Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C253/00—Preparation of carboxylic acid nitriles
  • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups

Definitions

• these objects are achieved by heating a mixture consisting essentially of an aminophenol, acrylonitrile, and glacial acetic acid at a temperature between about 25C. and the reflux temperature of the mixture.
• a mixture consisting essentially of an aminophenol, acrylonitrile, and glacial acetic acid
• the product may be recovered by quenching the reaction mixture with water provided the acetic acid content does not exceed about 70 percent of the aminophenol content. If excess acetic acid is present, it may be removed by distillation along with unreacted acrylonitrile prior to quenching the reaction mixture.
• the method of the present invention is applicable to p-, or m-aminophenols and to substituted derivatives thereof provided the substituents do not themselves react with acrylonitrile.
• reaction is essentially complete in eight hours, but reflux may be continued overnight or longer without deleterious effect.
• the preparation is convenient as all the reagents are added at once and reflux temperatures are sufficient. No pressure equipment is needed.
• the product is isolated in good yield by simply quenching in water.
• the product is obtained as a light colored solid which may be recrystallized if desired, but the crude material is suitable for further reactions, e.g., hydrolysis to the diacid.
• the products obtained using the present invention are light-colored even when prepared under normal atmospheric conditions although an inert atmosphere (e.g., nitrogen) may be provided if desired.
• an inert atmosphere e.g., nitrogen
• the product may be recrystallized from ethyl acetate or aqueous acetic acid.
• a sample purified by the latter method yielded light yellow needles, mp. -81C.
• N.m.r. and i.r. data confirmed the identity of the product.
• Example I is repeated but o-aminophenol is substituted for the p-aminophenol.
• the product secured was N,N-bis (2-cyanoethyl)-o-aminophenol.
• a method for preparing an N,N-dicyanoethylated aminophenol which comprises heating a mixture consisting essentially of an aminophenol at least 2 mols of acrylonitrile for each mol of the aminophenol, and glav cial acetic acid in an amount at least 50 percent by weight of the aminophenol, at a temperature between about 25C. and the reflux temperature of the mixture, and thereafter quenching the reaction mixture with water to precipitate a substantially pure dicyanoethylated phenol.

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

Priority Applications (10)

Applications Claiming Priority (1)

Publications (1)

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Citations (2)

• 1973
  • 1973-06-21 US US372315A patent/US3890368A/en not_active Expired - Lifetime
• 1974
  • 1974-06-17 NL NL7408084A patent/NL7408084A/xx not_active Application Discontinuation
  • 1974-06-18 GB GB2701374A patent/GB1405243A/en not_active Expired
  • 1974-06-20 BE BE145700A patent/BE816646A/xx not_active IP Right Cessation
  • 1974-06-20 CH CH844874A patent/CH587232A5/xx not_active IP Right Cessation
  • 1974-06-20 FR FR7421524A patent/FR2234279B1/fr not_active Expired
  • 1974-06-20 IT IT51640/74A patent/IT1016121B/it active
  • 1974-06-20 SE SE7408179A patent/SE411751B/xx unknown
  • 1974-06-21 DE DE2429781A patent/DE2429781C2/de not_active Expired
  • 1974-06-21 JP JP49070342A patent/JPS50157324A/ja active Pending

Patent Citations (2)

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