,transcrib]'s ,notes3 ,illu/ration has be5 mov$ s x does n break up ! p>agraph4 ,z ?is 0 a h&-writt5 !sis1 ! spell+1 punctuation & hyph5ation is v inconsi/5t4 ,! orig9al spell+1 hyph5ation & punctuation h be5 left un*ang$4 ,subscripts appe>s z ,x :]e ,x is an integ]4 ,multi-l9e curly brackets h be5 replac$ ) multi-l9e squ>e brackets4 ,,on ,,sulphonfluoresce,n ,,& ,,"s ,,( ,,its ,,d]ivatives4 ,,diss]tation ,pres5t$ = ! ,degree ( ,doctor ( ,philosophy at ! ,johns ,hopk9s ,univ]sity by ,c4 ,will>d ,hayes1 #ahhg4 ,cont5ts4 p4 ,introduction #c4 ,i ,or?o-sulpho-b5zoic acid4 ,prep>ation f tolu5e & ,h#b,,s#d #g4 0 0 p>a-nitro-tolu5e & ,h#b,,s#d #h4 ,oxidation ( tolu5e-o-sodium sulphonate #ab4 ,prep>ation ( ,sulph9ide f 0 0 #ad4 0 0 0 by *lorsulphonic acid4 #ag4 ,conv]sion ( sulph9ide into o-sulphob5zoic acid4 #be4 ,analysis ( & cry/allography ( 0 0 0 #bh4 ,,ii ,sulphonfluorescen--previ\s attempts #bi4 ,prep>ation & purification ( s-fluorescen #cj4 ,analyses ( 0 #cd4 ,prop]ties ( 0 #ce4 ,salts4 ,ba4 & ,ca4 ( 0 #cg4 ,acetyl d]ivative ( 0 #da4 ,br sub/itution products ( 0 #db4 ,action ( ,h#b,,s#d on 0 #dd4 ,action ( ,h,cl on 0 #de4 ,r$uction ( 0 #df4 ,conclusion4 #dg4 ,on ,sulphonfluorescen & "s ( its ,d]ivatives4 ,introduction4 ,! close analogy 9 composition & /ructure betwe5 ph?alic acid & or?o-sulpho-b5zoic acid sugge/s ! possibility ( obta9+ f ! latt]1 by its action on ph5ols1 sub/ances analog\s to ! ph?alens4 ,if su* comp\nds c\ld be made !y w\ld af=d a favorable opportunity ( /udy+ ! effects produc$ 9 ! prop]ties ( a comp\nd by ! replacem5t ( ,,co by ,,s#b4 ,x 0 ) a view to su* /udy t ! foll[+ discuss$ "w 0 und]tak5 at ! sugge/ion ( ,pr(4 ,rems5 & c>ri$ on "u 8 con/ant guidance4 ,"s exp]im5ts previ\sly p]=m$ by ,rems5 & ,palm] 7,a4,g47 indicat$ ! possibility ( ! =mation ( a fluoresc5t sub/ance by ! action ( or?o-sulpho-b5zoic acid on resorc9 b !y did n succe$ 9 obta9+ any def9ite cry/alliz$ comp\nd f ! reaction4 ,! *ief ob/acle to be ov]come 9 ! "w is ! difficulty 9 obta9+ ! o-sulpho-b5zoic acid & a l>ge proportion ( ! "w "h describ$ 0 appli$ 9 t direction4 ,or?o-sulpho-b5zoic acid3 ,me?ods = its prep>ation4 #a4 ,f tolu5e & ,h#b,,s#d4 ,a me?od employ$ by ,rems5 & ,fahlb]g 7,am4 ,*4 ,j\r4 ,vol4 #a4 p 7 = gett+ ! sulphonic acid gr\p 9 ! or?o position to me?yl 02 7a7 treat tolu5e ) fum+ ,h#b,,s#d =m+ ?us or?o- & p>a- tolu5e sulphonic acids1 7b7 make ! calcium salt ( ! sulphonic acids ?us =m$ & f ?is ! potassium salt4 7c7 treat ?is mixture ( potassium tolu5e sulphonates ) phosphor\s p5ta-*loride =m+ ! correspond+ sulphon*lorides4 ,"o ( ^! 7p>a7 be+ a solid & ! o!r 7or?o7 an oily liquid a ne>ly complete sep>ation c\ld be effect$4 ,! difficulty ) ?is me?od is h[ev] t ! l>g] "p ( ! product is ! p>a & only a comp>atively small proportion ( ! or?o comp\nd is =m$4 #b4 ,f p-nitro-tolu5e & ,h#b,,s#d4 ,a second me?od employ$ consi/s 9 />t+ ) p-nitro-tolu5e4 ,?is :5 treat$ ) ,h#b,,s#d =ms tolu5e p-nitro o-sulphonic acid4 ,if n[ a me?od c\ld be obta9$ = remov+ ! nitro gr\p ! desir$ result w\ld be atta9$4 ,! attempt 0 made by ,rems5 & ,palm] 7,a4,g47 to accompli% ?is by 7a7 r$uc+ ! nitro comp\nd to ! amide1 7b7 mak+ ! diazo comp\nd & 7c7 boil+ ?is ) absolute alcohol4 ,accord+ to g5]ally accept$ views ?is %\ld effect ! removal ( ! diazo gr\p & its replacem5t by hydrog54 ,exp]im5ts h[ev] %[$ t ! replacem5t 0 made n by hydrog5 b by ! e?oxy gr\p -,,oc#b;,h#e4 ,?is me?od 0 !re=e impracticable4 ,a modification ( ?is me?od 0 sugge/$ by an obs]vation ( ,baey] & ,lieb]mann t if ph5yl hydraz9e be boil$ ) a dilute solution ( copp] sulphate ! hydraz9e gr\p is replac$ by hydrog5 & b5z5e ?us =m$4 ,h5ce x 0 believ$ t if ! hydraz9e comp\nd %\ld be made f diazo comp\nd m5tion$ above1 ! correspond+ hydroc>bon1 i4e4 tolu5e o-sulphonic acid c\ld be obta9$4 ,! results ( exp]im5ts %[$ t ?is af=d$ a practicable me?od ( prep>+ tolu5e or?o-sulphonic acid4 ,aft] exp]im5t+ ) v>i\s modifications ( ! me?od ! foll[+ 0 f\nd to be ! be/ adapt$ to ! purpose4 ,! potassium salt ( tolu5e p-nitro-o-sulphonic acid is easily obta9$1 z already /at$1 by heat+ p-nitro tolu5e on ! wat] ba? ) ?ree times its weight ( fum+ ,h#b,,s#d1 neutraliz+ ) *alk & to ! solution ( calcium salt ?us obta9$ add+ a slight excess ( ,k#b;,,co#c4 ,on filt]+ f4 ! precipitat$ ,ca,c,o#c & evaporat+ slightly1 ! salt is obta9$ 9 long ne$le %ap$ cry/als ( a pale /raw yell[ color4 ,?is is ,,*#c ,c#f;,h#c,,s#b,,oh 7o7 ,,no#b 7p74 ,! r$uction ( ! nitro gr\p is be/ effect$ by means ( t9 & ,h,cl1 9 ! proportion1 salt #e p>ts1 t9 #f p>ts & conc5trat$ ,h,cl #cj p>ts4 ,! amido acid =ms a comp\nd ) t9 :i* cry/allizes f ! ,h,cl toge!r ) /ann\s *loride4 ,?is comp\nd may be brok5 up & ! t9 remov$ by cont9u$ boil+ ) wat]4 ,a bett] me?od ( remov+ ! t9 is by dissolv+ ! comp\nd 9 ,na#b;,,co#c4 ,?is =ms a salt ) ! amido acid & ?r[s d[n ! t9 z ,sn7,,oh7#b1 a :ite floccul5t precipitate4 ,on filt]+ & add+ to ! solution conc4 ,h,cl1 ! free amido acid is deposit$ 9 *>act]i/ic colorless1 rhombic cry/als1 hav+ ! =mula ,,*#c ,c#f;,h#c,,s#b,,oh 7o7 ,,nh#b 7p7 ,! me?od at fir/ employ$ = prep>+ ! hydraz9e comp\nd consi/$ 9 treat+ ! amido acid1 susp5d$ 9 ,h,cl1 ) potassium nitrite & !n ) /ann\s *loride4 ,! t9 0 !n remov$ f ! solution by ! addition ( sodium c>bonate & ! hydraz9e comp\nd ?r[n d[n ) ,h,cl4 ,?is me?od h[ev] gave poor results ! yield be+ only ab\t #ej ( ! !oretical4 ,ano!r me?od 0 accord+ly sub/itut$ = ! above1 namely t ( ,/reck] & ,rm] 7,b]4 ,,iv4 s #ghd47 ,by ?is ! diazo comp\nd is made fir/ & isolat$4 ,?is is done by susp5d+ ! f9ely p[d]$ acid 9 absolute alcohol1 cool+ & pass+ a curr5t ( ! oxides ( nitrog5 ?r\gh 9 ! ord9>y way4 ,! acid *anges 9 appe>ance1 becom+ m cry/all9e & slightly d>k] & settles quickly on be+ %ak54 ,! reaction "h may be express$ ?us-- ,,*#c ,,*#c ,c#f;,h#c ,,s#b,,oh ,,hno#b ,c#f;,h#c ,,s#c #b;,h#b,o ,,nh#b ,n,n ,:5 ! reaction is complet$ z %[n by ! appe>ance ( ! susp5d$ p[d] x is filt]$ & :ile /ill fre% is add$ to a solution ( acid sodium sulphite z long z x cont9ues to dissolve readily4 ,to ?is solution !re is add$ a quantity ( solution ( acid sodium sulphite equival5t to t already us$ & ! solution is !n boil$4 ,x has at fir/ a deep r$ color b 9 a few mom5ts becomes light r$di% yell[4 ,! reaction ( ,h,na,s,o#c on ! diazo comp\nd may be repres5t$ 9 two /ages1 ! fir/ portion =m+ an addition product & ! second act+ z a r$uc+ ag5t4 ,?us1 ,,*#c ,,*#c #a4 ,c#f;,h#c ,,s#c ,h,na,s,o#c ,c#f;,h#c ,,s#b,o,na ,n,n ,n,,nso#c;,h ,,*#c #b4 ,c#f;,h#c ,,s#b,o,na ,h,na,s,o#c ,h#b,o ,n,,nso#c;,h ,,*#c ,c#f;,h#c ,,s#b,o,na ,h,na,s,o#d4 ,,nh-,,nhso#c;,h ,to ! hot solution an excess ( conc4 ,h,cl is add$ :5 ! hydraz9e comp\nd sep>ates 9 a few mom5ts 9 lu/r\s yell[ scales :i* completely fill ! solution4 ,on ! addition ( ! ,h,cl a l>ge am\nt ( ,,s#b is giv5 (f f ! excess ( ,h,na,s,o#c & ! solution becomes deep r$4 ,:5 ! hydraz9e has sep>at$ ! "m liquor is aga9 yell[4 ,! reaction is repres5t$ z foll[s3 ,,*#c ,c#f;,h#f,,s#b,o,na ,h,cl ,h#b,o ,,nh-,,nhso#c;,h ,,*#c ,c#f;,h#c,,s#b,,oh ,h#b,,s#d ,na,cl ,,nh-,,nh#b ,! yield ( hydraz9e :5 bo? ! diazo & ! ,na,h,s,o#c are fre%ly prep>$ is practically quantitative4 ,! hydraz9e ?us prep>$ 0 treat$ ) a hot #aj solution ( copp] sulphate till a p]man5t blue color 0 obta9$ 9 ! solution4 ,nitrog5 is evolv$ & ! copp] sulphate is r$uc$ to cupr\s oxide :i* is precipitat$ z a r$ p[d]4 ,! reaction is z foll[s4 ,,*#c ,c#f;,h#c,,s#b,,oh #b;,cu,s,o#d ,h#b,o ,,nh-,,nh#b ,c#f;,h#d;,,*#c ,cu#b,o ,n#b #b;,h#b,,s#d ,,s#b,,oh ,*alk 0 add$ to ! solution to precipitate ! ,h#b,,s#d & =m a calcium salt ( tolu5e-o-sulphonic acid4 ,f ?is ! sodium salt 0 made by add+ a slight excess ( ,na#b,,s#c & evaporat+ to dryness4 ,! salt is v soluble be+ deliquesc5t 9 ! air :ile ! correspond+ potassium salt is n4 ,f #aech gr4 ( p>a-nitro-tolu5e1 #fee gr4 ( tolu5e or?o-sodium sulphonate 7 obta9$4 ,hav+ ?us obta9$ ! tolu5e or?o-sulphonic acid ! next /ep 9 ! problem 0 to f9d a conv5i5t me?od = conv]t+ ?is into or?o-sulph-b5zoic acid4 ,two ways pres5t !mselves = accompli%+ ?is end4 7#a7 direct oxidation ( ?is salt & 7#b7 conv]sion into b5zoic sulph9ide f :i* ! acid may be obta9$4 ,bo? ( ^! me?ods 7 tri$4 ,oxidation ( tolu5e-o-sodium sulphonate4 ,c#f;,h#d;,,*#c ,,s#b,o,na ,! sodium salt ( tolu5e-o-sulphonic acid is oxidiz$ to or?o-sulphob5zoic acid ) consid]able difficulty by ,k,mn,o#d 9 neutral solution4 ,?us two exp]im5ts %[$ t ! oxidation 0 n complete aft] #bd h\rs boil+ ) excess ( p]manganate4 ,if ! solution be made alkal9e h[ev]1 ! oxidation is complet$ 9 a few h\rs1 yet ! greate/ difficulty /ill rema9s 9 ! sep>ation ( ! free acid f ! products ( oxidation 9 ! solution4 ,if ,h,cl be add$ to ! solution ! acid salt ,,cooh ,c#f;,h#d ,,s#b,,ok is =m$ & ?is has ne>ly ! same solubility z ! ,k,cl also pres5t4 ,a bett] me?od !re=e is to add a slight excess ( ,h#b,,s#d & evaporate ne>ly to dryness4 ,9 ?is way are =m$ sulphates & ! free acid presumably4 ,! mixture is heat$ ) alcohol 7#ie7 :i* extracts ! acid leav+ ! great] "p ( ! manganese salts4 ,?is extract is evaporat$ & reextract$ ) alcohol4 ,to ?is solution ,ba,c,o#c is add$ to precipitate ! ,h#b,,s#d & =m ! ,b>ium salt ( ! o-sulphob5zoic acid4 ,! solution is filt]$ f ! ,ba,s,o#d & j en\gh ,h#b,,s#d is add$ to exactly precipitate ! b>ium4 ,! solution %\ld ?us conta9 only ! free acid s\ght1 :i* cry/allizes out on evaporat+ to a small volume4 ,:ile ! me?od is !oretically possible x pres5ts s _m difficulties t x is practically useless4 ,! yield is extremely small2 only en\gh acid be+ obta9$ 9 ?is way to %[ t x 0 possible4 ,=mation ( ,sulph9ide f tolu5e-o-sodium sulphonate4 ,! second me?od = obta9+ free o-sulphob5zoic acid f tolu5e-or?o-sulphonic acid is by ! conv]sion ( ! latt] fir/ into b5zoic sulph9ide & !n into ! free acid4 ,! sulph9ide 0 made ess5tially z describ$ by ,rems5 7,am4 ,*4 ,j\r4 ,vol4 ,i4 p4 #dbh7 ) a few *anges 9 ! details z foll[s4 ,! salt ,c#f;,h#d;,,*#c f9ely pulv]iz$ & 9 portions ,,s#b,o,na ( f #aj to #ej gr4 0 plac$ 9 a ,flor5ce flask2 an equival5t quantity ( ,p,cl#e add$2 ,an inv]t$ cond5s] 0 !n atta*$ & ! flask %ak54 ,! action takes place at once & involves suffici5t heat to di/ill (f ! oxy*loride =m$ 9 ! reaction4 ,?is be+ return$ to ! flask by ! cond5s] furni%es a liquid m$ium 9 :i* ! reaction takes place m readily & completely ?an :5 x is n pres5t4 ,x is be/ to cool ! flask at fir/ & aft]w>ds heat g5tly on ! wat] ba?4 ,! reaction :i* takes place may be repres5t$ z foll[s4 ,,*#c ,,*#c ,c#f;,h#d,,s#b,o,na ,p,cl#e ,c#f;,h#d,,s#b;,cl ,p,o,cl#c ,na,cl4 ,on ! addition ( wat] ! *loride sep>ates z a light yell[ oil4 ,?is is wa%$ ) wat] & conc5trat$ aque\s ammonia add$1 :i* =ms tolu5e-o-sulphonamide ?us4 ,,*#c ,,*#c ,c#f;,h#d ,,nh#c ,c#f;,h#d ,h,cl4 ,,s#b;,cl ,,s#b,,nh#b ,! reaction is accompani$ by a slight evolution ( heat & ! =mation1 app>5tly1 ( an int]m$iate product hav+ a yell[i% color1 :i* passes ov] on long] /&+ into ! :ite amide4 ,aft] /&+ sev]al h\rs ! excess ( ammonia 0 driv5 (f by v g5tle heat+ on ! wat] ba?4 ,if ! heat is too high a l>ge am\nt ( a t>ry product is =m$ & ! yield ( amide is correspond+ly small4 ,9 any case "s ( ?is t>ry product is =m$4 ,:5 ne>ly all ! ammonia _h be5 driv5 (f ! mass 0 boil$ ) wat] :i* dissolves ev]y?+ except ! t>4 ,! hot solution 0 filt]$ ?r\gh *>coal & on cool+ ! amide sep>at$ 9 :ite fea!ry cry/als :i* melt at #aee-aef4 ,! amide ?us obta9$ 0 oxidiz$ z describ$ by ,rems5 7loc4 cit47 ) potassium p]manganate 9 neutral solution4 ,! proportions are #aj gr amide4 #dj gr ,k,mn,o#d & #a ,l4 wat]4 ,! oxidation 0 usually effect$ 9 f f\r to six h\rs4 ,to obta9 ! sulph9ide f ?is solution aft] oxidation1 ! latt]1 aft] filtration f ! precipitat$ oxides ( manganese1 0 slightly acidifi$ ) ,h,cl & evaporat$ to ab\t "o f\r? its orig9al volume4 ,on ! addition ( conc5trat$ ,h,cl to ?is solution1 ! sulph9ide sep>at$ out 9 :ite or slightly yell[i% fea!r %ap$ cry/als melt+ at #bab & hav+ ! *>act]i/ic int5sely sweet ta/e4 ,=mation ( ,sulph9ide f ,tolu5e by means ( ! *lorsulphonic acid reaction4 ,be=e pass+ on to ! me?ods us$ = conv]t+ ! sulph9ide into free acid ano!r me?od %\ld be describ$ by :i* ! =m] 0 obta9$ 9 l>g] quantities & mu* m easily ?an by ! "o above describ$4 ,beckurts & ,otto 7,b]4 ,,xi4 #bjfa7 f\nd t by treatm5t ( tolu5e ) sulphuryl hydroxy-*loride or *lorsulphonic acid1 ,cl,s,o#b,,oh1 bo? o- & p- & z !y suppos$ also m-tolu5e sulphon*lorides 7 =m$ toge!r ) ! correspond+ sulphonic acid4 ,claesson & ,wall9 7,b]4 ,,xii4 p4 #ahdh7 repeat$ ! "w rea*+ practically ! same results & f9ally ,noyes 7,am4 ,*4 ,j\r4 ,vol4 ,,viii4 p4 #agf7 employ$ ! reaction z a conv5i5t me?od = obta9+ tolu5e o-sulphon-*loride4 ,*lorsulphonic acid is made by pass+ dry ,h,cl ov] solid sulphuric acid s long z x cont9ues to be absorb$4 ,s9ce no solid sulphuric acid 0 at h&1 ord9>y fum+ ,nordhaus5 acid 0 tak5 & f "o ( two equal portions ! ,,s#c 0 driv5 ov] into ! o!r4 ,h,cl 0 pass$ into ! latt] & ! result+ *lorsulphonic acid di/ill$ (f at ab\t #aef4 ,?is 0 plac$ 9 a flask1 provid$ ) a drop funnel & exit tube1 9 portions ( #aej gr4 & to ea* portion #fj gr4 ( tolu5e 0 add$1 v sl[ly1 ) con/ant %ak+1 ! temp]ature be+ kept ne> #aj4 ,! action is viol5t & if any tolu5e is all[$ to collect on ! surface ( ! liquid x is apt to produce disa/r\s results4 ,l>ge quantities ( ,h,cl are giv5 (f & ! liquid 9 ! flask assumes a br[n color4 ,:5 all ! tolu5e has be5 add$1 x is p\r$ into a l>ge quantity ( ice wat]1 :5 ! sulphon-*lorides sep>ate out1 ! or?o- z a heavy oil & ! p>a- z a :ite cry/all9e solid4 ,aft] all[+ to /& "s "t 9 ord] t z mu* ( ! p>a-*loride might cry/allize z possible ! or?o- 0 drawn (f & subject$ to a freez+ temp]ature = sev]al h\rs4 ,by ?is means m ( ! p-*loride 0 remov$ & ! op]ation 0 replicat$ z long z any cry/als cont9u$ to =m1 g5]ally two or ?ree times4 ,9 ?is way ! great] "p ( ! p>a- may be remov$1 ?\gh "s /ill rema9s dissolv$ 9 ! liquid *loride1 :i* _c be remov$ by repeat$ freez+s4 ,! *loride ?us obta9$ 0 treat$ ) /rong aque\s ammonia4 ,! conv]sion to ! sulphamide does n take place s readily z 9 case ( ! pure o-*loride obta9$ f ! sulphonic acid & phosphorus p5ta*loride4 ,aft] /&+ ab\t two days ! :ole ( ! oily *loride _h solidifi$ to a yell[i% br[n mass4 ,! excess ( ammonia 0 driv5 (f by g5tle heat+ on ! wat] ba? & ! mass !n boil$ ) wat]4 ,n en\gh wat] 0 add$ at fir/ = complete solution b :5 ! fir/ portion 0 saturat$ x 0 p\r$ (f ?r\gh a filt] & f x ! amide sep>at$ 9 yell[i% fea!ry cry/als :i* melt$ at #aje-abe & consi/$ !re=e z %[n by ,fahlb]g 7,am4 ,*4 ,j\r4 ,vol4 ,i4 p4 #agj7 ( a mixture ( o- & p-sulphonamides4 ,x 0 recry/alliz$ & f x 0 obta9$ a portion melt+ at #aec-e & "o at #ajh-bj4 ,s9ce ?is mixture _c be completely sep>at$ by recry/allization ano!r me?od 0 sugge/$4 ,rems5 has %[n t ,k#b;,cr#b,o#g 9 acid solution does n oxidize ! me?yl gr\p 9 ,,*#c ,c#f;,h#d ,,s#b,,nh#b 7o7 b does oxidize t 9 ,,*#c ,c#f;,h#d ,,s#b,,nh#b 7p74 ,x 0 ?\ght t 9 a mixture ( ! two ! =m] might be left un*ang$ :ile ! latt] 0 oxidiz$ to p-sulpham9e b5zoic acid4 ,to te/ ?is #ae gr ( ! mixture1 melt+ at #aje-abe1 0 heat$ ) #dj gr ,k#b;,cr#b,o#g1 #ee gr ,h#b,,s#d & #b vols4 ( wat] = ab\t two h\rs4 ,x 0 !n te/$ & %[n to be /ill a mixture ( p- o-amides1 s9ce x 0 aga9 heat$ = sev]al h\rs ) half ! orig9al quantity ( oxidiz+ mixture1 !n dilut$1 filt]$ & wa%$4 ,! :ite cry/all9e residue 0 treat$ ) sodium c>bonate to dissolve ! b5zoic p>a-sulphamide & ! residue 0 f\nd to be pure tolu5e o-sulphonamide melt+ at #aec-aee4 ,! small quantity rema9+1 #c gr41 indicat$ t "p ( ! o-amide _h be5 completely brok5 d[n by ! /rong oxidiz+ ag5t1 ?\gh ! proportion ( o- p-amides 9 ! orig9al mixtures 0 kn[n only approximately4 ,! evolution ( gas dur+ ! oxidation w\ld po9t to ! same conclusion4 ,al?\gh ?is effects a complete sep>ation x is h>dly economical s9ce x w be %[n lat] t a sep>ation c be conv5i5tly effect$ aft] ! oxidation ) ,k,mn,o#d s t ! o-amide conta9$ 9 ! mixture ne$ n be lo/4 ,! orig9al mass 0 treat$ ) successive portions ( wat] till no?+ rema9$ b a black t>ry sub/ance4 ,! amide :i* sep>at$ f ^! extracts 0 p]fectly :ite & melt$ at #aec-e4 ,x 0 !re=e reg>d$ z practically pure o-amide4 ,! yield 9 amide melt+ above #aec 0 a little ov] "o six? ! weight ( tolu5e us$4 ,! amide obta9$ 9 ?is way 0 oxidiz$ 9 ! mann] already describ$4 ,x 0 f\nd h[ev] t !re 0 always "s b5zoic p-sulphamide 9 ! solution ( ! oxidation1 due to ! slight admixture ( p- ) ! o-amide us$4 ,?is is ?r[n d[n ) ! sulph9ide on acidify+ ! solution & may be remov$ by re-cry/allization s9ce x is some:at less soluble 9 hot & cold wat] ?an sulph9ide4 ,a bett] way to effect ! sep>ation1 h[ev]1 0 f\nd to be ! foll[+4 ,aft] hav+ evaporat$ ! solution conta9+ ! products ( oxidation1 ne>ly neutraliz$ ) ,h,cl1 to ab\t "o fif? its orig9al volume1 x is made v slightly acid & all[$ to cool4 ,9 ?is way v ne>ly all ! b5zoic p-sulphamide is sep>at$ f ! solution & none ( ! sulph9ide4 ,aft] filt]+1 /rong ,h,cl is add$ & ! sulph9ide !n sep>ates 9 its *>act]i/ic =m4 ,?is indicates t sulph9ide =ms an alkal9e salt :i* is n decompos$ by dilut$ ,h,cl :ile ! p-sulphamide does n4 ,! mixture ( amides meet+ at #aje-abj 0 oxidiz$ & ! products sep>at$ 9 ?is way gave ab\t equal quantities ( sulph9ide & b5zoic p-sulphamide4 ,:5 tolu5e is treat$ ) *lorsulphonic acid !re are =m$ besides ! or?o- & p>a- *lorides also or?o & p>a sulphonic acids4 ,^! ( c\rse are 9 solution 9 ! wat] f :i* ! *lorides sep>at$4 ,9 ord] to recov] ! or?o-acid1 ! solution 0 neutraliz$ ) *alk =m+ ! calcium salt3 ?is conv]t$ into ! potassium salt :i* by evaporat+ ! solution to dryness 0 obta9$ z a :ite cry/all9e p[d]4 ,:5 treat$ ) ,p,cl#e 9 ! mann] already describ$ ?is gave a mixture ( or?o & p>a sulphon*lorides consi/+ ( ab\t or?o & p>a4 ,=mation ( ,or?osulphob5zoic acid f ,sulph9ide4 ,b5zoic sulph9ide may be conv]t$ into a sulpho-b5zoic acid 7#a7 by boil+ ) ,ba7,,oh7#b1 7#b7 by heat+ 9 a clos$ tube ) conc4 ,h,cl or 7#c7 by evaporat+ on ! wat] ba? ) ,h,cl4 #a4 ,?ree gramms ( sulph9ide 7 boil$ 9 a flask connect$ ) an inv]t$ cond5s] = ab\t two days ) an excess ( ,ba7,,oh7#b4 ,!re 0 =m$ 9 ! flask a h>d m9]al-l mass :i* 0 insoluble 9 wat] & cold dilut$ ,h,cl b dissolv$ 9 hot ,h,cl ) eff]ves5ce4 ,?is 0 a ,b>ium salt1 probably basic 787 ( or?o sulphob5zoic acid4 ,!re 0 also =m$ an easily soluble b>ium salt ( t acid4 ,! =m] 0 dissolv$ 9 ,h#b,,s#d & treat$ ) ,ba,c,o#c2 ! filtrate f ! ,ba,s,o#d :i* conta9$ a soluble b>ium salt 0 add$ to t above m5tion$ & ! b>ium exactly precipitat$ ) ,h#b,,s#d & ! filtrate evaporat$ to dryness giv+ ! free acid b n 9 a p]fectly pure condition4 #b4 #b4ge gr4 ( sulph9ide 0 seal$ up 9 a tube ) pure conc4 ,h,cl & heat$ two h\rs to #aej4 ,on cool+ no?+ sep>at$2 ! liquid 0 evaporat$ to dryness giv+ #c4b gr ( acid & ammonium *loride4 ,! reaction tak+ place "h may be repres5t$ ?us3 ,,co ,,cooh ,c#f;,h#d ,,nh #b;,h#b,o ,h,cl ,c#f;,h#d ,,nh#d;,cl4 ,,s#b ,,s#b,,oh #c4 ,a m conv5i5t me?od = obta9+ ! acid ?an ei!r ( ! above1 is to heat ! sulph9ide ) conc4 ,h,cl on ! wat] ba? = two days4 ,!n evaporate to dryness & dissolve ! residue 9 a small quantity ( wat]4 ,if ! sulph9ide conta9$ any p>a-sulphamide1 z is usually ! case1 ?is w be left undissolv$ & mo/ ( ! ,,nh#d;,cl w cry/allize on /&+4 ,?is solution by sl[ evaporation deposits l>ge colorless cry/als ( ! free acid4 ,?is acid is soluble 9 ab\t two p>ts ( cold wat]1 v difficultly soluble 9 absolute alcohol & almo/ completely insoluble 9 e!r4 ,x does n melt "u #bej b consid]ably above t x melts1 at fir/ app>5tly )\t *ange & !n ) slight sublimation ( a v deliquesc5t sub/ance1 probably ! anhydride4 ,two det]m9ations ( ! ,s4 made by ,mr4 ,a4 ,f4 ,l9n1 gave ! foll[+ results4 ,i #aceh gr sub/ance gave #ahee gr ,ba,s,o#d repres5t+ #aegb ,s4 ,,ii 0 0 0 0 0 0 ,,cooh ,calculat$ = ! =mula ,c#f;,h#d #aehd ,s4 ,,s#b,,oh ,illu/ration ,a cry/allographic exam9ation ( ! acid %[$ x to belong to ! or?orhombic sy/em4 ,axial ratio3 a3 b3 c #hejg3 #a3 #haba4 ,planes4 & 4 ,edge ,x #aca #h' 0 ,y #hb #ah' 0 ,z #aah #dj' ,angles measur$ #aad #ch' ,! cry/als are up to #h mm 9 l5g?4 ,! pyramidal faces are g5]ally et*$ s t ! image is poor4 ,sulphonfluorescen4 ,sev]al attempts _h already be5 made to obta9 f ! action ( o-sulphob5zoic acid & resorc9 a sub/ance analog\s to ! fluorescen obta9$ by ,baey]#a f ph?alic anhydride & resorc9 b :ile a /rongly fluoresc5t sub/ance 0 easily obta9$1 no def9ite comp\nd c\ld be sep>at$ f x4 ,?us ,palm] obta9$1 by heat+ toge!r ! above nam$ sub/ances to #afj787 a solid mass1 "p soluble 9 wat] & "p insoluble z a d>k br[n amorph\s p[d]4 ,bo? p>ts gave a /rong fluoresc5ce ) alkalis4 ,he 0 unable h[ev] to obta9 ! sub/ance itself or any d]ivative 9 a cry/all9e =m4 #a ,annal94 ,no4 #ahc4 ,s4 #a4 ,no4 #bjb4 ,s4 #cf ,s4 #aec4 ,b]i*te4 ,no4 ,,iv4 ,s4 #deg4 #eee4 #feh4 #ffb4 0 0 ,,viii4 ,s4 #ff4 #adf4 ,! fir/ exp]im5ts 9 ?is s]ies gave ! same negative results4 ,! mixture ( acid & resorc9 0 heat$ 9 a sulphuric acid bo? = sev]al h\rs to #aej-agj1 & z x %[$ no sign ( solidification ! temp]ature 0 rais$ to #bjj & !n to #bce :]e x 0 kept sev]al h\rs long]4 ,! black visc\s mass obta9$ 9 ?is way became vitre\s on cool+1 & 9 all respects resembl$ t describ$ by ,palm]4 ,?is h[ev] is n ! normal c\rse ( ! reaction z %[n lat] b is probably due to a decomposition ( ! normal product produc$ by too high heat+4 ,an exp]im5t 0 made ) ! acid salt ( or?o-sulphob5zoic acid4 ,,cooh ,c#f;,h#d ,,s#b,,ok1 resorc9 & ,h#b,,s#d heat+ ! mixture to #aej-agj4 ,a solid black mass 0 obta9$ /rongly fluoresc5t 9 alkal9e solution & 9 all o!r respects l ! sub/ance obta9$ above4 ,prep>ation ( ,sulphonfluorescen4 ,z ! result ( a numb] ( exp]im5ts ! foll[+ me?od ( prep>+ & purify+ ! sulphonfluorescen 0 f\nd to give ! be/ results4 ,! free acid is mix$ ) resorc9 9 ! proportion ( #a "p acid to #a4b p>ts resorc91 or a slight excess ov] two molecules ( ! latt] to "o ( ! =m]4 ,! mixture is plac$ 9 a deep vessel1 a te/ tube or beak]1 :i* is plac$ 9 a sulphuric acid ba?1 a !rmomet] be+ susp5d$ 9 ! mixture4 ,! ba? is heat$ & at ab\t #ajj ! resorc9 melts & ! acid sl[ly dissolves 9 ! liquid4 ,no action appe>s to take place till ! temp]ature rea*es #age :]e wat] beg9s to be giv5 (f & ! liquid sl[ly assumes a d>k] color4 ,:ite cry/als ( resorc9 collect on ! sides ( ! vessel4 ,aft] ! heat+ has be5 cont9u$ = ab\t sev5 h\rs at #agh-ahe ! liquid has a cle> deep r$ color b %[s no signs ( becom+ visc\s4 ,at l5g? lu/r\s yell[ cry/all9e plates appe> 9 ! liquid & soon ! :ole mass becomes a ?ick ne>ly solid yell[ pa/e4 ,cont9u\s heat+ at ! same temp]ature causes no fur!r app>5t *ange4 ,?is mass1 :i* on cool+ is made up ( yell[ cry/als imb$d$ 9 a r$ vitre\s matrix1 is !n dissolv$ 9 hot wat] =m+ a cle> r$ solution or at mo/ "o conta9+ b a small quantity ( a br[n floccul5t precipitate4 ,?is solution is filt]$ if necess>y & evaporat$ to a small volume f :i* ! sub/ance sep>ates on cool+ 9 r$di% yell[ radial cry/als4 ,^! are filt]$ & wa%$ ) e!r till ! wa%+s are p]fectly colorless4 ,! sub/ance on repeat$ cry/allization f wat] has a pale /raw yell[ color & :5 deposit$ sl[ly =ms transp>5t cry/al blocks f #bf mm long1 arrang$ 9 radial gr\ps4 ,a consid]able am\nt ( resorc9 is lo/ by sublimation dur+ ! reaction especially if ! op]ation is c>ri$ on 9 a beak] s t "s excess %\ld be add$4 ,b ev5 :5 ! resorc9 is pres5t 9 excess at ! end ( ! reaction "s free acid is always left :i* may be obta9$ f ! "m liquid 9 ! *>act]i/ic colorless or?orhombic cry/als4 ,! wat] ( cry/allization & sulphur 7 det]m9$ 9 ! new comp\nd4 ,9 e/imat+ ! wat]1 ! sub/ance 0 heat$ to #ajf-abc = ab\t t5 h\rs till x atta9$ a con/ant weight4 ,on /&+ 9 ! air x quickly rega9s its orig9al weight4 ,:5 heat$ to #acj-adj = "s "t x turns slightly r$di% & loses ov] #aj ( its weight :i* is n rega9$ by /&+ 9 ! air4 ,e/imation ,no4 ,i4 0 made by fusion ) ,,koh & ,,kno#c4 ,nos4 ,,ii & ,,iii 7 made by ,mr4 ,m9dileff by ,morse's me?od1 oxidiz+ ) ,k,mn,o#d 9 ,,koh solution4 #chhb gr4 heat$ to #ajf-abc lo/ #jcjb gr4 #he ,calculation = #b;,h#b,o - ,c#ai;,h#ab,o#f,s#b;,h#b,o #hi wat]4 ,i4 #bjjg gr sub4 gave #abhf gr ,ba,s,o#d #hgg ,s4 ,,ii4 gr 0 0 0 gr 0 #gia0 0 ,,iii4 gr 0 0 0 gr 0 #ghi0 0 ,calculation = ,c#ai;,h#ab,o#f,s#b;,h#b,o #gib ,s4 ,^! analyses %[ ) b little d\bt t ! sub/ance has ! composition indicat$ above i4e4 ,c#ai;,h#ab,o#f,s#b;,h#b,o4 ,! reaction !re=e :i* takes place betwe5 or?o-sulpho b5zoic acid & resorc9 f its analogy to t tak+ place betwe5 ph?alic anhydride & resorc9 may be repres5t$ ?us1 z %[n by ,baey] 9 8 second pap] 7,ann4 #bjb4 ,s4 #dc7 ,repres5t+ ! =mation ( ! anhydride z ! fir/ action4 ,,cooh ,,co ,c#f;,h#d ,c#f;,h#d ,o ,h#b,o ,,s#b,,oh7o7 ,,s#b & ! action ( resorc9 on ?is anhydride ?us4 ,,co ,,oh ,c#f;,h#d ,o #b;,c#f;,h#d ,,s#b ,,oh 7m7 ,o 7,,ho7,h#d;,c#f ,c#f;,h#d7,,oh7 ,c #b;,h#b,o ,c#f;,h#d ,o ,,s#b ,! sub/ance ?us =m$ w\ld naturally receive ! "n ,sulphonfluorescen f its analogy ) ,fluorescen4 ,,oh ,c#f;,h#c ,o ,c ,c#f;,h#c ,,oh ,c#f;,h#d,,s#b ,o ,sulphonfluorescen4 ,,oh ,c#f;,h#c ,o ,c ,c#f;,h#c ,,oh ,c#f;,h#d;,,co ,o ,fluorescen4 ,prop]ties ( ,s4fluorescen4 ,?is comp\nd %[s a m>k$ simil>ity to ! fluorescen describ$ by ,baey] z w\ld naturally be expect$ f its great simil>ity ( composition & con/itution1 b x also %[s decid$ diff]5ces :i* may be attribut$ to ! replacem5t ( ,,co by ,,s#b4 ,dissolv$ 9 wat] x %[s a weak gre5 fluoresc5ce :i* 9 alkal9e solution becomes mu* deep] b n by any means s /rong z t ( fluorescen4 ,! dilute alkal9e solution by transmitt$ light is almo/ p]fectly colorless & by reflect$ light a cle> gre54 ,unlike fluorescen x is extremely soluble 9 wat]1 ab\t "o "p 9 two or ?ree ( hot & five or six ( cold wat]4 ,x is also soluble 9 absolute alcohol =m+ a yell[ solution ) weak fluoresc5ce4 ,x is soluble ) difficulty 9 e!r b :5 9 solution is deposit$ only on evaporat+ to a small volume4 ,x does n melt at #bej b if held at a l[] temp]ature = a long "t becomes r$ und]go+ "s decomposition4 ,if quickly heat$ some:at above #cjj x melts to a deep r$ liquid & !n solidifies4 ,if ! mass is treat$ ) wat] x p>tly dissolves leav+ a d>k br[n floccul5t precipitate :i* dissolves on ! addition ( an alkali1 ! solution hav+ an int5se fluoresc5ce1 ne>ly if n q equal+ t ( fluorescen4 ,?is *ange produc$ by heat+ 0 n fur!r /udi$4 ,! cry/als are v ?9 blades1 app>5tly monocl9ic1 %[+ ! cl9op9acoid & a v n>r[ prism & cl9odome 4 ,! angle #ge & ! ext9ction angle aga9/ ! axis #bj4 ,! axial ratio c\ld n be accurately det]m9$4 ,salts ( sulphonfluorescen4 ,! influ5ce ( ! ,,s#b gr\p is %[n by ! fact t ! sub/ance acts z an acid decompos+ c>bonates & =m+ salts :i* is n ! case ) fluorescen4 ,b>ium salt4 ,! sub/ance 0 boil$ ) an excess ( c>efully purifi$ ,ba,c,o#c = two h\rs4 ,! filtrate f ! ,ba,c,o#c evaporat$ to a small volume deposit$ yell[ cry/als resembl+ ! orig9al sub/ance b 9 %ort] & ?ick] prisms4 ,^! 7 twice recry/alliz$ & _h !n a light /raw yell[ color4 ,a det]m9ation ( ! ,ba gave ! foll[+ results4 ,! salt 0 dri$ 9 ! air4 ,transcrib]'s ,note3 ,! foll[+ table 0 cross$ out on ! orig9al4 ,a note on ! previ\s page beside ! table 03 ,all ^! calculations are wrong4 ,j4,r4 ,i #ajgh gr salt gave #jcjd gr ,ba,s,o#d #aegc ,ba4 ,,ii #afda 0 0 0 #jdeg 0 0 #aeec0 0 ,,iii #bdbe 0 0 0 #jfhj 0 0 #aefe0 0 ,,iv #bhfj 0 0 0 #jgih 0 0 #aeed0 0 ,v #ahdc 0 0 0 #jdih 0 0 #aejh0 0 ,,vi #bfbj 0 0 0 #jgjh 0 0 #aejh0 0 ,,vii #cbcj 0 0 0 #jijf 0 0 #aefe0 0 ,,viii #bhge 0 0 0 #jhjg 0 0 #aeff0 0 ,calculat$ = ,c#ai;,h#ac,o#g,s,ba #aeaj ,ba4 ,9 ! above det]m9ations ! salt analys$ 0 tak5 f specim5s made at ?ree diff]5t times & purifi$ 9 slightly diff]5t ways1 ,nos #a1 #b1 #c be+ wa%$ ) absolute alcohol4 ,nos ,v & ,v 7 made by precipitat+ ! ,ba ) ,h#b,,s#d f a solution ( ! salt4 ,! wat] 0 det]m9$ by heat+ at #aaj till con/ant weight 0 rea*$4 ,"p only ( ! weight lo/ 0 rega9$ on /&+ 9 ! air4 #cidc gr salt lo/ at #aaj #jbhf gr #g4be ,wat] calculat$ = ,c#ai;,h#ac,o#g,s,ba#b;,h#b,o #g4ce ,al?\gh ^! analyses %[ a p] c5t4 ( ,ba some:at above t requir$ by a comp\nd hav+ ! =mula ,c#ai;,h#ac,o#g,s,ba /ill ?is appe>s to be ! mo/ probable =mula :i* c be assign$ to ! sub/ance4 ,if ?is is ! true composition ( ! salt1 !n 9 sulphonfluorescen ! anhydride condition mu/ be brok5 up by boil+ ) ,ba,c,o#c =m+ ! salt ?us4 ,,oh ,,oh _/ _/ ,c#f;,h#c ,c#f;,h#c ,o ,o _/ _/ ,c ,c#f;,h#c ,c#f;,h#c ,h#b,o ,c ,,oh ,,oh ,c#f;,h#d,,s#b ,c#f;,h#d,,s#b,,oh _/ ,o ,,oh ,,oh ,,oh _/ _/ ,c#f;,h#c ,c#f;,h#c ,o ,o _/ _/ ,c#f;,h#c ,c#f;,h#c #b ,c ,ba,c,o#c ,c ,ba4 ,,oh ,,oh ,c#f;,h#d,,s#b,,oh ,c#f;,h#d,,s#b,o ,,oh ,,oh #b ,by treat+ ! salt ) ,h#b,,s#d ! orig9al sub/ance is re=m$4 ,calcium ,salt4 ,attempts 7 made to prep>e ! calcium salt b )\t success4 ,! ,s-fluorescen 0 boil$ sev]al h\rs ) v f9ely p[d]$ calcite1 & "s salt 0 =m$ z %[n by ! ,,co#b evolv$ b on evaporat+ ! solution & recry/alliz+ ! sub/ance deposit$ x 0 f\nd to be ! un*ang$ ,s-fluorescen4 ,"s ,ca4 salt 0 9 ! "m liquors b its extreme solubility prev5t$ a sep>ation be+ made4 ,acetyl d]ivative ( ,s4fluorescen4 ,s4fluorescen 0 boil$ ) an excess ( acetic anhydride = ab\t ?ree h\rs4 ,! solution became q d>k & :5 evaporat$ on ! wat] ba? left a black t>ry residue4 ,?is 0 treat$ ) wat] :i* dissolv$ a "p leav+ a d>k floccul5t precipitate4 ,! solution 0 boil$ ) animal *>coal & evaporat$ ne>ly to dryness4 ,on cool+ !re sep>at$ a light yell[ floccul5t precipitate v soluble 9 hot wat] & b slightly less s 9 cold4 ,?is 0 dissolv$ 9 a small quantity ( alcohol f :i* x sep>at$ on evaporation 9 small radial cry/als hav+ a light lav5d] color sat9y lu/]4 ,!y also h a peculi> odor resembl+ slipp]y elm :i* is n remov$ by recry/allization4 ,!y %[ a t5d5cy to decompose1 becom+ yell[ on exposure to ! air4 ,! sub/ance does n melt or *ange 9 appe>ance "u #bde4 ,) alkalis x gives a slight gre5i% fluoresc5ce4 ,f ! me?od ( its =mation ?is 0 tak5 to be an acetyl d]ivative ( ,s4fluorescen b :e!r ! mono-or di-acetyl c\ld n be det]m9$ )\t analysis = :i* ! sub/ance did n suffice4 ,brom9e sub/itution products ( ,s-fluorescen4 ,x 0 especially int]e/+ to see :at influ5ce ! ,,s#b gr\p w\ld ex]t ^u ! introduction ( ,brom9e into ! comp\nd4 ,9 ! case ( fluorescen f\r ,brom9e atoms ent] easily & special precautions are necess>y to obta9 a product conta9+ a small] numb]4 ,! case h[ev] is diff]5t ) ,s4fluorescen4 ,! latt] 0 dissolv$ 9 glacial acetic acid 9 :i* x is soluble ) "s difficulty & to ! solution 0 add$ a #bj solution ( brom9e 9 acetic acid1 9 suffici5t quantity to make eight atoms ( brom9e to "o molecule ( ,s4fluorescen4 ,?is solution 0 evaporat$ on ! wat] ba? & :ile /ill hav+ a consid]able volume1 small1 r$1 %>ply def9$ cry/als began to sep>ate4 ,! solution 0 evaporat$ to a small volume & all[$ to cool b no?+ fur!r sep>at$4 ,^! cry/als are difficultly soluble 9 wat]1 alcohol & e!r4 ,! alkal9e solution %[s a gre5 fluoresc5ce & slight r$ color by transmitt$ light4 ,^! cry/als 7 dissolv$ 9 a l>ge quantity ( alcohol :i* on evaporation gradually deposit$ v small yell[ cry/als1 :i* 7 dri$ 9 ! air & tak5 = analysis4 ,! ,br4 0 det]m9$ by ,c>ius me?od4 ,i4 #bcde gr sub4 gave #agah gr ,ag,br #caag ,br4 ,,ii4 #bghf gr 0 0 #ahae gr 0 #bggb ,br4 ,calculat$ = ,c#ai;,h#aj;,br#b,o#f,s #cjdb ,br4 ,^! results1 ?\gh n conclusive1 indicate t "u ! giv5 conditions x is ! di-bromsulphonfluorescen :i* is =m$4 ,:e!r ?is is due to ! pres5ce 9 ! comp\nd ( ! ,,s#b gr\p or simply to ! great] insolubility ( ! di-?an ( ! tetra-brom product _c be def9itely /at$4 ,:5 ! orig9al acetic acid "m liquor 0 evaporat$ to dryness1 a r$ non-cry/all9e sub/ance rema9$ :i* m closely resembl$ ros9 ?an ! cry/als4 ,! conc5trat$ alkal9e solution _h a deep r$ color )\t fluoresc5ce & act$ z a r$ dye /uff4 ,! dilute alkal9e solution %[$ ! *>act]i/ic delicate p9k ( ros94 ,action ( ,h#b,,s#d on ,s4fluorescen4 ,a te/ tube 9 :i* ,s4fluorescen 0 be+ made j at ! end ( ! reaction broke & all[$ ! cont5ts to run out into ! sulphuric acid ba?1 :i* _h a temp]ature ( #age4 ,on /&+ sev]al days ! solution deposit$ a heavy precipitate :i* 0 sep>at$ by filt]+ ?r\gh glass wool4 ,:5 dry x =m$ a light yell[ p[d] extremely soluble 9 wat]1 alcohol & e!r4 ,! alkal9e solution _h an int5se gre5 fluoresc5ce ) delicate %ades ( p9k by transmitt$ light4 ,on acc\nt ( its great solubility x 0 impossible to purify x by cry/allization1 h5ce ! ,ba salt 0 made4 ,! sub/ance decompos$ ,ba,c,o#c ) great ease =m+ an easily soluble salt4 ,:5 x 0 attempt$ to evaporate ! solution ( ?is salt to cry/allization ! latt] came out 9 a h>d insoluble granul> =m & on cont9u\s boil+ ( ! solution turn$ br[n4 ,to avoid ?is undesirable =m x 0 conv]t$ into ! ,ca4 salt by treatm5t ) ,h#b,,s#d & !n ,ca,c,o#c4 ,?is also =m$ a h>d granul> insoluble mass on boil+ b did n *ange 9 color4 ,z !re 0 no gu>antee z to its purity & only a small quantity 0 obta9$ x 0 n analyz$4 ,action ( ,h,cl on ,s4fluorescen4 ,hydro*loric acid does n dissolve ,s4fluorescen b conv]ts x into a light yell[ granul> p[d]4 ,:5 recry/alliz$ f wat] 9 :i* x is q easily soluble x melts p>tially at #acj app>5tly ) "s decomposition4 ,?is comp\nd 0 n fur!r /udi$4 ,r$uction ( ,s4fluorescen4 ,:5 treat$ ) z9c du/ 9 a /rong alkal9e solution sulphonfluorescen is r$uc$ to a colorless sub/ance probably analog\s to fluorescen :i* is =m$ 9 ! same mann]4 ,on acc\nt ( its great solubility x c\ld n be obta9$ 9 ! free /ate4 ,x is quickly oxidiz$ to s4fluorescen by oxidiz+ ag5ts z ,k,mn,o#d & ,,hno#c & passes back spontane\sly on /&+ 9 ! air4 ,! latt] action is h[ev] mu* sl[] ?an 9 case ( fluorescen4 ,conclusion4 ,! pr9cipal results relat+ to s4fluorescen :i* h be5 rea*$ 9 ?is "w may be briefly summ>iz$ z foll[s4 ,or?osulphob5zoic acid acts on resorc9 at a temp]ature ( ab\t #ahj giv+ (f wat] & =m+ a sub/ance analog\s to fluorescen b hav+ ! ,,co gr\p replac$ by ,,s#b4 ,?is sub/ance sulphonfluorescen cry/allizes f wat] 9 light yell[ monocl9ic cry/als hav+ ! composition ,c#ai;,h#ab,o#f,s#b;,h#b,o4 ,x is v soluble 9 alcohol & wat] & ) difficulty 9 e!r4 ,x does n melt "u #bej b above #cjj melts ) decomposition4 ,x %[s 9 alkal9e solution a cle> gre5 fluoresc5ce4 ,x acts z an acid1 decompos+ c>bonates & =m+ salts1 ! ,ba salt hav+ ! composition ,c#ai;,h#ac,o#g,s,ba4 ,x =ms an acetyl comp\nd :5 boil$ ) acetic anhydride4 ,x =ms sub/itution products ) ,br1 probably ! dibrom-product mo/ easily4 ,x =ms a comp\nd ) ,h#b,,s#d1 probably a sub/itution product1 ^: composition 0 n det]m9$4 ,x is r$uc$ by z9c du/ & ,,koh to a colorless sub/ance analog\s to fluorescen4 ,f9ally 9 t]ms ( ! preval5t !ory ! sub/ance itself may be repres5t$ ?us-- ,h ,h ,c ,o ,c ,,oh 7,,ho7,c ,c ,c ,c7,,ho7 ,c#f;,h#c ,,hc ,c ,c ,,* ,o ,c ,c ,c ,c ,h ,h ,c#f;,h#c ,,hc ,,oh ,,hc ,c ,o ,c#f;,h#d,,s#b ,,hc ,c ,o ,c ,,s#b ,h