NAPHTHALIC GROUP. 



NAPIER'S BONES. 



Pktkalami: acid, or napitkalamidt piMalamult (CJUSOJ, result. 

 from the action of ammonia upon anhydrous phthalic acid. 



PllAalimidf, or ma^tAalimidt (C^H.^O.). sublimes in thin plts 

 when acid phtualato of ammonia u heat*.]. It is colourless, almost in- 

 soluble in water, but redilv soluble in boiling alcohol or ether. 



f/tnitlpltlkalimiilt, or pAOialaiile (C^H^NO.), is produced by tin- 

 action of aniline upon ammonia, Pka>i/l-plitl<alamic acid, or phftoMBdM 

 ac.W, contains (C - H, 1 NO.=C I .H.(C 1 ,H.)NO.>. 



Chlorine ami Bromine drriratiret t<f \ajAftal!*. 

 These are extremely numerous, and are of two kind*. First, tho.<c 

 which are simply naphthalins (C,,H,\ in which an atom or atoms of 

 en are replaced by equal quantities of chlorine or of bromine. 

 The following is a list of them : 



Chlor-aaphthiUn (cblonaphtaae) . . . . C,,!! 



Erom-naphtbalin (bronaphusr) . . . . C,,H 7 Hr 



Btchlor-napbtbalin (chlonaplitmr) . . . C. H,C1, 



Bibrom-iujihthalin ('orompbto-i ; . . . . C', l II l Br l ( 



Trichlor-naiibllulin (chlonaphUse) . . . C,.U 3 cl, 

 Tribroin-napbthalin (brouphtJM-) . ... C, n>Br., 



Bromo-bicblor-Raphtbalin (ehlorcbronnphtiac) . C :t HjCl,Br 



Quailrichlor.naphthalin (ilil napato-c) . . C. II,C1, 



Brttno-tricblor-naphthalin (cbluribro&apbtMc) . C t ,n,CljBr 



Hibromo-bichlor-naplithaUn (chlorcbronaphtow) . C,,II 4 CI,Br, 



Quadribrom-naphlbaliii (bronapbtou) . . . C l> II 1 l!r < 



Bibrom.tricblor.n.iphthalin (bromechlonapbtusc) . C, l ,n,C1,Br i 



Srxehlor-naphthalin (cblonupbthalase) . . . CjjIIjCl, 



Pcrchlor.niphthalin (chlonaphtbalii?) . . . C |U C1, 



Several of the above compounds exist in seven, or less, distinct modifi- 

 cation* ; Laurent, the completeness of whose researches on these bodies 

 is only equalled by their importance, accounts for this fact by supposing 

 that each of the eight equivalents of hydrogen in nnphthaliu has its 

 allotted position, and that according as one or other is replaced by the 

 chlorine or the bromine so do the properties of the resulting compound 

 differ. 



In naming the many derivatives of naphthalin, Laurent adopted the 

 word najJit as the root, prefixing it by Mo, bra, &c., to indicate the 

 substituting element; and introducing the vowels, a, t, i, <>. '. win n it 

 was necessary to show that one, two, three, four, or five atoms of the 

 element had been token into the compound molecule. When more 

 than fire replacing atoms were employed, the syllable al was intro 

 duced, and the use of the vowels recommenced. Numerous examples 

 of this useful, though scarcely euphonical, nomenclature will be < ' 

 throughout the article. 



The second class of chlorine and bromine derivatives of naphthalii 

 are combinations of the compounds just described, with addition.! 

 equiralenta of chlorine or bromine, ordinary chlaridet and ' 

 resulting. They are nearly all formed by the direct action of chlorine 

 or bromine upon the different naphthalins. When acted upon 1>\ 

 alcoholic solution of potash, they are split up into hydrochloric o 

 hydrobromic acids, and the chlor- and brom-naphthalins already 

 mentioned. The following is a list of these chlorides and bromides of 

 luphthaliu, or of iU derivatives : 



idif. Obtained by the reduction of nitronaphthalin, either with 

 acetic acid and metallic iron, or with sulphide of ammonium. 



+ 4HO + 9. 



C.^.tNO.) + 6H8 m 

 Nltronnpbthalln. Sulphuretted 



C..H.N 



Kaphtlivlamlne. 



Water, Sulphur. 



Naphthylamine forms white, silky needles. It melts at 122" Fahr., 

 and at 572* sublimes without alteration. It has a disagreeable 



Chloride of napbthalin . . . 

 brom-napblhalln . . 



Bromldf of tribrom-naphlhalln . . 



Blchlorid* of lupbthaltn 



Bleblorobromide of napbthalin . . 



Bichloride of chlor-iuphthalln 

 bicblor-napbtbalin 



,, bibrom-naphtbalin . 



Blbromlde of blcblor-napbthalin 



bromochlor.napbthaUn 



,, blbtom-Dapbtbalin . 



Blcblorlric of bibrom-cblor.naphtballn 



Ilibroinidr of trlbrom.napbUiaUn 



C,,H,, Cl, 

 , C,,H,Br, Cl, 



Cj.HjBr,, Br, 

 , C,,U,, SCI, 

 , C lo n,, Cl a nr 

 . C,.H,CI, 2C1, 

 > C t( II 4 Cl 3 , 2C1| 

 , C,.H.Br,. SCI. 

 , C..H.CI,, SBr, 

 , <'.,Il,I!rCI, SBr, 

 . C JS II,llr t , SBr, 



. C,,H,Br,, snr, 

 This polymeridc of najili 



. 



ind bitter taste, in almost insoluble in water, but very soluble in alcohol 

 or ether. It combines with acids to form white crystalline salts. The 

 hydrudJornU contains C.,,H.N,HC1 ; the nitrate C.,,11 .X.XHo.; the 

 neutral tu-alate 2C,,H ,N, C.O., '2HO : and the acid oxalite C t ,H N. 

 10. Dr. Schiff has also recently (' Ann. Chem. I'harm.'ci. !'"!. 

 obtained the following deriv.itivea of naphthylamine. lodiilf of 

 ua^lilli'.ltiinnwtiium (X(C,H,), (t^H.)!!,. 1) ; sliiniiiK four-sided prisms. 

 /;,v,.mV< <>f tthyl-HaiJithylamm-'. C '> 1 1 . H: I ; acicular 



crystals. X<tjilitl<yl-urea (C.II.M '.,.11 IH.O j j >-hining, flat needles. 



il,(C M H;), Br.) Oxynai>lithslamint 



- OAprodooad by the characteristic reacti-n oi iMphtliy- 

 L-uiiine with perchloride of iron, chlorides of gold, platinum, iwn-nry. 

 zinc, chromic acid, or nitrate of silver. It is the substanco 

 naplilhomtiii by Piria. />i.(y(/iM///-i(/y./i'vi. H,(C,,,H.),, 



C,S,) obtained on limiting napliUiyUimm- with bisuljiliidi- of carbon 

 in a sealed tube for some hours, lly lu-atin-r iwiihtliylsulpho-carba- 

 mide with anhydrous phosphoric aciil. Mr. Mull has jirodiuxtl 



/ naphthyl (C OT H,, C 



the action of potash oil naphthylaulphocarbamide, is also powerfully 

 attacked by anhydrous phosphoric acid anil yields, among other bodies, 

 Cyanate of nu/,htli;/l i(' !!-,( '.A'O.^. Hy]X>nitrousacid acts upon naph- 

 thylaiuiu, and gives rise, to Xitrut't-najJil/it/lin, a pur] 

 taining, according to Church and 1'erkin, (Cj,,ll.i N(MN) : it some- 

 what resembles Laurent's carat Inaji/itc obtained by the action of chromic 

 acid upon naphtholin. 



.\iln,:itt/,litJii/luminc (C BI H,(NO,)N) is a nitric derivative of naphthy- 

 lamine obtained on treating binitronanaphthalin with sulphn 

 hydrogen, the ultimate product, however, is 



Azunaiihthi/laminc, or semimiflttlutlidam (C M H, Nj). The following 

 equation explains its formation : 



+ 12HS = 



+ 8HO + S,, 



Binitronaphthalin. 



A/.onaplitliylamlnc. 



raranif,f,l!,alia, or ant/trad* (C,^!!,, ) f 



thalin accompanies the latter body towards the end of the process of 

 distilling coa]-Ur. It is insoluble in alcohol ; any naphthalin is tln-rc- 

 for* easily dissolved out by that liqui<l. It is a white solid: melting 

 point 354' Fahr. At a temperature above 672*. it boils, sublimes, and 

 oodgoso in Umcllar crystals. Turpentine readily dissolves it. Chlo- 

 rine converts it into cUaranthauin, a crystalline body containing 

 C^H, U,. A corresponding nitric derivative, C W H 10 (NO,),, also 



aiMnlin, or rttiHerin, is another polymcride of naphthalin, 

 obtained daring the distillation of rosin Its melting ; 

 Fahr., boiling point 617*. It is crystalline, slightly soluble 

 alcohol, but readily so when heated ; it is also soluble In ether, naphtha, 

 and turpentine. 



1 )). NapMalidam. 



It is deposited from alcohol in long, brilliant needles. Its salts are 

 crystalline, and have mostly an acid constitution. 



ni'iiin/iliii'" ' ' , I^.XsJjO,,) and n'^'liili'.n'.c (or Mil|>li 



thalidaiuii;) < > are isomeric sulphuric derivatives of 



ii..|ihthylaniine. They form crystallisable salts with bases. 



(>.:-i/na)iliiltiilic C ' i,,). This substance has not yet been 



produced (unless alizarin be identical with it), but two derivati 

 it, containing respectively one and live eijuiv.-ilonts of chlorine in tin- 

 place of one and live of the hydrogen in the above forniulic, are well 

 known. 



By the action of nitric ncid upon bichloride of chlornaphthalin we 

 obtain chloridfof dUoflaampttftyi (O^HtCLO,) called al* 



'liilnilotetmA u.ridc <>J ~< lit.ote. Alcoholic solution of 



converts it into chloroxyn.iphthahte of potash, and from this salt 

 chlonucynaplitlialic arid (C^jH s C10 ) is easily isolated. Chloride of 

 ''i/i'ii/'li'li!/l(C M Cl,0,) obt.iin.'d I iy the action of nitric acid \i\: ui 

 sexchlornaplithaliu is converted by alcoholic potash into pei 

 oxyiiaphthalatc of potash, and from this salt the perddoroxynapktiuilic 



/.] -,, litli.dctic acid (C,,,HC1 3 () ) is easily isolated. 



NAI'HTJIAUDAM. | X.M-IITIIAI.K- &BODP.1 



N Al'llTHALIDIXK. I XAI-IITIIM.U' CKOOP.] 



NAPHTIIAI.1MIDK. [ XAI'IITII M.I.- QB 



NAI'HTHAUX. (NAI-IITIH'. 



XAI'IITHAMKIX. [X.M-IITII.M.I.' Cnofi-.] 



XAI'MTHASK. f\M i 



NAi'iiriiKNi:. pTAnmu.1 



NAl'HTIIKIM-:. A name, given by MM. Jaubert de Bcaulicu and 

 Dosvaux, to a mineral found in the de|rtinent of the Maine-t-l 

 France. It much resembles the elastic bitumen found in i!>< > 

 shire lead mines, and i- pn.l.ably only a variety of ozokerite. [0/OKE- 



r. MIST. Div.] 

 NAPHTHIONIC ACID. [XAI-IITIIAI.IC GROUP.] 



1'IITHOLE. [NAI-HTMX ] 

 NAl'llTHVI.. I NM'inn.M.h- (iiioup.] 

 NAI'MTHYLAMIMv [ NANI uni.ii- (inorr.] 

 NAl'IITIIVI.CAKHAMIIH-:. | NAI-HTIIAI.I- 

 XAl'HTIIVl.lilTlllciM.' A i 1 1 >. | XAI-HTIIAUC OltOUP.] 

 KAPHTHYLSULPHOGAKBAMIDE. [H ,,!..] 



N \rimivi. sri.puriidCs Arm. [NAFBTBAUO OMVP.I 

 NAPHTHYL-TUIO8INN \.\IIXK. | Mr>,Aiu>, on, OF.] 

 NAPHTHYLUREA, (XAI-IITIIAI.H' (;i:.,n-.| 



ii.i:s r,ii\KS, or RODS, a contrivance of Napier to fad 

 the performance of multiplication and division. i-\p!a:nrd by him in 

 his ' HabdologiiC, seu niiine.nitionis ]>cr virgnlas libri ilno,' Ivlinburgh, 

 1C17, 12uio. The invention would have I i:-n perhaps more emi 





