Volume 1

Watts' dictionary of chemistry / revised and entirely rewritten by H. Forster Morley and M.M. Pattison Muir ; assisted by eminent contributors.

Date:: 1888-1894

Credit: Watts' dictionary of chemistry / revised and entirely rewritten by H. Forster Morley and M.M. Pattison Muir ; assisted by eminent contributors. Source: Wellcome Collection.

Provider: This material has been provided by the Royal College of Physicians of Edinburgh. The original may be consulted at the Royal College of Physicians of Edinburgh.

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$ACETONE-PHENYL-HYDRAZIDE: (CH3)2C:N.NHPh (165°) at 91 mm. Oil. Pre- pared by mixing acetone with phenyl-hydrazine. It dissolves in cold aqueous acids and on warm- ing the solution it is resolved into its constituents (Eeisenegger, B. 16, 662). DI-ACETONE-PHOSPHINIC ACID C6H13P04aq, i.e. (CH3)2CH.CHA.c.P0(0H)„ aq, or, less probably (CH3.CO.CH,)„PH(OH).,aq. Di- acetonyl-phosphinic acid, iso-propyl-acetonyl- phosphonic acid, a-acetyl-iso-butane w-phospho- nic acid [64°]. Formed, by the action of water upon di-acetone-phosphorous chloride (infra). (Michaelis, B. 17, 1273 ; 18, 902): C6H10O.,PCl + 2H20 = C6H,3P04 + HC1. Slender needles. V. e. sol. water or alcohol, v. sol. ether. Strong dibasic acid. Salts.—NH4HA. V. sol. water, si. sol. alco- hol. Crystals.—(NH.,)3HA2 2aq. Insol. alcohol. —BaH,A2 2aq. Needles ; v. sol. water, si. sol. alcohol.—BaA 6aq ; m. sol. hot water ; tri- metric tables, a : b : c = -785 : 1 : 2-525 — PbA.-PbA | PbO.-MgA 6aq; ppd. by al- cohol from aqueous solution in glittering plates. —KHA; deliquescent gum: v. sol. alcohol.— KH3A,; slender needles, v. sol. water, si. sol. alcohol.—Ag2A. Reactions.—1. HN03 forms a tribasic crys- talline acid C|HsPOr,possiblyj8-carboxy-propane- phosphonic acid : CH3.CH(C02H).CH,.P0(0H)2. The salts Ag3A', and Ba.jA'^ are crystalline. Oxim.—CttH16(NOH)P03 [170°]. Colourless crystals ; v. sol. water or alcohol; dibasic acid. Di-Acetone-phenyl-phosphinic Acid C6H1.>(C6Hr)P03, probably (CH3)2CH.CH(CO.CH3).PO(CliH-)OH. [86°]. Prepared by adding P205 to a mixture of acetone and phosphenyl chloride, and treating the pro- duct with water : (1) 2C3H60 + C6H5PCl2-H„0 = C6H1„(C6H5)POCU (2) CliH10(C6H5)POCl2+2H,O = C;H12(C6H,)P03 + 2HC1. Long colourless plates (+ H20). Sol. hot water, si. sol. cold water and ether, v. e. sol. alcohol. The anhydrous acid forms a glassy mass, v. sol. ether. A'Ag; crystals, v. sol. water. (Michaelis, B: 19, 1009.) Di-Acetone-2>tolyl-phosphinic Acid Ci;H1„(C,H,)POs, probably (CH3)2CH.CH(C0.CH3).P0(C7H7)0H. [103°]. Obtained by adding P205 to a mixture of acetone and ^j-tolyl-phosphorous chloride, and treating the product with water. Glistening plates ; sol. hot water, v. sol. alcohol and ether. A'Ag; slender glistening soluble needles. (Michaelis, B. 19, 1012.) DI-ACETONE-PHOSPHORIC-TRI-CHLORIDE C6H10OJ>C13 i.e. ( HsK ~ ? (?) CH...CO.CH-PCL, v ' [115°]. Formed by passing chlorine into a solu- tion of di-acetone-phosphorous chloride in pe- troleum-ether (Michaelis, B. 18, 901). Colour- less crystals ; si. sol. petroleum-ether. DLACETONEPHOSPHORIC-CHLORO-BROMIDE C6H1002PClBr2 i.e. *CH^-^ ~ °{ /?) CH3.CO.CH-PClBr2 K } [142°]. Formed by addition of bromine to a so- lution of di-acetone-phosphorous chloride inlight petroleum (Michaelis, B. 18, 900). Colourless crystals. SI. sol. light petroleum. It is decom- posed by water into mesityl oxide, phosphoric acid, HC1, and HBr. ACETONE-PHOSPHOROUS ACID v. Acetone. DI-ACETONE-PHOSPHOROUS CHLORIDE (CH3),C-0 C6H10O2PCl i.e. i i (?) 6 10 2 CH3.CO.CH.PCl v ' [36°]. (154°) at 100 mm.; (235°) at 745 mm. S.G. (liquid) if 1-209. Prepared by slowly add- ing A1,C16 (8 pts.) to a cooled mixture of PC13 (50 pts.) and 1\ times its volume of acetone; yield: 5 pts. It is decomposed by water into di-acetone-phosphinic acid C6HI3P04 and HC1. It readily combines with 1 mol. of chlorine or bromine (Michaelis, B. 17, 1273; 18, 898). ACETONE SULPHONIC ACID v. Acetone. ACETONIC ACID v. h-Oxy-iso-butyric Acid. DI-ACETONIC ALCOHOL v. Acetyl-butyl A1COHOL. ACETONINE C9H!8N2. This base described by Stadeler (A. Ill, 277),Hlasiwetz (4.76, 294), and Mulder (A. 168, 228), was found by Heintz (A. 201, 102) to be a mixture of di-acetonamine, tri-acetonamine, and tri-acetone-di-amine. ACETONINES. Bases obtained by dehy- drating acetone-alcamines by cone. H2S04. Ethylidene-di-acetonine CSH15N i.e. CH:CH.CH2 CH..CH-.CH i i or i i MeCH.NH. CMe2 MeCH.NH.CMe, Tri-metliyl-tetra-hydro-pyridine. (132°-i37°.) Formed from ethylidene-di-acetone-alcamine (1 pt.) and cone. H,S04 (3 pts.) by heating for li hours at 100°. Colourless oil with alkaline reaction. Volatile with steam. SI. sol. water, more soluble in cold than in hot water. Miscible with alcohol, ether, or chloroform. Heated with HI, it yields iodo- tri-methyl-piperidine, C5H7Me3IN [60°]. Salts.—B'HI ; slender, sparingly soluble needles.—B'HBr; small soluble trirnetric pyra- mids (Fischer, B. 17, 1795). Benzylidene-di-acetonine C]3H,,N i.e. H2C-CH = CH HC = CH-CH2 i i or i i PhHC-NH-CMe2 PhHC-NH-CMe2. Phenyl-di-methxjl-tetra-hydro-pyridine. Formed by the action of strong H2S04 on benzylidene- di-acetone-alcamine. Distils undecomposed. Volatile with steam. V. sol. alcohol or ether, v. si. sol. water. Salts.—B'HBr: colourless tables or needles, si. sol. cold water.—B'HI ; sparingly soluble needles.—xB'HAuCl4. (Fischer, B. 17, 1797.) Tri-acetonine H2C.CH:CH C,H,.N t.e. i i (146°) at 740 mm. 0 Me2C.NH.CMe2 v ' Tetra-methyl-tetra-hydro-pyridine. Prepared by heating tri-acetone-alcamine (1 pt.) with strong H2S04 (3 pts.) on a water- bath for an hour, pouring into water, neutralising the acid, and distilling the base over with steam (Fischer, B. 16, 1604). Properties.—Mobile fluid, smelling like pipe- ridine. It combines with water forming a hydrate crystallising in long white needles, which give off their water at a moderate temperature. Vo- latile with steam. Poisonous. By heating with HI it gives iodo-tetra-methyl-piperidine. Salts.—B'HBr; large white prisms, si. sol. cold water.—B'HCl; v. sol. water or alcohol.— B'HAuCl4; yellow needles.$