98 



POLYHYDRIC ALCOHOLS 



[48 C-L. 



and potassium acetate (Dusart, Ann. 

 97, 127). Also among the products 

 obtained by passing 1 the vapour of acetic 

 acid over heated zinc dust (Jahn, Ber. 

 13, 2111). 



[D.] Ethyl alcohol [14] by the inter- 

 action of zinc ethyl and carbon tetra- 

 chloride [methane; 1; L; O, &c.] (Beil- 

 stein and Rieth, Ann. 124, 242), or of 

 bromoform and zinc ethyl (Beilstein 

 and Alexejeff, Jahresber. 1864, 470). 



Also from dichloracetal (Lieben, Ann. 

 104, 114; Jacobsen, Ber. 4, 217; 

 Pinner, Ber. 5, 148; Krey, Jahresber. 

 1876, 474) by the action of zinc ethyl 

 (Paternb, Comp. Rend. 77, 458). 



[E.] Acetone [106] through 2 : 2- 

 dichlorpropane by the action of phos- 

 phorus pentachloride (Friedel, Ann. 112, 

 236) and the action of sodium at 130- 

 150 (Friedel and Ladenburg, Zeit. [2] 

 4, 48). Also from 2 : 2-dibrompropane 

 by the same process (Reboul, Ann. Chim. 



[5] 14, 488). 



Acetone combines with bromine to 

 form an unstable dibromide(Linnemann, 

 Ann. 125, 307) which gives acrol&in 

 [lOl] on distillation (Ibid. 310) ; or, by 

 the action of iodine trichloride on acetone, 

 diiodacetone is formed (Simpson, Journ. 

 pr. Ch. 1O2, 380), and this yields acrole'in 

 on treatment with silver cyanide (Ibid.}. 

 Acrolein when reduced with zinc and 

 hydrochloric acid gives allyl alcohol 

 (Linnemann, Ann. Suppl. 3, 260), and 

 the latter yields glycerol by oxidation 

 with potassium permanganate (Wagner, 

 Ber. 21, 1237). 



Or allyl alcohol can be converted into 

 allyl iodide (Tollens, Bull. Soc. [2] 9, 

 396), or allyl carbonimide (Cahours and 

 Hofmann, Phil. Trans. 1857, p. 555) and 

 allylamine (Ibid. Ann. 102, 301). The 

 latter on acetylation and bromination 

 gives acetyl-^3y-dibrompropylamine and 

 the dibrompropylamine by hydrolysis, 

 y-amino-a/3-propyleneglycol by heating 

 the latter with water, and glycerol by the 

 action of nitrous acid (Chiari, Monats. 



19, 571)- 



[P.] Butyric and isouutyric [Vol. II] 



acids ; propylene is among the products 

 of electrolysis of the potassium salts 

 (Bunge, Journ. Russ. Soc. 21, 552; 

 Hamonet, Comp. Rend. 123, 252 ; 



Petersen, Ch. Centr. 1897, 2, 519). 

 Propylene is also among the products 

 formed by passing butyric acid vapour 

 over heated zinc dust (Jahn, Ber. 13, 

 2115). 



[G-.] Isovaleric add [Vol. II] ; pro- 

 pylene is among the products (ethylene, 

 butylene, &c.) formed by passing the 

 vapour through a hot tube (Hofmann, 

 Journ. Ch. Soc. 3, 121) ; also among the 

 products of dry distillation of calcium 

 isovalerate (Dilthey, Ber. 34, 2115). 



[H.] Lactic acid [Vol. II] ; propylene 

 is among the products (ethylene, &c.) 

 formed by distilling calcium lactate 

 (Gossin, Bull. Soc. [2] 43, 49). 



[I.] Azela'ic acid [Vol. II] ; propylene 

 is among the products of distillation 

 with soda-lime (Miller andTschitschkin, 

 Journ. Russ. Soc. 31, 414; Ann. 307, 



375). 



[J.] Thymol [67] gives propylene on 

 heating with phosphorus pentoxide 

 (Engelhardt and Latschinoff, Zeit. [2] 

 5, 616). 



[K.] From acetic acid [Vol. II] and 

 ethyl alcohol [14] through ethoxychlor- 

 acetoacetic ester by the action of sodium 

 on ethylchloracetate in ethereal solution 

 and decomposition of the product by dilute 

 hydrochloric acid (Fittig and Erlenbach, 

 Ann. 269, 15). The ester on heating 

 with dilute hydrochloric acid gives sym- 

 metrical dichloracetone = I : 3-dichlor- 

 propanone (Ibid. 18), and this yields 

 diiodacetone on heating with potassium 

 iodide solution (Volker, Ann. 192, 89). 

 Diiodacetone can be converted into acro- 

 le'in, &c., as under E. 



Or acetic acid can be converted into 

 chloracetic acid and nitromethane by 

 distilling potassium chloracetate with 

 potassium nitrite (Preibisch, Journ. pr. 

 Ch. [2] 8, 316). Nitromethane gives 

 glycerol as below under L. 



[L.] From methyl alcohol [13] and 

 formic aldehyde [91] by converting the 

 alcohol into methyl iodide and nitro- 

 methane by the action of silver nitrite 

 (Bewad, Journ. Russ. Soc. 24, 1 26; Meyer, 

 Ann. 171, 32) ; the sodium or barium 

 compound of nitromethane gives brom- 

 nitromethane by the action of bromine 

 (Tscherniak, Ber. 7, 916; Ann. ISO, 

 128 ; Ber. 30, 2588), and this condenses 



