DE2336976A1 - Verfahren zur herstellung von n-(alphaalkoxyaethyl)-carbonsaeureamiden - Google Patents
Verfahren zur herstellung von n-(alphaalkoxyaethyl)-carbonsaeureamidenInfo
- Publication number
- DE2336976A1 DE2336976A1 DE19732336976 DE2336976A DE2336976A1 DE 2336976 A1 DE2336976 A1 DE 2336976A1 DE 19732336976 DE19732336976 DE 19732336976 DE 2336976 A DE2336976 A DE 2336976A DE 2336976 A1 DE2336976 A1 DE 2336976A1
- Authority
- DE
- Germany
- Prior art keywords
- electrolysis
- alanine
- current
- solution
- yield
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
- 238000005868 electrolysis reaction Methods 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 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 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003792 electrolyte Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 229960003767 alanine Drugs 0.000 description 25
- 239000000463 material Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- 230000005611 electricity Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 6
- 229910002804 graphite Inorganic materials 0.000 description 6
- 239000010439 graphite Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 241000976416 Isatis tinctoria subsp. canescens Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KTHDTJVBEPMMGL-UHFFFAOYSA-N N-Acetyl-DL-alanine Chemical compound OC(=O)C(C)NC(C)=O KTHDTJVBEPMMGL-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WFMJTCLDCCCFHE-UHFFFAOYSA-N n-(2-methoxyethyl)acetamide Chemical compound COCCNC(C)=O WFMJTCLDCCCFHE-UHFFFAOYSA-N 0.000 description 1
- KTHDTJVBEPMMGL-GSVOUGTGSA-N n-acetylalanine Chemical compound OC(=O)[C@@H](C)NC(C)=O KTHDTJVBEPMMGL-GSVOUGTGSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical class C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732336976 DE2336976A1 (de) | 1973-07-20 | 1973-07-20 | Verfahren zur herstellung von n-(alphaalkoxyaethyl)-carbonsaeureamiden |
| NL7409539A NL7409539A (nl) | 1973-07-20 | 1974-07-15 | Werkwijze voor het bereiden van n-((alpha)-alkoxy- ethyl)-carbonzuuramiden. |
| IT25341/74A IT1019727B (it) | 1973-07-20 | 1974-07-18 | Processo per la preparazione di n alfa alcossietil carbonammidi |
| US05/489,533 US3941666A (en) | 1973-07-20 | 1974-07-18 | Process for the preparation of N-(α-alkoxyethyl)-carboxylic acid amides |
| AU71367/74A AU7136774A (en) | 1973-07-20 | 1974-07-18 | N-%delta-alkoxyethyl<-carboxylic acid |
| AT593974A ATA593974A (de) | 1973-07-20 | 1974-07-18 | Verfahren zur elektrochemischen herstellung von n- (alpha-alkoxyathyl) -carbonsaureamiden |
| JP49081781A JPS5076014A (enExample) | 1973-07-20 | 1974-07-18 | |
| BE146821A BE817949A (fr) | 1973-07-20 | 1974-07-22 | Procede de preparation de n-(alpha-alcoxy-ethyl) carboxamides |
| FR7425364A FR2237980B3 (enExample) | 1973-07-20 | 1974-07-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732336976 DE2336976A1 (de) | 1973-07-20 | 1973-07-20 | Verfahren zur herstellung von n-(alphaalkoxyaethyl)-carbonsaeureamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2336976A1 true DE2336976A1 (de) | 1975-02-13 |
Family
ID=5887538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732336976 Pending DE2336976A1 (de) | 1973-07-20 | 1973-07-20 | Verfahren zur herstellung von n-(alphaalkoxyaethyl)-carbonsaeureamiden |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3941666A (enExample) |
| JP (1) | JPS5076014A (enExample) |
| AT (1) | ATA593974A (enExample) |
| AU (1) | AU7136774A (enExample) |
| BE (1) | BE817949A (enExample) |
| DE (1) | DE2336976A1 (enExample) |
| FR (1) | FR2237980B3 (enExample) |
| IT (1) | IT1019727B (enExample) |
| NL (1) | NL7409539A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51149225A (en) * | 1975-06-13 | 1976-12-22 | Tanabe Seiyaku Co Ltd | Preparation of alpha-alkoxyamino acid derivatives |
| EP0019226A1 (de) * | 1979-05-16 | 1980-11-26 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von N-alpha-Alkoxy-ethyl-carbonsäureamiden |
| US4322271A (en) | 1979-05-16 | 1982-03-30 | Hoechst Aktiengesellschaft | Process for the preparation of N-vinyl-N-alkyl-carboxylic acid amides |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7600544A (nl) * | 1975-01-25 | 1976-07-27 | Hoechst Ag | Werkwijze voor de bereiding van n-(gamma-alkoxy- ethyl)-carbonzuuramiden. |
| JPS5218978U (enExample) * | 1975-07-29 | 1977-02-10 | ||
| US4149941A (en) * | 1975-09-06 | 1979-04-17 | Hoechst Aktiengesellschaft | Process for preparing fungicidal monoalkoxy and dialkoxy N-substituted cyclic amines |
| US4138408A (en) * | 1975-12-20 | 1979-02-06 | Hoechst Aktiengesellschaft | ω-Alkoxy derivatives of lactams and process for their manufacture |
| US4567300A (en) * | 1984-01-14 | 1986-01-28 | Mitsubishi Chemical Industries Limited | Process for producing N-substituted formamides |
| DE3529531A1 (de) * | 1985-08-17 | 1987-02-26 | Basf Ag | Verfahren zur herstellung von carbamidsaeureestern |
| US4997984A (en) * | 1989-12-19 | 1991-03-05 | Shawa Denko K.K. | Process for preparation of N-(α-alkoxyethyl)-carboxylic acid amide |
| BR102013017403A2 (pt) * | 2013-07-05 | 2016-07-12 | Charles Adriano Duvoisin | equipamento compacto para esterilização por eletrólise de alimentos e utensílios |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643693B2 (de) * | 1967-11-11 | 1976-09-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von sebacinsaeuredimethylester durch elektrolytische kondensation von adipinsaeuremonomethylester |
| GB1238853A (enExample) * | 1968-02-28 | 1971-07-14 | ||
| DE2014985C3 (de) * | 1970-03-28 | 1978-06-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur elektrolytischen Kondensation von Carbonsäuren |
| DE2039991A1 (de) * | 1970-08-12 | 1972-02-17 | Basf Ag | Verfahren zur Herstellung von Sebacinsaeurediestern hoeherer Alkohole |
-
1973
- 1973-07-20 DE DE19732336976 patent/DE2336976A1/de active Pending
-
1974
- 1974-07-15 NL NL7409539A patent/NL7409539A/xx unknown
- 1974-07-18 AU AU71367/74A patent/AU7136774A/en not_active Expired
- 1974-07-18 AT AT593974A patent/ATA593974A/de not_active Application Discontinuation
- 1974-07-18 JP JP49081781A patent/JPS5076014A/ja active Pending
- 1974-07-18 US US05/489,533 patent/US3941666A/en not_active Expired - Lifetime
- 1974-07-18 IT IT25341/74A patent/IT1019727B/it active
- 1974-07-22 FR FR7425364A patent/FR2237980B3/fr not_active Expired
- 1974-07-22 BE BE146821A patent/BE817949A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51149225A (en) * | 1975-06-13 | 1976-12-22 | Tanabe Seiyaku Co Ltd | Preparation of alpha-alkoxyamino acid derivatives |
| EP0019226A1 (de) * | 1979-05-16 | 1980-11-26 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von N-alpha-Alkoxy-ethyl-carbonsäureamiden |
| US4288300A (en) | 1979-05-16 | 1981-09-08 | Hoechst Aktiengesellschaft | Process for the manufacture of N-α-alkoxyethyl-carboxylic acid amides |
| US4322271A (en) | 1979-05-16 | 1982-03-30 | Hoechst Aktiengesellschaft | Process for the preparation of N-vinyl-N-alkyl-carboxylic acid amides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2237980B3 (enExample) | 1977-05-20 |
| JPS5076014A (enExample) | 1975-06-21 |
| AU7136774A (en) | 1976-01-22 |
| NL7409539A (nl) | 1975-01-22 |
| FR2237980A1 (enExample) | 1975-02-14 |
| US3941666A (en) | 1976-03-02 |
| ATA593974A (de) | 1976-03-15 |
| BE817949A (fr) | 1975-01-22 |
| IT1019727B (it) | 1977-11-30 |
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