A historic example is that of the condensation of three molecules of acetone, CH 3 CO CH 3, in the presence of sulphuric acid, to s-trimethylbenzene or mesitylene, C 6 H 3 (CH 3) 3, first observed in 1837 by R.
Somewhat similar condensations are: of geranial or citral, (CH 3) 2 CH CH 2 CH :CH C(CH 3) :CH CHO, to p-isopropylmethylbenzene or cymene; of the condensation product of methylethylacrolein and acetone, CH3 CH2 CH:C(CH3) CH:CH CO CH3, to [1.3.
4]-trimethylbenzene or pseudocumene; and of the condensation product of two molecules of isovaleryl aldehyde with one of acetone, C 3 H 7 CH 2 CH:C(C 3 H 7) CH:CH CO.
CH :CH (OH), formed by acting on formic ester with acetone in the presence of sodium ethylate, readily yields [1.3.51-triacetylbenzene, C 6 H 3 (CO CH 3) 3; oxymethylene acetic ester or formyl acetic ester or ß-oxyacrylic ester, (HO)CH :CH CO 2 C 2 H 51 formed by condensing acetic ester with formic ester, and also its dimolecular condensation product, coumalic acid, readily yields esters of [1.3.
Torray's observations on nitromalonic aldehyde, N02 CH(CHO)2,formed by acting on mucobromic acid, probably CHO CBr:CBr:000H, with alkaline nitrites; this substance condenses with acetone to give p-nitrophenol, and forms [I.3.5]-trinitrobenzene when its sodium salt is decomposed with an acid.
Normal values of K were given by nitrogen peroxide, N204, sulphur chloride, S 2 C1 21 silicon tetrachloride, SiC1 4, phosphorus chloride, PC1 3, phosphoryl chloride, POC1 31 nickel carbonyl, Ni(CO) 4, carbon disulphide, benzene, pyridine, ether, methyl propyl ketone; association characterized many hydroxylic compounds: for ethyl alcohol the factor of association was 2.74-2.43, for n-propyl alcohol 2.86-2.72, acetic acid 3.62 -2.77, acetone 1 .
The a-oxime, on long continued boiling with a concentrated solution of a caustic alkali, is partially decomposed with formation of some acetone and acetoxime (C. Harries, Ber., 1898, 31, pp. 1381, 1808; 18 99, 32, p. 1 33 1).
It is a thick yellowish oil boiling between 242° C. and 250° C. It condenses with acetone in the presence of caustic soda to a quinoline.
Some solutions of nitroglycerin (in ether, acetone, &c.) burn quietly, and the same is the case when it is held in solution or suspension in a colloid substance, as gelatinized guncotton, &c.
Soc., 1901, 79, p. 828) has resolved benzyl-allyl-phenyl-methylamine iodide by boiling with silver d-camphorsulphonate in a nearly anhydrous mixture of acetone and ethyl acetate.
Dry distillation is extremely wasteful even when definite substances or mixtures, such as calcium acetate which yields acetone, are dealt with, valueless by-products being obtained and the condensate usually requiring much purification.
Prior to 1830, little was known of the process other than that organic compounds generally yielded tarry and solid matters, but the discoveries of Liebig and Dumas (of acetone from acetates), of Mitscherlich (of benzene from benzoates) and of Persoz (of methane from acetates and lime) brought the operation into common laboratory practice.
In France, the general denaturizing agent is wood-spirit of at least 58 over-proof, and containing 25% of acetone and 2.5% of "impurites pyrogenees"; 10 litres of this spirit denaturizes Too litres of alcohol.
The solubility of the gas in various liquids, as given by different observers, is zoo Volumes of Brine Water Alcohol Paraffin Carbon disulphide Fusel oil Benzene Chloroform Acetic acid Acetone It will be seen from this table that where it is desired to collect and keep acetylene over a liquid, brine, i.e.
The great solubility of acetylene in acetone was pointed out by G.
Hess, who showed that acetone will absorb twenty-five times its own volume of acetylene at a temperature of 15° C. under atmospheric pressure, and that, providing the temperature is kept constant, the liquid acetone will go on absorbing acetylene at the rate of twentyfive times its own volume for every atmosphere of pressure to which the gas is subjected.
The chief trouble was that acetone expands a small percentage of its own volume while it is absorbing acetylene; therefore it is impossible to fill a cylinder with acetone and then force in acetylene, and still more impracticable only partly to fill the cylinder with acetone, as in that case the space above the liquid would be filled with acetylene under high pressure, and would have all the disadvantages of a cylinder containing compressed acetylene only.
This difficulty was overcome by first filling the cylinder with porous briquettes and then soaking them with a fixed percentage of acetone, so that after allowing for the space taken up by the bricks the quantity of acetone soaked into the brick will absorb ten times the normal volume of the cylinder in acetylene for every atmosphere of pressure to which the gas is subjected, whilst all danger of explosion is eliminated.
The introduction of acetylene dissolved under pressure in acetone contained in cylinders filled with porous material drew attention again to this use of the gas, and by using a special construction of blowpipe an oxy-acetylene flame is produced, which is far hotter than the oxy-hydrogen flame, and at the same time is so reducing in its character that it can be used for the direct autogenous welding of steel and many minor metallurgical processes.
It is manufactured by distilling wood in iron retorts at about 50o C., when an aqueous distillate, containing methyl alcohol, acetone, acetic acid and methyl acetic ester, is obtained.
The amount of methyl alcohol present in wood spirit is determined by converting it into methyl iodide by acting with phosphorus iodide; and the acetone by converting it into iodoform by boiling with an alkaline solution of iodine in potassium iodide; ethyl alcohol is detected by giving acetylene on heating with concentrated sulphuric acid, methyl alcohol, !under the same circumstances, giving methyl ether.
The disadvantage in this process is that the by-products, such as pyroligneous acid, acetone, wood spirit, &c., are lost; as an alternative method, wood is frequently carbonized in ovens or retorts and the volatile products are condensed and utilized.
With aniline it forms benzylidine aniline C 6 H 5 CH: N C 6 H 5, and with acetone, benzal acetone C 6 H 5 CH: CH CO CH 3.
This compound condenses in alkaline solution with compounds containing the grouping - CH 2 - CO - to form quinoline or its derivatives; thus, with acetaldehyde it forms quinoline, and with acetone, a-methyl quinoline.
With ammonia they yield complex condensation products; acetone forming diand tri acetonamines (W.
For dimethyl ketone or acetone, see Acetone.
CH:C(CH 3) 2, forms yellow crystals which melt at 28° C. and boil at 197.2° C. When heated with phosphorus pentoxide it yields acetone, water and some pseudocumene.
Dilute nitric acid oxidizes it to acetic and oxalic acids, while potassium permanganate oxidizes it to acetone, carbon dioxide and oxalic acid.
Acetyl acetone, CH 3 CO CH 2 CO CH 3, may be prepared by the action of aluminium chloride on acetyl chloride, or by condensing ethyl acetate with acetone in the presence of sodium (L.
Acetonyl acetone, CH 3 CO CH 2 CH 2 CO -CH a liquid boiling at 194° C., may be obtained by condensing sodium aceto-acetate with mono-chloracetone (C. Paal, Ber., 1885, 18, p. 59), CH3000H2C1+Na CH [[Coch3(Coor) ->Ch3co Ch2 Ch 000h,(Coor) -Ch3co]] CH2 CH2 000H3; or by the hydrolysis of diaceto-succinic ester, prepared by the action of iodine on sodium aceto-acetate (L.
It has since been shown by Buchner and Albert that yeast-cells which have been killed by alcohol and ether, or with acetone, still retain the enzyme.
The first compound, containing a group COH, or more explicitly 0 = CH, is an aldehyde, having a pronounced reducing power, producing silver from the oxide, and is therefore called propylaldehyde; the second compound containing the group - C CO C - behaves differently but just as characteristically, and is a ketone, it is therefore denominated propylketone (also acetone or dimethyl ketone).
Duppa in 1865 examined the reaction and concluded that Geuther's sodium salt was a derivative of the ethyl ester of acetone carboxylic acid and possessed the constitution CH3COï¿½CHNaï¿½OOOC2H5.
Many derivatives are known, thus ortho-amino-benzophenone, melting at 106° C., can be obtained by reduction of the corresponding nitro compound; it condenses under the influence of heated lead monoxide to an acridine derivative and with acetone in presence of caustic soda it gives a quinoline.
Moissan, contains only a trifling amount of morphia, and the effect produced by it is apparently due, not to that alkaloid, but to such decomposition products as pyrrol, acetone and pyridine and hydropyridine bases.
ACETONE, or DIMETHYL KETONE', CH3.CO.CH3, in chemistry, the simplest representative of the aliphatic ketones.
Soc., 1895, 17, p. 187) manufactures it by passing the vapour of acetic acid through a rotating iron cylinder containing a mixture of pumice and precipitated barium carbonate, and kept at a temperature of from 500° C. to 600° C. The mixed vapours of acetone, acetic acid and water are then led through a condensing apparatus so that the acetic acid and water are first condensed, and then the acetone is condensed in a second vessel.
Crude acetone may be purified by converting it into the crystalline sodium bisulphite compound, which is separated by filtration and then distilled with sodium carbonate.
Acetone is largely used in the manufacture of cordite.
Acetone is a colourless mobile liquid of pleasant smell, boiling at 56.53°C., and has a specific gravity 0.819 (0 deg.
By the action of various reagents such as lime, caustic potash, hydrochloric acid, &c., acetone is converted into condensation products, mesityl oxide C6H10O, phorone C 9 1 14 0, &c., being formed.
Acetone has also been used in the artificial production of indigo.
Acetone has been employed medicinally in cases of dyspnoea.
Metaor iso-xylene, the most important isomer, may be prepared by nucleus-synthetic reactions, or by distilling mesitylenic acid, C 6 H 3 (CH 3) 2 CO 2 H, an oxidation product of mesitylene, C 6 H 3 (CH 3) 3, which is produced on the condensation of acetone, with lime; this reaction is very important, for it orientates meta-compounds.
Quinaldine may also be obtained by condensing ortho-aminobenzaldehyde with acetone in presence of caustic soda (P. Friedlander, loc. cit.).
Knorr, Ann., 1886, 236, p. 69) or from aniline, acetone, formaldehyde and hydrochloric acid (C. Beyer, Jour.
Y-Phenylquinoline, which is probably the parent substance of the cinchona alkaloids, is prepared by heating y-phenylquinaldic acid, the oxidation product of the y-phenylquinaldine, which results from the action of alcoholic potash on a mixture of orthoaminobenzophenone and acetone (W.
With a dissertation on acetone in 1858.
Citric acid digested at a temperature below 40° C. with concentrated sulphuric acid gives off carbon monoxide and forms acetone dicarboxylic acid.
Notwithstanding the inconsistency of his allocation of substances to the different groups (for instance, acetic acid was placed in the vegetable class, while the acetates and the products of their dry distillation, acetone, &c., were placed in the mineral class), this classification came into favour.
With sodium ethylate in ethyl acetate solution it forms the sodium derivative of benzoyl acetone, from which benzoyl acetone, C6H5.CO.CH2.CO.CH3, can be obtained by acidification with acetic acid.
It combines directly with acetone and with various amines.