Ether butyl

Experiments have been carried out under different conditions and reached apparently conflicting conclusions. 

Under aerobic conditions, a mixed bacterial culture was able to degrade the substrate with intermediate formation of tert-butanol (Salanitro et al. 1994). 

Evidence from field measurements indicated slow decay near the source of contamination but persistence further downstream. This was consistent with the results of laboratory experiments that showed only slow biodegradation of MTBE under aerobic condition (Borden et al. 1997). 

In a simulated spill, groundwater was spiked with BTEX, MTBE, and chloride as marker, and injected into a sandy aquifer (Schirmer and Barker 1998). Whereas the level of BTEX fell, loss of MTBE was much slower, and only ca. 3% remained after 8 years, although the mechanism of its loss was not resolved. 

Degradation of [U- C]-MTBE and [U- C]-tert-butanol was demonstrated within 105 d in laboratory micrososms containing stream sediments from a contaminated area (Bradley et al. 1994). 

For many natural and synthetic resins, gums, oils. Fats, organic acids, esters, and alkaloids. Beeswax and carnauba wax  

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MTBE Methyltert-butyl ether. Used as a gasoline additive. 

MTBE-ETBE (methyl- or ethyl-tertiary butyl ether)... 

Ecole Nationale Superieure du Petrole et des Moteurs Formation Industrie end point (or FBP - final boiling point) electrostatic precipitation ethyl tertiary butyl ether European Union extra-urban driving cycle volume fraction distilled at 70-100-180-210°C Fachausschuss Mineralol-und-Brennstoff-Normung fluid catalytic cracking Food and Drug Administration front end octane number fluorescent indicator adsorption flame ionization detector... 

The preparation of -butyl bromide as an example of ester formation by Method 1 (p. 95) has certain advantages over the above preparation of ethyl bromide. -Butanol is free from Excise restrictions, and the -butyl bromide is of course less volatile. and therefore more readily manipulated without loss than ethyl bromide furthermore, the n-butyl bromide boils ca. 40° below -butyl ether, and traces of the latter formed in the reaction can therefore be readily eliminated by fractional distillation. 

A small residue of di- -butyl ether, b.p. 142°, remains in the flask. 

Di-n-butyl ether. Technical n-butyl ether does not usually contain appreciable quantities of peroxides, unless it has been stored for a prolonged period. It should, however, be tested for peroxides, and, if the test is positive, the ether should be shaken with an acidified solution of a ferrous salt or with a solution of sodium sulphite (see under Diethyl ether). The ether is dried with anhydrous calcium chloride, and distilled through a fractionating column the portion, b.p. 140-141°, is collected. If a fraction of low boiling point is obtained, the presence of n-butyl... 

Mono-alkyl ethers of ethylene glycol, ROCHjCHjOH. The mono methyl, ethyl and n-butyl ethers are inexpensive and are known as methyl cellosolve, cellosolve, and butyl cellosolve respectively. They are completely miscible with water, and are excellent solvents. The commercial products are purified by drying over anhydrous potassium carbonate or anhydrous calcium sulphate, followed by fractionation after... 

This preparation is an example of the use of di-M-butyl ether as a solvent in the Grignard reaction. The advantages are it is comparatively inexpensive, it can be handled without excessive loss due to evaporation, simple distillation gives an ether free from moisture and alcohol, and the vapour does not form explosive mixtures with air. n-Butyl ether cannot, of course, be employed when the boiling point of the neutral reaction product is close to 140°. 

Prepare a Grignard reagent from 24 -5 g. of magnesium turnings, 179 g. (157 ml.) of n-heptyl bromide (Section 111,37), and 300 ml. of di-n-butyl ether (1). Cool the solution to 0° and, with vigorous stirring, add an excess of ethylene oxide. Maintain the temperature at 0° for 1 hour after the ethylene oxide has been introduced, then allow the temperature to rise to 40° and maintain the mixture at this temperature for 1 hour. Finally heat the mixture on a water bath for 2 hours. Decompose the addition product and isolate the alcohol according to the procedure for n-hexyl alcohol (Section 111,18) the addition of benzene is unnecessary. Collect the n-nonyl alcohol at 95-100°/12 mm. The yield is 95 g. 

The crude bromide contains a little unchanged alcohol and is said to contain some n-butyl ether (b.p. 141°). The former is removed by washing with concen. trated hydrochloric acid and this purification process is satisfactory for most purposes. Both the alcohol and the ether are removed by washing with 11-12 ml. of concentrated sulphuric acid the butyl bromide is not affected by this reagent. 

The preparation of diethyl ether is described here for the sake of completeness. It is an unsuitable exercise for beginners. Di-n-butyl ether (Section 111,57) offers an excellent alternative. 

An alternative method for isolating the n-butyl ether utilises the fact that n-butyl alcohol is soluble in saturated calcium chloride solution whilst n-butyl ether is slightly soluble. Cool the reaction mixture in ice and transfer to a separatory fimnel. Wash cautiously with 100 ml. of 2-5-3N sodium hydroxide solution the washings should be alkaline to litmus. Then wash with 30 ml. of water, followed by 30 ml. of saturated calcium chloride solution. Dry with 2-3 g. of anhydrous calcium chloride, filter and distil. Collect the di-n-butyl ether at 139-142°. The yield is 20 g. 

This separation utilises the fact that n-butyl alcohol is soluble in 50 per cent, sulphuric acid by weight, whilst n-butyl ether is only slightly soluble. 

If, however, the water formed is removed as formed (compare the preparation of di-n-butyl ether. Section 111,57), the sulphuric acid may react completely and the method may be employed for the preparation of the free sulphonic acid. 

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. 

Ethers. Di-re-butyl ether Anisole Diphenyl ether. 

Separations based upon differences in the chemical properties of the components. Thus a mixture of toluene and anihne may be separated by extraction with dilute hydrochloric acid the aniline passes into the aqueous layer in the form of the salt, anihne hydrochloride, and may be recovered by neutralisation. Similarly, a mixture of phenol and toluene may be separated by treatment with dilute sodium hydroxide. The above examples are, of comse, simple apphcations of the fact that the various components fah into different solubihty groups (compare Section XI,5). Another example is the separation of a mixture of di-n-butyl ether and chlorobenzene concentrated sulphuric acid dissolves only the w-butyl other and it may be recovered from solution by dilution with water. With some classes of compounds, e.g., unsaturated compounds, concentrated sulphuric acid leads to polymerisation, sulphona-tion, etc., so that the original component cannot be recovered unchanged this solvent, therefore, possesses hmited apphcation. Phenols may be separated from acids (for example, o-cresol from benzoic acid) by a dilute solution of sodium bicarbonate the weakly acidic phenols (and also enols) are not converted into salts by this reagent and may be removed by ether extraction or by other means the acids pass into solution as the sodium salts and may be recovered after acidification. Aldehydes, e.g., benzaldehyde, may be separated from liquid hydrocarbons and other neutral, water-insoluble hquid compounds by shaking with a solution of sodium bisulphite the aldehyde forms a sohd bisulphite compound, which may be filtered off and decomposed with dilute acid or with sodium bicarbonate solution in order to recover the aldehyde. 

Di re-butyl ether (111,57, scale use 100 ml. Pyrex bolt-head flask). 

Use Learning By Modeling to make models of water methanol dimethyl ether and di tert butyl ether Mini mize their geometries and examine what happens to the C—O—C bond angle Compare the C—O bond dis tances in dimethyl ether and di tert butyl ether... 

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