US622456A - Process of manufacturing salol - Google Patents
Process of manufacturing salol Download PDFInfo
- Publication number
- US622456A US622456A US622456DA US622456A US 622456 A US622456 A US 622456A US 622456D A US622456D A US 622456DA US 622456 A US622456 A US 622456A
- Authority
- US
- United States
- Prior art keywords
- salol
- soda
- phenol
- manufacturing
- salicylate
- 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 - Lifetime
Links
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N Phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 title description 20
- 238000000034 method Methods 0.000 title description 20
- 229960000969 phenyl salicylate Drugs 0.000 title description 20
- 238000004519 manufacturing process Methods 0.000 title description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 24
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 22
- 229960001860 salicylate Drugs 0.000 description 22
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 229960004889 salicylic acid Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 230000001264 neutralization Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
Definitions
- the manufacture of salol is thus very mate'- rially facilitated, for this process dispenses with the preliminary production of salicylic acid or its neutral salts, which was heretofore necessary, and can easily be combined with the manufacture of basic salicylate of soda, such as carried out in Kolbes process for the manufacture of salicylic acid.
- the mode of carrying out the process of my invention is to make a mixture of one equiva lent of basic salicylate of soda and one mole cule of phenol and to subject the sameto the action of phosphorus oxychlorid atatemperature of 120 to 140 Celsius, or in case it is con venient to combine this process with that of making basic salicylate of soda to allow the temperature which was necessary to form the latter to cool down to about 100 Celsius,subse quently adding so much phenol that there is exactly one equivalent of the same to one equivalent of the basic salicylate of soda, and then treating the mixture with PO01 or the other reagents at a temperature of 120 to 140 Celsius, as indicated, for instance, by the following equation:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
I; NTED STATES PATENT rricn,
HENRY CARL FEI-IRLIN, OF ST. LOUIS, MISSOURI, ASSIGNOR TO THE FINK & FEIIRLIN CHEMICAL COMPANY, OF MILWAUKEE, WVISCONSIN.
PROCESS OF MANUFACTURING SALOL.
SPECIFICATION forming part of Letters Patent No. 622,4:56, dated April 4, 1899.
Application filed February 25, 1898. Serial No. 671,691. [No specimens.)
To all whom it may concern:
Be it known that I, HENRY CARL FEHRLIN, doctor of philosophy, a citizen of the Republic of Switzerland, residing at St. Louis, State of Missouri, have invented certain new and useful Improvements in the Manufacture of Salicylate of Phenyl, of which the following is a full, clear, and exact description, which will enable others skilled in the art to which it appertains to use the same.
In the various processes for the manufacture of phenyl-salicylic-acid ester (or the so= calledsalol the same is formed as described in the patents now to be referred to and indicated by the following equations:
In Letters Patent No. 350,012, dated the 28th day of September, 1886, to Marcel von Nencki:
In Letters Patent No. 377,311, dated the 31st day of January, 1888, to Carl Kolbe:
-OII C l l ;COOH+C H,OH+COCI -OH C l'I -COOC II +CO +2HCI In Letters Patent No. 383,306, dated the 22d day of May, 1888, also to Carl Kolbe:
--Oll I E,-COOH+3C H OH+PCI ---()H V 30 1-1,-COOC Ilfi-3HC1+P(OI-l) According to the above patents salol could only heretofore be produced if salicylic acid or the neutral salts of same, such as C I-I (OH)COONa or C H,(OH)COOK, and phenol or phenolate of soda are used as raw materials, and, as stated in the Patents Nos. 377,311, and 383,306, the result obtained is a very impure product if in place of phenol salts of phenol are used. I have now discovered that salol or salicylate of phenyl can also be produced by employing a mixture of phe= 1101 and crude basic salicylate of soda instead of salicylic acid or the neutral salts thereof. The manufacture of salol is thus very mate'- rially facilitated, for this process dispenses with the preliminary production of salicylic acid or its neutral salts, which was heretofore necessary, and can easily be combined with the manufacture of basic salicylate of soda, such as carried out in Kolbes process for the manufacture of salicylic acid.
The mode of carrying out the process of my invention is to make a mixture of one equiva lent of basic salicylate of soda and one mole cule of phenol and to subject the sameto the action of phosphorus oxychlorid atatemperature of 120 to 140 Celsius, or in case it is con venient to combine this process with that of making basic salicylate of soda to allow the temperature which was necessary to form the latter to cool down to about 100 Celsius,subse quently adding so much phenol that there is exactly one equivalent of the same to one equivalent of the basic salicylate of soda, and then treating the mixture with PO01 or the other reagents at a temperature of 120 to 140 Celsius, as indicated, for instance, by the following equation:
ONa
I The product thus obtained will then give a pure colorless salol if it is treated with a solution of carbonate of soda and the salol distilled off in a current of steam.
I wish it distinctly understood that I do not limit myself to the employment of phosphorous oxychlorid in carrying out my process, as any other ingredient reacting similarly cule of basic salicylate of soda and one molecule of phenol with phosphorous oxychlorid at a suitable temperature.
2. The within-described process of producing salol from basic salicylate of soda and phenol, which consists, in treating one mole cule of basic salicylate of soda and one molecule of phenol with phosphorous oxychlorid at a temperature of from 120 to 140 Celsius.
3. The Within-described process of producing salol which consists in treating basic salicylate of soda with the necessary quantity of phenol, and phosphorous oxychlorid at a temperature of from 120 to 140 Celsius, subsequently adding a solution of carbonate of soda, and finally distilling off the salol in a current of steam.
In testimony whereof I aflix my signature in the presence of two witnesses.
HENRY CARL FEHRLIN.
Witnesses:
ALFRED A. MATHEY, O. F. KELLER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US622456A true US622456A (en) | 1899-04-04 |
Family
ID=2691062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US622456D Expired - Lifetime US622456A (en) | Process of manufacturing salol |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US622456A (en) |
-
0
- US US622456D patent/US622456A/en not_active Expired - Lifetime
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