GB787056A - Improvements relating to the production of tetracycline by the hydrogenolysis of chlortetracycline - Google Patents

Improvements relating to the production of tetracycline by the hydrogenolysis of chlortetracycline

Info

Publication number
GB787056A
GB787056A GB12923/55A GB1292355A GB787056A GB 787056 A GB787056 A GB 787056A GB 12923/55 A GB12923/55 A GB 12923/55A GB 1292355 A GB1292355 A GB 1292355A GB 787056 A GB787056 A GB 787056A
Authority
GB
United Kingdom
Prior art keywords
catalyst
chlortetracycline
carried out
hydroxide
reaction
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
Application number
GB12923/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB787056A publication Critical patent/GB787056A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
    • C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Tetracycline is produced by reacting hydrogen with chlortetracycline in the presence of a palladium hydroxide catalyst, preferably distributed on a porous carrier such as activated carbon, activated alumina gel and diatomaceous earth. The catalyst is preferably prepared by precipitation from a water solution of palladium chloride by adding a water-soluble base such as sodium hydroxide, potassium hydroxide and ammonium hydroxide until the pH is 9 to 10. In the case of the supported catalyst, the precipitation is carried out in the presence of the finely divided carrier. The catalyst may be used wet, i.e. as separated from the reaction media, or dry. The catalyst is used in proportions of 0.25 to 3 per cent by weight of the chlortetracycline. The supported catalyst contains 5 to 15 parts by weight of palladium hydroxide distributed on 95 to 85 parts of the porous carrier. The catalyst is suspended in a solution of chlortetracycline in an organic solvent and the reaction with hydrogen is carried out at a temperature of 0 DEG to 100 DEG C. and preferably 15 DEG to 40 DEG C. Suitable solvents are the ethyl ether of ethylene glycol, beta-methoxyethanol, n-butanol, methanol, ethanol and mixtures thereof. The reaction is preferably carried out at a pH of 7 to 9.5. Reference has been directed by the Comptroller to Specification 747,779.
GB12923/55A 1954-05-14 1955-05-04 Improvements relating to the production of tetracycline by the hydrogenolysis of chlortetracycline Expired GB787056A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US787056XA 1954-05-14 1954-05-14

Publications (1)

Publication Number Publication Date
GB787056A true GB787056A (en) 1957-11-27

Family

ID=22145726

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12923/55A Expired GB787056A (en) 1954-05-14 1955-05-04 Improvements relating to the production of tetracycline by the hydrogenolysis of chlortetracycline

Country Status (1)

Country Link
GB (1) GB787056A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117718042A (en) * 2024-02-09 2024-03-19 北京理工大学 Pd(OH) 2 Diatomite catalyst and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117718042A (en) * 2024-02-09 2024-03-19 北京理工大学 Pd(OH) 2 Diatomite catalyst and preparation method and application thereof
CN117718042B (en) * 2024-02-09 2024-05-28 北京理工大学 Pd(OH)2Diatomite catalyst and preparation method and application thereof

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