Dibutyl Phthalate (DBP), Dimethyl Phthalate (DMP), and Diethyl Phthalate (DEP) are dialkyl phthalates used primarily in cosmetics at concentrations of less than 10 percent as plasticizers, solvents, and perfume fixatives.These phthalates are rapidly absorbed, metabolized, and excreted. Acute animal feeding studies indicate that these ingredients are nontoxic. The results of most subchronic and chronic tests indicate that these ingredients are relatively nontoxic to rats. The oral administration of DBP produced testicular atrophy in various test rodents. The available data are not adequate to prove that these ingredients are teratogenic agents to experimental animals. This was not observed after the administration of DMP and DEP. Undiluted DBP, DMP, and DEP produced only minimal irritation t o eyes of rabbits.The mutagenic activity of DBP, DMP, and DEP toward Salmonella typhimurium mutants i s essentially negative, but some assays reported positive findings. Carcinogenesis was not observed in DBP feeding studies. limited clinical data on DBP, DMP, and DEP indicate that these ingredients are not human skin irritants, sensitizers, or phototoxic agents. On the basis of the available data, it i s concluded that these compounds are safe for topical application in the present practices of use and concentration in cosmetics.ethyl Phthalate. Di(2-ethylhexyl)phthalate, a compound currently of great concern, is not used in cosmetics. 267 at UNIVERSITE DE MONTREAL on June 16, 2015 ijt.sagepub.com Downloaded from 14 30 734 7 7 7 7 7 7 7 7 7 7 6 7 3 6 7 1.5049 7 7 1.5002 6
ReactivityThe alkaline hydrolysis products of phthalate esters are mono-and diacids.The second-order alkaline hydrolysis rate constants in water at 30°C are 1 .O x lo-', 6.9 x lo-', and 2.5 x lo-' M-' sec' for DBP, DMP, and DEP, respectively.Acid hydrolysis is generally slower than alkaline hydrolysis, and neutral hydrolysis is generally too slow to be d e t e~t e d . '~) DBP is stable in solutions with a near neutral pH.") The products of the thermal decomposition at 250 to 5OOOC of DBP are 1-butene, butanol, phthalic anhydride, and small amounts of benzoic acid, butyl at UNIVERSITE DE MONTREAL on June 16, 2015 ijt.sagepub.com Downloaded from 270 COSMETIC INGREDIENT REVIEW benzoate, phthalic acid, and monobutyl phthalate. ( l o ) The major products in the pyrolysis at 730°C of DBP are isobutene, butene, and propylene.'") DBP can be degraded by radiolysis. The major product of a 1 ppm aqueous DBP solution at pH 7 after a dose of 3 x lo4 rad of gamma radiation is monobutyl p hthalate. ( I 2 )
Methods of Manufacture and ImpuritiesPhthalate esters can be prepared by the reaction of phthalic acid with alcohol. DBP, DMP, and DEP are produced industrially by the reaction of phthalic anhydride with butyl alcohol, methyl alcohol, and ethyl alcohol, respecti~ely.(~,~.'~) DBP is manufactured by the esterification of phthalic anhydride with an excess of n-butyl alcohol. Vacuum stripping removes the unreacted n-butyl alcohol. Steam sparging ensures low odor. The phthala...