NANKEEN". 



NAPHTHALIC GROUP. 



sro 



Fabian, Ferdinand, Joscdine, Miles, Sylvester, Theobald, Theodore, and a 

 host of others. 



Some further information of a curious nature will be found in an 

 * Essay on Surnames/ by M. A, Lower. 



NANKEEN, a kind of cotton cloth, usually of a yellow colour, 

 imported from China, and taking its name from the city of Nankin, in 

 which great quantities are made. The peculiar colour is natural to the 

 cotton-wool of which the nankeen is made, and not the effect of- any 

 dye. White cloth of similar texture is imported from China; and 

 this, to distinguish it from the yellow kind, is called white nankeen. 

 Nankeen cloth was formerly very much used in England for gentle- 

 men's summer clothing ; but better fabrics of home manufacture being 

 now procurable at lower prices, these have taken the place of the 

 Chinese goods. 



NAPHTHA. The word naphtha is derived from the oriental term 

 nafata, signifying to ooze out, and was originally applied to a yellowish- 

 white, volatile, inflammable, liquid hydrocarbon, which exudes from 

 the soil in certain parts of Persia, Italy, &c. The very fluid portions 

 of those natural tar-like matters [ASPHALT; BITUMEN; PETROLEUM] 

 that issue from the ground in so many parts of the world, having been 

 found to be almost identical with the original nafata, have been in- 

 cluded under the term naphtha, and the latter word is therefore, or 

 rather should be, now used to designate any light, more or less colour- 

 less, inflammable fluid, of mineral origin and immiscible with water. 

 Naphtha is sometimes specifically termed mineral naphtha. 



Other liquids, resembling true naphtha in little else than the cha- 

 racters of volatility and inflammability, have also been called naphtha. 

 Thus wood-spirit has frequently been so named, and is still often 

 spoken of as wood-naphtha ; see METHYL, hydrated oxide of. ACETONE 

 is also sometimes described under the name of naphtha. Lastly, COAL 

 TAB yields by distillation a liquid having all the characters of natural 

 naphtha ; it is, however, generally distinguished as coal naphtha. 



The origin of naphtha is, in all probability, due to the action of 

 internal heat upon beds of coal or peat, these substances being, in nearly 

 all cases, found in the neighbourhood of the petroleum or naphtha 

 springs; moreover, the artificial production of coal naphtha, as just 

 described, gives considerable support to this theory. 



Crude naphtha is usually contaminated with much colouring matter, 

 but from this it may be freed by rectification. When quite pure it 

 contains no oxygen, and hence is usually the liquid in which potassium, 

 sodium, and other metals that have intense affinity for oxygen are 

 preserved. For the latter purpose it must be several times well 

 agitated with about a fifth of its bulk of strong sulphuric acid, then 

 washed with water, and finally distilled from quicklime. 



Pure naphtha is colourless, and of peculiar taste and odour. It is 

 insoluble in water ; soluble in about eight parts of alcohol ; and mis- 

 cible in all proportions with ether, and with the essential oils. With 

 the aid of heat it dissolves one-fourteenth of its weight of phospho- 

 rus, or one-twelfth of sulphur, but deposits them on cooling. It 

 dissolves one-eighth of its weight of iodine, absorbs ammoniacal and 

 hydrochloric acid gases, is attacked by chlorine and bromine, and de- 

 composed by hot concentrated nitric or sulphuric acids. It is an 

 excellent solvent for gutta percha, india-rubber, camphor, and oily or 

 resinous bodies generally ; is indeed largely used for these purposes, 

 but chiefly in lamps as a source of artificial light. Its specific gravity 

 varies from 0'7 to 0'85. 



Naphtha seems to be a mixture of several polymeric hydrocarbons. 

 Pelletier and Walter have extracted, and described three, namely, 

 naphtha (C, t H,.,), boiling point 190 ; naphtltene (C 10 H JO ), boiling point 

 239; and naphth'/le (C 24 H.,,,), boiling point 374. 



Great care should be observed in manipulating with the more vola- 

 tile descriptions of naphtha. It is exceedingly inflammable, and fatal 

 accidents have arisen from its vapour catching fire on the approach of 

 a naked flame. 



For the chief localities of the naphtha springs, and statistics con- 

 cerning their products, see NAPHTHA, in NAT. HIST. Div. 



NAPHTHALAMIDE. [NAPHTHALIO GROUP.] 



NAPHTHALASE. [NAPHTHALIC GROUP.] 



NAPHTHALENE. [NAPHTHALIC GROUP.] 



NAPHTHALIC ACID. [NAPHTHALIC GROUP.] 



NAPHTHALIC GROUP, a division of the Benzoic series of organic 

 compounds. It is chiefly composed of the derivatives of napththalin. 



Naphthalai (C go H 8 ), or hydride of naphthyl (C^H,, H), or naphtha- 

 lene, was first discovered by Garden in coal tar. Faraday determined 

 its composition, and Laurent has particularly investigated its consti- 

 tution. It is a very common product of the decomposition of organic 

 bodies by heat, but its most abundant source is coal-tar. Large quan- 

 tities of it are produced at all gas-works, and ita separation from the 

 tir may be accomplished by the following process : After exposure to 

 air for some time the tar is redistilled; the first portion of the distillate 

 is set aside, the second portion furnishes much naphthalin if artificially 

 cooled, but the last portion comes over in an almost semi-solid state, 

 and on standing for a short time sots into a solid mass of crystals of 

 naphthalin. Much oily matter ia got rid of on submitting the mass to 

 pressure, and the naphtha is finally obtained in a pure state by 

 successive sublimations or recrystallisations from alcohol. 



Naphthalin is colourless, has a somewhat tarry odour, and a burning 

 aromatic taste. It crystallises in large, thin, rhombic plates of pearly 



lustre, and unctuous feel. Exposed to light under a glass covering, it 

 gradually sublimes in magnificent crystals, and altogether presents a 

 very beautiful appearance. It fuses when heated to 174 Fahr., and 

 boils at 428. Its vapour density is 4'582. It is not very inflammable, 

 and when ignited gives off much smoke. It is very volatile in vapour 

 of water. It is insoluble in cold water, very slightly soluble in hot 

 water, but readily so in alcohol, ether, and the fixed and essential oils. 

 It appears also to be soluble in acetic or oxalic acids, but is not acted 

 upon by caustic potash. 



Sulphuric derivatives of Naphthalin. 



Sulphonaphthalic acid (C^H^Ou + 2Aq.). Naphthyl-stdphurous acid, 

 hypostdphonaphthalic acid, or naphthyl-dithionic acid. Obtained by 

 acting upon naphthalin with excess of sulphuric acid at a temperature 

 not exceeding 200 Fahr. ; it crystallises on cooling. It is very soluble 

 in water, alcohol, and oils, but only slightly so in ether. It has an 

 acid, astringent, metallic taste, and at a high temperature is decom- 

 posed. The sijphonaphthalates are monobasic; those of the alkalies 

 are readily obtained in crystals. By substitution processes, the follow- 

 ing compounds of Sulphonaphthalic acid are easily produced ; they 

 all form salts with bases, several of the compounds being crystalline : 



Chlor-sulphonaphthalic acid 

 Broni-sulphonaphthalie acid . 

 Bichlor-sulphonaphtkiilic acid 

 Bibvom-sulphonaphthalic acid . 



Trichlor-sulphonaphthalic acid . 

 Quadrichlor -Sulphonaphthalic acid . 

 Nitro-sulphonaphthal(or thcu)ic acid 

 Binitrc-Milphonaphthalic acid . 



. C, H,BrS s O. 

 . C 80 H 6 C1,S,0. 



C so H,(NO t )S,0 



C 20 H (i {N0 1 ) 2 S. ! 



Disulphonaphthalic acid (C., H g S,p 12 ). Thionaphthic acid, or Jti/po- 

 sulphonapht/dnic acid. This "acid is produced under circumstances 

 similar to those under which Sulphonaphthalic acid is obtained, but at 

 a higher temperature ; fuming sulphuric acid also facilitates the reaction. 

 It is dibasic. Both it and its salts crystallise with difficulty. 



Sulphonaphthalin (C^H^S^O^ C 20 H 8 + HO, S0 3 -2IIO). Produced 

 when vapours of anhydrous sulphuric aqid are passed into fused naph- 

 thalin, the latter being kept in excess. It is a granular body, slightly 

 soluble in water, but more so in alcohol. It is sometimes accompanied 

 by svlpJioglutinic acid (hyposulphoglutinic acid). 



Nitro-derii'atives of Naphtlialin. 



Nitronaphthalin (C 20 H 7 (N0 4 ) ). Nttronaphthalase. Naphthalin is 

 well stirred with five times its weight of cold nitric acid of sp. gr. 1'33. 

 After some days it is found converted into a lemon-yellow mass of 

 mtronaphthalin, insoluble in water, but soluble in hot alcohol or 

 ether, the solutions depositing it in brittle needles on cooling. Heated 

 with lime, it disengages ammonia, and, among other products, yields a 

 substance called by Laurent naphthalase, or, better, naphthase. 



Binitronaphthalin (C 20 H,,(N0 4 ),,). Nitronaphthalese. Naphthalin 

 added to hot strong nitric acid is converted into the above compound, 

 which crystallises out on cooling in pale yellow needles. It is only 

 slightly soluble in alcohol or ether. Boiled with alcoholic solution of 

 potash, ammonia is disengaged, and nitric acid then precipitates, from 

 the solution, dark brown flocks of nitronapkthalesic acid. 



Bromo-Unitronaphthalin (C., H, Br(NOJ ? ). A crystalline body 

 formed on dissolving bibromonaphthalin in nitric acid. 



Tiinitronaphthalin (C 20 H ? (N0 4 ) 3 ). Nitronaphthalise. This com- 

 pound occurs under tliree isomeric modifications. It is obtained on 

 boiling uaphthalin for some days in nitric acid. It is colourless, and 

 crystallises in irregular tables or prisms. Alkalies colour it red. 



The final product of the prolonged action of nitric acid upon naph- 

 thalin is a mixture of oxalic and phthalic acids, thus : 



C 20 H 8 + 10 = 2HO,C 10 H 4 + 2HO.C 4 O e 

 Naphthalin. Oxj-gen. Phthalic acid. Oxalic acid. 



Phthalic acid (C 16 H 6 S = 2HO, C 10 H t ). Naphthalic acid. Alizaric 

 acid. In addition to the method just mentioned, this acid results from 

 the long-continued action of nitric acid upon bichloride of naphthalin, 

 alizarin, or purpurin. [MADDER, COLOURING MATTERS OF.] It may 

 be obtained in the pure state by repeated crystallisation from water, 

 and then forms lamellar groups. It is very soluble in alcohol or ether. 

 By distillation with lime it is converted into carbonic acid and 

 BENZOLE and when heated alone it sxiblimes in beautiful elastic 

 needles of phthalic anhydride (C 10 H 4 ), called also anhydrous phthalic 

 acid, and pyroalizaric acid. It is a bibasic acid, and forms neutral and 

 acid phthalates. 



Trichlorophlhalic acid fC ls H,Cl,0,), clilorophthalmc acid is produced 

 by the action of nitric acid upon sexchlornaphthalin. 



Nitrophthalic add (C 1( ,H,(NOJO,) may be obtained in yellowish 

 rhomboidal crystals by evaporation of the mother liquors from the 

 preparation of the nitronaphthalius. It is bibasic, and forms crystalline 

 salts. By sublimation it is reduced to the anhydrous condition. 



