Tetramethylene bromide

The formic acid Is distilled off, and the remainder dissolved in warm benzene and washed with a bicarbonate solution to a neutral reaction. After the benzene has been distilled off, the aminomalonic ester xylidide is obtained. This Is treated with an equal quantity of sodium ethylate and boiled with twice the theoretical quantity of tetramethylene bromide in absolute alcohol. 

After 6 hours of boiling, the sodium bromide formed is separated, and the mixture Is steam-distilled in order to remove the excess of tetramethylene bromide. The remaining oil, which mainly consists of delta-bromobutylaminomalonic ester xylidide is separated from the water and boiled with 3 parts of concentrated hydrochloric acid for 3 hours. Thereafter carbonfiltering and evaporation to dryness under vacuum takes place. The residue is dissolved in water, and the pH adjusted with sodium hydroxide to 5.5. The solution is extracted twice with ether, and the water is made strongly alkaline with sodium hydroxide. 

Tetramethylene bromide, AE62 Tet ramethylformam i d i n i urn chloride, AF02... 

Fifty milliliters of 95% ethanol is heated to reflux in a flask equipped with two dropping funnels, a stirrer, and a condenser. In one funnel is placed 54 g. (0.25 mole) of tetramethylene bromide (p. 271) in 100 ml. of ethanol, and in the other a solution of 60 g. (0.25 mole) of sodium sulfide nonahydrate in a mixture of 100 ml. of ethanol and 50 ml. of water. The two solutions are added at such a rate that the additions are completed at the same time. About 3 hours is required to add the reagents, and the mixture is stirred and heated under reflux for an additional 6 hours. The same amounts of reagents... 

CaHsBra, Tetramethylene bromide. 271 CaHgClaO, , -Dichloroethyl ether. Ill CaHsCkS, Bis-2-chloroethyl sulfide... 34... 

The completely saturated unsubstituted molecule, octahydro-l,4-diazo-cine (1,4-diazacyclooctane 80, R = R = H) has been prepared by condensing tetramethylene bromide with N,/V -ditosyl-ED in refluxing alcoholic potassium hydroxide (74MI1). The unsubstituted and -dialkylated com-... 

Adipic acid (n=4) Despite its name (in Latin adipis is fat), this acid (hexanedioic acid) is not a normal constituent of natural lipids but is a product of oxidative rancidity (lipid peroxidation). It was obtained by oxidation of castor oil with nitric acid (splitting of the carbon chain close to the OH group). Synthesized in 1902 from tetramethylene bromide, it is now obtained by oxidation of cyclohexanol or cyclohexane. It has several industrial uses in the production of adhesives, plasticizers, gelatinizing agents, hydraulic fluids, lubricants, emollients, as an additive in the manufacture of some form of nylon (nylon-6,6), polyurethane foams, leather tanning, urethane and also as an acidulant in foods. Adipic acid is used after esterification with various groups such as dicapryl, di(ethylhexyl), diisobutyl, and diisodecyl. 

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