A new method for reacting cellulose and formaldehyde in the vapor phase using acid catalysts is described. Acids as weak as boric acid were effective in introducing up to 6% covalently bonded formaldehyde. The results of reaction conditions where catalyst concentration ranged from 1%-10% and reaction temperature ranged from 110°-150°C are presented.A chemical investigation of the structure of the product of the reaction showed that formalde-, hyde preferentially substitutes the secondary hydroxyl groups of cellulose to yield a 'structure represented by the general formula R~O-CH2-O~R', where R and R' indicate glucose residues in parallel chains. * This article is based on a thesis submitted by Robert E.
The crude acidic product was purified by filtering through a 1-inch layer of anhydrous potassium carbonate and was fractionated to give a neutral product.Cyclohexylamme Salt of C, Chlorofluorocarboxylic Acid. A solution of 24 grams (0.05 mole) of C, chlorofluorocarboxylic acid in 25 ml. of ethvl ether was added to 5 grams (0.05 mole) of cyclohexylamine in 15 ml. of ethyl ether.The solvent was evaporated and the remaining solid was recrystallized from cyclohexane to give 14 grams (48%) of white solid.Decarboxylation of C, Chlorofluorocarboxylic Acid. A 27-gram charge of C, chlorofluorocarboxylic acid was neutralized with sodium hydroxide, concentrated under a stream of nitrogen, and dried at 105 °C. in a vacuum oven. A 10.7-gram (0.0214 mole) sample of the dry sodium salt was heated in a small distillation apparatus. A liquid product (8.3 grams) distilled at ca. 160°C. as the pot temperature rose from 160°to 300°C. and gave a positive unsaturation test with aqueous potassium permanganate.A redistilled portion had a molar refractivity confirming the structure CF2C1(CFC1CF2)2CF =CF2.CF2C1(CFC1CF2)2CC1= CF2 is indicated by the presence of fluoride in the pyrolysis residue.
APPLICATIONSThe chlorofluorocarboxylic acids are resistant to thermal decomposition and are very stable toward strong acids, bases, and oxidants. This stability indicates that the acids or their derivatives will be excellent surfactants in some environments where hydrocarbon surfactants fail.The large number of derivatives of the chlorofluorocarboxylic acids potentially available should provide new classes of materials useful as hydraulic fluids, lubricants, plasticizers, and for other applications where a nonflammable, stable material is required.
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