detection, determination and separation of organic …
TRANSCRIPT
DETECTION, DETERMINATION AND SEPARATION OF ORGANIC AND INORGANIC SUBUSTANCES
A Dissertat ion Submi t ted t o tine Faculty of Science of Al igarh Musl im University, Al igarh in part ia l fu l f i lment of the requirements fo r the a\A/ard o f the Degree of
MASTER OF PHILOSOPHY IN
CHEMISTRY
BY
UMESH CHANDRA SHARMA
DEPARTMENT OF CHEMISTRY ALIGARH MUSLIM UNIVERSITY ALIGARH (INDIA) NOV. 1983
A G K N 0 H l > l l P € S W J g | I T jL^iXLL. Ill] I. mm III Jill mnmm'mitrnmTmuniuimmmtmmimmmaammmmtmmmmtmmimmmmmm
FiiHit of all X vottltH Itke to express wy profotind sonse
of girstltu e and gratefulnest to w Supervtsor Dr. J*P* lAVAT
for his valu«1>le gnldanoo, preetous snggostlons and constant
inspiration during the entire course of work reported In this
dissertation*
t an thankful to Prof. W, Rahman, Chairman, Departnent
of Chewietry, for providing all the necessary research
facilities,
I an Tety nuoh gi^teful to ny respected parents who
encouraged ne for pursnlng the researoh work:.
At last, bat not the least, I extend «y thanks to ny
research colleagues for the oo*operetion during this work*
( P.C. S! N.&o. (Agra)
Departnent of Chenis t iy , Al igei i i Nttslin VnlTersity, Allg«f1i-202001 ( I n d i a ) .
C O N T E N T S
PAGK
ACnfOWLEIKSEMENT (1)
LIST OF TABLES (ill)
LIST or riGURBS (IY)
CHAPTEB . t
THIN LATER CHROMATOGBAHIT OF PHENOLS
niTROOUCTlON 1
BIPERINBNTAL 15
flSSOLTS 18
DlSC08SfOlf 51
WFSIIENCES 60
( l i )
L I S T Ojr T A B L E S
PA«
TABLE I THIN LATER CniOMATOGllAIIlT OF PHENOLS ON
DIFrBRBNT ADSORBENTS 9
TABLE II IL fALOES OP JO FHEN(».S IN VABIOUS SOLVENT
STSIEMS 20
TABLE III B. VALUES OP 30 PHENOLS ON SILICA mh LATER
IN VARIOUS SOLVENT SYSTEMS 24
TABLE IV R^ VALUES OP 30 PHENOLS IN DIFFERENT CONOENTRA.
TION OF ANKCmiUlf HTDROXICB 26
TABLE V BINART SBPARATICmS ACHIEVED IN VARIOUS SOLVENT
SYSTEMS 27
TABLE VI TERNARY SEPARATIONS ACHIEVED IN VARIOUS
SOLVENT SYSTEMS «5
TABLE VII QUATERNARY SEPARATIONS ACHIEVED IN VARIOUS
SOLVENT SYSTEMS 49
C lit )
L I S T or r I 6 p » E s
vMm
PX6URB 2 (a.«)
rXOUBB 2 (e.ti)
rXGVIK 5 <a-«)
riOOHl! 3 (t«li)
rxcwa 3 (t.4)
pLOir or i^ AOAXNST MOLAR CC»ICBNTRATXOII
or AMUONIUH a r o s o n m
PLOT or Up AGAINST NOLAE COMCENTRATlQir
or AMNOHXim BTDEOXIDB
PLOT or S^ YS. MOIfBES OT BTDROXT GSOOPS
PLOT or iL TS, NOMBea or wnmoxt GROUPS
PLOT or Ry vs. mjNBBR OT BENZEME RINGS
PLOT or i^ VS, NONIIER Or aSNSSBNE RINGS
PLOT or R^ VS. NUMBER Or BENZENE RINGS
A DIAGRAMATIOAU.T IKPRESENTATION Or
QUATBRKASr SEPARATIONS IN VARIOUS
SOLVENT SrStlMS
5«
53
5*
55
56
57
58
59
( !• )
1
lliTlOIUfCTlOlt
Analytioai eii««tfttiy d««la with tta« developvaat of netboAt
far oli«iii«ftl «ii»ly»t» whtoh t» ln*i»p«tifiabl« tit «afiy branelHi* of
8el«no«. B0t«1>lltl»«iit of tho waobaiilsm of varloua raaotlons anA
fonralation of ttia fundaaaatal law* of Cbentstiy ha« largely b««n
baaadi on the reaulta of Obemloal Analyata, ft finds a oonatant
applieatiofi in teohnology, indoatry, awdtoine, agrionltura*
geology, criminology and otbar fields. The obenioal analysis is
ordinarily divided into qualitative analysis and qnantitative
analysis* The qnalitatiye analysis deals with the deteotion of
eonstittients or conponents present in a ooiBpotmd or sanple while
quantitatire analysis detemines the proportions in vhioh the
ctrostituents or the asiounts of the oonstituents ere present*
The oonstituents to be detected or determined aay be
fron inorganic or organic snbstences and the analysis correspon
dingly known aa Inorganic or Organic Analysis* Inorganic Analysis
has been developed to establish, in siany cases, important
fnndasiental laws of theories of eheaistry* Most of the reactions
are straight forward and there is less probability of side
reactions* The nature of Inorganic substances is governed by a
nnaber of selective and specific reactions and, therefore,
specificity and selectivity has been studied in greater detail.
Organic Analyais on the other hand, deals with the
organic reactions which are usually slower involving more coaiplez
2
araotianisa and vi th greater probattilltty of stcfa raaetlona.
Nanbara of tioMolognona serlaa ahov a la i lar behaviotir or oonpounds
oontatnini; aane fnnottonal group ara aora alilce «be«108lly, and
ttiarefore, the nixtures ere more complex, fifowerer, ourrently
the eltttflttcnfi 1» improirlnir anrt today, a large niraiber of analytical
obemists are ooeapled in tbe (feTeloiwent of organio analyala.
Separation in «ost of tbe oaaea, la one of the important
pretreatnent taetbod for qnalitatt-ve and ifuantitative analyeie.
For on analyeis eoise form of pretreatnent of aausple i s usually
re<|aired so QB to renove Interferenoe of other Gubstanoes.
Separation, a versat i le fors of pretreatmcnt, involves olassioal
and tno<!em techniques, fbe precipitation and d i s t i l l a t i o n are
tbe o lass ioal techniques and ere replaced marlcedly by modem
teohniqnea as Chroaiatograpby, Solvent extraoti(Ki, Ion«>excbange
and Bleotropboresis. The rapid developnent of these nodem
teohniqnee has increased the reqniremGnts placed in analytical
laboratories. One of these ohronatography i s a practical ly
itsportant, simple and convenient method of sepai^tions,
Thus separations find an important position in cheMioal
analysis while ohronatography has proved i t s e l f to be a powerful
tool to chemical separations. The wide scope of ohromatoiraphy
i s the result of the labours of many, many people. I t grew in
response to practical needs.
The technique of chromatography was discovered by a
Swedish Botanist, Michael Tswett ( i ) in iqo6. t a t e r on in 19IO
3
ht pul»ll^«d A <!«ta11e4 monograph, "Chlorophylls In th« plant and
anlMal world*. The dtffarent oomponenta of a pigpent ailxture ware
reaolvetl in the form of yarlona coloured sonea on a etmple oaletuM
oaTtKmate eolunn* Be deeorlhed that the reaolutlon la baaed on
the adsorption neohanisn. Since the eoteponent which la aore
strongly adsotlied on the coluanti displeoea the weaker adeoH>ed
ones downwards. Kuhn A bis coworkers (2,5) demonstrated the
yalne of this new technique of adsorptl<nt chromatography and
resolved plant carotlne Into several components.
Thereafter people were In persistent search for an
adsorption chromatographic micro-separation process* In this
course thin oaplllories were tried In place of broader Tswett-
oolunns. However, e euoeess In this field was obtained by the
development of »l>rop Chi^matography* bjr tamollov and Sohreiber (%)
in 1938 by the change of closed columne to open eolussne In the
form of adsof1)ent coated glass plates and this may be considered
as the historical start of thin layer chromatography. Meinhard
and ifall (5) in 19%8 added the use of binding agent to hold the
layer in place and named the technique as 'Surface Chromat(Hiraphy *.
A series of excellent papers were published by Klrchner et al.
(6t7t8) using this method and the name "Ohromatostrlp technique**
was employed. The most Important contribution to the development
of TtC was made by E.Stahl (9*1S) by the use of fine grain and
thlner sorption layers. Because of thin layers of very fine
grained naterial he called the method as «Thin tftyer Chromatography",
4
Oil sueb pl«t«s th« oonoentration of tbe Bep4iFat«d ooitposents la
••oh spot ar«a Is hlghar than on ooarae sorption layars uaad
•arliar. Vl»lng fine grains and thin layers ft lieoaiae posslhla
to achieve separations at an ultra nloro level. Thns E.Stahl
Is known as the *ploneer* of this teohnlqne.
The very proof se and sort one type of xtork started from
1958» Although several other authors (19*3^) have also contributed
a lot In the development of this branch of obrotaatography.
At present, thin layer ohroBMSitogrophy has proved to ho
highly sensitive for traces of materials. Preparation of thin
layer plates Is quite slnrple. An adsorbent (stationary phase)
such as sllloa or alumina In the forro of a slurry tilth or without
a binder Is spread as a thin layer of specified thlelcness (0.5-2 nm)
on a glass plate. Tt Is then allowed to dry and used for
ohronatography In the following way.
fhe sample solution is applied as a spot or a line at a
centimetre from one end of thin layer plate and the solvent is
allowed to evaporate. This end of the plate Is then dipped Into
a suitable developing solvent (noblle phase) placed in a closed
tank. The level of the developing solvent Is kept below the
line or spot of the satsple. The developing solvent rises
continuously upward because of capillary action. Although
developaent of thin layer can be made through ascending, descending,
horlsontal or radial «ovenent of the solvent. But ascending wode
tends to Mlnlalze problems of channeling of the solvent flow.
5
Tb* plate* are taken out of the tnnk anc the eolTent rlne le
•arkeA with pencil* After ^rsrlng the plates are sprayed by a
suttahle ffeteetor to t«?eiitlll the varlons o<mponentei for
Indlvtifnal oomponente of the aanple the nlis ration rotes are
different due to difference In dtetrlbation oo»effloients between
stationary phase and the esoblle phase and this resnlte In the
separation of zones of different oorsponents of the saisple* The
different rotes are tneasured as the ratio of distances titivelled
by the solute and the solvent In terns of Betardatton Paotor (llp)i
Where,
Metanee travelled by the centre of the gone of solute Distance travelled by the developing solvent
Thin hay^T Ohroaatography sofBetines is also Icnown as *planer* or
*open oolniro* chroisatf^raphy* This technique has got the
advantage of (1) low cost, (ii) sensitivity, (iii) slispllclty,
(iv) speed, (v) unaffected by high tenperaturee, (vi) unaffected
by aggressive spraying reagents, (vii) less diffusion of the
spots, (viii) possibility for cmantitative Measurements, and
(ix) a wide range of applicability in terms of adsox1»ent,
developing solvents and the sample,
A large number of stationary phases have been applied,
the most widely used being Silica, SiO^^X If O, a polar adsorbent.
Chromatographic silica typically has a surface area of about 9
900 m /gm, a pore volume of about 0.% ml/gm, and an average pore
6
dlan«t«r of aboat 10 ii«. Surface ar«a «ay be daoreased by aginn
in «taa«« Surface adeorptton altes are ooaposed of hyiSroxyl
groupa that are attached to alltoon atone and interact with
adsorttiog noleeulea throu{;h hydrogen bonding* The naximrai
oonoentratioQ of these surface hydroxyl groops ie obtained by
heating to about SOO 0, where moat of the adsorbed water la
reooved. At higher temperatures, hydroxyl groups interact with
each other to liberate water, and the surface activity decreases,
distinction Is made between several types of hydroxyl groups e.g.
Free, Bound, and Reactive. Reactive sites are presaoed to be
best for adsorption of polyfunotioaal: solutes (the west c OfflRon
type) whoreas monofunetional solutes adsorb e(|ually will on
reactive and free sites.
Next in lisportenoo to silica is Aluaina, an adsorbent
having basic sites. A problem with alumina is that B8se<43atalysed
reactions way cwcur with raany solutes, particularly when the
alumina has been activated at a high terapereture* Strong acid
solutes Riay be ehemieorbed, esters and antiydrides aay sapnify,
aldehydes and ketones aMsy form oondensation products, double bond
may change, double bonds nay ohange position and hydrogen halide
may be lost. Host oovMRonly need is low.temperature (200 C),
istpure* r-alnnina with a surface area of loO to 200 m /ga. It is
usually assuaed that oxide ions (o"***) are present la the surface
layer and AluainiiuR ions (Al^*^) In the layer below. Vater aay
be present as either hydroxyl groups or adsorbed water. Beating
to about 300 C reaoves aost of the adsorbed water and briags about
7
8 reaotlon to form hyi^roxyl groups, whlob In t»m oan b« renovwd
tiy heating to about 8(M) C snrfaoe aotlvity Inoreaaes with
tamperatnre. At h1j;b temperature (1100 C)c< •aluniaa ie fomed
which has low surface area anil is ohro»atographioaliy inactive,
Alunlna has been used as an edsotbent nainly in oolunn
ohro»atO|;raph3r, but it in not used to the aatse extent as atllea gel
for thin layer ohronotogrephy* The nutsber of papers reporting
the applioatioD of almiina in thin layer chromatography are far
lower than those for silica gel.
Mueiina nay be of three types nafflely Alkaline* Neutral
and Aoidowaehed el»0lne« Tt con be activated to different degrees.
Per the prepar8ti<Ma of neutral alumina, oomerotal alunina ia
covered with distilled water and a alight excess of 0«5K BK l is
added with stirring. After standing for an hour the liqnld is
decanted and the alumina repeatedly washed with distilled water
until the washings are free from chloride icms* It is then
dried at 100*190 C for at least 12 hours.
Phenols are hydroxy derivatives of aroaatio hydrocarbons.
The hydroxy derivatives of aroaatio hydrocarbons in general nay
be divided into three classes nnsely Alcohols, Snols and Phenols.
Phenols are conpounds in which a hydroxy group Is attached
directly to a benzene ring. They are nuoh acre aoldlo than
alcohols. Phenols ore very hydrophylllo compounds with varied
acidity. Certain phenols have got the importance in aedioinee
8
• • •ff«otlTe antisept ic , purfoBMtii toothpowd«r*, and aoath washas.
The tfenantfa of phenols are oonstantljr Inoreastng In a
nn«ber of ebenioal Indastrtea relatei) to nanufaeture of (fyea,
dletnfeotenta, antloxldents, prepai^tlons of explosives and
plas t ies e t c .
The separation of sooh en itsportant c lass of compound i s
naturally important• The raain problem oncountored for the
separation of phenols i s the eeporotion of strtiotural isomers.
The tise of ehroaatography in general end thin layer ohronatography
in porticnlar ean be made for the ir separation*
The earl ier wot* on Thin Layer Chroj»at<^rophy of Phenols
i s sutraiarised in the following table 1 .
s
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14
A eearob of the l i terature ehofws that a nunlier of atfeortieiite
and varied elaeees of developers have been need for tbe separation
of phenole. Host of the papers appear on 8 l l l«« gel as adeorbent.
Use of AlQi«ilna hae a lso been inade but lo a much l e s ser extent.
I t ties, therefore, decided to develop some simpler solvents
to separate i^enole on neatral alueilna plates , A syeteraatlo
chronatogi^phlo study has, therefore, been made with 24 developing
solvent systePTS for 30 phenols of varied c las ses . The use of
strong allcallne systems has been avoided as some of the phenols
taay oxidise In this medluin and pose d i f f icu l ty In deteotlem. The
results obtained on alumina are a lso compared with those obtained
on s i l i c a gel p lates .
15
BXPEBlMENfAt
ApparatuB
Thlo layer ohrowetography apparatus <T0SHin[VAl«,I!l15IA)
was naed for th« preparation of p la tes , fhe ohro«atography was
perforwe^t tn 24 x 10 x 2k em raotanijnlar chaBsber with a l i d ,
aeagents
A|jtl!4lNA (NEUTRAL) for TLC Of National Chemtoal Laboratory,
Poona was need and SI Ilea gel 6 for TtC (oontnlnlng 13* oalotuni
salphate) of Biogen, Bombay was used.
Solutions of different Phenols of 0*1' concent ration were
prepared by dissolving 100 ng of each phenol in 100 nl of
distilled alcohol,
!>eteotor
Perrlo chloride anhydrous (Laboratoiy Reagent) of Farabhai
M•Chemical8, India was used as 1* solution of it, prepared by
dissolving 1 giR in 100 nl distilled alcohol.
Other cbenloals and solvents were of analytical grade.
l»eveloper
The following solvent systems were used as developers*
1, Condnetivity water
2 . B l s t i l l e d alcohol
16
3 . Ethyl aeetat* (B.T^.H.)
4 . Ao«ton« (E.M«rek)
5* 1,4-Btoxane (B.I^.R*)
6* Metbea&l <B«B,ff»)
7» Btitanon««>2 (B«B»H*)
8, Benzene (B,D«R,)
9. Carbon at sulphide (Kooh light)
10. ©Imethyl enlphoxlde (Kooh light)
11, Aoetlo aoia (B.Mereb)
12, Toluene <B,B«B«)
13. Pyrliflne (B.ll.n,)
1%, Aeimonla (B.D.R.)
15. S B S (Kooh light)
16. Aniline (B.U.R.)
17. BataQone»2 andl Cyolohexane (lt3)
18. Aoetlo aold and l,%»B1oxane (Itl)
19. Methanol and Toluene (Itl)
20. Toluene, Chloroforo) and Acetone (39t30t35)
21. n-Butanol, Benzene end Aoetlc acid (99t40t5).
Preparation Of Thin Layer Platee
(i) Silica gel Q plateet The Blurry of ellloo gel wae prepared
by mixing 24 gai sllloa gel In k8 ml of 1» starch solution (prepared
by dleeolTlng 1 gm starch In 100 ml conductivity water). This
much slurry was sufficient for coating 3 plates of size 20 x 20 cm.
The slurry wae Immediately coated on the clean glass plates with
17
the h«lp of an applleator (Toshalwal,India) to give a layer of
0*50 «n tltlolmeafl for qnalltattve stabiles* Theae platea were
firat dried at room temperature for complete diylng and then
stores In an oven at room temperature until used.
(11) Alamlna (neutral) plateat The slurry of alumina was also
prepared hy mixing alumina (neutral) 24 g« In hB ml of 1*?* starch
solution (as prepared ahove) with constant shaking for 5 minutes.
This slurry was also sufficient for coating 3 plates of size
20 X SO cm and thloHness of the thin layer was also tcept constant
(0.50 nm). These were also dried as ahove and kept In an oven
at room temperature until used. iTntformlty of layer thickness
was the Important factor for optimum separations and reproduclhlllty
of Sp values*
Procedure
The plates were first activated hy heating them at a
temperature of 80-85 C for 15 minutes. Then one or two spots of
the test solutions were placed with the help of fine glass
capillaries and TtC Spotting Guide. The plates were then placed
In a chamher which was saturated with desired solvent vapours.
The solvent wns allowed to ascend for a specified distance. Then
the plates were removed from the chanher, dried end sprayed
hy alcoholic ferric chloride.
18
«BSm,TS
On dftteotton a vartety of ooloars w«re obaerved with
different i»l)«iiols which ar« l i s t ed as followat
- Qnlnol, 0-Cresol, tt^resol, S-^droatyqulnollne, Qnlntaydrone,
Oateehol, o( ^Naphthol, B-Kaphthol, 8-ByrlroaQr*7*todoqtt1iiollne>
5*Sulphonlo aoltl and Mienyl Plaorone (9-pheiiyl-2,3f7-trlbydrcay.
6-xflttorone) gave daric brown oolotired spots ,
• 0*Nltropheno1. oi^ Picric acid gave yellow spots.
«• !%enolphthal1ne gave plntc coloured spot when followed by
spray of WB solution*
• Resoreinol^ Vanllline» O-AMnophenol gave reddish-brown spots,
• Pyrogallol gave blaclcish spots*
• l»llltroso*2>Naphthol and Pentahydrosy flavone gave dark green
spots•
- Brono ore sol gmen and Brono phenol bine gave purple and
v io le t colours respectively.
- B-Nltrophenol and p*Hitrophenol gave reddish-yellow spots .
- k (^-Nitrophenyl-aso)-resorcinol gave orange coloured spot*
- Thyaol gave l ight grey spot,
- Phenol, Phlorogluoinol, 0-Ohlorophenol and p-Chlorophenol
gave reddish spots.
The results of ft. values in different solvent systeiss
are shown in tables I t , i n and IT.
19
Separations wera trleil for the different phenols having
differenoea in their R^ valuea. Spots of the mixtures were placed
on the plates and developed vlth the desired developer. Those
separations achieved praotioally are reported In tahles V, VI
and VTI.
20
S I . HO.
1 . 2 .
3. 4 .
5. 6. 7. 8 .
9 . 10 . t l . 12 .
1 3 . U .
15 . 16.
17. 18.
19 . 20. 2 1 . 22 .
2 3 . 24 .
25 . 26 . 27 .
2 8 . 29 .
30 .
1^ TALHES OF 30
T - • Phenols
O-Afsinopltefiol O-Hltrophenol Beeoroinol Cateeltol B.Kaphtbol Tani l l i t ie ftvjmol ftionol Plcrto aold flh-NttrophoQol Qulnol O-Cresol eioCresol 8-Hyflroxy Qoinoltne
O-Cbloropbenol Pyrogal lo l Gal l to aeid
p->Nltropli«iiol Phloroi laolnol 1 «Ni tro«o-2«Naph tliol < .Haphthol Bro«o oraaol grean BroMO phenol blue Phenolpbtbaltne
TABLE II
PHENOLS
Conduo-t l r i t y water
0 .38
0 .65 0 .70 0 .05 0 .00 0 .50 0 .00 0 .00
0 .09 0 ,52 0 . 7 3 0 .00 0 .00 0 .00 0 .00 0 .04 0 .02
0 .43 0 .71 0 .04
0 .51 0 .00
0 .00 0 .12
Qutnhy drone 0 .78 iM^hloroptaaaol 0 .22 4(%«»llltrophenyl aso)
Beaorelnol 0 .00 PentahydroxT flavone 0 . 0 0 8-4ly flroiy»7*T otloqnlno*
ltne»5«.attlphORto aold 0 .00 flianyl r inoreae 0 .00
IN TABIOtrS SOLVENT SYSTEMS
"7 > Bton
0.83 0 .27
0 .77 0 .03 0.81 0.36 0.84 0 .80 0 .06 0 .68 0 .70
0 .83 0 .85 0 .13 0 .02 0.04 0 .00
0.43 0.34
0 .80 0.81 0 .00
0 .00 0.76 0 .78 0 .76
0 .23 0 .00
0 .00 0 .00
f
ItOAO (Pora)
0 . 8 3 0 .40
0 .43 0 .02
0 .87 0 ,20 0 .88 0 .64 0 .00 0 .27 0 .52 0 .00
•
0.04
0 . 0 3 0 . 0 3 0 .00 0 .22 0.11
0 .03 0 .79 0 .00
0 .00 0 .26
0 .77 0 .88
0 .87 0 .00
0 .00 0 .00
f •
Acetone 1, (Pure)
0 .80
0 .09 0 .52 0 .02 0 .68 0 .08 0.12 0 .08
0 .00
0 .19 0.66 0 .87 0 .87 0 .03 0 .00 0 .05 0 .00 0.18 0.28 0.94 0 .88 0 .00 0 .00 0.22 0 .64 0.74
0 .00 0 .00
0 .00 0 .00
) 4*1)1 oxane (Pure)
0.91 0 .18 0 .48 0 .02
0 .75 0 .19 0 .93 0 .83 0 .00
0 .19 0 .57 0 .70 0 .90 0 .07 0 .00
0 .05 0 .00
0 .27 0 .20 0 .04
0 .80 0 .00
0 .00 0 .30 0 .64 0 .77
0.02 0 .00
0 .00 0 .00
<t«%l« f l oontinu«d)
21
S I , Ho.
t . 2 .
3. h.
5. 6. 7. 8 .
9. to. 1 1 . 12 .
13 . 1%.
15 . 16 . 17 . 18 .
19 . 2 0 . 2 1 , 2 2 .
2 3 . 2k.
25 . 26 .
27 .
28 .
2 9 .
3 0 .
itienol*
Oi»A«liiOfiticnot O-Nitroplienol Sesorolnol Cat«e}iol B«>Hephtbol Vanl l l ine Thywol Phenol Ptcrlc acta noNitrophenol Qttlnol O^reso l W'-CreBol
9»'By&ro%y Oalnoline O^hlorophenol Pyi^gfillol Gall10 sold p»lVltroph«nol Phloroglttolnol 1»N1troa o-2-Maph thol c< .HafAntbol BroMO or»to l green Bro«o plienol bine Plienolph thai ine
Qulnhy^rone p»Chlorophenol %(4«>lfttrophenyl axo)
Seaorelaol 3» 5»7»2,%, pentahyiJrosy
flavene
8<4i3r<lro3C]r.>7«»T odo4u Ino* ltBe->5-attlphonlo aold
nienyl fluorcme or ( 9 * n i e B y l . 2 , 3 , 7 . t r l h y . drQxy-6*f liioroBO )
Methanol (Pure)
0 .85 0 ,16 0 .7* 0 .03 0 .81 0 .18 0 .88 0 .84 0 .00
0 .57 0.81 0 .88
0 .87 0 .03 0 .77 0.0% 0 .02
0 ,23 0 .40 0 .00 0 .72 0 .00 0 .00 0 .44 0 .62
0 ,66
0 .02
0 .00
0 . 0 0
0 . 0 0
t Butanone
(Pure)
0 ,73 0 .06
0 .29 0.02 0.62
0 .06 0 ,90 0,75 0,00 0.28 0 .66 0 .88
0 ,89 0 .03 0 .74
0 .03 0 .00 0 .20
0 .13 0 .00 0 . 8 i 0 .00 0.00 0 .11 0 .00 0 .44
0 .00
0 .00
0 .00
0 .00
1
Benasene (Pure)
0 .04
0 .11 0 .00 0 .00
0 . 0 9 0 .04 0 .42
0 .13 0 . 0 0 0 . 0 0 0 . 0 0 0 .18 0 .16 0 . 0 0 0 .00 0 . 0 0 0 . 0 0
0 .03 0 . 0 0 0 . 0 0 0 ,04 0 . 0 0 0 .00
0 . 0 0 0 .00 0 .16
0 ,00
0 .00
0 .00
0 . 0 0
*CS2
(Pure)
0.00
0 .03 0 .00 0 .00 0.04 0 .00
0 .09 0,11 0 .00 0 .00 0 .00
0 .13 0 .06 0 .00
0 .09 0 .00 0 .00 0 .00 0 .00 0 .00 0 .00 0 .00 0 .00 0 .00 0 .00 0 .10
0 .00
0 .00
0 .00
0 .00
t
Toluene (Pure)
0 .00
0 .05 0 .03 0 .00
0 .05 0 .00 0 .24
0 . 0 9 0 .00 0 .04 0 .00
0 .16 0 .10 0 .00
0 .09 0 .00 0 .00
0 .03 0 .00 0 .00 0 .04 0 .00 0 .00
0 .00 0 .00 0.21
0 .00
0 .00
0 .00
0 .00
22 (Tal)l« IT cwttnuef l )
«— ,_,"* '1'"C—r:: —r:—rr_—*::':, i S I . PhMol* CH-COOR IPSO fyrfrtlna Pyridine SW Ani l ine
1 . 0->Amtnophettol 0*00 0 .00 0*00 0 .00 0 .06 0*00 2 . 0-Nltrophenol 0 .62 0.36 • - 0 .55 0 ,58 3 . R«8or«tnol 0 .77 0 .75 0,67 0 .7* 0,77 0 .75 4 . Catechol 0 « U 0.04 0 .03 0.04 0.06 0 .02 5 . B-Naphtbol 0 .00 0 .00 0 .00 0 .00 0,03 0 .00 6 . Voniltne 0 ,54 0 .43 0 .48 0 .63 0 .73 0 .62 7 . Thymol 0 .00 0 .00 0 .00 0 .00 0 .60 8 . rhenol 0 .00 0 .00 0 .00 0 .03 0.41 9 . Flcrlo acid 0 .62 0 .00 0.17 0.51 0 .43 0 .12
10 . »-Nltropbenol 0 .56 0.54 0 .58 0 .46 0.54 0 .52 1 1 . Culnol 0 ,76 0.76 0 .78 0.75 0.74 0 .34 12 . O-Creeol 0 .00 0 .00 0 .00 0 .00 0 .00 0 .00 13 . w-Creeol 0 ,00 0 .00 0 ,00 0,00 0,00 0 ,00 14 . 8-Tlyrtroxy Qulnollne 0 ,00 0 .00 0 .00 0 ,00 0,00 0 ,00 15 . 0-Chlorophenol 0 .00 0.00 0 .00 0 .08 0,62 0 .00 16. fyrogal lo l 0.11 0.08 0.06 0 .06 0,06 0 .06 17 . Oal l te a d d 0 .03 0,02 0 ,03 0.04 0.04 0.02 18. p-^ltrophenol 0 .33 0 .27 0.22 0 .18 0 .38 0 .27 19 . PhloroKlucinol 0 .68 0.67 0,62 0 .65 0.36 0 .38 2 0 . l-Nltro80-2-1«aphthol 0,11 0,04 0.04 0 ,08 0,08 0 ,04 2 1 . oC^Naphthol 0 .00 0 .00 0 ,00 0 .00 0.32 0 .00 2 2 . Broffio oreBol sreen 0 .30 0 .50 0 .13 0 .38 0 .38 0 .04 2 3 . Browo phenol hlue 0 .30 0 .59 0.15 0 .39 0 .38 0 .04 24 . Phenolphthellne 0 .00 0 .00 0 ,00 0 .00 0 .29 0 .13 25 . Qulnhydrone 0 .73 0 .80 0 ,76 0 .77 0.76 0 .00 26 . p-Chlorophenol 0 .00 0 .00 0 .00 0 .05 0.54 0 .15 27 . 4(4-Nltroplicnyl aao)
Resorelnol 0 .00 0 .00 0 .00 0 .54 0 .23 0 .20 28 . 3»5,7.2,4«Pentehydroxy
flavone 0 .00 0 .00 0 ,00 0,02 0 ,03 0 .00 29 . 8*nydroxy-7-Todoqulno*
11ne-5-9ulphon1c acid 0 ,00 0,00 0,02 0 ,03 0,06 0 ,00 3 0 . l^enyl Pluorone or
( 9 - P h e n y l . 2 , 3 , 7 - t r l h y -droiiy-6-flnorone) 0 .00 0 ,00 0 ,00 0 ,00 0 ,00 0 . 0 0
(T»bl« II eontiimed) 23
S I , No.
1 . 2 .
3. * .
5 . 6 .
7 . 8 .
9 . 10. I t . 12.
13 . 14. 15 . 16.
17. 19.
19. 20 . 2 1 . A r M tn
23 . 2* .
25. 26 . 27 .
28 .
29 .
50 .
Phenols
0>An1noph«nol 0-Nltrophenol Hesoretnol Catechol B«>Naphthol Vanl l l lne Thywol Phenol Ptcrto o d d noKltrophenol Qulnol 0-Cresol ii<i.Cre6ol
8-ny^rosy Qulnoltne O-Chlorophenol Pyrogallol G a l l i c ec ld p-Nltror»heool Phlorofitluolnol l»Hltroso-2-Naphthol o< «*9aphthol Bronio oreaol green Brono phenol blue Phenolphthaiine Qulnhy^rone p-Chl orophenol 4(4-lfltrophenyl aso)
Besorctnol 3» 5,7f 2 , %-Pentlihydroxy
flarone 8-Hy <« roxy-7-T ortocjii 1 n o»
11ne-5-eiilphonlo eolA Phenyl Fluorone or
(9 -Pheny l -2 ,3 ,7 - tr lhy <lfroxy-6-f 1 ttorone )
r •' Butanone tCyolo-hexane ( l t 3 )
0.3%
0.29 0.15 0 .00 0A2
0.06 0.82
0 .58 0 .00 0.21 0.12 0 .70
0 .53 0 ,03 0.45 0 .03 0 .00 0 ,20 0.04
0,03 0 .52 0.00 0 .00 0.04 0 .12 0 .46
0 .00
0 .00
0 .00
0 .00
Toluene 1 Chloro-forat Acetone (35t30t 35)
0«75 0 .47 0 .23 0 ,02 0 .74 0 . 2 0 0 .92
0 ,71 0 . 0 0
0 .25 0 .14 0 .80 0 .74 0 .02 0 .12 0 ,04
0 .00 0 .14 0 ,04
0 .06 0 .66 0 .00 0 ,00 0 .14
0 .13 0 .55
0 .00
0 .00
0 ,00
0 .00
Butanolt Bensene t Aoetto acid ( 5 5 J 4 0 8 5)
0 .92 0,82 0 .80 0.54 0.92 0 .78 0.94 0 .83 0,05 ^ 0.79 0.74 0,82
0 .79
0 .19 0 .30 0 .20
0.07 0.71 0 .59 0 .60 0,86 0.02 0.02 0,86 0 .89 0 .90
0 .70
0 .07
0 ,00
0 .00
Tol iiene t Methanol ( I j l )
0 . 8 0 0 ,42 0 ,59 0 ,02 0 ,64
0 .36 mm
mm
0,05 0 .55 0 .58
-
-
0.05 mt
0 .03 0 .02 0 .34
0 .26 0 .09 0 .72 0 .00 0 .00 0 .54 0 .63 0.71
0.12
0 ,00
0 . 0 0
0 .00
'O.IM Acdfi l,4-T»1ox-ane (1j1)
0 .92 0.42 0,87 0 ,07 0,91 0 ,85
-
4M»
««•
0,83 0.86
-
0 ^ 2
0.08
-
0.09 0.04 0.74 0.82
0 .10 0 .87
0 .17 0 .16 0,94
0 .93 0 .85
0 ,65
0.04
0 ,00
0 ,00
24
TABLE IIT
IT VALUES OP 30 PHENOLS ON STLICA GBL LAYBg - , i ' ^ . . • ' • » » • m , . . , . i . . . . „ ,
IN VARIOITS SOLVENT SYSTEMS
T 1 i i i Ethyl 1,4-Moxane Metbanol Butan- Aoetone acetate one-2
81 . No.
Flienole
(Pure) {VvLte) (Pure) (Pure) (Pore)
1 .
2 .
3 .
4 .
5 .
6 .
7 .
8 .
9 .
10 .
1 1 .
12 .
13 .
1*.
15.
16 .
17.
OoAnlnophenol
O-Nltrophcnol
BesoFOinol
Catechol
B-NapHthol
Ven l l l lne
Thynol
Phenol
Picr ic acid
n-Nltropbenol
Qulnol
O'-Creeol
• •Creeol
8»Ry4roxy Qnlnollne
0«Chl oroph enol
Pyrogallol
Gal l i c acid
0.9%
0.91
0.94
0 .90
0 .98
0 .75
0 .96
0 .96
0 .57
0.91
0 .91
0 .96
0 .98
0 .85
0 .95
0 .75
0 .03
0 .93
0.91
0 .89
0 .88
0 .89
0.86
0 .89
0 .94
0 .60
0.91
0 .90
0 .89
0 . 9 *
0.91
-
0.90
0 .09
0 .66
0 .87
0 .86
0 .86
0 .88
0 .85
0 .89
0 .88
0 .96
0 .93
0 .92
0 .94
0 . 9 3
0 .90
0 .95
0 .92
0 .74
0 .83
0.81
«
0.85
0 .88
0.77
0 .89
0 .86
0 .78
0 .88
0 ,87
0.91
0.91
0.82
-
0.68
0.10
0 .90
0 .95
0 .95
0 .95
0 .95
0.91
••
*m
0.94
0 .98
0 .99
mt
-
0.86
«•
0 .97
0.08T
(Table III continued)
25
S I . No.
18.
19 .
20 .
2 1 ,
2 2 .
2 3 ,
2h,
2 9 .
26 .
Pfienols
p«Nltrophenol
Phloroglaolnol
1 •.Ni troe o-2->na ph tb ol
cK .Krapbtbol
Brono ore s o l gi«en
Bromo pbenol blue
Pbenolpbtballne
i^uinbydrone
p-Cblorophenol
«
Ethyl acetate (Pure)
0.68
0.79
0.72
0.92
0.00
0.00
0.95
0.00
0.90
t
l ,4»Dioxane
(Pure)
0.75
0 .78
0 .76
0 .85
0 .03
0 .02
0.86
0 .98
0 .95
Metbanol
(Pure)
0 .82
0 .86
0 .88
0 .92
0 .92
0 .87
0 .87
0 .96
0.96
Butan~ one->2
(Pure)
0 .77
0 . 9 *
0.4%
0 .95
0 .03
0 .03
0 .91
0 .92
0 .98
Acetone
(Pure)
0 .91
0 .98
0 .97
0 .97
0 .09 T
0.10 T
0.96
0 .95
0.91
27. 4(%-llltrophenyl aao) Heeorolnol 0.16 0.82
28. 3»5»7t2,%~Pentabyaro«y flaTone 0.07 0.68
29. 8-.!tyflroxy-7»Toflo<?ul no-l ine* 5*enlpbonlo aeia 0.00 0.02
30. Pbenyl Vluorone or (9«Phenyl»2,3»7»tr1hy-4roxy-6*fluorone) 0.04 0.04
0.96 0.07 0.18
0.94 0.15 0.37 r
0.94 0.00 0.03 T
0.29 0.02 0.05 T
T • Tal l i sc
fABiJS IV 2 6 • ^ TiaOES or 30 FflKNOLS IH Pirr.CONCENTRATION OP AMNONIUN RTPROXinE:
SI. No.
Phenols O.OIM NH^OH O.IM NH^OB l.OM Nlf (»f
1. 2 . 3. k.
5. 6. 7. 8 .
9. 10 . 11 . 1 2 .
13 . 1*.
15. 16. 17. 18.
19. 2 0 . 2 1 . 23 .
2 3 . 2 * .
25 . 26 . 27 .
28 .
29 .
50 .
0>A8lnoph«nol 0-4fltroplieaol N«soreliiol Catechol B-Naphthol Vanl l l lne Thywol Phenol P ler lc aclfl • •Nltrophenol QalDOl 0»Creeol n-Cresol S-Hydroary Oulnollne OoChl oropheo ol
Pyrogallol Oa l l l e Aoid
p>Hltrophenol Phlorogloctnol t-.Nttro8o-2-Kaphthol o( -Naphthol Browooresol green Bromophenol bine PhenolphthaiIne QninhyArone p«>Chl orophen ol 4i(%«Nltrophenyl azo)
Seeorelnol 3,5,7f2,*-Pent8hyflroxy
flavone
8-Hy flrojty-T-I odociulno-line<-5-sulphonle aotd
Phenyl Fluorone or (9-Ph«Byl-2 ,3 ,7- trthy» drosy-e-f1«orone)
0 .00 0 , 7 1 0 .65 0 .03 0 .00 0 .68 0 .00 0 .00
0 .69 0 .60
0 .27 0 ,00 0 .00 0 .00 0 .00
0 .05 0 .03 0 .45 0 .39 0.34 0 .00
0.45 0 .49 0 .28 0 .20
0 .17
0 .22
0.02
0 .02
0 .00
0 .00 0*79 0 .69 0 .04 0 .39 0 .78 0 .00 0 .00
0.71 0 .75 0 .30 0 .00 0 .00 0 .00 0 .00
0.07 0 .06
0 .65 0 .41
0.45 0 .59 0.76 0 .78 0 .50
0 .55 0 .33
0 .43
0 .12
0 .13
0 .00
0 .00 0 .84 0.75 0.05 0.61 0.82
0 .00 0 .00
0 .77 0 .77 0 .35 0 .00 0 .00 0 .00 0 .00 0 .10 0 .08 0 .74
0.51 0 .56 0 .62 0 .80 0 .83
0 .57 0 .48
0 .39
0 .58
0 .18
0.23
0 .00
27
TABLE T
BIKAmr SEPARATIONS ACHTBVSD IK VARIOUS SOLVEHT SYSTEMS
8 1 . No.
Separation
Of «F Vrom
SEPARATIONS IN CO?JI>»CTIVITY WATBtl
1 . OoAntnophenoI (0 .39) 2 . 0->Nltropheno1 (0*00) 3 . O-Nltroptieool (0 .00) * , Resorelnoi (0 ,70) 5« Resorofnol (0*70) 6« Reaorolnol (0«70) 7 . Cateoliol (0»05) 8 . Ceteeliol (0*05) 9 . B-Nsphthol (0 .00)
t o . B^Naplithol (0 .00) 11 . Phenol (0«00) 12 . Phenol (0 .00) 13* Fhenol (0 .00 ) 1%, tnienol (0 .00) 13* Phenol (0 .00 ) 16 . Vani l l lne (0 .50 ) 17 . Vanl l l lne (0 .50) 18 . P icr i c acid (0 .09) 19 . P icr ic acta (0 .09) 20* ••NItrophenol (0 .52) 2 1 . «.Nitrophenol (0 .52) 2 2 . n^Nltrophenol (0 .52) 23 . Qutnol (0 .73) 2%. 8>flydrox3r Qulnollne (0 .00 ) 25. SJHydroxy Onlnollne (0.00)
26. Pyrogallol (0.04)
27. Phlorogluolnol (0.71)
0-Chlorophenol (O.OO) B-Nltrophenol (0 .52) p-Nltrophenol (0 .^3) Catechol (0 .05) Pyrogal lo l (0.0%) G a l l i c acid (0 .02) Qnlnol (0 .73) Phlorogluoinol (0 .71) o<.N&phthol ( 0 . 5 i ) Oalnhydrone (0 .78) n-Nltrophenol (0 .52) Resorelnoi (0 .70 ) p«Nltrophenol (0 .43) Phlorogluolnol (0 .71) Qutnol (0 .73) Thywol (0 .00) Phenol (0 .00) n»Nitrophenol (0 .52) p*Nltrophenol (0 .43) 0-Cresol (0 .00) • -Creeol (0 .00) l -Nltroeo-2.Naphthol (0 .04) Gal l i c ac id (0 .02) Oulnhydrone (0 .78) Qutnol (0 .73 ) Phlorogluolnol (0 .71) Gal l i c acid (0 .02)
(Table V eontinu«d)
28
S I , Separation J
Of \
fTCM
28* l~Nltro80.2-Naphtbol (0.04)
89• l-Nitro0O*2.Naphtbol (0.04)
30. o<:-Naphthol (0 ,51) 3 1 . Qolnhyflrone (0 .78)
(X.Hapbthol (0 .51) <>uinbydrone (0 .78) Qulnltydrone (0 .78) 8-ll3r(irox3r»7«to(!of!u tnol tne«
9-Sulpbonic a d d (0 .00)
SEPABAfXOKS IN ETBANOL
3 1 . O^Anlnopbenol (O.SS) 3 8 . O-Aalnophenol. (0*82) 3%. 0«>Antnophenol (0 .82) 3 5 . 0-Nttrophenol (0 .27) 36 . 0«Nttropbenol (0 .27) 37 . Besorotnol (0 .73) 3 8 . fteaorotool (0 .73) 39» Refiorolnol (0 .73) 4 0 . Cateobol (0 .03) 4 1 . Cateobol (0 .03) 4 2 . Oateobol (0 .02 ) 4 3 . B.Napbtbol (0 .80) 4 4 . y a n i l l i n e (0 .35) 4 5 . Vant l l ine (0 .35) 46 . Thjmol (0 .84) 47 . Tbywol (0 .84) 4 8 . rtieBol (0 .80 )
4 9 . Pbenol (0 .80) 50 . Phenol (0 .80) 51 . Fterlo acid (0 ,06) 52 . Plorlo acid (0 .06) 5 3 . a-Nltropbenol (0 .65)
0«I9itropbenol (0 .26) 0-Cbloropbenol (0 .02) p*Nttropbenol (0 .43) n«Nttropbeool (0 .66) P icr ic acid (0 .06) Catechol (0 .02) Pjrroi^allol (0 .04) Phloroglnolnol (0 .34) Phenol (0 .80 ) Qnlnol ( 0 .80 ) Phlorogltsoinol (0 .34) 8-I!ydrosy Qutnoline (0 .13 ) Tbynol (0 ,84 ) Phenol (0 .80 ) Broaooresol green (0 .00) Brono phenol blue (O.OO) P icr ic ac id (0 .06) Pyrogallol (0 .04) Phloroglnolnol (0 ,34) n-Vltrophenol (0 .68) p«Nitrophenol (0 .43) p-Nitrophenol (0 .33)
29
(Talilt T oontlnucd)
S I . No,
Separation T 0 f Frow «r
5*. 55, 56. 57. 58. 59. 60 .
Qnlnol (0.60) Qulnol (0*80) 8-B^droxy Qutnollne (0»13) lyrogallol (0.0%) Oalllc acta (0.00) i.!«rttro6o.s-frapbthol (0.60) 1*111 tro8o.2-ilaphthol (0.80)
6 1 . c3^-Naphthol (0 .81) 62. BrcMBOcreaol green (0.00) 6 3 . Bronoptienol blue (0«00) 6%. I^enolphtballne (0 .76)
6 5 . Phenolphthalln© (0 .76) 66 . Qnlnhydlrone (0 .78)
67 . B-Naphthol (0 .80) 6 8 . 4~(4*Nltropbenyl axo)
Resorelnol (0 .23)
Pyrogallol (0 .04 ) Phlorogluolnol (0 .3*) QttlnhycironQ (0 .78) Ttilox^gluclnol (0.3%) Flilorogluclnol (0.3%) S-Hytlroxy Qulnollne (0 .13) 8-Hydroagr-7»I o<lo«|«lnol Ine-
5»Snlphonlc aotd (0 .00) 8«I|)rdiroxy<|ulnollne (0 .13) Pbenolphthallne (0 .76) PhenolphtbAline (0 .76) 4»(4-9lltropbenyl azo)
Besorolnol (0 .23) Phenyl Plnorone (O.OO)
8-Hy droxy«7-t odoqiilnol 1 ne -5-Salpbonlc aold (0 .00)
Vanl l l lne (0 .35) Resorolnol (0 .73)
SEPARATIOHS IK BTRTL ACETA1S
69 . 0*Aiilnophenol (0 .83) 70 . 0-A«lnopbenol (0 .83) 71 . 0*A«lnophenol (0 .83) 72 . 0*A«ilnopbenol (0 .83) 73 . Heeorolnol (0.%3) 7%. Beaorolnol (0.%3) 75 . Resorolnol (0 .43 ) 76 . Resorolnol (0 .43 ) 77 . Cateohol (0 .02) 78 . Cateobol (0 .02)
OoNltropbenol (0 .40) p.>Nltropbenol (0 .22) ••Nltrophenol (0 .27) 0«Chloropbenol (0 .03 ) Catechol (0 .02) Pyrogallol (0 .03) Pblorogltiolnol ( O . i l ) Phenol (0.8%) Phenol (0 .84) Qttinol (0 .52)
(T«1»l« V oont1nti«4l)
30
8 1 , Sepamtlon
Of "r Wrvm «F
7 9 . B-N«phthol (0 .87) 80 . B-Naphthol (0 .87 ) 8 1 . nesoreinol (0«li3)
92, Vant l l lne (0 .20 ) 8 3 . Phenol (0.8%) 8 4 . Phenol (0 .84) 89* I^enol (0 .84 ) 86* Flienol (0 .84) 87 . Ptorlo a d d (o.OO) 8 8 . Picric aoti! (0 .00) 89 . H c r t e aotd (0«<K)) 90. Oolnol (0.52) 9 1 . Qulnol (0 .92 ) 9 2 . Qttlnol (0 .52 ) 9 3 . 8-Ily<!roxyqoiiiollne (0 .04) 94 . 8-fltydroxfctttliioltne (0 .04) 95 . 0-Chlorophenol (0 .05) 96 . p-Hitrophenol (0 .22) 97 . l-Nitro8o»2*Napbthol (0 .03 ) 9 8 . l-TVitroiio.2«Naphtbol ( 0 .03 ) 99* BroHC oraaol graen (0 .00)
100. nrono phenol blue (0 .00)
101. Phenolphthaline (0 .26) 102. Phenolphthallne (0 .26)
103* Phenolphthallne (0 .26)
8«>7!y(1rQ]cyqulnollne (0 .04) i'Nltroso-2'.Naphthol (0 .03) 4«(4-i;itrophenyl aiEo)
SeeorclDol (0*87) thjmol (0 .86) P lor le o d d (0 .00) O-Nltropbenol (0 .40) n*Nitropbenol (0 .27 ) p«Nltrophenol (0 .22 ) 0-Hltrophenol (0 .40) flk»Nltrophenol (0 .27) p*Nitropbenol (0 .22) 8-4l!jr^f03Q''qotnol1nc (0 .04) Pyrogailol (0 .03) Fhloroglnolnol (0 .11) o(-!?apbthol (0 .79) Qulnbydrone (0 .77) p-Chlorophenol (0 .88) p«0hlorophenol (0 .88) o( •Naphthol (0 .79) fUNaphthol (0 .87) Phenolphthallne (0 .26) Phenolphthallne (0 .27) Pentahydfroxy flavone (O.OO) 8«I{ydiroxy«>7*t odoqolnol Ine-
5.Sulphoalc acid (O.OO) Phenyl f loorone (0 .00)
SEPARATIONS IN ACETOMB
104. O-Aalaophenol (0 .80) 105* 0-A«lnophenol (0 .80)
0«Nltrophenol (0*09)
••Nltrophenol (0 .19 )
(T«I>1« T eontinoert)
31
S I . W o . w v .
106.
107. 108.
109. 110.
111. 112,
113. 114.
115. 116. 117. 118.
119. 120. 121 . 122.
123. 12%.
125. 126. 127. 128.
129.
" T ' " - • - """
Of Ip
0-Anlnopbenol ( 0 « ^ ) 0*Anlnoptieno] (0 .80) O-Kttropbenol (0 .09) l!«soreinol (0 .52) flesorolnol (0 .58)
Beeorelnol (0 .52) Resorelnol (0.52> Catechol (0 .02) B-Naplithol (0 .67) B»!l8phthol (0 .68) B*!raphthol (0 .67) Phenol (0 .08) Phenol (0 .08) Phenol (0 .08) (^uinol (0 .66) Qulnol (0 .66) 0<-Chlorophenol (0 .00) PhloroprlttOinol (0 .22) Gufnhyilrone (0 .6* )
Cainhydrone (0.6%) rhenolphthaline (0 .22) Phenolphthaltne (0 ,22) Phenolphthallne (0 .22) Phenolphthaltne (0 .22)
Separation
Prow ip
p«Nltrophenol (0 .18) 0«Chlorophenol (O.OO) p-43hlorophenol (0.7'k) Catechol (0 .02) ^•(^•.Hltrophenfl aaso)
Reeorolnol (0 .00) Pyrogal lol (0*05) Fhloroglnolnol (0 ,22) f l i lorogluolnol (0 .23) o(f-Waphthol (0 ,89) 8«Bydro]Qr(siilnollne (0 .03) l .Nlt i*oeo^.Naphthol (0.9%) p-Chlorophenol (0,7%) '^•Naphthol (0 .89) B^Nophthol (0 .67) Catechol (0 .02)
Pyrogallol (0 .05) p-4;{hlorophenol (0.7%) Qulnol (0 .66) 8-HyrtroxF-7-.TodoqulnoHne-5-
Solphonlo aoia (0 ,00) 8«Hyt!rojr3rqolnoltne (0 ,03) Brono creaol green (0 ,00) Brofflo phenol hlue (0 .00) Phenyl fluorone (O.OO) Penta hydrojiy flBTone (0 .00)
SEPARATIONS IN 1.4-PTOXANl
130. 0*A«lnophenol (0.91) 131* OoAalnophenol (0.91) 132. 0*A«lnophenol (0,91)
0«Nltrophenol (0.18) ••Nltrophenol (0.19) p«Nltropheaol (0.27)
(Table ? contlnusA)
32
S I . ' No.
133. 13* . 135. 136.
137. 138.
139.
1*0. 1*1. 1*2.
1*3. 1**.
1*5. 1*6.
1*7. 1*8.
1*9.
150. 151. 152.
153. 15*. 159. 156. 157. 158. 159. 160.
" ' •
Of Up
O-Anlnoptieiiol (0 .91) O-Nltrophenol (0 .18) Sesoroinol (0 .*8 ) Resorolnol (0 .*8 ) Resorcinol <0.*8) Resorotool (0 .*8 ) Reeorotnol (0 .*8)
Coteohol Cateohol
I (0 .02) i (0 .02)
B-Naphthol (0 .75) B-Napbthol (0 .75) B-Naphthol (0 .75)
Vant l l lne (0 .19) Vant l l lne (0 .19) Vanl l l tne (0 .19) Tbynol ( Tliynol 1
fhywol ( Thyaol I Ftienol < riienol I rhenol ( rbenol I Pfianol Ilienol 1 Plianol 1 P icr ic 1
»»)tltro;
(0.93) [0.93)
[0.93) [0.93) [0.83) 0 .83 ) [0.81) [0.81) [0.82)
[0.83) [0.83) lotfl (0 .00)
)h«nol (0 .19)
Separation * - " ' . . i ._
OoChloroptienol (0 .00)
Phenol (0 .83) Catechol (0 .02)
Hienol (0 .83) Pyrogallol ( 0 .05 ) Pbloroglfictnol (0 .20) 4*(**Hltrophenyl azo)
Besoroinol (0 .02) Phenol (0 .83 ) Qainol (0 .57 ) 8-Hy<^ro3Qrquinol1ne (0 .07) l.IVltroao.2.Naphthol (0 .0* ) 8»nydroxy«>7<»lodo(}t]lnol i n e - 5 -
Sulphonio aold (0 .00)
.ThinBOl (0 .93 ) 0<4:re8ol (0 .70) • ^ r e s o l (0 .90) PhenolphthaiIne (0 .30) 4-.(**191trophenyl ajso)
Resoroinol (0 .02)
Pentahydroxy flarone (0 .00) Phenyl flnorone (0 .00) l y r o g a l l o l (0 .05) Phloroglwotnol (0 .20) ••Nltrophenol (0 .19) p-Nltrophenol (0 .27) 0-Nltrophenol (0 .18) G a l l i c ac id (0 .00)
Ouinol (0 .57) p.¥lltrophenol (0 .27) p«Chlorophenol (0 .77)
(T8bl« T oonttnned)
33
S I , No.
Separation
Of Prow B.
161. Qnlnol (0 .57 ) 162. Qalnol (0 .57) 163. Qiitnol (0.57> 16%. 0«>Cre«ol (0 .68 ) 165. 8-Hyflro3i^<lulnbltne (0*07) 166. 8-Hydro3ryqulnoltne (0 .07) 167. Gal l ic ©eld (O.OO) 168. p-Wltrophonol (0 .27) 169* l-!7itro8o-2'.Naptithol (0 .04) 170. l-Nitro8o.2-Naplithol (0 .04) 171 . oC-Sfaphthol (0 .80) 172 . DroBto creso l green (O.OO) 173. Browo phenol blue (0 .00) 174 . Ftienolptithellne (0 .30)
175. Phenolphthaline (0 .30) 176. Phenolphthallne (0 .30)
177. Phenolphthallne (0 .30)
178. 179, 180 . 181 . 182.
183. 184.
185. 186. 187.
Pyrogollol (0 .05) Phlorogluclnol (0 .20) Gal l i c acid (0 .00)
n-Oreaol (0 .91) Quinhyflrone (0*64)
o( .Napbthol (O.8O) Reaoroinol (0 .48) p»Chlorophenol (0 .77) o< -Naphthol (0 .80) Oninhydrone (0 .64) 8<-liy^roaEyf)alnoline (0 .03) Phenolphthallne (0 .30) Phenolphthallne (0 ,31) ^•(^.Nltrophenyl aeo)
ftesorolnol (0 .02) Pentahydrojty flavone (0 .00) 8-Hy «!ro3ty-7-l od oqu In ol 1 ne-
5*Salphonlc acta (O.OO) Phenyl flnorone (O.OO)
SEPARATIONS ACHIIiVKD IN WiTHANOL
OoAmlnophenol (0 .85) O-Anlnophenol (0 .85) O'oAMlnophenol (0 .85) 0-Kltrophenol (0 .16) 0»Nltrophenol ( 0 . I 6 ) 0-Nltrophenol (0 .16) Resorclnol (0 .74) l e soro lno l (0 .74 ) Reaorolnol (0 .74) Catechol (0 .03)
0*Nltrophenol (0 .16) •-Nltrophenol (0 .57) p-Nltrophenol (0 .23) Phenol (0 .84) n-Nltrophenol (0 .57) 0*Chlorophenol (0 .77) Catechol (0 .03) Pyrogallol (0 .04) Phlorogliiclnol (0 .40) Phenol (0 .84)
(r«bl« T oontifiu«d)
34
S I . No,
Sef)a rat ion
Of T
Frew
188, 189. 190. 1 9 1 . 192.
193. 19*. 195. 196. 197. 198. 199. 200. 201 , 202. 205. 204 . 205. 206. 207. 208. 209. 210. 211 . 212. 213 . 2141. 215 . 216. 217.
Catechol (0 .03) Catectiol (0 .03) B-Haphthol (0 .81) 1!.N8phthol (0 .81) itesorolnol (0 .7^)
T&nllllne ( 0 . I 8 ) ThyiBOl (0 .88) Thyaol (0 .88) l ^ o l (0.88) rtienol (0 .84 ) Phenol (0 .84 ) Phenol (0 .84 ) Phenol (0 .84) Hi-Nttrophenol (0 .57) n>N1trophenol (0 .57) •u lno l (0 .81 ) Qulnol (0 .81) Qttlnol (0 .80) 0-Cresol (0 .88 ) • •Cresol (0 .97) 8»ny«ro3ry qalnol lne (0 .03) 0-<2hlorophenol (0 .77) Pyr<^allol (0 .04) Gal l i c acid (0 .02) p-Nltrophanol (0 .23) l - introso .2 .Naphthol (0 .00) l . iritroso»2.Kaphthol (O.OO) l .Nltroao.2.Naphthol (0 .02) Broiio eraaol graen (0 .00) Brono phenol blna (O.OO)
Oulnol (0 .81) rtilorogluolnol (0 .40) 8-l!yflroxy qulnoline (0 .03) l-.l(tltro9o-2*!faphthol (0*00) 4«.(4-Nltrophen3rl a«o)
Reaorclnol (0 .02) Thywol (0 .88) Bromo oreso l greee (0 .00) DroiBO phenol blue (O.OO) Phenolphthallne (0 .44) Picr ic aclfl (0 .11) O-Nltrophenol (0 .16) i9»Nltrophenol (0 .57) p*Hltrophenol (0 .23) p»Nltrophenol (0 .23) 0-?lltrophenol (0 .16) Fyrogallol (0 .04) Phlorogluclnol (0 .41) Gal l i c acid (0 .02) Broao oreeol green (O.OO) BroMo creaol gznan (0 .00) o<f-Waphthol (0 .72) Gal l i c acta (0 .00) Phlorogluclnol (0 .40) Phlorogluclnol (0 .40) p«Chlorophenol (0 .66) o^-Haphthol (0 .72) Qulnhydrone (0 .62) o( .Naphthol (0 .72) Phenolphthaltne (0.44)
PhenolphthaiIne (0.44)
(Tal)l« V oonttnuftiSI)
35
S I , iio.
Sepa rat ion
Of Rp Pros 8p
218. Quinhy&rone ( 0 ,63 ) 219• Oulnhyrtrone (0 .62 )
220, 4»(4*NUropheQyl aso) Heeorotnol (0 .02)
221 , Pentabydroiy flavon© (0 ,00) 222, Phenyl fluorono (O.OO)
* » 5 . 224.
225. 226. 227. 228. 229. 230,
231. 232, 233. 23* . 235. 236, 237. 238. 239. 240. 2%1. 242. 243.
8-Ily«!roayqnlnollne (0 ,03) 8-Hydroxy-.7-I odoqolaolin©.
5*Sul|^onlo acid (o ,00)
ThyiBQl (0 ,88) Thyeol (0 .88 ) Thyaol (0 ,87)
SEPARATIONS IN BIJTANONE-2
O-Anifioptienol (0.73 ) 0-<AiBtiioplienol (0 .75) O-Amlnophonol (0 .73) Reeorotnol (0 ,29) Reeorolnol (0 ,29) fteeorotnol (0 ,29) Sesorolnol (0 ,29) Re«orcliiol (0 ,29)
Catechol (0 .02) Catechol (0 .02) B.Nanhthol (0 ,62) B.Napbthol (0 ,62) B.Naphthol (0 .62) B.Naphthol (0 .62) Van l l l lne (0 .06) Tbynol (0 .90) Thywol (0 .90) Thyaol (0 .90)
PentahyAroxy flavone (0 .00) Phenyl fluorone (0 ,00) Phenol (0 ,84)
O-Nltropbenol (0 ,06) n-Nltrophenol (0 ,28) p»Nltrophenol (0 ,20) Catechol (0 ,02)
Phenol (0 .75 ) Qntnol ( 0 .66 ) Fyrogallol (0 ,03) 4 . (4-Nltrophenyl azo)
Besoroinol (0 ,00)
Phenol (0 .75) Quinol (0 .66 ) ^(-Napbthol (0 ,81) 8-l!ydro:iR^qulnoltne (0 ,03) l-Nltroso*2-Naphthol (0 .00 )
0«tnhy<Srone (0 .00) Tbynol (0 .90) Br<Mio creaol green (O.OO) Broao phenol blue (O.OO) Phenolphthaltne (0 .11) Thy«ol (0 .90) Tbjraol (0 .90)
Nitrophenol (0,28)
(Tabl« V continued)
36
SI. No.
Separation
Of from «F
2hk,
2^15. 246. 247. 248. 249. 250. 251 . 252. 255. 25*. 255. 256, 257. 258.
259. 260. 261.
262. 263. 264. 265. 266. 267. 266.
269. 270.
Phenol (0 .85 ) Plorlo ac id (0 .11) ii«|91trophenol (0 .28) Qalnol (0 .66) Qalnol (0 .66) 8i<*Creeol (0 .89) 8«Hydroxyi|nlnoltn© (0 .03) 8«Rydroacy<|ulnollne (0 .03) 0*Chlorophenol (0 .74 ) 0«Chlorophenol (0 .74) l-Hltroso-2-Nsptothol (0 .00) Gal l i c aoia (0 .00) Catechol (O.OO) P i c r i c acid (O.OO) D< -Naphthol (0 .81) o( -Napbthol (0 .81) Rt*Creeol (0 .88) Catechol (O.OO)
p»Nltrophenol (0 .20) Phenol (0 .74) 0«Nltrophenol (0 .06) Pyrogal lol (0 .03) Fhloro^laclnol (0 .13) V a n l l l l n e (0 .06) o(-Naphthol (0 .81) B-Naphthol (0 .62) O-Nltrophenol (0 .06) P«-Chl0rophenol (0 .44) <^*Nephthol (0 .81)
Qulnol (0 .67) B^Naphthol (0»62) Qolnol (0 .66) Brono creso l green (O.OO) Broao phenol hlue (O.OO) p»Nltrophenol ( O . l l ) o(.Napbthol (0 .80)
SEPABATIONS IN.IM PlfniT)T?JE
O^Anlnophenol (O.OO) nesorclnol (0 .74) Iteaorelnol (0 .74) Catechol (0.04)
Catechol (0.04)
B.iraphthol (O.OO) 4-(4.Nltrophenyl a t o )
Iteaorelnol (0 .5* ) Yanllllne (0.63)
Thy«ol (O.OO)
m*Nltrophenol (0 .46) Catechol (0 .04) Pyrogenol (0 .06) Phlorogluclnol (0 .63 ) Qulnbydrone (0 .76) Qulnhydrone (0 .76)
Resorclnol (0 .74) Thywol (0 .00) Broaocreaol green (0 .38)
37
(T«til« ? o on tinned)
S I , No,
271, 272.
273. 27*. 275. 276. 277. 278.
279. 280. 281 , 282.
283.
284.
289. 286,
287. 288,
289.
separat ion
0 f Bp
Ttaynol (0 .00) Thjrwol (0 ,00)
FhoBol (0 .03) Phenol (0 .03) P icr ic acid (0 .51) n-NltropTienol (0*46) Qttinol (0 .75) Oainol (0 .75)
O^Cresol (0 .00) 8-Hydro«yqainollne (O.OO) Pyifogellol (0 .06) PhlorojEiluetnol (0 ,65) l-Nitr080-2.Niilibtfcol (0 .08)
Pbenolphthallne (O.OO) Phenolphthaline (0 .00) 4»(4.Nltrof»henyl azo)
lies ore ino l (0 .5*) - d o . «»do» wdOw
SEPARATIONS
PrOB Hp
Brono phenol blue (0 .39 ) 4-(4»Nitrophenyl a«o)
Beeoroinol (0.5%) Qainol (0 .75 ) Reaoreinol (0.7%) p-Nltrophenol (0 . I8 ) p-Nltropbenol (0 .18) Pyrogallol (0 .06) 6*!lydroxy-7*Todoqttinoline-
f-Sulphontc acid (0 .03 ) Ver.i l l ine (0 .63) Qolnbydrone (0 .77) Phlorogluoinol (t>.65) Ool l i c actd (0 .04) Ah-(*-.Nltrophenyl a«o)
Hesoreinol (0.5%) Brono oreso l green (0 .38) Brono phenol blue (0 ,39)
Phenolphthaline (O.OO) Pentahydroary flavone (0 .02) Phenyl fluorone (0 .00 )
8*IIydr<wy-7»TodoqainoHne-5-Salrhonlc acid (0 ,03)
IN O.IM PywiDINE
290. 0«AMinophenol (O.OO) 291. 0-*«iinophenol (O.OO) 292. Reaoroinol (0,67) 293. Reeorcinol (0.67) 29%. Catechol (0,03) 295. Catechol (0.03)
n-Nitroplieuol (0.98) Quinol (0.78) Catechol (0.03) Pyrogallol (0.06) Phlorogluoinol (0.62) Quin<^, (0.78)
(Table V continued)
38
S I . No.
296. 297. ^"o «
299. 300. 301 . 302.
303. 304.
305. 306.
307.
308. 309 . 310.
311 . 312.
313. 31'!. 315. 316. 317. 318.
319. 320 . 321 . 322.
3 2 3 .
1 1 .1 1 1
Of ftp
Thynol (0 .00) Phenol (O.OO) neeorclnol (0 .67) P i c r i c ocirt (0 .17) m-Nltrophenol (0.5*?) Qufnol (0 .78) Pyrogallol (0 .06) Ga l l i c acifl (0 .03) Qulnhy^rone (0 .76) Quinhyilrone (0 .76) Quinhyitrone (0 .76) Ouinhydrone (0 .7*)
Separation
Prow Up
Vanit l ine (O.ftS) Ouinol (0 .78) Vanillin© (0 .47) w-fJitrophenol (0 .58 ) p*Kitror»henol (0 .22 ) Pyrogal lol (0 .06) Phloro»loclnol (0 .62 ) Phlorogluolnol (0 .61 ) B«wophthol (0 ,00) d -!9aphthol (0 ,00) 8-Hydrosy<3ulnol Ine (0 .00) 8-Hydroxy-7-t odoquinoline-
5-Su1^onic acid (0 .02) SEPAfiATlOJlS IN O.IW ACETTC ACIP
0*Ae9tnophenol (O.OO) OoAtninopbenol (O.OO) 0-A«1oophenol (O.OO) O-Nitroptienol ( 0 .62 ) Peeorcinol (f».77) Resorclnol (0 ,77) Catechol (O.H) Catechol (0 .11) Phenol (0 ,00) Phenol (0 ,00) Phenol (O.OO) P icr ic acid (0 .62) iB-Nitrophenol (0 .56) Ouinol (0 .76) PhloroRluciool (0 .68) Phlorofrlncinol (0 .68)
O-Kitronhenol (0 .62 ) «»Nitrophcnol (0 .56 ) p-NitroT)henol (0 .33 ) p«Nitrophenol (0 ,33) Catechol (0.1%) Pyrogallol (0 ,11) Ouinol (0 .76) PhlorOjejlncinol ( 0 .68 ) Weworcinol (0 .77) Ouinol (0 ,76) Phlorosrlucinol (0 .68) p-iritrophenol (0 ,33 ) p-Nitrof)henol (0 .33 ) Gal l i c acid (0 .03) Pyrogallol ( O . H ) Gal l i c acid (0 .03)
(Table • oontlnuftd)
39
Si , NO,
Separation
Of «P Prom
324, Quinhydrotie (0.73> 325 . Qutn!iy<irone (0 .73) 326 . Qolnbyflrone (0»73) 327, Ow1n*iy«^rone (0 .73)
8-Hy^roxy«[iilnol1ne (O.OO) c< -Naphthol (0 .00) B-Naphthol (0 .00) 8-ny<f roxy-.7-T odoquinoline.
5-s»lphonle aoi6 (o.OO)
SEPAHAflONS tn O.IW PMSO
328, O^Amlnophenol (O.OO) 329, 0-»Aiitfiophonol (0 .00) 330, O-Awtnophenol (0 ,00) 331 , Resorclnol (0 .75) 332, Qesorctnol (0 ,75) 333, Catechol (0 .04) 334, Catechol (0 ,04) 335, 0-43re90l (O.OO) 336, m-^resol (0 .00) 337, Htenol (0 .00)
338, Phenol (O.OO) 339, Wienol (0 .00) 340, Phenol (0 ,00) 341 , phenol (0 .00) 342, P i cr i c acta (0 .00) 343, P i cr i c acta (0 .00) 344, P icr ic acid (O.OO) 345, »-Nltrophenol (0 .54) 346, Quinol (0 .76) 347, Pyrogal lol (0 ,08) 348, G a l l i c aeiO (0 ,02) 349, Oolnhyilrone (0 .80 )
350, Qnlnhydrone (0 .80) 351, Qalnhy<'rone (0 .80)
0»19ltrophenol (0 .36) m-Nltrophenol (0 ,54) P-N1tropbenol (0 ,27) Catechol (0 ,04) Pyrogollol (0 .08) Qulnol (0 .76) Phlorogluclnol (0 ,67) Van l l l lne (0 .43) Vanl lUne (0 .43) 0-Kltrophenol (0 .36 ) in-Nitroplienol (0 .54 ) p-Nltrophenol (O.27) Resoroinol (0 .75) Phlorofljliicinol (0 .67) 0-^?4trophenol (0 .36 ) w-Nltrophenol (0 .54 ) p-Nltrophenol (0 .27) p-Nitrophenol (O.27) pyrogal lo l (0 .08) Phloroi?luclnol (0.G7) Phloroffladnol (0 .67) o(«i|aphthol (0 .00) B-Kaphthol (O.OO) 8-IIy^roxyno1noline (0,00)
40
(Table V continued)
S I . No,
Of «F
Separation 1 — ~ ~
Fron
352. Quinhyfirone (O.W))
SEPARATIONS IN Q.lW ANTU??B
8-IIy f'roxy-y-T odotro i nol ine. 5«»Sttlplsonie aoia (o.OO)
353. O-Amlnoptienol (O.OO) 35*• O.Aatnophenol (0 .00) 355, O-Nltrophenol (0 ,5S) 356, Hesorolool (0 ,75 ) 357, Iteaorcinol (0 ,75) 358, Resoroinol (0 ,75) 359, Resorclnol (0 ,75) 360, Catechol (0 ,02) 3 6 ) , Catechol (0 ,02) 362. Vanl l l lne (0 ,62)
363, JB-Nitrophenol (0 .52 )
36*. QulBol (0 .3*) 365. Oninol (0.3%) 366. Qttinol (0 ,3*) 367. Pyrogal lol (0 ,06 ) 368. Gal l ic acifl ( 0 . 02 ) 369. PhloroRlnclnol (0 .38) 370. ftcaoroinol (0 ,75)
37 t , Catechol (0 ,02)
a«-Nitropbenol (0 ,52) p.Nitropbenol (O.27)
p-Nitrophenol (0 ,27 ) Catechol (0 ,02) Ottinol (0 .3*) Pyrogallol (0 ,06) Phloro{<;luoinol (0 ,38 ) OulQol (0 .3*) Phloroglaolnol (0 ,38) P i cr i c acid (0 ,12 ) p-Nttrophenol (0 ,27 ) Pyrogallol (0,06)
Catechol (0,02)
Gallic aeid (0,02)
Vanilline (0.62)
Vanilline (0,62)
Pyrogallol (0,06)
^.(ii«Nitrophenyl ««o) Reaorcinol (0,20)
Vanilline (0.62)
SSPARATIOVS IK t * STO
372. O-Aninophenol (0 ,06) 373, O-Aninophenol (0 ,06) 37*. 0-AiilnopheROl (0 ,06) 375. n e s o r c i i o l (0 .77) 376, Reworcinol (0 ,77)
0-Nitrophenol (0.55)
•-Nitrophenol (0,5*)
p-Nltrophenol (0,38)
Catechol (0.06)
Pyrogallol (0,06)
(Table y oontinue<S)
41
S I . X1U«
377. 178. 379. 380 . 381 , 382 . 383 . JrCl" •
385. 386. 387. 388 .
389.
1
Of Rj,
Resorcfnol (0 .77) Catechol (0 .06 ) B-Naphthol (0 .03) Vani l l tne (0 .73 ) Vantllln© (0 .73 ) Ttiyiaol ( 0 .60 ) Picr ic acta (0.'i3) s-^Kitrophenol (0 .5*) Qttlnol (0.7J*) Qntnol (0.7%) Qotnhyarone (0 .76) Qalnhy<1rone (0 .76) Qoinhyflrone (0 .76)
SEPARATTOWS
Separation
Prom R.
Phloro^luclnol (0 .36) Qalnol (0 .7*) Qti1ntiy6rone (0 .76) 0<»Cre8ol (O.OO) (B-iCi«sol (O.OO) Phenolphthnline (0 .29) Gal l i c ac id (0 .04) Gal l i c aoia (0 .04) Pyrogallol (0 .06 ) Phlorogluclnol (0 .36) o( .Napbthol (0 .31) 8-Hy^roxyqulnoltn© (0 .00) t-.Nltroeo-2-.Nophtliol (0 .08)
IN B«TAN0^35«2j CYCLOllbXANE (2?f7?)
390. O-Awinophenol (0 .34 )
3 9 i . neeorclnol (0 .15) 392. B-Nophtbol (0 .42) 393 . B-Saphthol (0 .42) 394. B*Naphtbol (0 .42) 395. Vani l l tne (0 .06) 396. Van i l l lne (0 .06) 397. vanillin© (0.06)
598. Thywol (0.82)
399. BroBO oreeol green (0.00)
400. Brono phenol blue (O.OO)
401. Phenol (0.58)
402. Phenol (0.58)
403. Phenol (0.58)
404. Phenol (0.58)
Catechol (0 .00) Phenol (0 .58) 8.1lydroxyqtiinolitie (0 .03) 1-Nitro«o«2»lfarhthol (0 .03) Qainhyflrone (0 .12) ThjniOl (0 .82) 0»Crefiol (0 .70) n<-Cresol (0 .53) Phenolphthaline (0 .04) Thymol (0 .82) Thywol (0 ,82) 0-Nitrophenol (0 .29) ••Nitrophenol (0 .22) p.Hltrophenol (0 .20) Ouinol (0 .14)
(Table V continued)
42
SI . No.
%05. 406. 407. 408.
409. 410. 4J1 . 412.
413. 414.
415.
Separation
Of Hp
8-I^tfro3yqulnol1no (0 .03) p.Cblorophenol (0 .46) Pyrogallol (0 .03 ) Pyrogallol (0 .03) Gal l i c a d d ( 0 . 0 0 ) l-Nttroso-2-Naplithol (0 .03) Qolnbydron© (0 .12) 4.(4-.Nltropheny3 BBO)
Qeaorclnol (O.OO) Pentahydroxy flavone (0 .00) Phenyl fluorone (0 .00) BroBio ere so l green (O.OO)
SEPARATIONS IN TOtllENB {?^ 1 ,:?<?
1 " - - — -
Fron ftp
o( -Napbthol (0 .52) p*Nltrophenol (0 .20) oi .Napbthol (0 .52) B«Naphtbol (0 .43) o(-Napbthol (0 .52) o( -Napbthol (0 .52) cC-Napbthol (0 .52)
Thyraol (0 .82) Thymol (0 .82) Thyiaol (0 .82) B-Napbtbol (0 ,43)
S CHLOROFORM t ACETONE ' 1 ??) ....-,
416. 0-A«ntnopbenol (0 .75) 417. 0-Affl1nopbeool (0 .75) 418. O-Awlnophcnol (0 .75) 41q. 0-Nltrophenol (0 .48) 420. 0-Nftrophenol (0 .48) 421 . Reaorolnol (0 .23) 422. Ga l l i c aciff (O.OO) 425. Catechol (0 ,02) 424. Catechol (0 ,02) 425. B-Naphthol (0 .74) 426. B-Naphthol (0 .73) 427. B-Naphthol (0 .74) 428. Vanl l l tne (0 .20) 429. Broao crc«ol green (0 .00) 430. Bromo phenol blue (0 ,00) 431 . PhenolphthaiIne (0 .14)
0-Nltrophenol (0 .47) w«Nltrophenol (0 .25) p-Nttrophenol (0 .14) «-Nltrophenol (0 .23) p-Nitrophenol (0 .16) Catechol (0 .02) ftesorclnol (0 ,23) Phenol (0 .71) o<-Napbthol (0 .66) l-Nltro»o-2-Naphthol (0 .06) Qntnhyrtrone (0 .13) 8-!lyaroxyqutnollne (0 .02) Thywol (0 .92) Thymol (0 .92) Thymol (0 .92) Thymol (0 .92)
(Tftble V eontinii«A)
43
» 1 , No.
*32 .
%33. ^3%, 435. *36 ,
437. 438 ,
439. 440. 441 , 442 .
443 . 444 .
445. 446.
447. 448.
449. 450.
451 . 452. 453. 454. 455.
456.
457.
f
Of Up
4*(4.Nitroph«ny1 azo) flefcorotnol (0 .00)
Pentahy«!roxy flovone
Separation
(0 ,00) riienyl flttorono (O.OO) Phenol (0 .71) Phenol (0 .71) P icr ic aclfl (O.OO) Plorlo acid (0 .00)
O-Creeol (0 ,80) tt-^ro8ol (0 .74) 8«Hy<1roxy<inlnollne (0 .02) O-Chlorophenol (0 .12) l-Nitro8o-2-Naplithol
Quinbydirone (0 .13)
SBPARATIONS IN
Qeeorcinol (0 .80) fteaoroinol (0 .80) BeBorc"?.nol (0 .80)
Catechol (0 .54) B-Nanhthol (0 .92) 1-.Ni t ro90-2-!r*iph th ol y a n l l l l n e (0 .78) Van i l l lne (0 .78) Thywol (0.94) Thynol (0 .94) 4-(4-H^trophenyl«zo)
Resorolnol (0 .70) Ptntahydrojiy flavona
(0 .06 )
BBTANOL (55 I
(0 .60)
(0 .07) Phenyl fluorone (0 .00)
From Bp
Thywol (0 .92) Thymol (0 .92) Thymol (0 .92 ) Gal l ic acl«s (0 .00) Pyrogallol (0 .04) Thyraol (0 .92) o<: -Nophthol (0 .66) Brotno ere s o l green (0 .00) Bromo creeo l green (0 ,00) o<.Naphthol (0 .66) p«.C!hlorophenol (0 .55) o< -Kaphthol (0 .66) c< .Naphthol (0 .66)
t WJNZKW; J ACr.TIC ACTP 40 f 5)
Catechol (0 .54) Pyrogal lol (0 ,20) Phlorofflncinol (0 .59) Pyrofal lo l (0 .20)
8«Hyaroxy9«lncHn« (0 ,19) B^Naphthol (0 ,92) Gal l i c acid (0 ,07) Pyroisallol (0 ,20) Brono oreaol icre^n (0 .02) Broffo phenol bine (0 .02)
Thy«ol (0 .94) Thy«ol (0 .94) Thywol (0 .94)
(fabl« V continued)
44
No.
*58.
*59 . hSO, %61, 462, 463. 464.
465. 466.
467. 46f. 469. 470. 4 7 t . 472.
473 . 474.
475. 476. 477. 478. 479. 480.
"T - " " •
OtRp.
Phenol (0 .83) Pjrrogallol (0 .20) Phenol (0 .83) n c r l c ac ia (0 ,05) Ptcrtc ac id (0 ,05) P i c r i c acifl (0 .05) Ouinol (0 ,72) 8-.Hyaroxyq«inollne Bromo c r e s o l greeti Browo c r e s o l green 8.fiy <i9oxyqu tnol loe 8-.Hydroi3ri|ttinoline
—Feparattiwi
,
1
(0 .19) (0 ,02) (0 ,02 )
(0 .19 ) (0 ,19 )
(MJhlorophenol (0 .50) PhloroflttCinol (0 .59) Gal l to aoi«? (0 .07) l*!fttro»o-?*Naptit»iol (0 .60)
o( -Haphthol (0 .86) c<-Napbtliol (0*86) Pheoolphthallne (0 .86) Pliettolphthaltne (0 .86) Phenyl flnorone (0 ,00 ) Pentahydroxy flavone (0 .07) Qulnhyarone (0 .89)
~ - » ^ - -
Catechol (0 .54) Phenol (0 .83) Phlorogluolnol (0 ,58) Pheisol (0.92> Ven i l l ine (0 ,78) Tbywol (0 .94) Pyrogeno l (0 ,20) dainol (0 .72) 0»Creeol (0 ,82)
fli«Creeol (0 ,79) i-Httroso-2-Waphthol (0 ,60 ) <?ulBhydrone (0 .89) p^Chlorophenol (0 .90) pyrogal lo l (0 .20) Pbloroglacinol (0 .59) Qulnhydrone (0 .89) Ga l l i c acid (0 .07) S-HydroxyquIncline (0 ,19) UroaofiheBol hlue (0 ,02) Brooio ereeo l green (0 ,02) Phenolplithallne (0 .85) Phenolphthaline (0 ,85) 8*lfy drosyo7-l odoquinol ine»
5-Siilfilionlc acid (O.OO)
45
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*<* o ¥>*
l-»
ce ^ u t
~«
8 • O
' w
•e •-o «
o I N
m 9
« i i ^
CM O
•
3 »«* e Si • •»»
o •
o ^ • K '
« B «*« fa*
o 6 •»* 0 O" fe £
4
* ^ rk o t
o >m^
H O « •» «
IB il
* ^ VO o • e Sm^
c! O c •
4 * «
*<^ lA c •
O S v '
<C ** o «
o t V
CM KN M>
50
PISCOSSION
rhenols were also ohroMatographed on Sllioa gel 6 thin
layers and developed la alooei dll the soliretitci used for Altmtna
coated plates. On oomparlson, it was found that different phenols
are better separable on Alamtna layer than on Silica gel layer.
On Alumina layer the spots were compact, distinct and easily
detected while on the silica gel layer the spots were irregular
with tailing end the detection was less distinct. The result of
R- values of different phenols on alumina layers and silica gel
layers are shown in tables If and Tfl respectively. It can be
seen from the tables that silica coated plates show poor resolution
in almost all the solvents systems tried. Alumina layers,
however, ei^ibit greater resolution and offer better possibility
of separations of various phenols.
Results given in table TV reveal that the 8- values of
phenols on alumina loaded plates in aqueous aeneonia follow a
definite trend. Plots of «-, against molar concentration of
ammoniun hydroxide as shown in Figure 1 (a • f) are generally
straight lines and R. values increases as the concentration of
ammonium hydroxide increases. This fact is owed to the weakly
acidic nature of phenols which in ammoninm hydroxide media are
more ionised as the eoneentration of ammonium hydroxide increases,
R. values of phenols remain quite low in most of the cases
when conductivity water, benxene, carbon dieulphide, and toluene
51
w«re u»9(l as d«v«loptni solvents which can be seen tn table Tt.
fhe plots of 11 •&• namher of hydroxy groups keeping
ntmber of bensene rlni;s constant, as shown tn Pigure 2 (a • h)
are plotted for 0<>AiBinophenol, Resorclnol, Pyrogallol, Phenol,
Qulnol, and Gallic acid tn different developing solvent systens.
From the f isures i t can be Inferred that IL, valnes of phenols
having one hydrcwry group i s greater than the phenol having two
hydroxy groups which in turn Is greater than the one with three
hydroxy groups.
The plots of Rp v s . nueAter of beneene rings as shown in
Figure 3 (a - J) show whon number of hydroxy groups are kept
constant.Rp values increases as the noisber of beneene rings
increases In phenols, AlutBlna worths as a good adsorbent hence
i t s a f f in i ty should be greater for the phenol wblch can furnish
greater number of hydrogen Ions, So the phenols l ike pyrogallol
are store strongly adsox1»ed than resoroinol and thynol* As a
result of Up values of trthydroxy phenols are the least In the
comparison of dihydroxy and raonohydroxy phenols.
On the basis of difference in R values a number of
important separations were tried and those practically achieved
are given In tables V, VT and VTT,
Tt w i l l be interesting to plot the quaternary separations
diagramatieally as represented in Figure 4, which gives a view
to confirm quite sharp separations.
52
t
cc
0 8
0-6
0-2
0
(a) ® Q u l n h y d r o n c & 1-Ni t roBO,2-Naph-
tho t 0 4 ( A - N l t r o p h e n y t a z o )
Reso rc ino l
( c )
6 P i c r i c a c i d O P h l o r o g l u c i n o t
A 0-8 -
0-6 -
- 0 4 o >
u. 0 2
( b )
0
o R e s o r c i n o l ^ o - N i t r o p h e n o l © Van i l l l ne
© P e n t o h y d r o K y F lovone X 8-Hydro«y-7- lodoqu lno l inc
5 -Su lphon ic acid
(d)
& P h e n o l p h t h a l i n e o p - C h l o r o p h e n o l
A. X 001M 0-1M 1-OM 0 0-OlM 0•1^5 1 0 M
:*> MOLAR CONCENTRATION OF AMMONIUM HYDROXIDE
FIGURE 1 ( a - d ) PLOTS OF Rp AGAINST MOLAR CONCENTRATION
OF AMMONIUM HYDROXIDE
53
2 o > u.
( f )
m - N11 r o p h n n o t X p - M i l r o p h s n o l
o Pyro^a l lo l 6 CaUic acid o Catechol
O'OIM 0-1M 1-0 M 0 0-01M 0-1 'i 1-0./.
'=i> MOLAR CONCENTr?ATION OF AMMONIU.V. HVDHOXIDZ
FIGURE K c - f ) PLOTS OF Rp AGAINST .viOLAR CONC ENT:^ A T : 0 \ '
OF AWMONIUW HVDRO«iDE
1 0
0-8
0-6
0-4 -
0-2
0
1-0
54 (a ) • ETHYL ALCOHOL
* ETHYL ACETATE o 1.4D10XANE & ACETONE
n)0 -AMINO PHENOL •C2) RESORCJNOL (3) PYROGALLOL
( b ) * ETHYL ALCOHOL • ETHYL ACETATE t 1i4-0»0XANE o aUTANONE-2
CI) PHENOL (2) QUINOL C3) GALLIC ACID
08
0-6
0-4 -
(C) n)0-AMINOPHENOL (2>RES0RCIN0L (3)PYR0GALL0L
& 0-lMCH3C00H-^ 1,4-OIOXANE
, o L « 8u0H4 BENZENE + ACOH
A METHANOL o M«OH-»-TOLUENE
(d) CD PHENOL (2)0UIN0L 13)GALLJC ACIO
» BuOH + BENZENE* ACOH
, A METHANOL
1 2 3 0 1 2 3 NUMBER OF HYDROXY GROUPS
FIGURE 2 ( a - d ) PLOTS OF Rp VS. NUMBER OF HYDROXY GROUPS (NUMBER OF BENZENE RING REMAINS CONSTANT)
I.e. ONE BENZENE RING PHENOLS
55
: • c r
\
4
in
-J <
Q:
\ A C j i T O A . ; i i> a ouTA^orr-r-i^-CYCL. .IXA.X
c (•- suTA,\c :: I ' l-cvci . ; : / , . . i
ACETONE t;u TA XON" -:. -> c 7 c . 0; " /
r':-:r:OL
CALMC .•.CI :i
A
in tu 3
vo
0-3
0-3
C-/:
S)70LUEN2 + CHLOeOrORM+ACETONS
o p-NAPHTHOt. O •• • OUlNHyORONS
VLAZOJFISSORCINOS MAPMTHOl
- r 1
0-2 1-
I
J
( h )
0
0UTANONE •^C^ZlO.-^ZSi:.y'.
V j3 -NAPHTHOL Q QUtNHYDRO.N':
yLAZO'RESORClMO^ o K-MAPHTHOL
NU'/iD'::-! o;-" •IVDnOJIV GROUPS
r i G U R E 2 ( e - h ) PLOYS Oi- Rp VS. MUMSER OF HYHROXV GROUPb
( N L ; . T t H OF 3i-:iMZEKE R lHC i ! cU.A i.' iS CO:^ ST;-. i\ T )
i :•-. OiMc B'TK'ZENE R I . \ G P H L ' V Q ! 5
56
t
u.
0-8
0 6
o >
0-2
0
(a)
"o >
0-6 h
2 0 1 2
NUMBER OF BENZENE RINGS
FIGURE 3 ( a - d ) PLOTS OF Rp AGAINST NU.VI3ER OF BENZENE RINGS. (—OH GROUPS REMAINS CONSTANT)
57
4
3 O > U.
0-8
0-6
0-4
( e )
. 0 W 0-2
0
A
O > u.
0-8
0-6
0-4
0-2
0
(g) 8u«anone-2 + Cyclohcxane
( 2 5 : 7 5 )
( h )
MsOH*PhCH3 ; ( i n ) I
X J
I'-.- ••&>•
2 0 1
NUMBER OF BENZENE RINGS
FIGURE 3 ( e - h ) PLOTS OF Rp AGAINST NUMBER OF
BENZENE R I N G S .
( - 0 H GROUPS REMAINS CONSTANT)
58
:,\
CEC
0-0
0-6
0-4
0-2
C
. il)
?
1
/
'CKCl3*MG2CO
1 0 1 2 0 1 - :
- ^ ^ > aUWSZ:^ OF BSKZc.VE RIMG5
FIGURE 3 { ! - ] ) P L 0 7 S OF Re AGAUs:5V .\'J>:3Z.": OF BENZENE Rl.VGS-( - 0 H GROUPS RE.v.AIK'S COXSTATCT)
59 • 0
\ 0 8
0-6
>
u. r
0-2
0
QUINHYDRONE
« - NAPHTHOL
0-AMINOPHENOL
p , 1 -NJTRSO-! ( 2-NAPHTHOL
1
( ^ TKYMOL
"O-AMINOPHENOL
_ RESOftCINOL
-
OPYROGALLOL
2
t J THYMOL
OUINHYDRONE
PHLOROGLUCINOL
GALLIC ACID
3
/ ^
_0-AMINOPKENOL
_ RESORCINOL
r~^
O-NlTROPHENOL
/^CATECHOL
4
CONDUTIVITY BUTANONE-2 METHANOL 1-4 OlOXANE WATER
1-0
1 0-8
0-6
n ii
i 0-4 > u. r
0-2
0
o _ «<-NAPHTHOL
-O OUINHYDRONE
-
PHLOROGLUCINOL
8 HYDROXY -^ OUmOLINE
5
-0 RESORCINOL
(y O-NITROPHENOL
-
«<- NAPHTHOL -
p - N A P H T H O L
C5 8
o - QUINOL
_ o A C A - N I T R O P H E N -YLAZO;RESORCINOL
O-AMJNOPHENYL
1
CATECHOL
f! 7
1
'o ^- NAPHTHOL
m-NITROPHENOL ' 1
1
P-NlTROPHi£NOi- '
1
1
PICRIC ACID
•' V
a
ACETONE r/o SOS 0-lMACETIC ACID METHANOL " + ^-U DIOXANE TOLUNE
FIG 4 OIAGRAMATIC REPRESENTATION OF QUATERNARY SEPARATIONS ACHIEVED IN DIFFERENT SOLVENT SYSTEMS
60
HEFEBSNCSS
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