Document RaXa3p8Rn0YbZVX2QmqpDoBEk

Dr. I. Gubelmannj Dr. H. W. ElleyJ Dr. E. K. Bolton Dr. William Kirk Mr. J. S. Groves for I.C.I. J. L. Piles ,.x Uj (1) (1) (3) V"' (2^#^ E. I. duPont de .Nemours & Company Jackson Laboratory February 12, 1941 Preparation of Intermediates for Miscellaneous Products Research N40783 JLR-62-N, No. 5 Serial Number 18050 B. I. duPont de Nemours & Company Jackson laboratory New Products Division G. :E> Holbrook Progress Report February 12, 1941 Preparation of Intermediates for Miscellaneous Products Research Group Leader - C. W, Croco Work Done By - J. R. Schaffer Reported By - J. R. Schaffer Work Started - 12-25-40 Completed - 1-14-41 J. M. TINKER ASSISTANT DIRECTOR W. S. CALCOTT DIRECTOR DUP050059056 Preparation of Intermediates for Miscellaneous Products Research (Proieot Ho. 2079) J. R. Schaffer JLR-62-N, No. 3 Serial Number 18030 0b.1eot of the Investigation: To prepare compounds for evaluation as Nullapon B substitutes. Period Covered by this Report: December 23, 1940 to January 14, 1941. Historical Background: The compounds were requested by the Miscellaneous Products Division. Summary and Conclusions: N, N, N1, N-Tetracarboxymethy1-4-phenylenediamine, (208.2/1772) was prepared by condensing 1 mol. of 4-phenylenediamine with 4 moles of chloroacetic acid. The yield was 24.5$ based on p-phenylenedlamine. Hexacarboxymethyl melamine, (309/3988) N(OH2COOH)2 0 I (H00CH2C)2N-C C-N(CH2COOH)2 DUP050059057 was not obtained by reacting 1 mol. of melamine with 6 moles of chloroacetic acid. Melamine did not react with the chloroacetic acid under the conditions used. Patent Situation; 4 The compounds are believed to be new but no action will be taken pending their evaluation. EXPERIMENTAL PART N.N.N* .N1 -Tetracarboxymethy1-4-Phenylenedlamlne: (JLNB 3392-78) A solution of the sodium salt of 4 moles of chloroacetic acid was added to a mixture of 1 mol. of p-phenylenedlamine and 2 moles of soda ash in a 5-liter flask with stirring and the mixture was heated at 90-95C. for 12 hours with stirring. One mol. additional of Na-salt of chloroacetic acid was added and the mixture was heated at 90-95G, for 20 hours. The product was filtered off. Yield: 24.5$ based on p-phenylenediamine. Analysis: N = 6.98$, Calculated for N,N,N* ,N`-tetracarboxymethyl-p-phenylenediamine- . tetra-Na-salt = 6.54$. Hexacarboxymethy1 Melamine: (JLNB 3392-80) A solution of the sodium salt of 6 moles of chloroacetic acid was added to a mixture of 1 mol. of melamine and 3 moles of soda ash in a 5-liter flask with stirring. The mixture was heated at 90-95 C. for 12 hours. When 1 mol. additional of the sodium salt of chloroacetic acid was added and heating at 90-95*0. was con tinued for 20 hours, the precipitate which separated out of the solution was filtered and dried at 50C . Analysis: N = 27.61$, Calculated for hexacarboxymethyl melamine * N 17.72$, Calculated for melamine, N * 66.7$ which indicates that reaction' did not take place. * Further work on this preparation was abandoned on advice o'f C. W. Croco. Submitted for Typing May 27, 1942 Typed June 8, 1942 RED -2- DUP050059058