Formaldehyde and Its Polymers'

1220. INDUSTRIAL AND .ENGINEERING CHEMISTRY. Vol. 23, xo. 11. Literature Cited. (8) Egloff and Morrell, Ibid., 18, 364 (1926). (9) Elm, Federation of ...
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I N D U S T R I A L A N D .ENGINEERING CHEMISTRY

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Literature Cited American Society for Testing Materials, Standard No. D236-27 (1930). American Society for Testing Tentative Standard No' D235-26T (1930). Browne, IND.ENG.CHEM.,19, 982 (1927). Browne, Federation of Paint and Varnish Production Clubs, O.@cial W e s t , 96, 106 (1930): Am. Paint J . , 14, 22 (April 7. 1930); Paint, Oil Chem. Rev., 89, 9 (March 20, 1930). Browne, IND.ENG.CHEM..12, 847 (1930). Browne, Ibid., 23, 868 (1931). Browne, Ibid.,as, 874 11931).

Vol. 23, xo. 11

( 8 ) Egloff and Morrell, Ibid., 18, 364 (1926). (9) Elm, Federation of Paint and Varnish Production Clubs, OBcial Digcsf, 105, 474 (1931). (10) Federal Specifications Board, Master Specification 16, Bur. Standards, Circ. 98 (1923). (11) Federal Specifications Board, Master Specification 7b, Bur. Standards, Circ. 86 (1926). (12) Gardner and Holdt, Mfrs. Assocn. u.s,, Tech. Circ. 199 (1923), (18) Nelson, Proc. Am. SOL.Testing Materials, 12, Pt. 2, 485 (lQZ2). (14) Nelson, Schmutz, and Gamble, Ibid.. 16, Pt. 2, 563 (1926). (15) Rhodes and Wells, IND.ENO.CHRM., 21, 1273 (1929).

Formaldehyde and Its Polymers' Frederic Walker T H EROESSLBR & HASSLACHER CHBMIC.\L COXPANY, INC., PBRTKAMBOY,N. J .

LTHOUGH from a structural standpoint formaldehyde is the simplest member of the aldehyde group, its chemistry is exceedingly complicated. In general, the first member of any homologous series of organic compounds is the most unorthodox in its behavior and this is especially true in the case of formaldehyde. This compound shows many reactions that are peculiar to itself and does not take part in some of the standard aldehyde reactions. However, even disregarding its chemical reactions with compounds other than itself and water, volumes could be devoted to the chemistry of its polymers, hydrates, and solutions. Our knowledge concerning these things has been greatly clarified in recent years. At present, however, most of this information remains scattered through the literature, and much of the information that is easily available is confusing and in some cases incorrect. The object of this paper is to summarize briefly the present status of our knowledge of formaldehyde, its solutions and its polymers. Formaldehyde was first prepared by Butlerow (3) in 1859 in the form of one of its polymers by the action of silver oxide on methylene iodide. On the basis of this study he came to the conclusion that the compound thus obtained was dioxymethylene, an "isomer" of the unknown formaldehyde. He gave an account of its characteristic reactions, prepared aqueous formaldehyde solutions by heating it with water and also described