tfl 



Bl'TYI.V 



BUTYRIC ACID. 



By Ik* act** of MM chloride of butyl on sulphide 

 I.SH.produoed; and by iu action 

 a. Aytr^.t, o/ o*y< (fi.HAHS), 

 alcohol i* formed. 



of pboaphoru. (PBr.), and of iodide of phos- 

 phorus (PI.), on butylic alcohol U analogous to that of chloride of 

 phosphorus, and the bnmidt of butyl. C.H.Br, and !</< o/ butyl, 

 C.H.I, which are formed, eloaly r*ssnible the chl-.ri.le. 



HM action of iodide of butyl on ammonia, like that of iodide of 

 ethyl on the MUM mibstanee, gives rise to the formation of various 



a*, in which one or more equivalentii of hydrogen 

 are replaced by the radical butyl (C.U.). One of these, butylaaute, 



tC.H. 

 H , ha* alao been formed by Anderson, along with 

 H 



vthyhuuinc. methylauune, and propyUmine, in the basic part of Dippel's 

 nbmloU. 



By acting with iodide of butyl on variou* silver aalU, Wurtz 

 obtained a number of compound butylic ethers. The carbonate of 

 *"// (C,rL,O,CO.), nitrate of butyl (C.H.O,NO,). afrtate of butyl 

 tC.H.O.C.H.O,), were obtained in this manner. They ctrongly re- 

 mble the corresponding ethyl compound*. 



Cyai,t, of butyl (C.H.C.N). Valerianate of ammonia, by the action 

 of anhydrou* phosphoric acid, lose* four equivalent* of water, and is 

 mmrted into this *ub*tance : 



NH.O. C,,H,0, 4 HO = C.H.C.N 



Valrrianatc of Ammonia. 



Cyanide of Butyl. 



It i* alao obtained, along with other product*, by the oxidation of 

 gelatine, and of caseine, by means of chromic acid. It is a colourless, 

 highly refracting liquid, of a burning aromatic odour and bitter taste ; 

 iU spec. gr. is 0-81, and it boils at 257 Fahr. In it* chemieal deport- 

 ment it resemble* the cyanides of the other alcohol radicals. By 

 boiling with potash it is converted into valerianic acid and ammonia. 



C.H.C.H + KOHO + SHO = KOC 10 H,O, + Ml 



1 ' Valerianate Ammonia. 



Cyanide 



r i p . - 



Valerianate 

 of i'otaah. 



By the careful addition of sulphuric acid to butylic alcohol, BO 

 a* to avoid too great an increase of temperature, lulpkobutytic arid 

 (C.H.O SO,, HO SO,) is obtained, corresponding to sulphovinic'acid. It 

 form* *a)U which crystallise well, and bear the most striking resem- 

 blance to the sulphovinatos. 



If butylic alcohol be treated with excess of chloride of zinc, gaseous 

 and liqukl iiroduct* are formed ; the gases contain, among others, 

 H.), homologous with olefiant 'gas, and hydridt of butyl 

 II , homologous with hydride of ethyL 



Butylene ha* alao been obtained by Faraday, among the product* 

 formed when fatty acid* are passed through a red-hot tube. K.-1U- 

 abo obtained it by the electrolyai. of valerianate of potash. At the 

 ordinary temperature it i* a ga. of the *p. gr. 1-926. It combine* with 

 chlorine in equal volume*, forming a colourless, limpid, aromatic liquid, 

 which boil* at S53* Kahr. Iu formula U C.H.CL; it i* the cl,l.,iide 

 of butylene, and u homologous with the chloride of ethylene, or I Hit, -h 

 liquid, C.H.CI,. Iu iu chemical deportment it perfectly resembles 

 that substance. Bromine al*o combine* with butylene, forming bromide 

 ofbutyttmt (C.H.Br,). 



If, in the preparation of *u]phobutylio acid, the temperature be not 

 kept down, a violent reaction ensues, with the disengagement of sul- 

 phurous acid, and formation of variou* oily hydrocarbon*, which appear 

 to be polymeric with butylene. 



(('Ill \ 



C^H { j h ** not yet been P re P are<1 in P" state. 

 It i* formed by the action of iodide of butyl on a solution of butylate 

 of pota.li in butylic alcohol 



C.11,0, KO -r C,H,I - XI + I C.H.O 



Botflatt of 



of But) I. 



Bl-TYI.AMINK. [BiTTiJ 



VI. h ALCOHOL. [BtTTUl 

 III-TYI.Ic KTIIKIt. [BI-TTI..I 



OK. .|-|. THrJi, ,* P . Thi. group of organic com- 

 to th VAttlllAMc Sr.R.M. The principal iubrtance. 



i P S l""^ U0der * 



'' .. in.] 



BPTYRAI.DKHYDK i , ] 



TYHAMIDK. [AMII.U; BCTTBUAim] 

 Itl-TYKATr-S. [BrTrmi' Ann.] 





. 

 .'.' TYRIC ACID ( C - H '^}0.). Thi. *ub*u,o. occur, in nature 



^ i2^2^? 7 th b '" '" il 



with glycwta., tm the form of butyrine. Thi,, 



which i* a neutral ub*tanoe, become* decomposed on being k< 

 ome time, more especially in] a warm atmosphere, butyric acid being 

 liberated, which then impart* to the butter its peculiar rancid odour. 

 Butyric acid is a frequent product of the action of oxidising agent* on 

 organic substances, and it occur* not les* frequently a* a product of 

 putrefaction and fermentation. Grape sugar, under certain circum- 

 stances, undergoes a peculiar fermentation, by which it is converted 

 into a lubstance, lactic acid, iaomeric with itself. If the fermentation, 

 instead of being arrested at this stage, be allowed to proceed, another 

 change take* place, and the lactic acid become* entirely changed into 

 butyric acid. It U on this process of fermentation that the best 

 methods of preparing butyric acid are based. The method originally 

 described by Pelouze and Gelis baa since been essentially improved by 

 Bensch, by whom the following process ha* been given. 



Six pound* of cane sugar and half an ounce of tartaric acid are 

 dissolved in 26 Ib. of boiling water, and the mixture left for a few day* 

 to allow the cane sugar to become converted into grape sugar. To this 

 mixture, about half a pound of decayed cheese diffused in a gallon of 

 sour skim milk, together with 3 Ib. of finely -powdered chalk, are 

 added, and the whole exposed in a warm place, the temperature of 

 which must not exceed 8595 Fahr. The mass U stirred daily, and 

 generally solidifies in eight or ten days to a mass of lactate of lime. On 

 standing, this gradually becomes more liquid ; carbonic acid and hydro- 

 gen gases escape ; and when, after five or six weeks, the disengagement 

 of gas ceases, the whole of the sugar has passed first into lactic acid, 

 and subsequently into butyric acid, which is present as butyrate 



of li II II-. 



The change may be thus expressed : 



Cnn.,0,, 

 Lactic Acid. 



C.H.O, + 4 CO, + 4I1O 



Butyric 

 Acid. 



(.,!.,,,, 



Acid. 



The solution of butyrate of lime is then mixed with an equal volume 

 of water, and a solution of 8 Ib. of crystallised carbonate of soda is 

 added. The liquid is filtered off from the precipitated carbonate of 

 lime, evaporated to a smaller bulk, and dilute sulphuric acid added. 

 This liberates the butyric acid, which rises to the surface as a dark oily 

 layer, and is removed by means of a siphon. It is then dehydrated by 

 chloride of calcium, and purified by fractional distillation. 



When pure it is a colourless, mobile liquid, a little lighter than 

 water, with on odour at once like acetic acid and rancid butter, and an 

 acrid and burning taste. It boils at 327 Fahr., and distils wit In. in 

 change. It vapour is inflammable, burning with a blue flame, \\li.n 

 exposed to the great cold produced by solid carbonic acid and ethn . it 

 crystallises in large plates. It attacks the skin and produces blisters, 

 like the most powerful acids. 



It is not attacked by sulphuric acid in the cold, and only feebly 

 when hot. Butyric acid dissolves in nitric acid without alteration, but 

 by prolonged boiling it is oxidised, and converted into succinic acid. 



C . H . + <O = C.H.O, + JIIO 



Butyric Acid. 



Succinic Acid. 



The action of chlorine on butyric acid gives rise to new acids, 

 Hifhlorobuti/ric aritl (C.H.CljO.), and JMtsVioJUdrgbttorit arid 

 (C.H.Cl.O.l, which contain 2 and 4 equivalents of chlorine in the 

 place of the same number of equivalents of hydrogen. 



The formula of butyric acid is C.H.O., and it is isom,ii< with 

 acetate of ethyl, and propionate of methyl. By its chemical com- 

 position and relations, and by its physical properties, butyric acid belongs 

 to the series of volatile fatty acids of the general formula CnHnO. 

 it is hence homologous with formic and acetic acids, and it bears the 

 greatest resemblance to those acids, both in its properties, and iu those 

 of its compounds ; the difference being no greater than might be pre- 

 dicated from it* higher position in the series. Analogous to acetic 

 arid wo may consider butyric acid as containing the organic radical 

 bntyryl (C.H,O.), and butyric acid would thus be the hydrated oxide 

 of biityryl(C,H,l .!! 



The butyrates are monobasic, their general formula is C.H.MO., 

 or MO, C,H,O,. When dry, they are inodorous : for the most 

 |rt they are soluble in water and orjntallisable. Hatyrale of toda 

 (NaO, C,H,O,), and butyrate nfpotiuA (KO C.H.O,) are deliquescent 

 alt*. Sutyrate of baryta (BaO, C.H,0, + 2aq) crystallises in long 

 flattened prism*, perfectly transparent ; when thrown on wat.-i . it 

 assumes curious gyratory movement*. Jlulyrate of lime (CaO, C,M.n,i 

 form* transparent fusible needles : it present* in water the same phi -n.i 

 mena a* the baryta salt. Hutyralf a/ajmr(OriO, C,H,O, + aq) forms 

 hratitiful green crystal* of thr ni"ii< hnic system. 



IMyratt of t*yl, or bulyr, H,O, 1 1 " , ) is obtained by 



diRtilling a mixture of bntyrir and, .il.-.ihol, and sulphuric acid. In a 

 state of purity it is a colourless, inllnmm.-.l.l,. liquid, with a prrnliar 

 odmir nwmhlitiK pine apples. A solution of this ether in alcoli.,1 j* 

 used in confectionery mult T the name i.f /,;, ,1,,,,/r nil. The pe. n!i:n 

 fl.-iM.nr of old rum is due to the presence of a miml! quantity of thin 

 ether. 



Alkalies decompile butyric ether Into a butyrate and free alcohol. 



