Dimethylaminopropylamine Explained

Dimethylaminopropylamine should not be confused with N,N′-Dimethyl-1,3-propanediamine.

Dimethylaminopropylamine (DMAPA) is a diamine used in the preparation of some surfactants, such as cocamidopropyl betaine which is an ingredient in many personal care products including soaps, shampoos, and cosmetics. BASF, a major producer, claims that DMAPA-derivatives do not sting the eyes and makes a fine-bubble foam, making it appropriate in shampoos.^[1]

Preparation and reactions

DMAPA is commonly produced commercially via the reaction between dimethylamine and acrylonitrile (a Michael reaction) to produce dimethylaminopropionitrile. A subsequent hydrogenation step yields DMAPA:^[2]

DMAPA is readily converted to the mustard dimethylaminopropyl-3-chloride, a powerful alkylating agent.^[3]

Health effects

Dimethylaminopropylamine is a known skin irritant and its presence as an impurity in cocamidopropyl betaine is thought to be the cause of irritation experienced by some individuals.^{[4] [5]}

See also

• 1,1-Dimethylethylenediamine
• 1,2-Dimethylethylenediamine

Notes and References

1. News: BASF ups capacity at DMAPA plant . 2003-10-28 . Cosmetics Design.
2. 3-Aminopropyldimethylamine . OECD Screening Information Dataset . UN Environment . 2019-05-12 . 2017-07-06 . https://web.archive.org/web/20170706080222/http://www.inchem.org/documents/sids/sids/109557.pdf . dead .
3. 10.15227/orgsyn.055.0127. Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-Hepthanedione. P.. Loeliger. E.. Flückiger. Organic Syntheses. 1976. 55. 127.
4. Angelini. Gianni. Foti. Caterina. Rigano. Luigi. Vena. Gino A.. 3-Dimethylaminopropylamine: a key substance in contact allergy to cocamidopropylbetaine?. Contact Dermatitis. February 1995. 32. 2. 96–99. 10.1111/j.1600-0536.1995.tb00754.x. 7758328 . 20508515 .
5. PIGATTO. P. Contact dermatitis to cocamidopropylbetaine is caused by residual amines: Relevance, clinical characteristics, and review of the literature. American Journal of Contact Dermatitis. March 1995. 6. 1. 13–16. 10.1016/1046-199X(95)90062-4.