CA1180723A - Process for preparing 4-aminomethylbenzoic acid from 4-hydroxyiminomethylbenzoic acid - Google Patents
Process for preparing 4-aminomethylbenzoic acid from 4-hydroxyiminomethylbenzoic acidInfo
- Publication number
- CA1180723A CA1180723A CA000385925A CA385925A CA1180723A CA 1180723 A CA1180723 A CA 1180723A CA 000385925 A CA000385925 A CA 000385925A CA 385925 A CA385925 A CA 385925A CA 1180723 A CA1180723 A CA 1180723A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- catalyst
- amount
- hydroxyiminomethylbenzoic
- rhodium
- 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
- UYCPLAQBBAOCGQ-UHFFFAOYSA-N 4-(hydroxyiminomethyl)benzoic acid Chemical compound ON=CC1=CC=C(C(O)=O)C=C1 UYCPLAQBBAOCGQ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229960003375 aminomethylbenzoic acid Drugs 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 2
- TWTQUXBHIQGPFI-UHFFFAOYSA-N 4-hydroxyiminocyclohexa-1,5-diene-1-carboxylic acid Chemical compound ON=C1CC=C(C(O)=O)C=C1 TWTQUXBHIQGPFI-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 abstract description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract description 6
- 239000013078 crystal Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 6
- -1 oxime compound Chemical class 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 150000002941 palladium compounds Chemical class 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 150000003284 rhodium compounds Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- IHVPBONIOHGKDJ-UHFFFAOYSA-N 2-(dichloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Cl)Cl IHVPBONIOHGKDJ-UHFFFAOYSA-N 0.000 description 1
- VLRVPJCWMLBRTQ-UHFFFAOYSA-N 2-(hydroxyiminomethyl)benzoic acid Chemical compound ON=CC1=CC=CC=C1C(O)=O VLRVPJCWMLBRTQ-UHFFFAOYSA-N 0.000 description 1
- OITNBJHJJGMFBN-UHFFFAOYSA-N 4-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCl)C=C1 OITNBJHJJGMFBN-UHFFFAOYSA-N 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- KKZMIDYKRKGJHG-UHFFFAOYSA-N methyl 4-cyanobenzoate Chemical compound COC(=O)C1=CC=C(C#N)C=C1 KKZMIDYKRKGJHG-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
-
- 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
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| JP128963/80 | 1980-09-17 | ||
| JP55128963A JPS6017780B2 (ja) | 1980-09-17 | 1980-09-17 | ４−アミノメチル安息香酸の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1180723A true CA1180723A (en) | 1985-01-08 |
Family
ID=14997738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000385925A Expired CA1180723A (en) | 1980-09-17 | 1981-09-15 | Process for preparing 4-aminomethylbenzoic acid from 4-hydroxyiminomethylbenzoic acid |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6017780B2 (OSRAM) |
| CA (1) | CA1180723A (OSRAM) |
| DE (1) | DE3137091C2 (OSRAM) |
| FR (1) | FR2490220A1 (OSRAM) |
| GB (1) | GB2084146B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101002061B1 (ko) | 2010-01-14 | 2010-12-17 | 에스케이유화 주식회사 | 4-아미노메틸벤조산 제조방법 |
| KR101263405B1 (ko) * | 2011-01-13 | 2013-05-10 | 한국화학연구원 | 디메틸 테레프탈레이트 제조 공정으로부터 발생하는 부산물로부터 고순도의 메틸-4-포밀벤조에이트의 정제방법 |
| CN102816077A (zh) * | 2012-09-21 | 2012-12-12 | 上海现代哈森（商丘）药业有限公司 | 乌洛托品作为催化剂在合成氨甲苯酸中的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1093822A (fr) * | 1953-02-23 | 1955-05-10 | Courtaulds Ltd | Procédé de fabrication d'acide oméga-amino-nonanoïque |
| JPS5152159A (en) * | 1974-10-31 | 1976-05-08 | Toray Industries | 44 asechiruaminomechirushikurohekisankarubonsan mataha sonojudotaino seizoho |
| JPS5612348A (en) * | 1979-07-09 | 1981-02-06 | Nippon Terupen Kagaku Kk | Production of 4-aminomethylcyclohexane-1-carboxylic acid |
| JPS5612350A (en) * | 1979-07-09 | 1981-02-06 | Nippon Terupen Kagaku Kk | Production of p-aminomethylbenzoic acid or its derivative |
-
1980
- 1980-09-17 JP JP55128963A patent/JPS6017780B2/ja not_active Expired
-
1981
- 1981-09-15 CA CA000385925A patent/CA1180723A/en not_active Expired
- 1981-09-16 GB GB8128015A patent/GB2084146B/en not_active Expired
- 1981-09-16 FR FR8117502A patent/FR2490220A1/fr active Granted
- 1981-09-17 DE DE3137091A patent/DE3137091C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3137091A1 (de) | 1982-05-13 |
| JPS6017780B2 (ja) | 1985-05-07 |
| GB2084146A (en) | 1982-04-07 |
| JPS5753441A (en) | 1982-03-30 |
| FR2490220A1 (fr) | 1982-03-19 |
| DE3137091C2 (de) | 1986-07-17 |
| FR2490220B1 (OSRAM) | 1985-01-25 |
| GB2084146B (en) | 1984-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |