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Dimethylaminopropylamine

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.

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: :[[File:Manufacture_of_DMAPA.png|400px]] DMAPA is readily converted to the mustard dimethylaminopropyl-3-chloride, a powerful alkylating agent.

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.

References

References

  1. (2003-10-28). "BASF ups capacity at DMAPA plant". Cosmetics Design.
  2. "3-Aminopropyldimethylamine". UN Environment.
  3. (1976). "Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-Hepthanedione". Organic Syntheses.
  4. (February 1995). "3-Dimethylaminopropylamine: a key substance in contact allergy to cocamidopropylbetaine?". Contact Dermatitis.
  5. (March 1995). "Contact dermatitis to cocamidopropylbetaine is caused by residual amines: Relevance, clinical characteristics, and review of the literature". American Journal of Contact Dermatitis.
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diamines dimethylamino-compounds
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