DE2259072C3 - Verfahren zur Herstellung von Arylessigsäuren - Google Patents
Verfahren zur Herstellung von ArylessigsäurenInfo
- Publication number
- DE2259072C3 DE2259072C3 DE2259072A DE2259072A DE2259072C3 DE 2259072 C3 DE2259072 C3 DE 2259072C3 DE 2259072 A DE2259072 A DE 2259072A DE 2259072 A DE2259072 A DE 2259072A DE 2259072 C3 DE2259072 C3 DE 2259072C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- reaction
- optionally substituted
- carried out
- cobalt
- 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
Links
- 239000002253 acid Substances 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 9
- 150000007513 acids Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- -1 Aryl acetic acids Chemical class 0.000 claims description 9
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229960003424 phenylacetic acid Drugs 0.000 description 9
- 239000003279 phenylacetic acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
- 229940073608 benzyl chloride Drugs 0.000 description 8
- 239000000292 calcium oxide Substances 0.000 description 8
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000006315 carbonylation Effects 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 2
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 2
- CDPKJZJVTHSESZ-UHFFFAOYSA-N 4-chlorophenylacetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1 CDPKJZJVTHSESZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GKGPLSQWIBJJPC-UHFFFAOYSA-N 1,2-dichloro-3-(trichloromethyl)benzene Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=C1Cl GKGPLSQWIBJJPC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- RRCDOVBQOMYGGJ-UHFFFAOYSA-N 1-(methoxymethyl)naphthalene Chemical compound C1=CC=C2C(COC)=CC=CC2=C1 RRCDOVBQOMYGGJ-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- GXXXUZIRGXYDFP-UHFFFAOYSA-N 2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-N 0.000 description 1
- XBLYVSAKBBNYDO-UHFFFAOYSA-N 2-ethoxy-2-phenylacetic acid Chemical compound CCOC(C(O)=O)C1=CC=CC=C1 XBLYVSAKBBNYDO-UHFFFAOYSA-N 0.000 description 1
- RHOPUUFLVKWWFP-UHFFFAOYSA-N 2-phenylacetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=C1 RHOPUUFLVKWWFP-UHFFFAOYSA-N 0.000 description 1
- SFXXYKYOGGWUHX-UHFFFAOYSA-N 2-phenylpentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=CC=C1 SFXXYKYOGGWUHX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000005109 Cryptomeria japonica Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229910000914 Mn alloy Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 150000005840 aryl radicals 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
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- IYPQZXRHDNGZEB-UHFFFAOYSA-N cobalt sodium Chemical compound [Na].[Co] IYPQZXRHDNGZEB-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940087654 iron carbonyl Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SVMGVNXXUVNGRK-UHFFFAOYSA-N oxomethylideneiron Chemical compound O=C=[Fe] SVMGVNXXUVNGRK-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2259072A DE2259072C3 (de) | 1972-12-02 | 1972-12-02 | Verfahren zur Herstellung von Arylessigsäuren |
| US416566A US3928429A (en) | 1972-12-02 | 1973-11-16 | Method of preparing aryl acetic acids |
| CH1667373A CH589593A5 (enExample) | 1972-12-02 | 1973-11-27 | |
| BE138254A BE807910A (fr) | 1972-12-02 | 1973-11-28 | Procede pour l'obtention d'acides arylacetiques |
| IT53993/73A IT1000175B (it) | 1972-12-02 | 1973-11-29 | Procedimento per la produzione di acidi arilacetici |
| GB5551873A GB1410400A (en) | 1972-12-02 | 1973-11-29 | Preparation of arylacetic acids |
| FR7342877A FR2208878B1 (enExample) | 1972-12-02 | 1973-11-30 | |
| NL7316426A NL7316426A (enExample) | 1972-12-02 | 1973-11-30 | |
| JP48135636A JPS5824415B2 (ja) | 1972-12-02 | 1973-12-03 | アリ−ルサクサン ノ セイホウ |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2259072A DE2259072C3 (de) | 1972-12-02 | 1972-12-02 | Verfahren zur Herstellung von Arylessigsäuren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2259072A1 DE2259072A1 (de) | 1974-06-20 |
| DE2259072B2 DE2259072B2 (de) | 1975-06-19 |
| DE2259072C3 true DE2259072C3 (de) | 1978-10-05 |
Family
ID=5863336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2259072A Expired DE2259072C3 (de) | 1972-12-02 | 1972-12-02 | Verfahren zur Herstellung von Arylessigsäuren |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3928429A (enExample) |
| JP (1) | JPS5824415B2 (enExample) |
| BE (1) | BE807910A (enExample) |
| CH (1) | CH589593A5 (enExample) |
| DE (1) | DE2259072C3 (enExample) |
| FR (1) | FR2208878B1 (enExample) |
| GB (1) | GB1410400A (enExample) |
| IT (1) | IT1000175B (enExample) |
| NL (1) | NL7316426A (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1522721A (en) * | 1975-01-09 | 1978-08-31 | Rhone Poulenc Ind | Process for the carbonylation of aralkyl halides |
| US4350825A (en) * | 1976-05-10 | 1982-09-21 | Exxon Research & Engineering Co. | Process for the manufacture of styrene |
| IT1076234B (it) * | 1977-01-18 | 1985-04-27 | Montedison Spa | Processo per la preparazione di acido fenilacetico |
| DE2828041C2 (de) * | 1978-06-26 | 1984-05-10 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Arylbrenztraubensäuren |
| IT1198337B (it) | 1980-07-01 | 1988-12-21 | Montedison Spa | Processo per la preparazione di composti organici carbossilati |
| US4440663A (en) * | 1981-09-14 | 1984-04-03 | The Procter & Gamble Company | Alkaline aqueous liquid detergent compositions containing normally unstable ester perfumes |
| IT1139455B (it) * | 1981-09-21 | 1986-09-24 | Montedison Spa | Processo per la preparazione di acidi alfa-arilpropionici e loro sali alcalini |
| IT1198351B (it) * | 1981-09-21 | 1988-12-21 | Montedison Spa | Processo per la carbonilazione di alogenuri benzilici secondari |
| US4492798A (en) * | 1982-03-01 | 1985-01-08 | Ethyl Corporation | Process for preparing arylalkylpyruvic acids |
| JPS5993020A (ja) * | 1982-11-19 | 1984-05-29 | Denki Kagaku Kogyo Kk | フエニル酢酸エステルとフエニルアセトアルデヒドを併産する方法 |
| US4575561A (en) * | 1983-03-28 | 1986-03-11 | Texaco Inc. | Carboxyalkylation of aryl-substituted alkyl halides to the corresponding esters |
| US4642370A (en) * | 1983-07-16 | 1987-02-10 | The British Petroleum Company P.L.C. | Process for the production of carboxylic acid esters |
| US4481368A (en) * | 1983-07-28 | 1984-11-06 | Ethyl Corporation | Process for preparing α-keto-carboxylic acids from acyl halides |
| US4689431A (en) * | 1985-02-21 | 1987-08-25 | Japan As Represented By General Director Of Agency Of Industrial Science And Technology | Method for the preparation of phenyl pyruvic acid |
| US4990658B1 (en) * | 1989-12-18 | 1994-08-30 | Ethyl Corp | Process for preparing ibuprofen and its alkyl esters |
| US6831191B2 (en) | 2001-12-20 | 2004-12-14 | Em Industries | Photo stable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom |
| US6602515B2 (en) | 2001-07-16 | 2003-08-05 | Em Industries | Photo stable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom |
| US6699463B2 (en) | 2002-04-10 | 2004-03-02 | Em Industries | Photostable cationic organic sunscreen compounds with antioxidant properties and compositions obtained therefrom |
| US6936735B2 (en) * | 2002-08-27 | 2005-08-30 | Emd Chemicals, Inc. | Photostable cationic organic sunscreen compounds and compositions obtained therefrom |
| CN113548954A (zh) * | 2021-07-30 | 2021-10-26 | 四川信乙化工有限公司 | 苯乙酸制备系统 |
| CN114774973B (zh) * | 2022-04-22 | 2024-03-08 | 河北师范大学 | 一种纳米花状钴钼硫化物负载型催化剂及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL170622C (nl) * | 1969-07-23 | 1982-12-01 | Montedison Spa | Werkwijze om fenylazijnzuur te bereiden. |
| BE757742A (fr) * | 1969-10-20 | 1971-04-20 | Montedison Spa | Procede de preparation de composes aromatiques |
-
1972
- 1972-12-02 DE DE2259072A patent/DE2259072C3/de not_active Expired
-
1973
- 1973-11-16 US US416566A patent/US3928429A/en not_active Expired - Lifetime
- 1973-11-27 CH CH1667373A patent/CH589593A5/xx not_active IP Right Cessation
- 1973-11-28 BE BE138254A patent/BE807910A/xx unknown
- 1973-11-29 GB GB5551873A patent/GB1410400A/en not_active Expired
- 1973-11-29 IT IT53993/73A patent/IT1000175B/it active
- 1973-11-30 FR FR7342877A patent/FR2208878B1/fr not_active Expired
- 1973-11-30 NL NL7316426A patent/NL7316426A/xx not_active Application Discontinuation
- 1973-12-03 JP JP48135636A patent/JPS5824415B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE807910A (fr) | 1974-03-15 |
| DE2259072B2 (de) | 1975-06-19 |
| JPS5824415B2 (ja) | 1983-05-20 |
| CH589593A5 (enExample) | 1977-07-15 |
| US3928429A (en) | 1975-12-23 |
| IT1000175B (it) | 1976-03-30 |
| DE2259072A1 (de) | 1974-06-20 |
| FR2208878A1 (enExample) | 1974-06-28 |
| GB1410400A (en) | 1975-10-15 |
| FR2208878B1 (enExample) | 1977-08-05 |
| NL7316426A (enExample) | 1974-06-05 |
| JPS4986339A (enExample) | 1974-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |