JPH046798B2 - - Google Patents
Info
- Publication number
- JPH046798B2 JPH046798B2 JP59089878A JP8987884A JPH046798B2 JP H046798 B2 JPH046798 B2 JP H046798B2 JP 59089878 A JP59089878 A JP 59089878A JP 8987884 A JP8987884 A JP 8987884A JP H046798 B2 JPH046798 B2 JP H046798B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- palladium
- cathode
- solution
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 38
- NOJZBJAFCSWMKC-VIFPVBQESA-N p-nitrobenzoyl-l-glutamic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=C([N+]([O-])=O)C=C1 NOJZBJAFCSWMKC-VIFPVBQESA-N 0.000 claims description 21
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- GADGMZDHLQLZRI-VIFPVBQESA-N N-(4-aminobenzoyl)-L-glutamic acid Chemical compound NC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 GADGMZDHLQLZRI-VIFPVBQESA-N 0.000 claims description 12
- 229910001252 Pd alloy Inorganic materials 0.000 claims description 10
- FMJNVBYVHPUUOT-VIFPVBQESA-N (2s)-2-[[4-(hydroxyamino)benzoyl]amino]pentanedioic acid Chemical compound ONC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FMJNVBYVHPUUOT-VIFPVBQESA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 description 52
- 239000000243 solution Substances 0.000 description 27
- 238000006722 reduction reaction Methods 0.000 description 24
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 21
- 229910052719 titanium Inorganic materials 0.000 description 21
- 239000010936 titanium Substances 0.000 description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000002994 raw material Substances 0.000 description 19
- 238000007747 plating Methods 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 229910052697 platinum Inorganic materials 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- -1 aromatic nitrides Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000008151 electrolyte solution Substances 0.000 description 4
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 4
- 239000003014 ion exchange membrane Substances 0.000 description 4
- 238000004445 quantitative analysis Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 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
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
- JQZGDCMJFOHYEW-VIFPVBQESA-N (2S)-2-[benzoyl(nitro)amino]pentanedioic acid Chemical compound OC(=O)CC[C@H](N(C(=O)c1ccccc1)[N+]([O-])=O)C(O)=O JQZGDCMJFOHYEW-VIFPVBQESA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960000304 folic acid Drugs 0.000 description 2
- 235000019152 folic acid Nutrition 0.000 description 2
- 239000011724 folic acid Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- BSIDXUHWUKTRQL-UHFFFAOYSA-N nickel palladium Chemical compound [Ni].[Pd] BSIDXUHWUKTRQL-UHFFFAOYSA-N 0.000 description 2
- 150000002940 palladium Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- BCQYMCKNCJYKFA-VIFPVBQESA-N (2s)-2-[(4-hydroxybenzoyl)amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=C(O)C=C1 BCQYMCKNCJYKFA-VIFPVBQESA-N 0.000 description 1
- LPJXPACOXRZCCP-VIFPVBQESA-N (2s)-2-benzamidopentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 LPJXPACOXRZCCP-VIFPVBQESA-N 0.000 description 1
- ZDPIKEVTLBBVHC-VIFPVBQESA-N (2s)-5-amino-2-[(4-aminobenzoyl)amino]-5-oxopentanoic acid Chemical compound NC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=C(N)C=C1 ZDPIKEVTLBBVHC-VIFPVBQESA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- DWIRHNMDQFNXPZ-FVGYRXGTSA-M sodium (2S)-5-hydroxy-2-[(4-nitrobenzoyl)amino]-5-oxopentanoate Chemical compound [Na+].OC(=O)CC[C@@H](C([O-])=O)NC(=O)C1=CC=C([N+]([O-])=O)C=C1 DWIRHNMDQFNXPZ-FVGYRXGTSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59089878A JPS60234986A (ja) | 1984-05-04 | 1984-05-04 | Ｐ−アミノベンゾイルグルタミン酸の製造法 |
| DE19843419817 DE3419817A1 (de) | 1983-05-31 | 1984-05-26 | Herstellung von p-aminobenzoylglutaminsaeure durch elektrochemische reduktion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59089878A JPS60234986A (ja) | 1984-05-04 | 1984-05-04 | Ｐ−アミノベンゾイルグルタミン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60234986A JPS60234986A (ja) | 1985-11-21 |
| JPH046798B2 true JPH046798B2 (fr) | 1992-02-06 |
Family
ID=13983021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59089878A Granted JPS60234986A (ja) | 1983-05-31 | 1984-05-04 | Ｐ−アミノベンゾイルグルタミン酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60234986A (fr) |
-
1984
- 1984-05-04 JP JP59089878A patent/JPS60234986A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60234986A (ja) | 1985-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Chamoulaud et al. | Biomass conversion II: simultaneous electrosyntheses of furoic acid and furfuryl alcohol on modified graphite felt electrodes | |
| US4521285A (en) | Electrolytic process for the preparation of organic compounds | |
| US4589963A (en) | Process for the conversion of salts of carboxylic acid to their corresponding free acids | |
| US4454012A (en) | Process for the preparation of methionine | |
| US4256550A (en) | Method for producing vitamin B1 and its intermediate | |
| JPH046798B2 (fr) | ||
| JPS6342713B2 (fr) | ||
| US4931155A (en) | Electrolytic reductive coupling of quaternary ammonium compounds | |
| US4505788A (en) | Production of p-aminobenzoylglutamic acid by electrochemical reduction | |
| JPH0657471A (ja) | 蓚酸をグリオキサル酸に還元する電気化学的方法 | |
| RU2135458C1 (ru) | Способ получения янтарной кислоты | |
| KR910005058B1 (ko) | 파라-아미노페놀의 제조방법 | |
| JPS6342712B2 (fr) | ||
| DE3419817C2 (fr) | ||
| JPH045757B2 (fr) | ||
| JPS62294191A (ja) | アルコキシ酢酸の製法 | |
| JP2902755B2 (ja) | ｍ―ヒドロキシベンジルアルコールの製造法 | |
| SU485113A1 (ru) | Способ получени скатилгидантоина | |
| JPS619587A (ja) | ２，４，５−トリアミノ−６−ハイドロオキシピリミジンの製造法 | |
| GB1583466A (en) | Electrochemical manufacture of p-hydroxymethylbenzoic acid | |
| SU1558997A1 (ru) | Способ получени сероводорода | |
| JPH04246187A (ja) | イリジウムの回収方法 | |
| JPH0160554B2 (fr) | ||
| JPS5953355B2 (ja) | ４−ヒドロキシ−２，４，６−トリアルキルシクロヘキサ−２，５−ジエノンの製法 | |
| JPS61257490A (ja) | 芳香族ジアミンの製造方法 |