DD141019A5 - Verfahren zur herstellung von salicylsaeure und derivaten davon - Google Patents
Verfahren zur herstellung von salicylsaeure und derivaten davon Download PDFInfo
- Publication number
- DD141019A5 DD141019A5 DD78210229A DD21022978A DD141019A5 DD 141019 A5 DD141019 A5 DD 141019A5 DD 78210229 A DD78210229 A DD 78210229A DD 21022978 A DD21022978 A DD 21022978A DD 141019 A5 DD141019 A5 DD 141019A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- item
- pressure
- atom
- psig
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title claims description 11
- 229940051879 analgesics and antipyretics salicylic acid and derivative Drugs 0.000 title description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000001569 carbon dioxide Substances 0.000 claims description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 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 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- UZUGIHHGLRFGMJ-UHFFFAOYSA-N (2-phenylphenyl) acetate Chemical group CC(=O)OC1=CC=CC=C1C1=CC=CC=C1 UZUGIHHGLRFGMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 7
- 229960004889 salicylic acid Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- -1 phenylacetic acid ester Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052799 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/865,563 US4131618A (en) | 1977-12-29 | 1977-12-29 | Preparation of salicylic acid and derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD141019A5 true DD141019A5 (de) | 1980-04-09 |
Family
ID=25345788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78210229A DD141019A5 (de) | 1977-12-29 | 1978-12-28 | Verfahren zur herstellung von salicylsaeure und derivaten davon |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4131618A (cs) |
| EP (1) | EP0002834A3 (cs) |
| JP (1) | JPS5495539A (cs) |
| AR (1) | AR220923A1 (cs) |
| AT (1) | ATA932678A (cs) |
| AU (1) | AU4242978A (cs) |
| CS (1) | CS203028B2 (cs) |
| DD (1) | DD141019A5 (cs) |
| DK (1) | DK584678A (cs) |
| ES (1) | ES475906A1 (cs) |
| FI (1) | FI783888A7 (cs) |
| GR (1) | GR66837B (cs) |
| HU (1) | HU176293B (cs) |
| IT (1) | IT1109344B (cs) |
| NO (1) | NO784317L (cs) |
| NZ (1) | NZ189141A (cs) |
| PL (1) | PL212192A1 (cs) |
| PT (1) | PT68946A (cs) |
| ZA (1) | ZA787365B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190926B (it) * | 1982-07-22 | 1988-02-24 | Zambon Spa | Procedimento per preparare l'acido 2',4'-difluoro-4-idrossi-(1,1'-difenil)-3-carbossilico |
| IT1250736B (it) * | 1991-08-01 | 1995-04-21 | Zambon Spa | Processo per la preparazione dell'acido 5-(2',4'-difluorofenil) salicilico in forma ii pura |
| IL118657A0 (en) | 1996-06-14 | 1996-10-16 | Arad Dorit | Inhibitors for picornavirus proteases |
| JP3814742B2 (ja) * | 1996-10-18 | 2006-08-30 | イハラケミカル工業株式会社 | ４−フルオロサリチル酸類 |
| IL122591A0 (en) | 1997-12-14 | 1998-06-15 | Arad Dorit | Pharmaceutical compositions comprising cystein protease inhibitors |
| WO2015057881A1 (en) | 2013-10-17 | 2015-04-23 | Si Group, Inc. | Modified alkylphenol-aldehyde resins stabilized by a salicylic acid |
| EP3058005B1 (en) | 2013-10-17 | 2023-06-07 | SI Group, Inc. | In-situ alkylphenol-aldehyde resins |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2816137A (en) * | 1954-08-09 | 1957-12-10 | Eastman Kodak Co | Method of preparing hydroxy aromatic carboxylic acids |
| US3714226A (en) * | 1970-06-09 | 1973-01-30 | Merck & Co Inc | Phenyl benzoic acid compounds |
| US3992459A (en) * | 1975-05-01 | 1976-11-16 | Merck & Co., Inc. | Preparation of biphenyl compounds |
-
1977
- 1977-12-29 US US05/865,563 patent/US4131618A/en not_active Expired - Lifetime
-
1978
- 1978-12-11 ES ES475906A patent/ES475906A1/es not_active Expired
- 1978-12-11 NZ NZ189141A patent/NZ189141A/xx unknown
- 1978-12-12 AU AU42429/78A patent/AU4242978A/en active Pending
- 1978-12-13 AR AR274785A patent/AR220923A1/es active
- 1978-12-16 GR GR57904A patent/GR66837B/el unknown
- 1978-12-18 FI FI783888A patent/FI783888A7/fi unknown
- 1978-12-20 PT PT68946A patent/PT68946A/pt unknown
- 1978-12-21 NO NO784317A patent/NO784317L/no unknown
- 1978-12-27 CS CS788922A patent/CS203028B2/cs unknown
- 1978-12-27 JP JP16028378A patent/JPS5495539A/ja active Pending
- 1978-12-27 PL PL21219278A patent/PL212192A1/xx unknown
- 1978-12-28 HU HU78ME2237A patent/HU176293B/hu unknown
- 1978-12-28 IT IT52475/78A patent/IT1109344B/it active
- 1978-12-28 DK DK584678A patent/DK584678A/da unknown
- 1978-12-28 AT AT932678A patent/ATA932678A/de not_active Application Discontinuation
- 1978-12-28 DD DD78210229A patent/DD141019A5/de unknown
- 1978-12-28 ZA ZA787365A patent/ZA787365B/xx unknown
- 1978-12-29 EP EP78101862A patent/EP0002834A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5495539A (en) | 1979-07-28 |
| HU176293B (en) | 1981-01-28 |
| EP0002834A2 (en) | 1979-07-11 |
| EP0002834A3 (en) | 1979-07-25 |
| PL212192A1 (pl) | 1979-08-13 |
| PT68946A (en) | 1979-01-01 |
| NO784317L (no) | 1979-06-30 |
| IT7852475A0 (it) | 1978-12-28 |
| US4131618A (en) | 1978-12-26 |
| CS203028B2 (en) | 1981-02-27 |
| NZ189141A (en) | 1980-08-26 |
| FI783888A7 (fi) | 1979-06-30 |
| IT1109344B (it) | 1985-12-16 |
| ES475906A1 (es) | 1979-11-01 |
| AR220923A1 (es) | 1980-12-15 |
| AU4242978A (en) | 1979-07-05 |
| ATA932678A (de) | 1981-01-15 |
| ZA787365B (en) | 1980-08-27 |
| DK584678A (da) | 1979-06-30 |
| GR66837B (cs) | 1981-05-04 |
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