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propionic acid by the action of hydrochloric acid (40 per cent.) in sealed tubes at 80°.

Dichloropropionic acid crystallises in colourless prisms and melts at 56. The acid dissolves freely in alcohol, ether, chloroform, benzene, and water. The ethylic salt, C2H,Cl2 COOEt, is a colourless liquid, possessing a fruit-like odour. It is slightly heavier than water and boils between 171° and 175°. When saponified with alcoholic potash, it yields ẞ-nonochloracrylic acid, showing that the dichloropropionic acid is really the B-compound. The amide, C2H,Cl2 CONH2, crystallises in white needles or plates. It melts at 140°, and is soluble in water and alcohol, forming fluorescent solutions. W. C. W.

Acids from Drying Oil. By K. HAZURA (Monatsh. Chem., 8, 260— 270. Compare this vol., pp. 359, 798).--Peters (this vol., p. 126, Dieff and Reformatzky (this vol., p. 716), and the author (this vol., p. 359) have on different grounds concluded that the formula of linoleic acid is C18H32O2 and not C16H2802. In order to set this point at rest, the author has undertaken the present research. When sativic acid (Abstr., 1886, 868) is oxidised with alkaline potassium permanganate, the only solid product obtained is azelaic acid.

When linoleic acid is treated with bromine, the hexabromo-compound, C1HBrO2, is the only product. When the tetrabromoderivative of the acid from hemp oil is treated with excess of bromine, no further bromination takes place, showing that the above-mentioned hexabromo-compound is not derived from this.

The linoleic acid from linseed oil gave an "iodide value" which corresponds with a mixture of two acids, one with the formula C18H32O2, the other with the formula C18H30O2. The formation of a tetra- and hexa-bromo-derivative and of linusic acid and sativic acid on oxidation also support the view that linoleic acid is a mixture. The author prepared the CH2O2 acid from the tetrabromo-compound and the C18H30O2 from the hexabromo-derivative; for the former, he proposes the name linolic acid, for the latter linolenic acid.

If linolic acid, prepared from the tetrabromo-derivative, is oxidised with alkaline potassium permanganate, it yields sativic and azelaic acids, but no linusic acid; when treated with bromine, it gives tetrabromolinolic acid, melting at 114-115°.

Linolenic acid, C18H30O2, prepared from the hexabromo-compound melting at 177°, has an "iodine value" of 245, and yields on oxidation no solid acid but linusic acid (m. p. 201°). With bromine, nothing but the hexabromolinolenic acid is formed.

These experiments clearly show that the acids from drying oils contain both linolic acid, CH2O2, and linolenic acid, C1,H3002. The author proposes to examine the acids from poppy oil, hemp-seed oil, and nut oil, which give only sativic acid on oxidation. He enunciates the following law for the oxidation of the unsaturated fatty acids: these acids when oxidised in alkaline solution with potassium permanganate add as many (OH)-groups as they contain free valencies, and form saturated acids which contain the same number of carbon-atoms in the molecule. On this law, he founds an exact qualitative method for the examination of fats and oils. G. H. M.

Turkey-red Oil. By R. BENEDIKT and F. ULZER (Monatsh. Chem., 8, 208-217).-The authors review previous work on this subject (see Abstr., 1884, 946; 1885, 313 and 315) and have prepared the sulpho-acid of a higher fatty acid in order to compare its behaviour with that of the Turkey-red oil soluble in water.

Sulpholeic acid was prepared by heating pure oleic acid (10 parts) at 200-220° with sulphur (1 part). Sulphuretted hydrogen is copiously evolved, and the sulphur is completely dissolved. The sulpho-acid was separated from the unaltered oleic acid by means of the barium salt. When sulpholeic acid is oxidised with potassium permanganate in alkaline solution, it yields a sulpho-fatty acidsulphohydroxystearic acid; this substance and the soluble fatty acid of Turkey-red oil from olive oil behave in many respects in the same manner. Both are miscible with water in all proportions, and are precipitated by sodium chloride and dilute acids; neither are decomposed when boiled for some hours with aqueous potash. In other respects the two acids differ in behaviour, and the author concludes that the Turkey-red oil is the acid sulphate of hydroxystearic acid, thus confirming Liechti and Suida's results (loc. cit.). The authors are satisfied by repeated experiments that the soluble fatty acid of Turkey-red oil from olive oil, and that from oleic acid are absolutely identical, and that in each case the pure acid is not decomposed by boiling with water.

In order to compare the turkey-red oil from olive, cotton-seed and castor oil respectively, the authors prepared the "total fatty acids" from these Turkey-red oils; in order to do this, it was necessary to saponify the triglyceride and also to decompose the sulphates of the fatty acids. This was effected by first boiling the washed crude Turkey-red oil with potash, and then with dilute acid. The resulting fatty acids, of which those from cotton-seed and olive oils were solid whilst that from castor oil was fluid, were then examined by the method proposed by the authors in a former paper (this vol., p. 620). The results are expressed in the following table. It will be seen that the " acetyl-values" of the acids from olive and cotton-seed oils correspond with the conversion of the unsaturated acids in these oils into hydroxy-acids, whilst the number for castor oil remains nearly the same. The table also shows the "acetyl-values of the fatty acids from different commercial Turkey-red oils and also for the insoluble and soluble portion of Turkey-red oil from castor oil.

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The difference in the behaviour of olive oil and castor oil is explained by the different constitution of oleic and ricinoleic acid, the latter being an hydroxy-acid which reacts with sulphuric acid with the elimination of water forming a sulphate, which is again decomposed into the hydroxy-acid and sulphuric acid, whilst the former combines with sulphuric acid forming hydroxystearic sulphate. The acid from Turkey-red oil from olive oil does not take up any iodine, whilst the iodine value of the acid from Turkey-red oil from castor oil is 773, and that of the ricinoleic acid is 85.3. The authors conclude from this that Turkey-red oil from castor oil is of much greater value as a mordant than that from olive oil.

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Action of Sulphur Dichloride on Ethyl Acetoacetate. By A. DELISLE (Ber., 20, 2008-2009).—When ethyl acetoacetate (2 mols.) is treated with sulphur dichloride, a vigorous reaction takes place with evolution of hydrogen chloride, and the whole solidifies to a crystalline mass. The new compound, which has the formula CHOS, crystallises from alcohol in thin, lustrous, colourless prisms, sparingly soluble in ether, insoluble in water, soluble in barytawater with formation of a barium salt. It softens at 75°, and melts at 90-91°. N. H. M.

Constitution of Ethyl Propiopropionate. By A. GEUTHER (Annalen, 239, 386-388).-As Israel (Abstr., 1886, 334) has recently shown that ethyl propiopropionate is decomposed by treatment with sodium ethoxide and ethyl iodide, yielding ethyl propionate and -ethylpropionic acid or methylethylacetic acid, the author concludes that the constitution of ethyl propiopropionate is correctly represented by the formula OH.CEt CMe COOEt.

W. C. W.

Action of Phosphoric Chloride on Chloralide. By R. ANSCHÜTZ and A. R. HASLAM (Annalen, 239, 297-300).-Ethereal oxalates are converted into ethereal salts of dichloroglycollic acid by the action of phosphoric chloride (Abstr., 1886, 786 and 1011); but when chloralide is heated with phosphoric chloride at 290° for several days, the product is an oily liquid of the composition C, HClO3. The new compound boils at 134-136° under 12 mm. pressure, and its density at 20° is 1.7426. W. C. W.

Dissociation of Hydrated Oxalic Acid. By H. LESCOEUR (Compt. rend., 104, 1799-1800).—Crystallised oxalic acid readily

becomes anhydrous, its vapour-pressure at 45° being 10'6 mm. No intermediate hydrate is formed. In moist air, the dehydrated acid not only absorbs 2 mols. H2O, but at 5° the absorption continues until the acid has the composition H2C2O, + 241H2O, and has a vapour-pressure of 5.5 mm. The vapour-pressures of the dihydrate at different temperatures are as follows:

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At 100°, the phenomenon becomes complicated by the decomposition. of the oxalic acid, the vapour-pressure increases continually and becomes equal to 980 mm. after 24 hours.

In order to obtain oxalic acid of constant composition for the preparation of standard solutions, the ordinary crystals must be dried over sulphuric acid of 55° B.

C. H. B.

Action of Iodine on Derivatives of Ethyl Sodiomalonate. By C. A. BISCHOFF and A. HAUSDÖRFER (Annalen, 239, 110-131).— By the action of iodine on ethyl benzylsodiomalonate in ethereal solution, ethyl benzyliodomalonate is produced. It is a colourless oil, and decomposes on hydrolysis, yielding benzaldehyde, alcohol, acetic acid, and carbonic anhydride, that is, the products of decomposition of ethoxybenzylmalonic acid. Iodine replaces the sodium in ethylsodiomalonate, and the product on saponification with alcoholic potash yields potassium ethylethoxymalonate, OEt CEt (COOK), and on treatment with baryta-water yields barium ethyltartronate. Ethyl dicarbontetracarboxylate is formed by the action of iodine on the ethylic salt of sodium acetylenetetracarboxylate.

The properties of the product have been previously described by Bischoff and Rach (Abstr., 1885, 244). W. C. W.

Isomerism of Fumaric and Maleïc Acids. By R. ANSCHÜTZ (Annalen, 239, 161-184).-The author is in favour of the following formule for fumaric and maleïc acids :

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His reasons for regarding maleïc acid as the dioxy-lactone of 7-hydroxycrotonic acid are as follows:-The formation of maleic acid when trichlorophenomalic acid is decomposed by baryta, and the occurrence of maleïc and not fumaric acid in the products of decomCBrCH(OH).

position of bromopyromucic acid, CBr CO COO. The author,

in conjunction with Wirtz, has just shown that maleïnanil is decomposed by baryta, yielding the salt of fumaranilic acid (p. 934). The relation between mesaconic and citraconic acids is probably similar to that between fumaric and maleïc acids

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The conversion of maleïc into fumaric acid by the action of hydrochloric acid is explained by the following equation:



This also explains why fumaric and maleïc acids yield the same product when treated with hydrobromic acid. W. C. W.

Conversion of Fumaric and Maleïc Acids into Aspartic Acid. By ENGEL (Compt. rend., 104, 1805-1807).—Fumaric or maleïc acid is heated for 20 hours at 140-150° with an excess of alcoholic ammonia, the ammonia is expelled, the residue dissolved in water, and the solution acidified with hydrochloric acid. After a short time, white crystals separate and are recrystallised from boiling water. Aspartic acid is the product in both cases; it crystallises in long, rhombic prisms which are identical with the inactive aspartic acid obtained by Dessaignes, and not with the active acid obtained from asparagin. The yield is not theoretical, owing to the fact that aspartic acid is somewhat readily decomposed when heated in sealed tubes at 140150° with aqueous ammonia or even with water. If active aspartic acid is heated under these conditions for 20 hours, 60-70 per cent. of the acid is decomposed and the remainder becomes optically inactive. C. H. B.

Synthesis of Xeronic Acid from a-Dibromo-normal-butyric Acid. By G. FROMME and R. OTTO (Annalen, 239, 272-285).—By the action of molecular silver on a-dichloropropionic acid, Otto and Beckurts (Abstr., 1885, 753) obtained a-pyrocinchonic (dimethylfumaric) acid. By the same process, the authors convert -dibromobutyric acid into xeronic and butyric acids. These acids are separated by the difference in the solubility of the calcium salts in hot water. The butyrate is more soluble than the xeronate. By the action of hydriodic acid at 180°, xeronic anhydride is converted into diethylsuccinic acid. This confirms the accuracy of Roser's hypothesis (Abstr., 1882, 1114) that xeronic acid is diethylfumaric acid.

The silver and copper salts of diethylsuccinic acids, CH12(COOAg) and CH12(COO),Cu + H2O, are amorphous powders sparingly soluble in hot water. W. C. W.

Action of Ethyl Oxalate on Acetone. By L. CLAISEN and N. STYLOS (Ber., 20, 2188-2191).-Ethyl acetopyruvate, CH,Ac-COOEt, is formed by adding a mixture of acetone and ethyl oxalate drop by drop to an alcoholic solution of sodium ethoxide cooled in ice; much heat is developed, and a yellow crystalline sodium compound separates, which yields the ethyl salt on treatment with a dilute acid. It is a colourless oil of sp. gr. = 1·124 at 21°, boils at 134-135° under 40— 41 mm., and at 213-215° under the ordinary pressure, and solidifies

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