Ether propyl

Matthews, Melton, and Forman, J. Am. Chem. Soc., 64,1222 (1942). 

A mixture of 180 g. (3.0 moles) of n-propyl alcohol and 90 g. (1.0 mole) of trioxymethylene is cooled, and dry hydrogen chloride is passed into the mixture until it is saturated (4 hours). The upper layer is separated, dried, and fractionally distilled. The product (210 g., 64%) is collected at 26-28°/32 mm., n ° 1.4106. 

Hydrogen chloride gas is passed into a rapidly stirred mixture of 525 ml. of concentrated hydrochloric acid, 450 ml. of 40% aqueous formaldehyde, and 465 ml. (508 g. or 6.0 moles) of thiophene. The reaction mixture is held at 0-10° during this operation, and the hydrogen chloride is passed in until the mixture is saturated. Pouring the mixture into 2 1. of water precipitates an oil which is removed by ether extraction. The ethereal solution is dried over anhydrous potassium carbonate and distilled to give 373 g. (47%) of 2-chloromethyl-thiophene boiling at 78-82°/18 mm. 

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Ethers. Diethyl ether, di-n-propyl ether, di-isopropyl ether, ani ... 

Diethyl ether, b.p. 35 . Di n-propyl ether, b.p. 90. Di propyl ether, b.p. 67 5. Anxsole methyl phenyl ether), b.p. 154 . Phenetole (ethyl... 

The inflammable solvents most frequently used for reaction media, extraction or recrystallisation are diethyl ether, petroleum ether (b.p. 40-60° and higher ranges), carbon disulphide, acetone, methyl and ethyl alcohols, di-Mo-propyl ether, benzene, and toluene. Special precautions must be taken in handling these (and other equivalent) solvents if the danger of Are is to be more or less completely eliminated. It is advisable to have, if possible, a special bench in the laboratory devoted entirely to the recovery or distillation of these solvents no flames are permitted on this bench. 

Di-teo-propyl ether. The commercial product usually contains appreciable quantities of peroxides these should be removed by treatment with an acidified solution of a ferrous salt or with a solution of sodium sulphite (see under Diethyl ether). The ether is then dried with anhydrous calcium chloride and distilled. Pure di-iao-propyl ether has b.p. 68-5°/760 mm. 

CAUTION. Ethers that have been stored for long periods, particularly in partly-filled bottles, frequently contain small quantities of highly explosive peroxides. The presence of peroxides may be detected either by the per-chromic acid test of qualitative inorganic analysis (addition of an acidified solution of potassium dichromate) or by the liberation of iodine from acidified potassium iodide solution (compare Section 11,47,7). The peroxides are nonvolatile and may accumulate in the flask during the distillation of the ether the residue is explosive and may detonate, when distilled, with sufficient violence to shatter the apparatus and cause serious personal injury. If peroxides are found, they must first be removed by treatment with acidified ferrous sulphate solution (Section 11,47,7) or with sodium sulphite solution or with stannous chloride solution (Section VI, 12). The common extraction solvents diethyl ether and di-tso-propyl ether are particularly prone to the formation of peroxides. 

Compounds which dissolve in concentrated sulphuric acid may be further subdivided into those which are soluble in syrupy phosphoric acid (A) and those which are insoluble in this solvent (B) in general, dissolution takes place without the production of appreciable heat or colour. Those in class A include alcohols, esters, aldehydes, methyl ketones and cyclic ketones provided that they contain less than nine carbon atoms. The solubility limit is somewhat lower than this for ethers thus re-propyl ether dissolves in 85 per cent, phosphoric acid but re-butyl ether and anisole do not. Ethyl benzoate and ethyl malonate are insoluble. 

CH3CH=CH2 + CH3CH2CH2OCH2CH3 Propene (9%) Ethyl propyl ether (91%)... 

Silanes react with alkyllithium compounds, forming various alkylsilanes. Complete substitution is generally favored however, less substituted products can be isolated by proper choice of solvent. AH four methylsHanes, vinylsHane [7291-09-1and divinylsilane [18142-56-8] have been isolated from the reaction of SiH and the appropriate alkyllithium compound with propyl ether as the solvent (35). MethylsHane and ethyldisHane [7528-37-2] have been obtained in a similar reaction (36). 

Cationic Starches. Commercial cationic starches are starch ethers that contain a tertiary amino or quaternary ammonium group, eg, the diethylaminoethyl ether of starch or the 2-hydroxy-3-(trimethylammonio)propyl ether of starch [9063-45-0], sold as its chloride salt [56780-58-6]. 

Cyclohexane 60 QHij Methyl propyl ether 103 C4Hi 0... 

Ethyl propyl ether 109 C5Hi20 Sulfur trioxide 2.30 S02... 

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