Phthalimide
Encyclopedia
Phthalimide is an imide
, which is a chemical compound
with two carbonyl
groups bound to a primary amine
or ammonia
. It is a white solid at room temperature.
with aqueous ammonia giving 95-97% yield. Alternatively, it may be prepared by fusing the anhydride with ammonium carbonate.
, and in research.
, made by reacting phthalimide with potassium carbonate
in water at 100°C or with potassium hydroxide
in absolute ethanol, is used in the Gabriel synthesis
of primary amines, and the Gabriel synthesis of glycine
has yields as high as 85%.
Imide
In organic chemistry, an imide is a functional group consisting of two carbonyl groups bound to nitrogen. These compounds are structurally related to acid anhydrides. The relationship between esters and amides and between imides and anhydrides is analogous, the amine-derived groups are less reactive...
, which is a chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with two carbonyl
Carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....
groups bound to a primary amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
or ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
. It is a white solid at room temperature.
Preparation
Phthalimide can be prepared by heating phthalic anhydridePhthalic anhydride
Phthalic anhydride is the organic compound with the formula C6H42O. It is the anhydride of phthalic acid. This colourless solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2002, approximately 4.6 billion kilograms were...
with aqueous ammonia giving 95-97% yield. Alternatively, it may be prepared by fusing the anhydride with ammonium carbonate.
Uses
Phthalimide is used in plastics, in chemical synthesisChemical synthesis
In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...
, and in research.
Reactivity
It forms salts with various metals such as potassium and sodium due to its high acidity caused by the electrophilic carbonyl groups attached to the nitrogen atom, which can be made by reacting phthalimide with metal carbonates. Potassium phthalimidePotassium phthalimide
Potassium phthalimide is a chemical compound of formula C8H4KNO2. It is commercially available, and usually presents as fluffy, very pale yellow crystals. It is the potassium salt of phthalimide...
, made by reacting phthalimide with potassium carbonate
Potassium carbonate
Potassium carbonate is a white salt, soluble in water , which forms a strongly alkaline solution. It can be made as the product of potassium hydroxide's absorbent reaction with carbon dioxide. It is deliquescent, often appearing a damp or wet solid...
in water at 100°C or with potassium hydroxide
Potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula KOH, commonly called caustic potash.Along with sodium hydroxide , this colorless solid is a prototypical strong base. It has many industrial and niche applications. Most applications exploit its reactivity toward acids and its corrosive...
in absolute ethanol, is used in the Gabriel synthesis
Gabriel synthesis
The Gabriel synthesis is named for the German chemist Siegmund Gabriel. Traditionally, it is a chemical reaction that transforms primary alkyl halides into primary amines using potassium phthalimide....
of primary amines, and the Gabriel synthesis of glycine
Glycine
Glycine is an organic compound with the formula NH2CH2COOH. Having a hydrogen substituent as its 'side chain', glycine is the smallest of the 20 amino acids commonly found in proteins. Its codons are GGU, GGC, GGA, GGG cf. the genetic code.Glycine is a colourless, sweet-tasting crystalline solid...
has yields as high as 85%.