JPS60234986A - Ｐ−アミノベンゾイルグルタミン酸の製造法 - Google Patents
Ｐ−アミノベンゾイルグルタミン酸の製造法Info
- Publication number
- JPS60234986A JPS60234986A JP59089878A JP8987884A JPS60234986A JP S60234986 A JPS60234986 A JP S60234986A JP 59089878 A JP59089878 A JP 59089878A JP 8987884 A JP8987884 A JP 8987884A JP S60234986 A JPS60234986 A JP S60234986A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- reaction
- cathode
- nitrobenzoylglutamic
- palladium
- 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.)
- Granted
Links
- 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 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 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 abstract description 23
- 229910045601 alloy Inorganic materials 0.000 claims abstract description 4
- 239000000956 alloy Substances 0.000 claims abstract description 4
- 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 abstract description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 35
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- 241000833020 Padilla Species 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 abstract description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 13
- 229910001252 Pd alloy Inorganic materials 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 4
- 238000005868 electrolysis reaction Methods 0.000 abstract description 4
- 239000011780 sodium chloride Substances 0.000 abstract description 4
- 229910052715 tantalum Inorganic materials 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 238000005341 cation exchange Methods 0.000 abstract description 3
- 239000012528 membrane Substances 0.000 abstract description 3
- 229910052759 nickel Inorganic materials 0.000 abstract description 3
- 229910052709 silver Inorganic materials 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 229910010977 Ti—Pd Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 50
- 239000000243 solution Substances 0.000 description 27
- 239000002994 raw material Substances 0.000 description 21
- 239000010936 titanium Substances 0.000 description 21
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 20
- 238000006722 reduction reaction Methods 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 15
- 238000007747 plating Methods 0.000 description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- -1 aromatic nitro compounds Chemical class 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000008151 electrolyte solution Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004445 quantitative analysis Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000003014 ion exchange membrane Substances 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 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
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 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 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BSIDXUHWUKTRQL-UHFFFAOYSA-N nickel palladium Chemical compound [Ni].[Pd] BSIDXUHWUKTRQL-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 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
- BCHONLIBKIBVRS-VIFPVBQESA-N (2s)-2-[amino(benzoyl)amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)N(N)C(=O)C1=CC=CC=C1 BCHONLIBKIBVRS-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 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 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride 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
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013305 food Nutrition 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
- 150000002500 ions Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 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
- 150000002940 palladium Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 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
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 true JPS60234986A (ja) | 1985-11-21 |
| JPH046798B2 JPH046798B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1984
- 1984-05-04 JP JP59089878A patent/JPS60234986A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH046798B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-02-06 |
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