lihn ctl SrondrF19un 3. Changms In vlrcoslty with Increose ond decrees. in tmmpwotum In a PVM/MA-HA dispwslon prepared at 17OoF. t h i s point the solution became slightly more turbid and assumed a n amber color (5).No appreciable change in viscosity w a s observed when PVM/MA copolymer solutions were heated a t different temperatures for varying periods of time (5). Thus, if the decrease in viscosity, observed in the case of solutions of t h e half amide, is due t o oxidative degradation, it is poss i b l e that t h e reactivity of t h e tertiary hydrogen atoms is governed in part by t h e nature of the carboxylate groups.T h e replacement of carboxyl hydrogens with t h e amide and/or ammonium groups may favor t h e formation of hydroperoxides, which in turn readily decompose to bring about chain scission.Unfortunately, no attempt w a s made to investigate the fundamental a s p e c t s of t h e observed viscosity behavior. However, t h e experiments reported were helpful in devising methods for t h e preparation of improved lithographic plate coating solutions. ACK NOWL EQGYENTT h e author wishes t o express h i s appreciation to F. Trusheirn and L. R. Wickland for their interest and c o o p e r e tion in t h i s work and to W. W. Rinne for h i s suggestions in the preparation of the manuscript. Acknowledgment is also made t o t h e Corps of Engineers, U. S. Army, Anny Map Service, for permission to publish t h e r e s u l t s of this work. LITERATURE CITED (1) Cletc, L P., "Ilford Yanud of P m c e m Work," p 237, Word (2) General Anlllne L Fllrn Cop., New Product Bull. P-103 (JM.

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some l,2-epoxy-2-methyipropane (8%) was also present. For the case of 1-butene the epoxide mixture consisted largely of 1,3-and 2,3-epoxybutanes as well as some ethylene and propylene oxides. No 1,2-epoxybutane was found.

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Products obtained from vapor-phase oxidation of 1 -hexene and n-hexane differ considerably. Hexane is attacked mainly at the second carbon in the chain and gives a mixture of cyclic ethers (largely 2,5-dimethyltetrahydrofuran and 2,4-epoxyhexane), carbonyls (acetaldehyde and formaldehyde), and olefins (C2-Ce). Hexene apparently is attacked all along the chain and gives 1,2-epoxyhexane, C1-C3 carbonyls including acrolein, and hexenals as major products. Minor products from hexene are 2,5-dimethyltetrahydrofuran, 2,4-, 1,3-, and 3,4-epoxyhexanes (all via the abstraction of a hydrogen atom by the intermediate free radical), 2-methyl-5-ethyl-tetrahydrofuran (via the addition of a methyl group to the intermediate free radical), and 2-oxabicyclo [2,2,1 ] heptane (resulting from attack on the terminal methyl group). Hexene, unlike C2-C4 olefins, does not give Ci and Cs aldehydes in equivalent amounts. This work was undertaken to determine exactly how 1hexene compares with lower molecular-weight (C2-C4) olefins and n-hexane on vapor-phase oxidation. All experiments were carried out in the presence of a "rain" of fine particulate inert solids to prevent inflammation and achieve temperature control. Earlier work in this laboratory (Jones et al., 1969a,b) demonstrated that: The major products from C2-C4 olefins consisted of the olefin oxides plus the carbonyl or carbonyls formed by cleavage of the double bond; the inert solids eitherTable I. Distillation of Hydrocarbon-Rich Layer Product from Oxidation of 1-Hexene" Charge: 9232 grams Fractions Column efficiency Fraction Bp range, Ref. index, collected theor. plates6 wt, g °C n™D range