CA1070640A - PROCESS FOR PREPARING N-(.alpha.-ALKOXYETHYL)-CARBOXYLIC ACID AMIDES - Google Patents
PROCESS FOR PREPARING N-(.alpha.-ALKOXYETHYL)-CARBOXYLIC ACID AMIDESInfo
- Publication number
- CA1070640A CA1070640A CA244,163A CA244163A CA1070640A CA 1070640 A CA1070640 A CA 1070640A CA 244163 A CA244163 A CA 244163A CA 1070640 A CA1070640 A CA 1070640A
- Authority
- CA
- Canada
- Prior art keywords
- electrolysis
- carbon atoms
- formula
- group
- current
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000005868 electrolysis reaction Methods 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical group CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- -1 tetrafluoroborates Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001298 alcohols Chemical class 0.000 abstract description 4
- 150000002431 hydrogen Chemical class 0.000 abstract description 4
- 239000013067 intermediate product Substances 0.000 abstract description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical class C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 17
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 15
- 238000010626 work up procedure Methods 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 5
- 206010001497 Agitation Diseases 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- ABMDIECEEGFXNC-UHFFFAOYSA-N n-ethylpropanamide Chemical compound CCNC(=O)CC ABMDIECEEGFXNC-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 101100230376 Acetivibrio thermocellus (strain ATCC 27405 / DSM 1237 / JCM 9322 / NBRC 103400 / NCIMB 10682 / NRRL B-4536 / VPI 7372) celI gene Proteins 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021135 KPF6 Inorganic materials 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000110 cooling liquid Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- SSQTXMAIJVOVIP-UHFFFAOYSA-N n-(2-methoxyethyl)formamide Chemical compound COCCNC=O SSQTXMAIJVOVIP-UHFFFAOYSA-N 0.000 description 1
- SDIDYFBTIZOPLA-UHFFFAOYSA-N n-ethylbenzamide Chemical compound CCNC(=O)C1=CC=CC=C1 SDIDYFBTIZOPLA-UHFFFAOYSA-N 0.000 description 1
- DHCJWWQFOMHARO-UHFFFAOYSA-N n-ethylbutanamide Chemical compound CCCC(=O)NCC DHCJWWQFOMHARO-UHFFFAOYSA-N 0.000 description 1
- 229960005419 nitrogen Drugs 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- WAWBMJIRULKJPO-UHFFFAOYSA-N tetraethylazanium borate Chemical compound [O-]B([O-])[O-].CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC WAWBMJIRULKJPO-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 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
- 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)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2503114A DE2503114C3 (de) | 1975-01-25 | 1975-01-25 | Verfahren zur Herstellung von N-(α-Alkoxyäthyl)-carbonsäureamiden |
| DE2539767A DE2539767C2 (de) | 1975-09-06 | 1975-09-06 | Verfahren zur Herstellung von N-(α-Alkoxyäthyl)-carbonsäureamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070640A true CA1070640A (en) | 1980-01-29 |
Family
ID=25768403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA244,163A Expired CA1070640A (en) | 1975-01-25 | 1976-01-23 | PROCESS FOR PREPARING N-(.alpha.-ALKOXYETHYL)-CARBOXYLIC ACID AMIDES |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4036712A (enExample) |
| JP (1) | JPS5837393B2 (enExample) |
| AT (1) | AT346301B (enExample) |
| BE (1) | BE837906A (enExample) |
| CA (1) | CA1070640A (enExample) |
| CH (1) | CH599354A5 (enExample) |
| FR (1) | FR2298614A1 (enExample) |
| GB (1) | GB1535123A (enExample) |
| IT (1) | IT1054978B (enExample) |
| NL (1) | NL7600544A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE2842760A1 (de) * | 1978-09-30 | 1980-04-10 | Bayer Ag | Verfahren zur herstellung von n-(alpha- methoxy-alkyl)-urethanen und n-(alpha- methoxy-alkyl)-urethane |
| DE2919756A1 (de) * | 1979-05-16 | 1980-11-27 | Hoechst Ag | Verfahren zur herstellung von n- alpha -alkoxyethyl-carbonsaeureamiden |
| DE2919755A1 (de) * | 1979-05-16 | 1980-11-27 | Hoechst Ag | Verfahren zur herstellung von n-vinyl- n-alkyl-carbonsaeureamiden |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3140276A (en) * | 1961-07-11 | 1964-07-07 | Exxon Research Engineering Co | Continuous electrolytic polymerization process |
| US3193476A (en) * | 1961-12-29 | 1965-07-06 | Monsanto Co | Electrolytic hydrodimerization of two different alpha, beta-olefinic compounds |
| US3459643A (en) * | 1967-02-03 | 1969-08-05 | Sprague Electric Co | Alkoxylation of n-methyl-n-hydrocarbylamides |
| DE2113338C3 (de) * | 1971-03-19 | 1978-08-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Alkoxylierung von am Stickstoff alkylierten Carbonsäureamiden |
| DE2336976A1 (de) * | 1973-07-20 | 1975-02-13 | Hoechst Ag | Verfahren zur herstellung von n-(alphaalkoxyaethyl)-carbonsaeureamiden |
-
1976
- 1976-01-20 NL NL7600544A patent/NL7600544A/xx not_active Application Discontinuation
- 1976-01-21 CH CH73176A patent/CH599354A5/xx not_active IP Right Cessation
- 1976-01-23 JP JP51006056A patent/JPS5837393B2/ja not_active Expired
- 1976-01-23 GB GB2674/76A patent/GB1535123A/en not_active Expired
- 1976-01-23 AT AT44576A patent/AT346301B/de not_active IP Right Cessation
- 1976-01-23 IT IT19550/76A patent/IT1054978B/it active
- 1976-01-23 US US05/651,693 patent/US4036712A/en not_active Expired - Lifetime
- 1976-01-23 CA CA244,163A patent/CA1070640A/en not_active Expired
- 1976-01-26 BE BE163799A patent/BE837906A/xx not_active IP Right Cessation
- 1976-01-26 FR FR7601967A patent/FR2298614A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ATA44576A (de) | 1978-03-15 |
| FR2298614A1 (fr) | 1976-08-20 |
| CH599354A5 (enExample) | 1978-05-31 |
| GB1535123A (en) | 1978-12-06 |
| US4036712A (en) | 1977-07-19 |
| JPS5837393B2 (ja) | 1983-08-16 |
| NL7600544A (nl) | 1976-07-27 |
| IT1054978B (it) | 1981-11-30 |
| AT346301B (de) | 1978-11-10 |
| BE837906A (fr) | 1976-07-26 |
| FR2298614B1 (enExample) | 1980-03-28 |
| JPS5198207A (en) | 1976-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |