56 SCIENCE [N. S. VOL. LIV. No. 1385
THE AMERICAN CHEMICAL SOCIETY line solution it yields a crystalline acid (m. p.
DIVISION OF ORGANIC CHEMISTRY 151°) from which no crystalline salts could be
obtained. It yields no acetyl derivative, and can
(Continued) not be reconverted into the lactone. It is readily
Symmetrical tribro'mphenylpropiolic acid and oxidized by permanganate. The lactone, like
its reaction with acetic anhydride: ROBERT CHAM- coumarin, yields a crystalline compound with bi-
nBas. Phenylpropiolic acid eondenses with acetic sulfite. Analysis indicates the empirical formula:
anhydride to form a phenylnaphthalene dicarbox- C16111803.
ylic anhydride. This reaetion holds for deriva- The bromination of 2-ainino-p-cymene: ALVIN
tives of phenylpropiolic acid where there is a S. WHiEEL.T ER and IRA W. SMITHEY. Pure p-cymene,
free ortho hydrogen. It was desired to investi- obtained from spruce turpentine, was nitrated and
gate the action of acetic anhydride on a di ortho the 2-nitro-p-cymene was reduced with Sn and
substituted phenyl propiolic acdd. The above HCI. The acetyl derivative of 2-amino-p-cymene
acid was prepared from meta nitro cinnamic acid in C014 solution was boiled with bromine. Bromo
as follows: reduction with zinc and hydroehlorie derivative, needles, m. 1220; yield 60 per cent.
acid gave meta amido hydrocinnamie acid. Bro- Hydrolysis gave free amine, liquid, b. 1690-1700
mination and subsequent diazotization in boiling at 20 mm., du 1.3012, nD2 1.5781. HCI salt,
ethyl alcohol gave 2.4.6 tribromhydrocinnamic plates, m. 2060-2100. HBr salt, plates, m. 2050.
acid. Heating to 1450 in a sealed tube with Diazobromoaminocymene, canary yellow needles,
bromine gave aa dibrom 2.4.6 tribromhydrocin- m. 1460-1480 (decomp.). Oxidtion of bromo-
namic acid. The latter with hot alcoholie potash acetylaminoeymene with neutral permanganate
gave 2.4.6 tribromphenylpropiolic acid. With gave a toluic acid derivative, m. 2130. Hydrolysis
acetie anhydride the above acid does not condense with acid gave the bromoamino acid, needles, m.
to a phenylnaphthalene derivatives but forms an 1510; HC1 salt, plates, m. 1900 (deeomp.). No
anhydride which may be hydrolyzed to the original bromoamino toluic acid of this description could
acid. be found in the literature. The Br atom appears
The reactions of alpha anthroquinonesulfonic to be in the 3 position.
adds with iercaptans: E. EmMET REID, GOLIN New derivatives of 2, 3, 8-tribromto-5-hydroxy-1,
M. MACKALL and G. E. MILLER. Sodium anthro- 4-naphthoquinone: ALVIN S. WHEELER and T. M.
quinone-alpha-monosulfonate and the 1.5 or 1.8 ANDREWS. Action of NaOH on the tribromo-
disulfonates react readily with mereaptans in quinone (A) gave the 2, 3-dibromo-5, 8-dihydroxy-
water solution to replace the sulfonic acid group 1, 4-naplithoquione (B), which, reduced with Zn
by -SR to give anthraquinone alkyl thio-ethers and H,SO,, gave 2, 3-dibromo-1, 4, 5, 8-tetra-
or dithio-ethers, a-Q4H,O,H,.SR, 1, 5-C04sH02(SR)2 hydroxynaphthalene, greenish needles, m. 1640-
and 1.8-0,,H(,0,(SR)2. The disulfonates may give 166°. Tetracetyl derivative, yellow needles, m.
the intermediate alkyl thio-ether sulfonato. 1490-1500. Acetyl derivative of B, yellow prisms,
The polymers of pinene: G. B. and 0. J. m. 1970. Methyl ether of A, yellowish red plates,
FRANKFORTER and E. R. KRYGER. m. 2090-2100. Ethyl ether of A, yellow needles,
Contribution to our knowledge of the chemistry m. 1340-136°. Aniline derivative of A (Br No.
of calcium cao-bide: G. B. FRANKFORTER and A. 8 replaced), purplish chip-like crystals, m. 2350.
E. STOPPEL. A is converted by Zn and H SO4 into the tri-
hydroxy derivative, yellowish needles, m. 106°-
A new lactone from oil of orange: FRANCIS D. 1070; triacetyl derivative, colorless prisms, m.
DODGE. Essential oils of citrus species, obtained 2200. Br. No. 8 in A is replaced by C1 with 1101
by ex2pression, on standing generally deposit solids and alcohol, golden bronze plates, m. 1520; acetyl
from which certain lactones derived from coumarin derivative, yellow prisms, m. 1600. Ketone re-
have ibeen obtained. In the present communica- agents on A do not give well defined products.
tion is described a new lactone of rather unusual
properties obtained from the sediment of West The bromination of 3-amino-p-cymene: ALVIN
Indian oil of orange. It forms colorless needles S. WHEEL and I. W. SMIrrEEY. (By title.)
(m. p. 88-900) easily soluble in alcohol and The production of furfural by the action of su-
ether, slightly so in ligroin. Optical rotation is perheated water on aqueous corn cob extract: F.
about - 380 in alcohol. On aeidifying an alka- B. LAFoRGE. (By title.)
JULY 15, 1921 ] SCIENCE 57
DIMSION OF AGRICULTURAL AND FOOD CHMISTRY copper compounds of the eprays did not. The
C. E. Coates, chairmnan. extra lime of the Bordeaux spray did not reduce
T. J. Bryan, secretary. the amount of copper absorbed by the plants com-
pared with the results on the Pickering plants.
Suggestions for mnore rapid and exact nethods Where the sprays and copper sulfate solution were
of analyses for the cheese factory: S. K. ROBINSON. added to the soil directly practically the same
Some problems of the pure food manufacturer: amounts of copper were recovered from the soil
H. A. Noyzs. The preserver of fruit and fruit samples. Samples of soil from sprayed potato
products has two important problems to solve: fields showed hbut minute amounts of copper.
(1) The obtaining of a high quality and uniform Pickering Bordeaux sprays: F. C. COO.
fruit supply each year, and (2) the processing of
fruit in such a way that its natural properties are Analysis of the Jerusalem artichoke: A. T.
retained. The pure food manufacturer's inability SHroirr. The Jerusalem artichoke, Heianthus tu-
to accomplish these two things up to the present berosus, gives the analysis:
has allowed the artificial flavor and color manu- Water Nx6.25 Fat Carb. Fiber Ash
facturer to develop his products and befuddle the Per cent.. .79.0 3.1 .2 16.5 .8 1.1
taste of the average consumer. The plans and
organization of one large concern, to study the The wastage by peeling is 31 per cent., the hy-
production of quality fruits and to apply research drogen ion concentration (colorimetrie) pH 5.0.
methods to its business, were given. The carbohydrate is inulin, as determined by po-
Variations in the Concord grape during ripen- lariscope and quantitated after inversion by Bene-
ing: H. A. NoyEs, H. T. KING, J. H. MART- diet 'a solution. Experiments show it is utilized,
SOLF. Variations in the Coneord grape during and not excreted by diabetics. The nitrogen is
ripening that are of interest to the juice and jam largely extracted with boiling water. This non-
manufacturer were investigated. Results show a protein fraction represents 71.5 per cent. of total
gradual increase in sugar content, a decrease in nitrogen. Of the water soluble non-protein nitro-
total acids and irregularities in tannin and color- gen 26 per cent. is free amino acid nitrogen and
ing matter. Weather conditions were an impor- 12 per cent. ammonia nitrogen.
tant factor affecting sugar content, warm days Measuring soil toxicty, acidity and basicity:
and cool nights seeming to be the optimum con- R. H. CARP.
dition for developing sugar. What puts the "pop" in pop corn? R. H.
The absorption of copper from the soil by CAnn. (Lantern.)
potato plants: F. C. CooK. Insoluble copper The rate of oxidation of line-sulfur: C. A.
compounds present in a Bordeaux spray contain- PETERS and A. L. PRINCE. The rate of oxidation
ing an excess of lime and present in Piekering of lime-sulfur is largely independent of the con-
spray containing no excess of lime, also a solu- centration and also of the temperature up to about
tion of sulfate of copper, were added to the soil 800, when the rate is inereased in all but the
near the roots of potato plants in equal strengths very dilute solutions.
and amounts at various intervals durimg the grow-
ing season. Samples of vines, tubers and soil A oolor test for "remade" mnilk: OseAR L.
were taken for analyses at frequent intervals. The EviNsoN.
leaves of the plants grown in the soil receiving the Effect of aging on leoithin-phosphoric aoid de-
insoluble copper, i.e., the sprays, held the largest termination of egg noodles: R. C. HUmmELL. The
part of the copper, the roots but little and the results of these experiments indicate that aging
stems an intermediate amount. The tubers con- does have considerable effect on the lecithin-phos-
tained hbut traces of copper. Where the soil phoric acid determination in egg noodles. By the
was treated with the copper sulfate solution the end of six months this value had deereased to less
roots were injured and the normal metabolism of than two thirds of the original value and in eigh-
the vines interfered with. The tubers from these teen. months had decreased to one half or less
vines were smaUl and the vines stunted. In these than one half of the original amount. Inasmuch
plants the roots held more copper than the leaves. as considerable time may elapse from the time
The soluble copper sulfate added directly to the at which egg noodles are manufactured until they
soil caused injury to the plants while the insoluble reach the consumer, it would seem to be quite in
58 SCIENCE [N. S. VoL. LIV. No. 1385
error to judge the egg content by the value ob- Cases of supercooling during the freezing of ice
tained in the aforesaid determination. cream mixes: HARPER F. ZOLLER and OWEN E.
Peanut by-products: J. B. REED. WILLIAMS. By the use of the rotating thermo-
couple we have examined the point of separation
Some factors governing the crystallization of
lactose in ice cream: HARPER F. ZOLLER and of ice in a variety of mixes. The measurements
OWEN E. WILLIAMS. A curve is presented as a were made in a commercial ice cream machine of
result of experimental evidence which serves to the Miller type with a capacity of five gallons.
separate those mixes which will produce sandiness The freezing point lowering of the mix was not
from those which will not, and is based upon the in harmony with the calculated value, but showed
relationship existing between the protein-serum a high supercooling in the mix even in the presence
solids concentration and the concentration of lac- of the swiftly moving beaters and scrapers. The
tose within the mix. It is erroneous to calculate addition of fine particles of substances to promote
the concentration of lactose on the water basis the formation of crystal nuclei prevented the
since the total water in the mix is not available supercooling of the mix and consequently the
to the lactose because of the competition of the freezing was done in a shorter time, and the
other solids. The effect of the proteins within the product was smoother. Both fat and gelatin seem
mix is not to repress the crystallization of lactose, to reduce supercooling in the average mixes.
but they aet oppositely in increasing concentration. When sand is added to an ice cream mix con-
Because of its slow rate of crystallization lactose taining 10 per cent. fat and 0.5 per cent. of gela-
hydrate is subject to much supercooling and over- tin ice begins to separate at only a slightly higher
saturation. Protein has very little effect upon its temperature when the brine is at 100 F. during
rate of growth. The solubility of lactose hydrate the freezing process. If the brine is much lower
according to the best of experimental deductions there is a greater difference in the supercooling
is 11.15 per cent. at 0° C. In an ice cream mix effect when no sand is present in the above mix.
containing 10 per cent. fat, 14 per cent. of cane When mixes are frozen which have been made
sugar and 65 per cent. of water, the above value from evaporated milk containing lactose crystal
for lactose reduces to about 8.9 per cent. calcu- nuclei and they have not been destroyed by pas-
lated on the water basis. teurization, or other means, no supereooling oc-
A rotating thermocouple and cold junction de- curs. A great deal of importance is attached to
signed for temperature studies inr horizontal power the degree of supercooling and its influence upon
ice cream machines: HARPER F. ZOLLER. A sen- the texture of the ice cream as it comes from the
sitive and experimental thermocouple is described freezer.
and illustrated which has been designed for the Black discoloration in canned sweet potatoes:
purpose of accurately measuring the temperature EDW. F. KOiaMAN. The black discoloration which
of the ice cream mix within the freezer when the occurs in canned sweet potatoes begins in the
latter is rotating at full speed. By maintaining bottom of the can where there is usually a semi-
an ice-water cold junction affixed to the shaft of liquid starch paste which affords close contact
the freezer along with the thermocouple junctions with the can. Eventually it may penetrate the
the small temperature differences within the freezer entire content of the can. The black formation
can be measured with an accuracy of .020 C, This is due to the combination of iron dissolved from
latter is also made possible by the use of a five the can with a tannin-like substance in the po-
junction copper-constantan thermocouple (of fine tatoes. This is lwalized to a considerable extent
wire for small temperature lag effect) and a po- just beneath the peel. But as there is also some
tentiometric setup embracing a galvanometer of throughout the potato and especially about the
low internal resistance with a potentiometer of center no change in present methods of peeling
microvolt capacity. The unique feature of the would be of advantage. Tannins do not form
instrument is the method of conducting the small black compounds with iron unless the latter is in
e.m.f. from the rapidly rotating shaft to the po- its highest state of oxidation. As air is essential
tentiometer without frictional thermoelectric ef- to bring it into this condition, the necessity of
fects. The instrument has been in regular service tight seams in canned sweet potatoes is emphasized.
for a number of months, has given no trouble,
and has measured the rapidly fluctuating tempera- CHARLES L. PARSONS,
tures within the mix simply and accurately. Secretary