GB760086A - Process for the production of ú-aminomethyl benzoic acid esters - Google Patents
Process for the production of ú-aminomethyl benzoic acid estersInfo
- Publication number
- GB760086A GB760086A GB28683/54A GB2868354A GB760086A GB 760086 A GB760086 A GB 760086A GB 28683/54 A GB28683/54 A GB 28683/54A GB 2868354 A GB2868354 A GB 2868354A GB 760086 A GB760086 A GB 760086A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzoic acid
- ester
- methyl
- liquid ammonia
- aminomethyl
- 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 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 3
- AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 abstract 3
- OITNBJHJJGMFBN-UHFFFAOYSA-N 4-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCl)C=C1 OITNBJHJJGMFBN-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical class NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- JTTXRFNOFFGPFI-UHFFFAOYSA-N ethyl 4-(chloromethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CCl)C=C1 JTTXRFNOFFGPFI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- SATDLKYRVXFXRE-UHFFFAOYSA-N methyl 4-(chloromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCl)C=C1 SATDLKYRVXFXRE-UHFFFAOYSA-N 0.000 abstract 2
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229960003375 aminomethylbenzoic acid Drugs 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- WCTQEHGXBKFLKG-UHFFFAOYSA-N ethyl 4-(aminomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CN)C=C1 WCTQEHGXBKFLKG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In a process for the production of p-aminomethyl benzoic acid esters an ester of a p-halogen methyl benzoic acid with an alcohol is reacted under pressure with ammonia, for example liquid ammonia, at a temperature of 0 DEG to 30 DEG C., preferably 10 DEG to 15 DEG C., during a reaction period of up to two hours. In a modification of the process a p-halogen methyl benzoic acid is first reacted with ammonia, for example liquid ammonia, under the conditions specified above and the acid formed is esterified with an alcohol. Esters may be prepared from monovalent alcohols to give, e.g., the methyl, ethyl, butyl and amyl esters in diprimary alcohols, e.g. glycol may be employed for the esterification. The free acid may be recovered from the ester by hydrolysis with cold hydrochloric acid. In examples: commercial liquid ammonia is filtered through alkali-treated alumina to eliminate traces of iron and copper, is reacted under pressure with p-chloromethyl benzoic acid methyl ester to obtain p-aminomethyl benzoic methyl ester (1) and p-aminomethyl benzoic acid ethyl ester is similarly prepared from liquid ammonia and p-chloromethyl benzoic acid ethyl ester (4); p-aminomethyl benzoic acid methyl ester is obtained by reacting p-chloromethyl benzoic acid with liquid ammonia under pressure to obtain p-aminomethyl benzoic acid which is reacted with methanol (2); and the corresponding ethyl ester is similarly prepared (3). p-Chloromethyl benzoic acid methyl ester may be prepared by half oxydizing p-xylylene dichloride with, e.g. 50 per cent nitric acid at elevated temperature, separating the reaction product and esterifying the p-chloromethyl benzoic acid with methyl alcohol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE760086X | 1953-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB760086A true GB760086A (en) | 1956-10-31 |
Family
ID=6660875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28683/54A Expired GB760086A (en) | 1953-12-01 | 1954-10-05 | Process for the production of ú-aminomethyl benzoic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB760086A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108623488A (en) * | 2018-06-20 | 2018-10-09 | 湖南文理学院 | A kind of synthetic method of aminomethylbenzoic acid |
-
1954
- 1954-10-05 GB GB28683/54A patent/GB760086A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108623488A (en) * | 2018-06-20 | 2018-10-09 | 湖南文理学院 | A kind of synthetic method of aminomethylbenzoic acid |
| CN108623488B (en) * | 2018-06-20 | 2021-10-01 | 湖南文理学院 | Synthetic method of aminomethylbenzoic acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1095088A (en) | Esters of acrylic acid | |
| GB1131981A (en) | Improvements in the production of acylated hydroxy sulphonates | |
| GB760086A (en) | Process for the production of ú-aminomethyl benzoic acid esters | |
| GB903613A (en) | Improvements in or relating to the production of acetoacetic acid esters | |
| US2413077A (en) | d(+)-alpha, gamma-dihydroxy-beta, beta-dimethyl-butyric-acid-(hydroxy-alkyl)-amides and process for the manufacture of same | |
| US2877264A (en) | Process for preparing hydroxyalkyl acrylates and methacrylates | |
| GB2008111A (en) | A process for the production of gamma -Chlorocarboxylic Acid Esters | |
| US1584907A (en) | Production of esters from amide acid sulphates | |
| US1829208A (en) | Processes of producing acrylic acid esters | |
| US2421233A (en) | Ureido acid esters and method of making the same | |
| GB1066117A (en) | Process for the manufacture of cyanoacetic acid esters | |
| US2665308A (en) | Process for making n-(1, 1-dimethyl-3-hydroxybutyl)-lactamide | |
| GB987274A (en) | Improvements in and relating to the production of halides of unsaturated aliphatic acids or derivatives thereof | |
| US2659750A (en) | Process for esterifying carbocyclic carboxylic acids | |
| GB707709A (en) | Process for the production of n-[-a:-g-dihydroxy--a:-a-dimethyl-butyryl]--a-alanine--a-mercaptoethylamide | |
| GB740005A (en) | Manufacture of acrylates | |
| ES222824A3 (en) | A procedure for sterification of superior fatty acids (Machine-translation by Google Translate, not legally binding) | |
| GB579333A (en) | Improvements in or relating to the production of monoesters of ascorbic acid | |
| ATE65495T1 (en) | ESTERS MANUFACTURE. | |
| GB764664A (en) | Process for the production of pentaerythritol trichlorohydrin | |
| GB789328A (en) | Improvements in or relating to production of l-glutamine | |
| GB851029A (en) | A process for the production of bis-(beta-hydroxy-alkyl)-terephthalates and isophthalates | |
| GB722594A (en) | Improvements in the manufacture of cellulose esters | |
| GB1149460A (en) | A process for producing esters of dicarboxylic acids and diols | |
| ES224974A1 (en) | Purification of dimethyl terephthalate |