GB803478A - Improvements in and relating to the manufacture of nitriles - Google Patents

Improvements in and relating to the manufacture of nitriles

Info

Publication number
GB803478A
GB803478A GB1062257A GB1062257A GB803478A GB 803478 A GB803478 A GB 803478A GB 1062257 A GB1062257 A GB 1062257A GB 1062257 A GB1062257 A GB 1062257A GB 803478 A GB803478 A GB 803478A
Authority
GB
United Kingdom
Prior art keywords
para
acid
phenylenediamine
amine
products
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
GB1062257A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Priority to GB1062257A priority Critical patent/GB803478A/en
Publication of GB803478A publication Critical patent/GB803478A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
    • C07C37/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen by substitution of a NH2 group

Landscapes

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

Abstract

Hydrocyanic acid is prepared and recovered as a by-product in the preparation of nitriles by reacting an amine with carbon monoxide at an elevated pressure and an elevated temperature in the presence of a dehydration catalyst. The reaction is preferably carried out in the gas phase using pressures of above 300 atmospheres and temperatures of between 300 DEG and 500 DEG C. Specified catalysts are aluminium oxide, g -alumina, magnesia, zinc oxide and boron trioxide. The amine reactant may be a primary or secondary, aliphatic or aromatic monoamine or diamine; those exemplified being aniline, diphenylamine, para-toluidine, para-phenylenediamine, meta-phenylenediamine, propylamine, ethylene diamine and 1 : 4-diaminobutane. The hydrocyanic acid and phenolic by-products are separated from the final products by a preliminary alkali-extraction treatment (e.g. using sodium hydroxide) and are subsequently separated from each other by conventional methods.ALSO:Nitriles are prepared by reacting an amine with carbon monoxide at an elevated pressure and an elevated temperature in the presence of a dehydration catalyst. The reaction is preferably carried out in the gas phase using pressures of above 300 atmospheres and temperatures of between 300 DEG and 500 DEG C. Specified catalysts are aluminium oxide, g -alumina, magnesia, zinc oxide and boron trioxide. The amine reactant may be a primary or secondary, aliphatic or aromatic monoamine or diamine; those exemplified being aniline, diphenylamine, para-toluidine, para-phenylenediamine, meta-phenylenediamine, propylamine, ethylene diamine and 1:4 - diaminobutane. Secondary and heterocyclic amines, phenols, amides and hydrocyanic acid are formed as by-products during the reaction, and these and unreacted amine may be separated from the nitrile product by successive alkali extraction, acid extraction and fractional distillation. The nitrile and dinitrile products may be hydrolysed to mono- and di-carboxylic acids respectively. The examples describe the preparation and recovery of benzonitrile, isophthalic acid-dinitrile, para-tolunitrile, butyronitrile, succinic acid dinitrile, adipodinitrile, phenol, resorcinol, para-cresol, benzanilide, butyramide, adipic acid diamide, diphenylamine and pyrrolidine. The para-tolunitrile product may be hydrolysed to toluic acid and the latter oxidized to terephthalic acid.
GB1062257A 1957-04-01 1957-04-01 Improvements in and relating to the manufacture of nitriles Expired GB803478A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1062257A GB803478A (en) 1957-04-01 1957-04-01 Improvements in and relating to the manufacture of nitriles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1062257A GB803478A (en) 1957-04-01 1957-04-01 Improvements in and relating to the manufacture of nitriles

Publications (1)

Publication Number Publication Date
GB803478A true GB803478A (en) 1958-10-29

Family

ID=9971254

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1062257A Expired GB803478A (en) 1957-04-01 1957-04-01 Improvements in and relating to the manufacture of nitriles

Country Status (1)

Country Link
GB (1) GB803478A (en)

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