2 29088,542 aluminum compound formed in the reaction. Flnaby the resulting A-cid mixture Is placed in a fL&& and subjected to steam distiu&tion. This removes carbon disulphide and any exoeas of dibenwfurane. During the steam distihation, the dibenzoluryl heptadecyl ketone sepamtes from the aqueous reaction niixture in the distiuing flask as an oily suvematant liquid. It does not di&Ul over with the carbon disulphide and can 10 be separated from the aqueous solution of aluminum chloride in the distuling flask bY simple decmtation. It is then taken up in ocetone, carA bon tetrachloride or other organie wlvent anu crystaulzed therefrom. in a itimil manner we can start with furane aikyl-substituted furanes and other substitution products. lakewise, as stated, we can start with any acid chloride of the higher fattir acids. Generally we start with the L acid chlorides of fatty go acids having twelve or,more carbon atoms since these fatty acids are readfly available and cheap. Our inventiorx is therefore not limited to the speci:dc compounds described above, sinee we are the first to describe mlxed ketones in which one radical attached to the carbonyl is a furyl radical, orlts.substitution products, and the other radical Is the alkyl residue of a Iligher fatty acid. And by higher fatty acid we mean those acids having six or more carbon atoms. Having,thus described our invention what we clli- is: 1. Mlxed ketones hglving the structural formula R-C-R, 10 wherein R is a furyl radical and R' is an alkyl radical having at least:ftve carbon atoms. 2. Mxed ketones having the structural formula 15 R-C-R' wherein R is a furyl radical and R' is an alkyl radical having at leglst eleven carbon atoms. 20 3. A furyl heptadecyl ketone. 4. A furyl undecyl ketone. ANDERSON W. RALSTON. CARL W. CHRISTENSEN.

Patented Mar. 10, 1936 2,033@542 UNITED STATES PATENT OFFICE 2,033 542 MIXED FURYL-ALKYL KETONES Anderson W. Ralston and Carl W. Christensen Chicago, Ul., assignors tG Armour and Com-' pany, Chicago, Ill., a corporation of IlUnois No Drawing. Application Apr.U @3, 1935, Serial No. 17,875 4 Claims. (Cf. 260-54) T'bis inven("Ion relates to mixed ketones and it compiises, as new compounds, ketones having the generic stru-cture wlierei-n P. is a furyl radical and RI is an alkyl racucal having five or more carbon atonis. The higher fatty acids, and by that we mean lo those fatty acids derived from vegetable and animal oils and fats are e2ctremely abundant materials md can be obtained et little expense. They have never, however, been used to any great extent as raw materials for the synthesis of more 1 5 valuable substances. These fatty acids have been uqed almost exclusively in the soap industry' for making candles, etc., and in but relatively few instq-nces have they been used as raw materials in what might be termed the "fine" organic 2( chemical fleld. 'VVe have now discovered a new class of compouncl,v, which can be made from the higher fatty acids qpd which have chemical and physical propei-tles of marked technical and conunercial 25 interest. We have discovered that the higher fatf@y acid clilorides such as stearyl chloride, myris't,Yl chloride, lauryl chloride, caproyl chloride, and other acid chlorides derived from, and corresponding to the higher fatty acids, can be 30 made to react with furane, or substituted furanes, to give mixed ketones having valuable properties which suit them for use in many technical applications. Many of these mixed ketones are waxy solids and can be crystallized from organic 35 solvents such as benzene, alcohol and others, to give pure ketones. The crystalline products, when melted and allowed to cool, yield substances of cleaxly defined "waxy" character, appearance' and "feel". Others are very high @oiling liquids. 40 We have discovered that they are excellent dielectrics and can be used in electrical insulation. We have also discovered that -these new substances are desirable constituents in.waxing and polishing compounds. When added to lubricating !@5 oils, the ketones of the present invention confer benefleial properties on the oil. In its broacl aspects, our invention cori2prises new products having the generic formula wherein R is a furyl radicai which may be substituted or not, and R' is an all@Yl radical containing the alkyl residue of a Wgher fatty acid. Thus, as an example, one of the new products falling within the scope of our inventioii Lq furyl heptadecyl ketone, which can be written structurally as follows: C-0171IM 5 In this case the C17H35, or heptadecyl radicel, is the alkyl residue of stearic acid, Ci7H35COOH. This particular ketone has a melting poliit of 10 52.5-54, C. Other typical ketones falling within the scope of idur invention are, furyl undecyl ketone, boiling at 165-167, C. at 5 mm. pressure, and methyl furyl heptadecyl ketone melting at 68-69, C. and 16 having the formula: 0 20 The dibenzofuryl compounds are especially interesting and valuable materials. Dibenzofur@l heptadecyl ketone melts at 83- 841 C. and has the formula: 25 30 The corresponding undecyl compound melts at 74-751 C. . All of the kptones of our invention can be made b@ the Friedel-Crafts reaction or by the 35 Grignard synthesis. We find that the FriedelCrafts gives high yields. Thus, for example, when we wish to make dibenzofuryl heptadecyl ketone, We start v;ith dibenzofurane and stearyl chloride. The stearyl 40 chlorid6,can be made in any of the known ways from stearic acid. Generally the stearic acid is reacted with phosphorous pentachloride or other chlorinating agent commonly used for converting aliphatic carboxylic acids to their correspond- 45 ing acid cworides. We then prepare a mixture containi,,ig about 29 parts by weight of stearyl chloride, 16 parts by weight of dibenzofurane and about 200 parts by weight of carbon disulphide. Thi mixture is cooled in an ice bath and about r)o 26 parts of aluminum chloride (dry) are slowly added with stirring until there is no further evolution of hydrochloric acid. The. reaction mixture is then poured into a mixture of Ice and dilute hydrochloric acid to hydrolyze the co,mplex 54