carbonyl compounds including novel acetophenones |
| US6819284B2 (en) | 2001-09-21 | 2004-11-16 | Bayerische Motoren Werke Aktiengesellschaft | System for assisting the parking of motor vehicles in parking spaces |
| DE102014208826A1 (de) * | 2014-05-12 | 2015-11-12 | Zf Friedrichshafen Ag | Kurbelwelle für eine Innenzahnradmaschine zum Ansteuern mehrerer Durchströmebenen eines Rotors |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5098847U (enrdf_load_stackoverflow) * | 1974-01-11 | 1975-08-16 | ||
| JPS5128746U (enrdf_load_stackoverflow) * | 1974-08-26 | 1976-03-02 | ||
| JPS5294944U (enrdf_load_stackoverflow) * | 1976-01-13 | 1977-07-15 | ||
| JPS5581091U (enrdf_load_stackoverflow) * | 1978-11-30 | 1980-06-04 | ||
| JPS5765896U (enrdf_load_stackoverflow) * | 1980-10-08 | 1982-04-20 |
-
1970
- 1970-02-25 NL NL7002680A patent/NL153513B/xx not_active IP Right Cessation
- 1970-03-03 JP JP1770270A patent/JPS4820538B1/ja active Pending
- 1970-03-04 GB GB1052070A patent/GB1244456A/en not_active Expired
- 1970-03-04 CH CH316570A patent/CH507178A/fr not_active IP Right Cessation
- 1970-03-04 BE BE746845D patent/BE746845A/xx unknown
- 1970-03-04 BR BR21721070A patent/BR7017210D0/pt unknown
- 1970-03-05 DE DE19702010534 patent/DE2010534A1/de not_active Withdrawn
- 1970-03-05 SU SU1412644A patent/SU438175A3/ru active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0084417A1 (en) * | 1982-01-07 | 1983-07-27 | Sumitomo Chemical Company, Limited | Production of aromatic carbonyl compounds including novel acetophenones |
| US6819284B2 (en) | 2001-09-21 | 2004-11-16 | Bayerische Motoren Werke Aktiengesellschaft | System for assisting the parking of motor vehicles in parking spaces |
| DE102014208826A1 (de) * | 2014-05-12 | 2015-11-12 | Zf Friedrichshafen Ag | Kurbelwelle für eine Innenzahnradmaschine zum Ansteuern mehrerer Durchströmebenen eines Rotors |
| DE102014208826B4 (de) | 2014-05-12 | 2019-03-21 | Zf Friedrichshafen Ag | Kurbelwelle für eine Innenzahnradmaschine zum Ansteuern mehrerer Durchströmebenen eines Rotors |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7002680A (enrdf_load_stackoverflow) | 1970-09-08 |
| NL153513B (nl) | 1977-06-15 |
| BR7017210D0 (pt) | 1973-01-18 |
| GB1244456A (en) | 1971-09-02 |
| SU438175A3 (ru) | 1974-07-30 |
| CH507178A (fr) | 1971-05-15 |
| BE746845A (fr) | 1970-09-04 |
| JPS4820538B1 (enrdf_load_stackoverflow) | 1973-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2404855A1 (de) | Verfahren zur verhinderung von emulsionsbildung bei der aufbereitung von butyraldehyden und kobalt enthaltenden reaktionsgemischen | |
| DE1194393B (de) | Verfahren zur Herstellung von Benzoldicarbonsaeuren oder deren Gemischen | |
| DE2855231C3 (de) | Kontinuierliches Verfahren zur Herstellung von Glykolen | |
| DE2061113C3 (de) | Verfahren zur Herstellung von Gemischen aus Ketonen und den entsprechenden Alkoholen | |
| DE1251763B (de) | Verfahren zur Herstellung von gesattigten aliphatischen Carbonsauren, Alkoholen und/oder Ketonen | |
| DE2010534A1 (de) | Verfahren zur Herstellung von aromatischen Aldehyden und den entsprechenden Alkoholen | |
| DE2722741A1 (de) | Verfahren zur stereoselektiven hydrierung von alpha-pinen | |
| DE2365131A1 (de) | Verfahren zur herstellung von p-nitrobenzoesaeure | |
| DD263520A5 (de) | Kontinuierliches verfahren zur extraktion von carbonsaeuren, aldehyden, ketonen, alkoholen und phenolen aus verduennten waesserigen loesungen | |
| DE1543032C3 (de) | Verfahren zur Herstellung von Styrolen | |
| DE1643081B2 (de) | Verfahren zur herstellung von alkylenchlor- oder -bromhydrinen und/oder alkylenglykolen mit 2 bis 4 kohlenstoffatomen | |
| DE879985C (de) | Verfahren zur Reinigung von Aldehyden und Ketonen | |
| DE2539045C2 (de) | Verfahren zur Extraktion eines Dialkylbenzol-dihydroperoxids | |
| DE2049113A1 (de) | Verfahren zur Herstellung von Adipin saure | |
| DE3784633T2 (de) | Verfahren zur oxydierung von aromatischen verbindungen. | |
| DE1002754B (de) | Verfahren zur Herstellung von zur Adipinsaeureherstellung geeigneten Gemischen aus Cyclohexanon und Cyclohexanol | |
| DE1959621C3 (de) | Verfahren zur Gewinnung von Adipinsäure aus 6-Hydroperoxyhexansäure | |
| DE2010534C (de) | Verfahren zur Herstellung eines Gemisches aus einem aromatischen Aldehyd und einem aromatischen Alkohol mit überwiegendem Aldehydanteil | |
| DE2017068C3 (de) | Verfahren zur Herstellung von Oxiranverbindungen | |
| DE2010534B (de) | Verfahren zur Herstellung eines Gemisches aus einem aromatischen Aldehyd und einem aromatischen Alkohol mit überwiegendem Aldehydanteil | |
| DE602005001551T2 (de) | Verfahren zur herstellung von alkylenoxid | |
| DE962527C (de) | Verfahren zur Herstellung von Oxyhydroperoxyden | |
| DE2034014C3 (de) | Verfahren zur Herstellung von geradkettigen aliphatischen Carbonsäuren | |
| DE1593343C (de) | Verfahren zur Herstellung von Cyclo hexanol und Cyclohexanon | |
| DE2116947A1 (de) | Verfahren zur Herstellung von Formaldehyd |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |