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MALONE—MALONIC ACID

Grande river. Pop. (1903), after the annexation of Barasoain and Santa Isabel, 27,02 5. There are thirty-eight. villages, or barrios, of which eight had, in 1903,1000 inhabitants or more. The principal language is Tagalog, but Spanish is spoken to some extent. Malolos is served by the Manila & Dagupan railway, and is a trade centre of considerable importance. The cultivation of rice is an important industry. In 1898-QQ, during the Filipino revolt, Malolos was the seat of the rebel government, but it was captured and reduced to desolation in March 1899. In 1904 a new municipal school building, a municipal market and a provincial building were erected.


MALONE, EDMOND (1741-1812), Irish Shakespearian scholar and editor, was born in Dublin, on the 4th of October 1741, the son of a barrister and a member of the Irish House of Commons. He was educated at Trinity College, Dublin, and was called to the Irish bar in 1767. The death of his father in 1774 assured him a competency, and he went to London, where he frequented literary and artistic circles. He frequently visited Dr Johnson and was of great assistance to Boswell in revising and proofreading his Life, four of the later editions of which he annotated. He was intimate with Sir ]oshua Reynolds, to whom he sat for a portrait now in the National Portrait Gallery. He was one of Reynolds' executors, and published a posthumous collection of his works (1798) with a memoir. Horace Walpole, Burke, Canning, Lord Charlemont, and, at first, George Steevens, were among Malone's friends. Encouraged by the two last he devoted himself to the study of Shakespearian chronology, and the results of his “ Attempt to ascertain the Order in which the Plays of Shakespeare were written” (1778) are still largely accepted. This was followed in 1780 by two supplementary volumes to Steevens's version of Dr Johnson's Shakespeare, partly consisting of observations on the history of the Elizabethan stage, and of the text of doubtful plays; and this again, in 1783, by an appendix volume. His refusal to alter some of his notes to Isaac Reed's edition of 1785, which disagreed with Steevens's, resulted in a quarrel with the latter. The next seven years were devoted to Malone's own edition of Shakespeare in eleven volumes, of which his essays on the history of the stage, his biography of Shakespeare, and his attack on the genuineness of the three parts of Henry VI., were especially valuable.' His editorial work was lauded by Burke, criticized by Walpole and damned by Joseph Ritson. It certainly showed indefatigable research and proper respect for the text of the earlier editions. Malone published a denial of the claim to antiquity of the Rowley poems (see CHATTERTON), and in this (1782) as in his branding (1796) of the Ireland MSS. (see IRELAND, WILLIAM HENRY) as forgeries, he was among the first to guess and state the truth. His elaborate edition of Dryden's works (1800), with a memoir, was another monument to his industry, accuracy and scholarly care. In 1801 the university of Dublin made him an LL.D. At the time of his death, on the 25th of April 181 2, Malone was at work on a new octavo edition of Shakespeare, and he left his material to James Boswell the younger; the result was the edition of 182I*g€I1€1'3.lly known as the Third Variorum edition-in twenty-one volumes. Lord Sunderlin (1738-1816), his elder brother and executor, presented the larger part of Malone's splendid collection of books, including dramatic varieties, to the Bodleian Library, which afterwards bought many of his MS. notes and his literary correspondence. The British Museum also owns some of his letters and his annotated copy of Johnson's, Dictionary

A memoir of Malone by James Boswell is included in the Prolegomena to the edition of 1821. See also Sir ]. Prior's Life of Edmond Malone (1860).


MALONE, a village and the county-seat of Franklin county, in the township of Malone, in the N.E. part of New York, U.S.A., about 60 m. E.N.E. of Ogdensburg. Pop. (1890), 4986; (1900), 5935 (910 foreign-born); (1905, state census), 6478; (1910), 6467. It is served by the New York Central & Hudson River; and the Rutland (N.Y. Central Lines) railways. The village has a Memorial Park, Arsenal Green, on the site of an arsenal and parade-ground sold by the state in 1850, a state armoury, the Northern New York Institute for Deaf Mutes, Franklin Academy, St Joseph's Ursuline Academy, and a detention-house for Chinamen entering the state from Canada. From Malone tourists visit the Great North Woods, in the Adirondack foothills, about 15 m. distant. Iron ore and Potsdam sandstone are found near Malone. In the surrounding region hops, potatoes, &c., are grown, and there are dairying and livestock interests. The village is a centre for the collection of hides and pelts. It manufactures woollen goods, paper and pulp, &c., and has foundry and machine shops and car repair shops. Malone, being on the line of communication between lakes Champlain and Ontario, was of strategic importance in the war of 1812, and later was twice the rendezvous of Fenians for attacks on Canada. The township of Malone was settled and erected from Chateaugay in 1805. The village was first known as Harison, was named Ezraville, in honour of Ezra L'Hommedieu in 1808, received its present name in 1812, and was incorporated in 1853.


MALONIC ACID, C3H404 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, IO7, 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 cyan acetic acid (H. Kolbe, Ann., 1864, 131, p. 349; H. Muller, Ann., 1864, 131, p. 352), and by the action of silver oxide on B-di-chloracrylic ester at 125° C. (O. Wallach, Ann., 1878, 193, 2

p S) CCl2:CH-COOCZH5 + Ag2O -l- H2O=

2AgCl + HOOGCH2-CO0C2H, .

It crystallizes in mono clinic 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 an hydride), it combines with aldehyde's 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 wei ht of alcohol, and saturated with hydrochloric acid gas. The wiiole 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 formingvsodium derivatives, that by further treatment with alkyl halides yield the di-alkyl malonic esters. These esters are readily hydrolysed and yield the monoand 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: R'I I

CH2(COOR)2$CHNa(COOR)2%CHR'(COOR)z

lNaoH

co, + CHQR'-COOH Q- cHR'<coo1~1lg, ,I

CHR'(COOH)2NaOH »cNaR'<cooR>. -> cR'R"<cooR>, L NaOH

co, + cHR'R"-cooH<-cR'R"<cooH>,

When sodio-malonic ester is heated to 145° C., it undergoes condensation, with elimination of alcohol and formation of the benzene derivative, phlorogluc-in 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)