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【Shandong Rich】Major in Phthalimide

Writer:Rich chemistrySource:Rich chemistry Number of visits: Date:2017-11-17 20:08:01

Preparation[edit]

Phthalimide can be prepared by heating phthalic anhydride with aqueous ammonia giving 95-97% yield. Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea. It can also be produced by ammoxidation of ortho-xylene.

Uses[edit]

Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin.[2]

Alkyl phthalimides are useful precursors to amines in chemical synthesis, especially in peptide synthesis where they are used "to block both hydrogens and avoid racemization of the substrates".[3] Alkyl halides can be converted to the N-alkylphthalimide:

C6H4(CO)2NH + RX + NaOH → C6H4(CO)2N-R + NaX + H2O

The amine is commonly liberated using hydrazine:

Reactivity[edit]

It forms salts upon treatment with bases such as sodium hydroxide. The high acidity of the imido N-H is the result of the pair of flanking electrophilic carbonyl groups. Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100 °C or with potassium hydroxide in absolute ethanol,[5]is used in the Gabriel synthesis of primary amines, such as glycine.

Natural occurrence[edit]

Kladnoite is a natural mineral analog of phthalimide.[6] It is very rarely found among a few burning coal fire sites.

Safety[edit]

Phthalimide has low acute toxicity with LD50 (rat, oral) of greater than 5000 mg/kg.

TypeInfo: Company News

Keywords for the information:Phthalimide  Zinc Oxide.