DE2558148C2 - Verfahren zur Herstellung von Bis-(N-acylaminomethyl)-äthern - Google Patents
Verfahren zur Herstellung von Bis-(N-acylaminomethyl)-äthernInfo
- Publication number
- DE2558148C2 DE2558148C2 DE2558148A DE2558148A DE2558148C2 DE 2558148 C2 DE2558148 C2 DE 2558148C2 DE 2558148 A DE2558148 A DE 2558148A DE 2558148 A DE2558148 A DE 2558148A DE 2558148 C2 DE2558148 C2 DE 2558148C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- acylaminomethyl
- ethers
- preparation
- reaction
- 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
- 238000000034 method Methods 0.000 title description 7
- 150000002170 ethers Chemical class 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SMGLHFBQMBVRCP-UHFFFAOYSA-N 3-hydroxypropanamide Chemical compound NC(=O)CCO SMGLHFBQMBVRCP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- -1 formamide methylolacetamide Chemical compound 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- MRHQBBSKCLIMRH-UHFFFAOYSA-N n-(acetamidomethoxymethyl)acetamide Chemical compound CC(=O)NCOCNC(C)=O MRHQBBSKCLIMRH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2558148A DE2558148C2 (de) | 1975-12-23 | 1975-12-23 | Verfahren zur Herstellung von Bis-(N-acylaminomethyl)-äthern |
| GB50985/76A GB1516428A (en) | 1975-12-23 | 1976-12-07 | Process for the manufacture of bis-(n-acylaminomethyl)ethers |
| ES454194A ES454194A1 (es) | 1975-12-23 | 1976-12-14 | Procedimiento para la obtencion de bis-(n-acilaminometil) eteres. |
| SE7614227A SE7614227L (sv) | 1975-12-23 | 1976-12-17 | Forfarande for framstellning av bis-(n-acylaminometyl)etrar |
| NL7614058A NL7614058A (nl) | 1975-12-23 | 1976-12-17 | Werkwijze voor de bereiding van bis-(nacylamino- methyl)ethers. |
| PT66003A PT66003B (de) | 1975-12-23 | 1976-12-22 | Verfahren zur herstellung von bis-(n-acylaminomethyl)athern |
| CH1618976A CH605665A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-23 | 1976-12-22 | |
| AT954276A AT347912B (de) | 1975-12-23 | 1976-12-22 | Verfahren zur herstellung von bis- (n- acylaminomethyl)-aethern |
| IT30760/76A IT1071484B (it) | 1975-12-23 | 1976-12-22 | Processo per la preparazione di bis-(n-acilamminometil)eteri |
| FR7638675A FR2336382A1 (fr) | 1975-12-23 | 1976-12-22 | Procede de preparation d'oxydes de bis-(n-acylaminomethyles) |
| BE173604A BE849817A (fr) | 1975-12-23 | 1976-12-23 | Procede de preparation d'oxydes de bis(n-acylamino-methyles) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2558148A DE2558148C2 (de) | 1975-12-23 | 1975-12-23 | Verfahren zur Herstellung von Bis-(N-acylaminomethyl)-äthern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2558148A1 DE2558148A1 (de) | 1977-07-07 |
| DE2558148C2 true DE2558148C2 (de) | 1984-02-16 |
Family
ID=5965359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2558148A Expired DE2558148C2 (de) | 1975-12-23 | 1975-12-23 | Verfahren zur Herstellung von Bis-(N-acylaminomethyl)-äthern |
Country Status (11)
-
1975
- 1975-12-23 DE DE2558148A patent/DE2558148C2/de not_active Expired
-
1976
- 1976-12-07 GB GB50985/76A patent/GB1516428A/en not_active Expired
- 1976-12-14 ES ES454194A patent/ES454194A1/es not_active Expired
- 1976-12-17 SE SE7614227A patent/SE7614227L/xx unknown
- 1976-12-17 NL NL7614058A patent/NL7614058A/xx not_active Application Discontinuation
- 1976-12-22 FR FR7638675A patent/FR2336382A1/fr active Granted
- 1976-12-22 PT PT66003A patent/PT66003B/pt unknown
- 1976-12-22 AT AT954276A patent/AT347912B/de not_active IP Right Cessation
- 1976-12-22 IT IT30760/76A patent/IT1071484B/it active
- 1976-12-22 CH CH1618976A patent/CH605665A5/xx not_active IP Right Cessation
- 1976-12-23 BE BE173604A patent/BE849817A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| ES454194A1 (es) | 1977-12-01 |
| AT347912B (de) | 1979-01-25 |
| GB1516428A (en) | 1978-07-05 |
| FR2336382B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-31 |
| SE7614227L (sv) | 1977-06-24 |
| NL7614058A (nl) | 1977-06-27 |
| PT66003A (de) | 1977-01-01 |
| FR2336382A1 (fr) | 1977-07-22 |
| ATA954276A (de) | 1978-06-15 |
| IT1071484B (it) | 1985-04-10 |
| BE849817A (fr) | 1977-06-23 |
| PT66003B (de) | 1978-06-16 |
| CH605665A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-13 |
| DE2558148A1 (de) | 1977-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |