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tomatic monitoring of column effluents able that the position of a n y skewed These resins should have relatively low
by available methods are necessarily peaks would advance if more solute were cross linkages to allow rapid exchange of
coniplicatcd by the prcsence of the present and retard if less material were dissolved solutes, and high mechanical
eluting solute, usually present in much put on the column. This uncertainty rigidities to allow useful flow rates
higher concentration than the substance in the posit'ion of a peak Tould give even when finely divided. If all the
being separated. Successful water elu- rise to inconstant results with different resins now available had this combina-
tion chromatography might make pos- mixtures and would cause the most tion of properties, both series would be
sible the detection and measurement trouble when separations are incomplete. nearly complete.
of eluted peaks by a simple physical This type of difficulty is encountered in
means such as a refinement of the con- other types of preparative chromatog- ACKNOWLEDGMENT
ductivity mcthod demonstratd here, raphy but in some, such as carrier
ultraviolet absorbance, p H measure- displacement chromatography ( I ) , it The authors are indebted to the
ment, or possibly others. -4s pointed is less conspicuous. Rohm & Hans Co.for generous gifts of
out by Thompson and Morris ( I S ) , the Many of the resins tested seemed to the Amberlite resins XE-89, XE-168,
chemical mildness to which the separat- have acidic or basic properties in the IR-45. XE-112, and XE-58. The Ka-
ing substances arc subjected might be desirablt, range but behaved sluggishly, tional Aluminate Corp. kindly donated a
advantageous with labile compounds. perhaps because of high cross linkage. sample of Xalcite X-219 and the
I n prcparative work the ease with which Xmberlite IRC-50 is such a material. Chemical Procws Co. furnished the
the purified material c a n be recovered .A carboxylic resin of lower cross linkage, Duolite rwins C-62. C-63, and A-4.
cannot bc escet,ded by any ot,her rlnibcrlite SI<-89. cschanged more rap-
method of chromat,ogrLipliy. In large idly but, perhaps bccause of a less LITERATURE CITED
scale separations, such as those that dense structure, is somrivhat gelatinous
might be carried out indust~rially. the in tcsturc and n.Iit11 vc'ry finely ground (1) Biic:hanan. 11. L . , A s . 4 ~ .CHEar. 31,
elimination of reagcnt cost \vould bc a n allows so litth flo\v of n-atc'r as to be 833 (1959).
(2) Buchanan, 1). I,, J . Biol. Cheni. 229,
important factor. nearly usc~lcs~.I t is possiblc that r&ns 211 (195ij.
X disadvantage of this typt, of chro- might, be prqiarecl \vith tlie desired (3) Davies, C. l V . j Biochem. .I. 45, 38
matography as dewloped so far, lies nciditicxs or bxsicities and yet possess (1949).
in its lack of versatility. From avail- wtisfactorj- pliysit>al p i m p c ~ t i t ~Es-
. ( 4 ) Fisher, 5 . F.,Kunin, R., J . Pliys.
Chem. 60, 1030 (1956).
able data it ~vouldbe diffiidt to devise a periment,s dcsc:ribetl here intlicut,c, that ( 5 ) Hamilton. P. B..ANAL.Cr-mar.30, :314
uwful schcme for tlie scyaration of all only a few s w h resins would hr~nec~led; (1958).
the protclin amino acids on a single columns of an>. rcquisitcs acidity or ( 6 ) IToore, S., Stein, IT. H., J . R i d .
column or even by an orderly succcssioii basirity could be prq)Lirid b>- mising. Chem. 176,367 (1948).
of diffc,rent columns. If the isolation ( 7 ) Ibid., 211, 803 (1954).
Hon-ever, tlie mising of ver!. -trong and 18) Pai.tridw. S. 11.. Brimlev. 11. C..
\ -
of ccvtniii individual amino acids is w r y w : t k a ( d resins in iiixiiy propor- Biociiem.2.'49, 153 11931). "
intendcd, a successful mctliod (mild cer- tions would wcni g e n t ~ t l ltlisadvan-
~~ (9;) Ihid., 51, 628 (1952).
t a i n l ~ i. i o be
~ drvelopcd. tagcous i i i that the rrcalc resin xould (11.)) Partridge, S. M., Kestall, I!. G.,
P u t of tlir difficulty ill pcrforniing act niainlj, as a nicchaniixl rlilucnt or ' Ibid., 44, &l8(1949).'
(11) Iteichcnberg, D., "Ion Exchangers in
prcy:trntivc, c-hromatography n i t h these filler and little of its t~wliangr~ c.al)ac.ity Organic :ind Biochemistry," C. Calmon
techiliqrics lit's in the e f h t of column v-ould bc utilized. -1 scrics of acidic and T. R . E. Krrssman, eds., p. 90, In-
loatling t i n tht' iiosition of peaks. (cation) csc~huiigi~rcyitis with suitnble terscience, S c w York, 1957.
(12) Spies, J . R., Charnliers, D. C., J . B i d .
'The ~licwdslin~icof clution p d s that physical propCrtiw :ind app:iwnt pK Cherri. 191,79ti !1951).
oceurs xhenever a relatively abundant v ~ l u o s bitn.c,cm 1 antl 6, pcrlixps a t (13) Thompson, J. F., Iloi-ris, C:. ,J.>
solute, is present a n d wliich is h ~ l dhack int(n:ils uf :ipprosim:itc~ly 1 to 2 p K Arch. Biochern. Biophys. 8 2 , 380 (1959).
to some degree by tlw resin is ade- units. antl a similar 5erit.r of basic
quately t~sp1:iiiii~d by a tlit~orc~tical (anion) psclimigc resins with a n up- RECEIVEDfor review Ilarch 24, 1960.
hccepted .July 22, 1960. LVork was slip-
c o i i d i w t i o n of self-sl~ar~~t~riirig
ant1 parent pI< range bctwccw 8 and 12 ported i n part by the V.s. Pulilic Hralth
self-(liffiising boinidariw ( 2 1 ) . Froni n-oultl prolxihly allow useful chromnto- Pcrvice.
RESULTS A N D DISCUSSION
Table I. Commercial Stable Diazo Salts"
YO. Commercial Nameb Stabilized Diazo Salt of The colors of all 1200 possible com-
binations were noted and recorded in
1 Fast Red AL Salt a-Aminoanthraquinone
Naphthanil Diazo Red AL accordance with Ridgway's color stand-
2 Fast Red 3GL Salt 4Chloro-2-nitroaniline ards and nomenclature (4). However,
Naphthanil Diazo Red 3G only representative data are given here,
3 Fast Scarlet GB Salt 2,5-Dichloroaniline and only common names for colors are
Xaphthanil Diazo Scarlet 2G employed. Several of the compounds
4 Fast Scarlet R Salt 2-Amino-4-nitroanisole
Naphthanil Diazo Scarlet R tested gave essentially the same color
5 Fast Blue B Salt o-Dianisidine with all diazo reagents, indicating that
Xaphthanil Diazo Blue B
-
6 Fast Orange GG Salt
Fast Ponceau L Salt
m-Dichloroaniline
2-Amino-5-nitrotoluene
in these cases, the nature of the phenolic
compound had little influence on the
;i Fast Red GL Salt 4-.4mino-3-nitrotoluene resulting azo dye. Thus, acetosyringone
9 2-.4mino-5-chlorotoluene gave a yellow-brown to brown color
10 4-Amino4 '-methoxydiphenylamine with every diazo reagent. Similarly! 2,5-
11 2-Amino-4-chlorotaluene
12 2-Amino-3-nitroanisole dihydroxyacetophenone yielded a green,
13 4-Amino-2,5-dimethoxy-4 '-nitroazobenzene and vanillil gave a yellow to gold color
14 Fast Blue Salt BBX 4-Benzamido-2,5-diethoxyaniline with every diazo reagent test'ed. For
15 Fast Bordeaux Salt BD 4-Amino-2,5-dimethoxybenzonitrile the most part, however, each phenolic
16 Fast Brown Salt Y 2-Amino-2'-chloro-4-methoxy-5-methyl-4'-
nitroazobenzene compound gave a variety of colors with
17 Fast Corinth Salt V 4-Amino-2,4'-dimethvl-5-methoxy-2'-nitro- the different diazo reagents. I n no
azobenzene instance did a diazo reagent give essen-
18 Fast Garnet Salt GBC 4-Amino-2',3-dimethylazobenzene t'ially the same color with every phenolic
19 Fast Orange Salt GR o-Xitroaniline
20 Fast Red Salt GG p-Nitroaniline compound, although some reagents did
21 Fast Red Salt ITRN N,N-diethyl. 3-amino-4-methoxybenzene- give much less variation in colors than
sulfonamide most.
22 Fast Red Salt PI)C S-n-butyl-3-amino-4-methoxybenzene- Although it is not a phenolic com-
sulfonamide pound. quinic acid wm included in this
23 Fast Red Salt R C S 2-Amino-4-chloroanisole
24 Fast Red Salt R L 2-Amino-3-nitrotoluene study because of its occurrence in so
25 Fast Scarlet Salt G 2-Amino-initrotoluene many natural products and because of
2ti Fast Violet Salt B S 4-Benzamido-2-methoxy-5-met hylaniline its close relationship to many of the
27 Fast Yellow Salt GC o-Chloroaniline phenolic acids encountered in our
28 Variamine Blue Salt RT 4-Aminodiphen ylamine
29 Variamine Blue Salt FG 4-Amino-3-methoxydiphenylamine studies. Furthermore, i t w m thought
30 Fast Orange Salt RDN 2-Chloro-5-trifluoromethylaniline that, quinic acid might give colors
similar to those given by syringic acid
a Sources of diazo salts: Kos. 1-12, Koppers Co., Inc.; Nos. 1-5, E. I. du Pont and the like which do not have ring
de Nemours & Co., Inc.: Nos. 13-30, Antara Chemicals Division of General Aniline and positions available for diazo coupling.
Film Corp.
b The h a hthanil" names for diazo salts 1-5 are names employed by E. I. du Pont de However, results obtained with quinic
Xemouriii Zo., Inc. acid indicated that no coupling or color
formation took place with any of the