JPH0114891B2 - - Google Patents
Info
- Publication number
- JPH0114891B2 JPH0114891B2 JP4454683A JP4454683A JPH0114891B2 JP H0114891 B2 JPH0114891 B2 JP H0114891B2 JP 4454683 A JP4454683 A JP 4454683A JP 4454683 A JP4454683 A JP 4454683A JP H0114891 B2 JPH0114891 B2 JP H0114891B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alkali metal
- carbon dioxide
- aromatic hydroxy
- aromatic
- 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 66
- -1 aromatic hydroxycarboxylic acids Chemical class 0.000 claims description 52
- 239000001569 carbon dioxide Substances 0.000 claims description 33
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910052783 alkali metal Inorganic materials 0.000 claims description 21
- 239000008187 granular material Substances 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000007790 solid phase Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 150000001896 cresols Chemical class 0.000 claims description 3
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 3
- GWPGDZPXOZATKL-UHFFFAOYSA-N 9h-carbazol-2-ol Chemical class C1=CC=C2C3=CC=C(O)C=C3NC2=C1 GWPGDZPXOZATKL-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000004780 naphthols Chemical class 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 10
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229960004889 salicylic acid Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229940031826 phenolate Drugs 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 229960004025 sodium salicylate Drugs 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- VOYOUEKVKQKBNT-UHFFFAOYSA-M potassium;2-hydroxynaphthalene-1-carboxylate Chemical compound [K+].C1=CC=CC2=C(C([O-])=O)C(O)=CC=C21 VOYOUEKVKQKBNT-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- NZZAIBUHIBBEOQ-UHFFFAOYSA-M sodium;phenyl carbonate Chemical compound [Na+].[O-]C(=O)OC1=CC=CC=C1 NZZAIBUHIBBEOQ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3210599.1 | 1982-03-23 | ||
| DE19823210559 DE3210559A1 (de) | 1981-03-30 | 1982-03-23 | Schleifverfahren und vorrichtung zur durchfuehrung des verfahrens |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58172346A JPS58172346A (ja) | 1983-10-11 |
| JPH0114891B2 true JPH0114891B2 (enrdf_load_stackoverflow) | 1989-03-14 |
Family
ID=6159024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4454683A Granted JPS58172346A (ja) | 1982-03-23 | 1983-03-18 | 芳香族ヒドロキシカルボン酸類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58172346A (enrdf_load_stackoverflow) |
-
1983
- 1983-03-18 JP JP4454683A patent/JPS58172346A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58172346A (ja) | 1983-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4918245A (en) | Process for preparing bisphenol A | |
| KR20050042061A (ko) | 포름산 포르메이트의 제조 방법 | |
| DK155879B (da) | Fremgangsmaade til fremstilling af granulerede metalsaeber | |
| MXPA05001090A (es) | Procedimiento y dispositivo para la obtencion de formiato de acido formico y su uso. | |
| JP2002255880A (ja) | ビスフェノールａの製造方法 | |
| ZA200502074B (en) | Method and device for producing formates and the use thereof | |
| US4508920A (en) | Process for the preparation of aromatic hydroxycarboxylic acids | |
| US4529817A (en) | Process for preparing aromatic hydroxycarboxylic acids | |
| EP0092772B2 (en) | Process for producing aromatic hydroxy compound | |
| US3813445A (en) | Preparation of dihydroxybiphenyls | |
| US4477682A (en) | Process for producing 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-diene-1-one | |
| JPH0114891B2 (enrdf_load_stackoverflow) | ||
| US4168390A (en) | Process for continuous alkylation of phenol using ion exchange resins | |
| US2974172A (en) | Preparation of aromatic ketones | |
| US4946877A (en) | Process for producing bisphenol A | |
| EP0674611B1 (en) | Selective hydroxylation of phenol or phenolic ethers | |
| JP2000128817A (ja) | ビスフェノールａの製造方法 | |
| JPS6127940A (ja) | ピルビン酸塩の製造方法 | |
| US3342857A (en) | Process for the preparation of hydroxytrimesic acid | |
| KR20060013536A (ko) | 포름산 포름산염의 제조방법 | |
| JPS60231625A (ja) | トリメチロ−ルプロパンのアリルエ−テル化物の製法 | |
| US3359310A (en) | Process for producing potassium malonate | |
| JPH10279511A (ja) | ビスフェノールａの製造方法 | |
| US4655974A (en) | Manufacture of phenyl esters | |
| JPS643175B2 (enrdf_load_stackoverflow) |