CA1179369A - Process for preparing 4-aminomethylcyclohexane-carboxylic acid or mineral acid salt thereof - Google Patents
Process for preparing 4-aminomethylcyclohexane-carboxylic acid or mineral acid salt thereofInfo
- Publication number
- CA1179369A CA1179369A CA000385915A CA385915A CA1179369A CA 1179369 A CA1179369 A CA 1179369A CA 000385915 A CA000385915 A CA 000385915A CA 385915 A CA385915 A CA 385915A CA 1179369 A CA1179369 A CA 1179369A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- process according
- mineral acid
- hydroxyiminomethylbenzoic
- mineral
- 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 abstract description 37
- 229910052500 inorganic mineral Inorganic materials 0.000 title claims abstract description 29
- 239000011707 mineral Substances 0.000 title claims abstract description 29
- 150000003839 salts Chemical class 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 title claims abstract description 8
- UYCPLAQBBAOCGQ-UHFFFAOYSA-N 4-(hydroxyiminomethyl)benzoic acid Chemical compound ON=CC1=CC=C(C(O)=O)C=C1 UYCPLAQBBAOCGQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012736 aqueous medium Substances 0.000 claims abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- 229910052703 rhodium Inorganic materials 0.000 claims description 10
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 12
- 238000005984 hydrogenation reaction Methods 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IQKLOQHWKQYTQZ-UHFFFAOYSA-N 4-(aminomethyl)benzoic acid;hydrochloride Chemical compound Cl.NCC1=CC=C(C(O)=O)C=C1 IQKLOQHWKQYTQZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002923 oximes Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000009615 deamination Effects 0.000 description 2
- 238000006481 deamination reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- QLEXWMVQURJMLJ-UHFFFAOYSA-N 4-hydroxyimino-2-methylcyclohexa-1,5-diene-1-carboxylic acid Chemical compound ON=C1CC(=C(C(=O)O)C=C1)C QLEXWMVQURJMLJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 238000005902 aminomethylation reaction Methods 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- VVHXCSFDEMZQFY-UHFFFAOYSA-N methyl 4-(hydroxyiminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=NO)C=C1 VVHXCSFDEMZQFY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- -1 or further Chemical compound 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55128962A JPS5951934B2 (ja) | 1980-09-17 | 1980-09-17 | ４−アミノメチルシクロヘキサンカルボン酸およびその鉱酸塩の製造方法 |
| JP128962/80 | 1980-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1179369A true CA1179369A (en) | 1984-12-11 |
Family
ID=14997713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000385915A Expired CA1179369A (en) | 1980-09-17 | 1981-09-15 | Process for preparing 4-aminomethylcyclohexane-carboxylic acid or mineral acid salt thereof |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5951934B2 (cs) |
| CA (1) | CA1179369A (cs) |
| DE (1) | DE3137092C2 (cs) |
| FR (1) | FR2490218A1 (cs) |
| GB (1) | GB2084145B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2316811B1 (en) | 2008-07-23 | 2015-12-16 | Mitsubishi Gas Chemical Company, Inc. | Process for producing hydrogenated aromatic polycarboxylic acid |
| CN102276490B (zh) * | 2011-06-30 | 2014-03-19 | 常州寅盛药业有限公司 | 一种对氨甲基苯甲酸催化加氢制备止血环酸的方法 |
| JP7628505B2 (ja) * | 2019-11-29 | 2025-02-10 | 株式会社Ｄｎｐファインケミカル宇都宮 | ４－（アミノメチル）シクロヘキサンカルボン酸の製造方法 |
| CN113042040B (zh) * | 2021-03-26 | 2023-07-28 | 白云山东泰商丘药业有限公司 | 一种用铂碳催化剂制备氨甲环酸的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2265725A1 (en) * | 1974-03-27 | 1975-10-24 | Asahi Chemical Ind | 4-Aminomethyl-cyclohexane carboxylic acid prepn. - by hydrogenating para-aminomethyl benzoic acid in presence of ruthenium catalysts and alkal-ine hydroxides |
| JPS5152159A (en) * | 1974-10-31 | 1976-05-08 | Toray Industries | 44 asechiruaminomechirushikurohekisankarubonsan mataha sonojudotaino seizoho |
-
1980
- 1980-09-17 JP JP55128962A patent/JPS5951934B2/ja not_active Expired
-
1981
- 1981-09-15 CA CA000385915A patent/CA1179369A/en not_active Expired
- 1981-09-16 GB GB8128010A patent/GB2084145B/en not_active Expired
- 1981-09-16 FR FR8117501A patent/FR2490218A1/fr active Granted
- 1981-09-17 DE DE3137092A patent/DE3137092C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2490218A1 (fr) | 1982-03-19 |
| GB2084145A (en) | 1982-04-07 |
| DE3137092C2 (de) | 1983-02-03 |
| JPS5753440A (en) | 1982-03-30 |
| GB2084145B (en) | 1984-07-11 |
| FR2490218B1 (cs) | 1984-04-20 |
| DE3137092A1 (de) | 1982-04-08 |
| JPS5951934B2 (ja) | 1984-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPWO2001034543A1 (ja) | ジオール混合物の製造方法 | |
| EP0201957A2 (en) | Process for the preparation of a carboxylic acid salt | |
| CA1179369A (en) | Process for preparing 4-aminomethylcyclohexane-carboxylic acid or mineral acid salt thereof | |
| US4950629A (en) | Process for catalyst recovery | |
| US4814444A (en) | Process for the selective reduction of 2-hydroxyquinoxaline-4-oxides | |
| DE4333642A1 (de) | Verfahren zur Herstellung von Formylimidazolen | |
| EP0083224A1 (en) | Process for producing aromatic polycarboxylic acid with high purity | |
| EP0448899B1 (en) | Preparation of a para-aminodiphenylamine | |
| EP1495806B1 (en) | Chiral zirconium catalyst | |
| JPH0597826A (ja) | ６−アミノ−７−フルオロ−２ｈ−１，４−ベンズオキサジン−３（４ｈ）−オンの製造法 | |
| CA1180723A (en) | Process for preparing 4-aminomethylbenzoic acid from 4-hydroxyiminomethylbenzoic acid | |
| EP0170520B1 (en) | Process for the production of cinnamic acid | |
| US5206430A (en) | Method for obtaining high-purity cinnamic acid | |
| US3658905A (en) | Process for the purification of p-aminophenol | |
| JPH06157461A (ja) | ５，６，７，８−テトラヒドロキノリン類の製造方法 | |
| JP3168079B2 (ja) | ２−アルキルホルミルイミダゾールの製造法 | |
| US4676933A (en) | Method for purification of amido acids | |
| JP3864995B2 (ja) | ピリジンカルボン酸類の精製方法 | |
| FI92586B (fi) | Uusi stereoselektiivinen hydrausmenetelmä | |
| JPS6272636A (ja) | ジメチルエ−テル、酢酸メチルまたはメタノ−ルのカルボニル化の際得られたカルボニル化生成物からヨウ素およびその化合物を分離する方法 | |
| JP3443583B2 (ja) | シス−２，６−ジメチルピペラジンの製造方法 | |
| JPS63112562A (ja) | ５，６，７，８−テトラヒドロキノリン類の製造法 | |
| US5420336A (en) | Catalyst recovery and dialkyl ester synthesis | |
| RU1824393C (ru) | Способ получени п-аминобензоилцианоуксусноэтилового эфира | |
| JPH0782211A (ja) | 脂環式カルボン酸の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |