MALONIC ACID, C3H4O4 or CH2(COOH)2, occurs in the form of its calcium salt in the sugar beet. It was first prepared in 1858 by V. Dessaignes, who obtained it by oxidizing malic acid (Ann., 1858, 107, p. 251). It may also be obtained by oxidizing allylene and propylene with cold potassium permanganate solution, by the hydrolysis of barbituric acid (malonyl urea) with alkalis (A. Baeyer, Ann., 1864, 130, p. 143); by the hydrolysis of cyanacetic acid (H. Kolbe, Ann., 1864, 131, p. 349; H. Muller, Ann., 1864, 131, p. 352), and by the action of silver oxide on β-di-chloracrylic ester at 125° C. (O. Wallach, Ann., 1878, 193, P. 25)
CCl2:CH·COOC2H5 + Ag2O + H2O =
2AgCl + HOOC·CH2·COOC2H5.
It crystallizes in monoclinic tables, and is readily soluble in water, alcohol and ether. The acid melts at 132° C., and at a higher temperature it rapidly decomposes into acetic acid and carbon dioxide. When heated with bromine and water to 100° C. it forms tribromacetic acid, some bromoform being produced at the same time. Malonic acid, as well as its esters, is characterized by the large number of condensation products it can form. In the presence of a dehydrating agent (such as acetic anhydride), it combines with aldehydes to form compounds of the type R·CH:C(COOH)2, or their decomposition products (formed by loss of CO2) R·CH:CH·COOH.
Many salts of the acid are known and, with the exception of those of the alkali metals, they are difficultly soluble in water. Many esters of malonic acid have been prepared, the most important being the diethyl ester (malonic ester), CH2(COOC2H5)2, which is obtained by dissolving monochloracetic acid in water, neutralizing the solution with potassium carbonate, and then adding potassium cyanide and warming the mixture until the reaction begins. When the reaction has finished, the whole is evaporated and heated to about 130°-140° C. and then allowed to cool. The mass is then covered with two-thirds of its weight of alcohol, and saturated with hydrochloric acid gas. The whole is then poured into ice-cold water, extracted by ether and the ethereal solution distilled (L. Claisen, Ann., 1883, 218, p. 131). It is a colourless liquid boiling at 197°.7-198°.2 C. (W. H. Perkin). It is a most important synthetic reagent; with sodium or sodium ethylate it forms sodio-malonic ester, which reacts readily with alkyl halides, forming alkyl malonic esters, which are again capable of forming sodium derivatives, that by further treatment with alkyl halides yield the di-alkyl malonic esters. These esters are readily hydrolysed and yield the mono- and di-alkyl malonic acids which, on heating, are readily decomposed, with evolution of carbon dioxide and the formation of mono- and di-alkyl acetic acids. The scheme of reactions is shown thus:
When sodio-malonic ester is heated to 145° C., it undergoes condensation, with elimination of alcohol and formation of the benzene derivative, phloroglucin tricarboxylic ester. The addition of urea to an alcoholic solution of sodio-malonic ester results in the formation of barbituric acid (A. Michael, Jour. pr. Chem., 1887 [2], 35, p. 456) The half nitrile of malonic acid is cyanacetic acid, CN·CH·2 COOH, which, in the form of its ester, may be obtained by the action of a solution of potassium cyanide on monochloracetic acid. The solution obtained is neutralized, concentrated on the water-bath, acidified by sulphuric acid and extracted with ether. It is then converted into the lead salt, which is decomposed by sulphuretted hydrogen and the solution is carefully concentrated (Th. Meves, Ann., 1867, 143, p. 201). It melts at 70° C. and at higher temperatures decomposes, with evolution of carbon dioxide and formation of aceto-nitrile, CH3·CN. The true nitrile of malonic acid is methylene cyanide, CH2(CN)2, which is obtained by distilling a mixture of cyanacetamide and phosphorus pentoxide. It is a crystalline solid, which melts at 29°-30° C. and boils at 218°-219° C., and is readily soluble in alcohol and ether.
MALORY, SIR THOMAS, translator and compiler of the famous English classic, the Morte d’Arthur. Previous to the publication of Professor Kittredge’s monograph, Who was Sir Thomas Malory? the identity of this writer remained an unsolved problem. Mr. Sidney Lee, in the Dictionary of National Biography, was compelled to admit that he could find no one of that name fulfilling the necessary conditions. Of direct evidence we have very little; in the concluding passage of the book the author asks the prayers of the reader for “Syr Thomas Maleore knyght,” and states that the book was ended “the ix. yere of the reygne of Kyng Edward the fourth.” Caxton, in his preface, says that he printed the book “after a copye unto me delivered whyche copye Syr Thomas Malorye dyd take oute of certeyn bookes of frensshe and reduced it in to Englysshe”; in his colophon he repeats this statement, adding that he himself is responsible for the division of the work into books and chapters, and that it was printed in 1485. It will be noted that Caxton does not say that he received the book from Malory, only that he had received a copy made by Malory; from this Professor Kittredge draws the conclusion that the compiler was no longer living. The problem then is to find a Thomas Malory who was (a) a knight, (b) alive in the ninth year of King Edward IV. (Mar. 4, 1469-Mar. 3, 1470), and (c) who was no longer living in July (or June) 1485.
All these conditions Professor Kittredge finds fulfilled in the life of Sir Thomas Malory, knight, of Newbold Revell (or Fenny Newbold), M.P. for Warwickshire in 1445. The date of Sir Thomas’s birth is uncertain, but he succeeded his father, Sir John, in 1433 or 1434. Previously to this he had served in France, in the retinue of the earl of Warwick, most probably during the time that that nobleman held the office of captain of Calais. It seems probable that he is also to be identified with a “Thomas Malorie, miles,” who in 1468 was, on account of the part played by him in the Wars of the Roses, excluded with several others from the operation of a pardon issued by Edward IV. As, however, on the death of Sir Thomas on the 14th of March 1470, there was no difficulty as to inheritance, his estates passing to his grandson, he must, if this identification be correct, have come under the general amnesty of 1469. It will be seen, therefore, that so far as it is in our power to state the question this Sir Thomas Malory fulfils all the necessary conditions.