JPS6318929B2 - - Google Patents

Info

Publication number

JPS6318929B2

JPS6318929B2 JP12555881A JP12555881A JPS6318929B2 JP S6318929 B2 JPS6318929 B2 JP S6318929B2 JP 12555881 A JP12555881 A JP 12555881A JP 12555881 A JP12555881 A JP 12555881A JP S6318929 B2 JPS6318929 B2 JP S6318929B2

Authority

JP

Japan

Prior art keywords

reaction

cyclodextrin

acid

parahydroxybenzoic acid

product

Prior art date

1981-08-11

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

• Espacenet
• Global Dossier
• Discuss

• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 29
• 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
• 229920000858 Cyclodextrin Polymers 0.000 claims description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 6
• 238000000034 method Methods 0.000 claims description 5
• 239000003054 catalyst Substances 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 238000006243 chemical reaction Methods 0.000 description 13
• 239000000047 product Substances 0.000 description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• 238000000862 absorption spectrum Methods 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000002994 raw material Substances 0.000 description 3
• 229960004889 salicylic acid Drugs 0.000 description 3
• 230000002194 synthesizing effect Effects 0.000 description 3
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 239000001116 FEMA 4028 Substances 0.000 description 2
• 241000581652 Hagenia abyssinica Species 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
• 235000011175 beta-cyclodextrine Nutrition 0.000 description 2
• 229960004853 betadex Drugs 0.000 description 2
• 230000000052 comparative effect Effects 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
• 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 1
• 239000003905 agrochemical Substances 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
• 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• -1 cyclic oligosaccharide Chemical class 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 229920001542 oligosaccharide Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 238000007086 side reaction Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1