Faraday's discovery of butylene, isomeric with ethylene, in 1825.
This discovery he worked out very thoroughly in investigations of ethylene oxide and the polyethylene alcohols.
To see how this law follows from Dalton's theory let us consider his diagrams for the molecules of water, ethylene and the oxides of carbon.
In water and in ethylene experiment shows that 8 parts by weight of oxygen and 6 parts of carbon, respectively, are in union with one part of hydrogen; also, if the diagrams are correct, these numbers must be in the ratio of the atomic weights of oxygen and carbon.
Ethylene glycol, C2H4(OH)2, was first prepared by A.
Chim., 18 59 , 55, p. 400) from ethylene dibromide and silver acetate.
For example, ethylene, C2H4 j is formed with absorption of 16200 cal., acetylene, C 2 H 2, with absorption of 59100 cal., and liquid benzene, C 6 H 6, with absorption of 9100 cal.
A consequence of this empirical division was that marsh gas, ethylene and cyanogen were regarded as inorganic, and at a later date many other hydrocarbons of undoubtedly organic nature had to be included in the same division.
The binary conception of compounds held by Berzelius received apparent support from the observations of Gay Lussac, in 1815, on the vapour densities of alcohol and ether, which pointed to the conclusion that these substances consisted of one molecule of water and one and two of ethylene respectively; and from Pierre Jean Robiquet and Jean Jacques Colin, showing, in 1816, that ethyl chloride (hydrochloric ether) could be regarded as a compound of ethylene and hydrochloric acid.
However, in 1833, Berzelius reverted to his earlier opinion that oxygenated radicals were incompatible with his electrochemical theory; he regarded benzoyl as an oxide of the radical C 14 H 1Q, which he named " picramyl " (from 7rucp6s, bitter, and &uvyalk, almond), the peroxide being anhydrous benzoic acid; and he dismissed the views of Gay Lussac and Dumas that ethylene was the radical of ether, alcohol and ethyl chloride, setting up in their place the idea that ether was a suboxide of ethyl, (C2H5)20, which was analogous to K 2 0, while alcohol was an oxide of a radical C 2 H 6; thus annihilating any relation between these two compounds.
Instances had already been recorded of cases where a halogen element replaced hydrogen with the production of a closely allied substance: Gay Lussac had prepared cyanogen chloride from hydrocyanic acid; Faraday, hexachlorethane from ethylene dichloride, &c. Here the electronegative halogens exercised a function similar to electro-positive hydrogen.
Thus ethane gives H3C CH2 CH3, propane; ethylene gives H 2 C:CH CH 3, propylene; and acetylene gives HC: C CH 3, allylene.
Perkin, junr., in 1883, that ethylene and trimethylene bromides are capable of acting in such a way on sodium acetoacetic ester as to form triand tetramethylene rings.
The readiness with which ethylene is acted on in comparison with other types of hydrocarbon, for example, is in harmony, he considers, with the circumstance that the greatest distortion must be involved in its formation, as if deflected into parallelism each valency will be drawn out of its position through 2.109° 28'.
From these results Baeyer concluded that Claus' formula with three para-linkings cannot possibly be correct, for the Q2.5 dihydroterephthalic acid undoubtedly has two ethylene linkages, since it readily takes up two or four atoms of bromine, and is oxidized in warm aqueous solution by alkaline potassium permanganate.
In general, therefore, it may be considered that the double linkages are not of exactly the same nature as the double linkage present in ethylene and ethylenoid compounds, but that they are analogous to the potential valencies of benzene.
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.).
It is remarkable that the position of the halogen in the molecule has no effect on the heat of formation; for example, chlorpropylene and allylchloride, and also ethylene dichloride and ethylidene dichloride, have equal heats of formation.
As a general rule, hydrocarbons are colourless; the exceptions include the golden yellow acenaphthylene, the red bidiphenylene-ethylene, and the derivatives of fulvene CH: CH >CH 2, which have been discussed by CH: CH J.
Dihydrothiazoles, or thiazolines, are obtained by condensing ethylene dibromides with thio-amides; by the action of a-haloid alkylamines on thio-amides (S.
When heated with zinc dust, it yields ethylene and water.
Dumas, who regarded them as hydrates of olefiant gas (ethylene); on the other they yielded chloroform, chloral and aldehyde, as well as other compounds of less general interest, and also the method of forming mirrors by depositing silver from a slightly ammoniacal solution by acet aldehyde.
It is an alkaline liquid, which when anhydrous boils at 116.5° C. Nitrous acid converts it into ethylene oxide.
NH2, is prepared by reducing ethylene dicyanide (succinonitrile) with sodium in absolute alcoholic solution (A.
Methane and its homologues give origin to the " paraffin " or " fatty series " of the general formula C,H 2, ,+ 1 000H, ethylene gives origin to the acrylic acid series, C n H 27, - 1 000H, and so on.
If a solution of potassium acetate be electrolysed the products are ethane, carbon dioxide, potash and hydrogen; in a similar manner, normal potassium succinate gives ethylene, carbon dioxide, potash and hydrogen; these reactions may be represented: CH 3 ï¿½CO 2;K CH 3 CO 2 K' CH 2 ï¿½CO 2 1K CH 2 CO 2 K' --> I + + I I -i iI + CH 3 ï¿½CO 21 K CH 3 CO 2 K' CH 2 ï¿½CO 2 iK CH 2 CO 2 K' By electrolysing a solution of potassium ethyl succinate, KO 2 Cï¿½(CH 2) 2 CO 2 C 2 H 5, the KO 2 Cï¿½ groups are split off and the two residues ï¿½(CH 2) 2 CO 2 C 2 H 5 combine to form the ester (CH2)4(C02C2H5)2.
It may be obtained synthetically by heating sodium in a current of carbon dioxide to 360° C.; by the oxidation of ethylene glycol; by heating sodium formate to 400° C. (V.
Soc., 1897, 60, p. 360; " Note on the Dielectric Constant of Ice and Alcohol at very low Temperatures," ib., 1897, 61, p. 2; " On the Dielectric Constants of Pure Ice, Glycerine, Nitrobenzol and Ethylene Dibromide at and above the Temperature of Liquid Air," id.
In contact with nascent hydrogen it builds up ethylene; ethylene acted upon by sulphuric acid yields ethyl sulphuric acid; this can again be decomposed in the presence of water, to yield alcohol, and it has also been proposed to manufacture sugar from this body.
Before the commercial production of calcium carbide made it one of the most easily obtainable gases, the processes which were most largely adopted for its preparation in laboratories were: - first, the decomposition of ethylene bromide by dropping it slowly into a boiling solution of alcoholic potash, and purifying the evolved gas from the volatile bromethylene by washing it through a second flask containing a boiling solution of alcoholic potash, or by passing it over moderately heated soda lime; and, second, the more ordinarily adopted process of passing the products of incomplete combustion from a Bunsen burner, the flame of which had struck back, through an ammoniacal solution of cuprous chloride, when the red copper acetylide was produced.
Alcohol is produced by fermentation from vegetable substances containing starch or sugar, from fermentable sugars produced by the hydrolysis of cellulosic bodies, and synthetically from calcium carbide and from the ethylene contained in coal and coke-oven gases.
The olefines - ethylene, &c. - are generally absorbed by a very strong sulphuric acid prepared by adding sulphur trioxide to sulphuric acid to form a mixture which solidifies when slightly cooled.
Ethane, when heated to this degree, splits up into ethylene and hydrogen, whilst ethylene decomposes to methane and acetylene, and the acetylene at once polymerizes to benzene, styrolene, retene, &c. A portion also condenses, and at the same time loses some hydrogen, becoming naphthalene; and the compounds so formed by interactions amongst themselves build up the remainder of the hydrocarbons present in the coal tar, whilst the organic substances containing oxygen in the coal break down, and cause the formation of the phenols in the tar.
There is very little doubt that the general course of the decompositions follows these iines; but any such simple explanation of the actions taking place is rendered impossible by the fact that, instead of the breaking-down of the hydrocarbons being completed in the coal, and only secondary reactions taking place in the retort, in practice the hydrocarbons to a great extent leave the coal as the vapours of condensible hydrocarbons, and the breaking down of these to such simple gaseous compounds as ethylene is proceeding in the retort at the same time as the breaking up of the ethylene already formed into acetylene and methane, and the polymerization of the former into higher compounds.
Starting with a solid hydrocarbon of definite composition, it would be theoretically possible to decompose it entirely into carbon, hydrogen, ethylene and methane, and, by rapidly removing these from the heating zone before any secondary actions took place, to prevent formation of tar.
The chief unsaturated hydrocarbons present in coal gas are: ethylene, C2H4, butylene, C 4 H 8, acetylene, C 2 H 2, benzene, C 6 H 61 and naphthalene,C 10 H 8, and the saturated hydrocarbons consist chieflyof methane, CH 4, and ethane, C2H6.
The idea held up to about 1890 was that the illuminating value depended upon the amount of ethylene present.
The '1.1' dicarboxylic acid is prepared from ethylene dibromide and sodio-malonic ester.
These acids are obtained by the reduction of the hydrobromides of the diand tetra-hydroterephthalic acids or by the action of ethylene dibromide on disodio-butane tetracarboxylic acid.
It extracts the elements of water from formic acid, giving carbon monoxide; from oxalic acid, giving a mixture of carbon monoxide and dioxide; from alcohol, to give ether or ethylene according to the conditions of the experiment; and from many oxygenated compounds (e.g.
Lithium hydride, LiH, obtained by heating the metal in a current of hydrogen at a red heat, or by heating the metal with ethylene to 700° C. (M.
1889, 22, p. 2220), or by the action of alkali on the compounds formed by the interaction of ethylene chlorhydrin on nitriles.