N-NITROSODIETHANOLAMINE FROM NITRITE AND NO2 41 able. Likewise, the effectiveness that nitrite scavengers might have in products could easily be examined. ACKNOWLEDGEMENTS The author would like to thank Edward Winstead of The Bionetics Corporation, Hampton, Virginia, for some important analytical work early in the project, and Ruby James and Marion Kirk of Southern Research Institute, Birmingham, Alabama, for some valuable discussions. A special word of thanks also goes to Bernard Kabacoff and Ira Rosenberg for their review and encouragement. REFERENCES (11) (12) (13) (14) (15) (16) (17) (1) T. Y. Tan, U. Goff, L. Song, D. H. Fine, G. P. Arsenault, and K. Biemann, N-Nitrosodiethanol- amine in cosmetics, lotions, and shampoos, Food Cosmetic Toxicology, 15, 423-430 (1977). (2) J. A. Wenninger, Progress Report on the Analysis of Cosmetic Products and Raw Materials for Ni-Nitroso- diethanolamine (United States Food and Drug Administration, Cosmetics Division, Washington, D.C., 1978). (3) J. A. Wenninger, Progress Report on the Analysis of Cosmetic Products and Raw Materials for N-Nitroso- diethanolamine (United States Food and Drug Administration, Cosmetics Division, Washington, D.C., 1980). (4) B. Kabacoff, M. Douglass, I. Rosenberg, L. LeVan, J. Punwar, L. Vielhuber, and R. Lechnir, Formation of nitrosamines in non-ionic and anionic emulsions in the presence and absence of inhib- itors. IARC Scientific Publication No. 57, 347-352 (1984). (5) I. Rosenberg, The CTFA program on nitrosamines: An overview, CTFA Cosmetic Journal, 30-37 (July-September 1981). (6) B.C. Challis and S. A. Kyrtopoulos, Nitrosation under alkaline conditions, J.C.S. Chem. Comm.,' 877-878 (1976). (7) V. R. Holland, BNPD and nitrosamine formation, Cosmetic Technology, 5, 31-36 (1981). (8) J. T. H. Ong and B. S. Rutherford, Some factors affecting the rate of n-nitrosodiethanolamine for- mation from 2-bromo-2-nitroporpane-1,3-diol and ethanolamines. J. Soc. Cosmet. Chem., 31, 153-159 (1980). (9) Nitrogen Dioxide and Nitric Oxide in Air, Method No. P&CAM 231 (United States Environmental Protection Agency, Washington, D.C., (1976). (10) J. Alary, P. Bourbon, P. Chovin, C. Delaunay, J. Esclassan, andJ. Lepert, Sur une nouvelle methode de dosage du diozyde d'azote present dans les atmospheres polluees, derivee de la methode de Griess- Saltzmann, Water, Air and Soil Pollution, 3, 555- 562 (1974). D. Levaggi, W. Siu, and M. Feldstein, A new method for measuring average 24-hour nitrogen dioxide concentrations in the atmosphere, Journal of the Air Pollution Control Association, 1, 30- 33 (1973). B. C. Challis and D. G. Shuker, Chemistry of nitroso-compounds. Part 16: Formation of N-nitrosa- mines from dissolved NOC1 in the presence of alkanolamines and related compounds, Fd. Cosmet. Toxicol., 18, 283-288 (1980). B. C. Challis and S. A. Kyrtopoulos, Rapid formation of carcinogenic N-nitrosamines in aqueous alkaline solutions, Br. J. of Cancer, 35, 693-696 (1977). I. S. Krull, E. U. Goff, G. H. Hoffman, and D. H. Fine, Confirmatory methods for the thermal energy determination of N-nitroso compounds at trace levels, Anal. Chem., 51, 1706-1709 (1979). I. S. Krull, T. Y. Fan, and D. H. Fine, Problem of artifacts in the analysis of N-nitroso compounds, Anal. Chem., 50, 698-701 (1978). B.C. Challis and J. A. Challis, Chem. Amino, Nitroso, Nitro Compd. & Their Deriv., 2, 1151-1223 (1982). B. C. Challis and S. A. Kyrtopoulos, "The Chemistry of Nitroso-Compounds. Part II: Nitrosation of

42 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS Amines by the Two-Phase Interaction of Amines in Solution with Gaseous Oxides of Nitrogen," in JCS Perkin I, 299-304 (1979). (18) U. V. Kozlov and B. I. Belov, Investigations in the field of diazo compounds. XVII. The nature of the diazotiating agents in carboxylic acid media, Zhurnal Obshchei Khimii, 33, 1951-1955 (1963). (19) R. M. Angeles, L. K. Keefer, P. P. Roller, and S. J. Uhm, Chemical models for possible nitrosa- mine artifact formation in environmental analysis, IARC Scientific Publication No. 19, 109-115 (1978). (20) D. Levaggi, W. Siu, and M. Feldstein, Quantitative separation of nitric oxide from nitrogen dioxide at atmospheric concentration ranges, Environmental Science and Technology, 6, 250-253 (1972). (21) R. N. Loeppky, T. J. Hansen, and L. K. Keefer, Reducing nitrosamine contamination in cutting fluids, Fd. Chem. Toxic., 21, 607-613 (1983). (22) B. Spiegelhalder, M. Hartung, and R. Preussmann, Biological monitoring in the metal working industry. IARC Scientific Publication No. 57, 943-946 (1984). (23) I. C. Hisatsune, J. Phys. Chem., 65, 2249 (1961).