It yields both esters and ethers since it is an acid and also a phenol.
His first original paper (1799) was on the compounds of arsenic and antimony with oxygen and sulphur, and of his other separate investigations one of the most important was that on the compound ethers, begun in 1807.
They are compounds which greatly resemble the mixed ethers of the aliphatic series.
Taking as types hydrogen, hydrochloric acid, water and ammonia, he postulated that all organic compounds were referable to these four forms: the hydrogen type included hydrocarbons, aldehydes and ketones; the hydrochloric acid type, the chlorides, bromides and iodides; the water type, the alcohols, ethers, monobasic acids, acid anhydrides, and the analogous sulphur compounds; and the ammonia type, the amines, acid-amides, and the analogous phosphorus and arsenic compounds.
Oxidation of thio-ethers results in the formation of sulphoxides, R2: S: 0, and sulphones, R2: S02; oxidation of mercaptans yields sulphonic acids, R S0 3 H, and of sodium mercaptides sulphinic acids, R S0(OH).
We may also notice that thio-ethers combine with alkyl iodides to form sulphide or sulphonium compounds, R3; SI.
Of these, undoubtedly the simplest are the ethers (q.v.), formed by the elimination of the elements of water between two molecules of the same alcohol, " simple ethers," or of different alcohols, " mixed ethers."
By replacing the chlorine in the imido-chloride by an oxyalkyl group we obtain the imido-ethers, R C(OR') :NH; and by an amino group, the amidines, R C(NH 2): NH.
As a useful preliminary it is convenient to divide heterocyclic ring systems into two leading groups: (I) systems resulting from simple internal dehydration (or similar condensations) of saturated aliphatic compounds - such compounds are: the internal anhydrides or cyclic ethers of the glycols and thioglycols (ethylene oxide, &c.); the cyclic alkyleneimides resulting from the splitting off of ammonia between the amino groups of diaminoparaffins (pyrrolidine, piperazine, &c.); the cyclic esters of oxycarboxylic acids (lactones, lactides); the internal anhydrides of aminocarboxylic acids (lactams, betaines); cyclic derivatives of dicarboxylic acids (anhydrides, imides, alkylen-esters, alkylenamides, &c.).
The same difference attends the introduction of the methyl group into many classes of compounds, for example, the paraffins, olefines, acetylenes, aromatic hydrocarbons, alcohols, aldehydes, ketones and esters, while a slightly lower value (157.1) is found in the case of the halogen compounds, nitriles, amines, acids, ethers, sulphides and nitro compounds.
He has also shown that the nitrophenols yield, in addition to the colourless true nitrophenol ethers, an isomeric series of coloured unstable quinonoid aci-ethers, which have practically the same colour and yield the same absorption spectra as the coloured metallic salts.
For other methods of preparation see Ethers.'
Chemically they appear to be ether anhydrides of the hexoses, the union being effected by the aldehyde or alcohol groups, and in consequence they are related to the ethers of glucose and other hexoses, i.e.
They behave in most respects as unsaturated compounds; they combine with hydrogen to form amines; with water to form acidamides; with sulphuretted hydrogen to form thio-amides; with alcohols, in the presence of acids, to form imido-ethers R C(:NH) OR'; with ammonia and primary amines to form amidines R C(:NH) NH 2 i and with hydroxylamine to form amidoximes, R C(:NOH) NH 2.
By the alchemists the word was used principally to distinguish various highly volatile, mobile and inflammable liquids, such as the ethers, sulphuric ether and acetic ether having been known respectively as naphtha sulphurici and naphtha aceti.
The hydroxyl group is more reactive than in the phenols, the naphthols being converted into naphthylamines by the action of ammonia, and forming ethers and esters much more readily.
Jochem (Ber., 1901, 34, p. 3337), who arrived at the conclusion that the normal decomposition of diazonium salts by alcohols results in the formation of phenolic ethers, but that an increase in the molecular weight of the alcohol, or the accumulation of negative groups in the aromatic nucleus, diminishes the yield of the ether and increases the amount of the hydrocarbon formed.
These oxygen ethers contain the grouping - N: N -, since they couple very readily with the phenols in alkaline solution to form azo compounds (E.
They behave, however, as tautomeric substances, since their alkali salts on methylation give nitrogen ethers, whilst their silver salts yield oxygen ethers: potassium salt - R N(CH 3).NO 2 nitramine.
Wallach, Ber., 1882, 15, p. 208); and by the action of ammonia or amines on imino-ethers (A.
OH series, also certain ethers, and members of the C„H 27, + 1 CO 2 H series of fatty acids.
Villiger (Be y ., 1901, 34, pp. 2679, 3612) showed that many organic compounds (ethers, alcohols, aldehydes, ketones, &c.) behave towards acids, particularly the more complex acids, very much like bases and yield crystallized salts in which quadrivalent oxygen must be assumed as the basic element.
ETHERS, in organic chemistry, compounds of the general formula R O R', where R, R' =alkyl or aryl groups.
They may be regarded as the anhydrides of the alcohols, being formed by elimination of one molecule of water from two molecules of the alcohols; those in which the two hydrocarbon radicals are similar are known as simple ethers, and those in which they are dissimilar as mixed ethers.
They may be prepared by the action of concentrated sulphuric acid on the alcohols, alkyl sulphuric acids being first formed, which yield ethers on heating with alcohols.
The formation of esters and ethers are generally facilitated by the presence of this acid.
Although nominally tribasic the commonest metallic salts are dibasic. Organic ethers, however, are known in which one, two and three of the hydrogen atoms are substituted (Michaelis and Becker, Ber., 1897, 30, p. 1003).
The /3 compound is hydroxylic in character, whilst the a and -y derivatives behave frequently as if they possess the tautomeric ketostructure, yielding according to the conditions of the experiment either N- or 0-ethers (H.
Investigation of the cyanic ethers (1848) yielded a class of substances which opened out a new field in organic chemistry, for, by treating those ethers with caustic potash, he obtained methylamine, the simplest organic derivative of ammonia (1849), and later (1851) the compound ureas.
Maxwell saw that it was unphilosophical to assume a multiplicity of ethers or media until it had been proved that one would not fulfil all the requirements.
Triphenylmethyl also combines with ethers and esters, but the compounds so formed are unsaturated.
The ethers are neutral volatile liquids (the first member, methyl ether, is a gas at ordinary temperature).