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Amine oxide
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Amine oxide
In chemistry, an amine oxide, also known as an amine N-oxide or simply N-oxide, is a chemical compound that has the chemical formula R3N+−O−. It contains a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-groups attached to nitrogen. Sometimes it is written as R3N→O or, alternatively, as R3N=O.
In the strict sense, the term amine oxide applies only to oxides of tertiary amines. Sometimes it is also used for the analogous derivatives of primary and secondary amines.
Commonly, amine oxides are white, water-soluble solids:
Long-chain alkyl amine oxides are used as amphoteric surfactants and foam stabilizers.
Amine oxides are surfactants commonly used in consumer products such as shampoos, conditioners, detergents, and hard surface cleaners. Alkyl dimethyl amine oxide (chain lengths C10–C16) is the most commercially used amine oxide. They are considered a high production volume class of compounds in more than one member country of the Organisation for Economic Co-operation and Development (OECD); with annual production over 26,000, 16,000 and 6,800 tonnes (28,700, 17,600 and 7,500 short tons) in the US, Europe, and Japan, respectively. In North America, more than 95% of amine oxides are used in home cleaning products. They serve as stabilizers, thickeners, emollients, emulsifiers, and conditioners with active concentrations in the range of 0.1–10%. The remainder (< 5%) is used in personal care, institutional, commercial products and for unique patented uses such as photography.
Amine oxides are highly polar molecules and have a polarity close to that of quaternary ammonium salts. Small amine oxides are very hydrophilic and have an excellent water solubility and a very poor solubility in most organic solvents.
Amine oxides are weak bases with a pKb of around 4.5 that form R3N+−OH, cationic hydroxylamines, upon protonation at a pH below their pKb.
Formation of amine oxides can also be an unwanted process, such as the oxidation of amine-based reagents. Amines left exposed to air can undergo oxidation from atmospheric oxygen, slowly reacting with oxygen to form N-oxides. This process can cause the amines to turn a yellowish color and the N-oxides can decompose further into byproducts. Oxidation due to air can be prevented by storing reagents under inert atmosphere.[citation needed]
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Amine oxide
In chemistry, an amine oxide, also known as an amine N-oxide or simply N-oxide, is a chemical compound that has the chemical formula R3N+−O−. It contains a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-groups attached to nitrogen. Sometimes it is written as R3N→O or, alternatively, as R3N=O.
In the strict sense, the term amine oxide applies only to oxides of tertiary amines. Sometimes it is also used for the analogous derivatives of primary and secondary amines.
Commonly, amine oxides are white, water-soluble solids:
Long-chain alkyl amine oxides are used as amphoteric surfactants and foam stabilizers.
Amine oxides are surfactants commonly used in consumer products such as shampoos, conditioners, detergents, and hard surface cleaners. Alkyl dimethyl amine oxide (chain lengths C10–C16) is the most commercially used amine oxide. They are considered a high production volume class of compounds in more than one member country of the Organisation for Economic Co-operation and Development (OECD); with annual production over 26,000, 16,000 and 6,800 tonnes (28,700, 17,600 and 7,500 short tons) in the US, Europe, and Japan, respectively. In North America, more than 95% of amine oxides are used in home cleaning products. They serve as stabilizers, thickeners, emollients, emulsifiers, and conditioners with active concentrations in the range of 0.1–10%. The remainder (< 5%) is used in personal care, institutional, commercial products and for unique patented uses such as photography.
Amine oxides are highly polar molecules and have a polarity close to that of quaternary ammonium salts. Small amine oxides are very hydrophilic and have an excellent water solubility and a very poor solubility in most organic solvents.
Amine oxides are weak bases with a pKb of around 4.5 that form R3N+−OH, cationic hydroxylamines, upon protonation at a pH below their pKb.
Formation of amine oxides can also be an unwanted process, such as the oxidation of amine-based reagents. Amines left exposed to air can undergo oxidation from atmospheric oxygen, slowly reacting with oxygen to form N-oxides. This process can cause the amines to turn a yellowish color and the N-oxides can decompose further into byproducts. Oxidation due to air can be prevented by storing reagents under inert atmosphere.[citation needed]
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