DE2547464A1 - Verfahren zur herstellung von hydrochinondimethylaethern - Google Patents
Verfahren zur herstellung von hydrochinondimethylaethernInfo
- Publication number
- DE2547464A1 DE2547464A1 DE19752547464 DE2547464A DE2547464A1 DE 2547464 A1 DE2547464 A1 DE 2547464A1 DE 19752547464 DE19752547464 DE 19752547464 DE 2547464 A DE2547464 A DE 2547464A DE 2547464 A1 DE2547464 A1 DE 2547464A1
- Authority
- DE
- Germany
- Prior art keywords
- process according
- solvent
- approx
- noble metal
- general formula
- 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- Withdrawn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 17
- 238000004519 manufacturing process Methods 0.000 title description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 17
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical class COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 9
- 235000019260 propionic acid Nutrition 0.000 claims description 9
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 9
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 229910000510 noble metal Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- QMXZSRVFIWACJH-UHFFFAOYSA-N 2-chloro-1,4-dimethoxybenzene Chemical compound COC1=CC=C(OC)C(Cl)=C1 QMXZSRVFIWACJH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000005218 dimethyl ethers Chemical class 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- IQISOVKPFBLQIQ-UHFFFAOYSA-N 1,4-dimethoxy-2-methylbenzene Chemical compound COC1=CC=C(OC)C(C)=C1 IQISOVKPFBLQIQ-UHFFFAOYSA-N 0.000 description 1
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 1
- WOGWYSWDBYCVDY-UHFFFAOYSA-N 2-chlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C=CC1=O WOGWYSWDBYCVDY-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019987 cider Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 230000008451 emotion Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VTWDKFNVVLAELH-UHFFFAOYSA-N methyl-p-benzoquinone Natural products CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N monomethylhydroquinone Natural products CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752547464 DE2547464A1 (de) | 1975-10-23 | 1975-10-23 | Verfahren zur herstellung von hydrochinondimethylaethern |
| NL7611492A NL7611492A (nl) | 1975-10-23 | 1976-10-18 | Werkwijze voor het bereiden van hydrochinondi- methylethers. |
| CH1327776A CH622761A5 (enExample) | 1975-10-23 | 1976-10-20 | |
| IT28583/76A IT1069002B (it) | 1975-10-23 | 1976-10-21 | Processo per la preparauione di idrochinondimetileteri |
| US05/734,455 US4057586A (en) | 1975-10-23 | 1976-10-21 | Process for the manufacture of hydroquinone dimethyl ethers |
| JP51125571A JPS5251332A (en) | 1975-10-23 | 1976-10-21 | Process for preparing hydroquinone dimethyl ether |
| GB43716/76A GB1535343A (en) | 1975-10-23 | 1976-10-21 | Process for the manufacture of hydroquinone dimethyl ethers |
| CA263,983A CA1065900A (en) | 1975-10-23 | 1976-10-22 | Process for the manufacture of hydroquinone dimethyl ethers |
| BE171787A BE847635A (fr) | 1975-10-23 | 1976-10-25 | Procede de preparation d'ethers dimethyliques de l'hydroquinone, |
| FR7632064A FR2328683A1 (fr) | 1975-10-23 | 1976-10-25 | Procede de preparation d'ethers dimethyliques de l'hydroquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752547464 DE2547464A1 (de) | 1975-10-23 | 1975-10-23 | Verfahren zur herstellung von hydrochinondimethylaethern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2547464A1 true DE2547464A1 (de) | 1977-04-28 |
Family
ID=5959891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752547464 Withdrawn DE2547464A1 (de) | 1975-10-23 | 1975-10-23 | Verfahren zur herstellung von hydrochinondimethylaethern |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4057586A (enExample) |
| JP (1) | JPS5251332A (enExample) |
| BE (1) | BE847635A (enExample) |
| CA (1) | CA1065900A (enExample) |
| CH (1) | CH622761A5 (enExample) |
| DE (1) | DE2547464A1 (enExample) |
| FR (1) | FR2328683A1 (enExample) |
| GB (1) | GB1535343A (enExample) |
| IT (1) | IT1069002B (enExample) |
| NL (1) | NL7611492A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039484A1 (de) * | 1980-05-07 | 1981-11-11 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Hydrochinonmonoäthern sowie die dabei als Zwischenprodukte gebildeten Chinolketale |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4204076A (en) * | 1977-01-26 | 1980-05-20 | Hoechst Aktiengesellschaft | Hydroquinone dimethyl ether |
| DE2703453A1 (de) * | 1977-01-28 | 1978-08-03 | Hoechst Ag | Cyclohexen-(1)-dion-(3,6)-tetraalkyldiketale, verfahren zu deren herstellung und ihre verwendung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1919580A (en) * | 1933-07-25 | Hermann wagnee |
-
1975
- 1975-10-23 DE DE19752547464 patent/DE2547464A1/de not_active Withdrawn
-
1976
- 1976-10-18 NL NL7611492A patent/NL7611492A/xx not_active Application Discontinuation
- 1976-10-20 CH CH1327776A patent/CH622761A5/de not_active IP Right Cessation
- 1976-10-21 US US05/734,455 patent/US4057586A/en not_active Expired - Lifetime
- 1976-10-21 JP JP51125571A patent/JPS5251332A/ja active Pending
- 1976-10-21 GB GB43716/76A patent/GB1535343A/en not_active Expired
- 1976-10-21 IT IT28583/76A patent/IT1069002B/it active
- 1976-10-22 CA CA263,983A patent/CA1065900A/en not_active Expired
- 1976-10-25 BE BE171787A patent/BE847635A/xx unknown
- 1976-10-25 FR FR7632064A patent/FR2328683A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039484A1 (de) * | 1980-05-07 | 1981-11-11 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Hydrochinonmonoäthern sowie die dabei als Zwischenprodukte gebildeten Chinolketale |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5251332A (en) | 1977-04-25 |
| GB1535343A (en) | 1978-12-13 |
| BE847635A (fr) | 1977-04-25 |
| CH622761A5 (enExample) | 1981-04-30 |
| US4057586A (en) | 1977-11-08 |
| FR2328683B1 (enExample) | 1980-06-06 |
| NL7611492A (nl) | 1977-04-26 |
| IT1069002B (it) | 1985-03-21 |
| FR2328683A1 (fr) | 1977-05-20 |
| CA1065900A (en) | 1979-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2460754C2 (de) | Verfahren zur Herstellung von p-Benzochinondiketalen | |
| DE3872566T2 (de) | Verfahren zur herstellung von 2-arylpropionsaeuren. | |
| DE3127975C2 (de) | Elektrochemisches Verfahren zur Herstellung von acetoxylierten aromatischen Verbindungen | |
| DE3874195T2 (de) | Reduktion von carbonsaeureestern. | |
| EP0293739B1 (de) | Verfahren zur Herstellung von 4-Isopropyl-cyclohexylmethanol bzw. dessen Alkylethern | |
| DE1945479B2 (de) | Bismonocarbonsäureester des 3-Formylbutandiol-(1,2) sowie ein Verfahren zu deren Herstellung | |
| EP0072914B1 (de) | Verfahren zur Herstellung von alkylsubstituierten Benzaldehyden | |
| EP0012942B1 (de) | Elektrolytisches Verfahren zur Herstellung von Benzaldehyden | |
| DE2547464A1 (de) | Verfahren zur herstellung von hydrochinondimethylaethern | |
| DE2240398C3 (de) | Verfahren zur Herstellung von Arylessigsäurealkylestern | |
| EP0577949B1 (de) | Verfahren zur Herstellung von chlorfreiem Cyclopropancarbonsäuremethylester | |
| DE3322399A1 (de) | Verfahren zur herstellung von benz aldehyddialkylacetalen | |
| EP0087585A1 (de) | Verfahren zur Herstellung von 3-Alkoxi-acrylnitrilen | |
| EP1004564B1 (de) | Verfahren zur Herstellung von Hydroxyethylcyclohexanen und Hydroxyethylpiperidinen | |
| DE60034446T2 (de) | Verfahren zur herstellung von tetrafluorbenzaldehyden und tetrafluorbenzolmethanolen | |
| DE2547383A1 (de) | Verfahren zur herstellung von p-benzochinondiketalen | |
| DE2410782C2 (de) | Phenylendiessigsäuredialkylester und Verfahren zu deren Herstellung | |
| DE10132526A1 (de) | Verfahren zum Herstellen eines Alkanderivats | |
| EP0222988B1 (de) | Verfahren zur Herstellung von Hydroxymethylcyclopropan (Cyclopropylmethanol) | |
| DE2953189C1 (de) | Verfahren zur Herstellung von Ketonen | |
| DE2703077A1 (de) | Verfahren zur herstellung von cyclohexandion-(1,4)-tetramethyl- diketal | |
| DE2208155A1 (de) | Verfahren zur herstellung von 4-endotricyclo(5,2,1,0 hoch 2,6-endo)-decylamin | |
| EP0030588B1 (de) | Verfahren zur Herstellung von p-tert. Butylbenzaldehyd | |
| DE3447070C1 (de) | Verfahren zur Herstellung von N-Acetyl-4-(aminomethyl-)-cyclohexancarbonsäure-methylester | |
| DE2334928A1 (de) | Verfahren zur herstellung von cis-ptert.-butyl-cyclohexanol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |