1
912 should therefore be very useful to the analyst of azo dyes, since it would enable him to split dyes of unknown composi- tion into their components without the addition of any foreign material. Fierz and WiessenbachZ2 report that the reduction of 1,5- and 1,8-nitronaphthalenesulfonic acids, and 1,3,6,8-nitro- naphthalenetrisulfonic acid proceeds auite satisfactorilv to the THE JOURNAL OF INDUSTRIAL AND ENGl NEERING CHEMISTRY Vol. 14, No. 10 country an organic reaction is being conducted electrolyt- ically on a paying commercial scale, lead to a firm optimism that organic electrochemistry will play a very considerable part in the establishment of America’s organic chemical industry. corresponding amines. The dye-makers would do well to consider seriously the use of this method of reduction in the factory, since it has much to commend it for the manufacture of H-acid. On the other hand, the reductiop of 1,6- and 1,7- nitronaphthalene sulfonic acids produces principally the cor- responding hydroxylamines, which rapidly form tarry sub- stances, a statement that sounds quite plausible to anyone who has ever made Cleve acid. A. Lowy reports the results of a study of the electrolytic oxidation of leucomalachite green.2s The role of electrochemistry in the dyeing industry has been discussed by F. Mollwo PerkhZ4 The possibility of modifying the oxidizing or reducing power of an electrode by altering its potential, and thus ex- ercising control over the products of electrolysis was empha- sized by all the early workers in this field who were apparently unaware that the electrode potential is not easy to control, since it is conditioned by the acidity or alkalinity of the electrolyte, and that this in turn frequently affects the course of the reaction more powerfully than the electrode poten- tial does. Furthermore, specific catalytic action of the electrode material is a greater factor in determining the prod- ucts of electrolysis than over-voltage is. These consider- ations, coupled with the practical difficulty of producing a reversible electrode of organic material, have resulted in a dearth of information on the single electrode potentials of organic reactions. Two researches have been published re- cently on this subject, one establishing the potential of the hydroquinone-quinone electrode26 and the other the oxidizing potential of several anthraquinone-sulfonic acids.26 It is disappointing that the authors of the latter article did not exercise that care in establishing the identity and purity of their materials for which their laboratory is famous. No strikingly new features are embodied in recent patents of cells for the electrolysis of organic materials. Several-call for a porous electrode through which the organic material may be forced. Others seek to eliminate the diaphragm by em- ploying difference of density to keep the anolyte and catholyte apart, or depend on rotating parts and centrifugal force or an immiscible solvent for this purpose. One particularly interest- ing looking device allows benzene to rise through the electro- lyte to the anode, above which it collects in a layer and is pumped back to the bottom of the cell again. Circulation is maintained until the desired degree of oxidation is accom- plished. The literature on the electrochemistry of organic materials gives the casual reader a sense of a great deal of disorganized effort. Such is partly the case, but in this field, as in many of the newer fields of chemical investigation, a great many ex- ploratory experiments must be performed before investiga- tors can define and limit the problem before them. The exploratory work is by no means complete, yet out of the chaos there arise a few guiding generalizations. These, coupled with the knowledge that here and there through the 22 Helvetica Chzm. Acta, 3 (1920), 305. 23 Trans Am Electrochem. Soc , 1921 (Preprint). x4 J. SOL. Dyers Colour., 36 (1920), 138 26 Biilmann, Ann chim., 16 (1921), 109, Sbrensen and Linderstrom-Lang, 26 Conant, Kahn, Pieser, and Kurtz, J. Am Chem SoC, 44 (19221, 17 U. S Patent 1,322,580 (1919). Ibsd., 16 (l920), 283. 1382. Bibliography of the Grignard Reagent The National Research Council has recently issued, as Re- print and Circular Series No. 24, a bibliography of the Grig- nard reagent, entitled “Organomagnesium Compounds in Syn- thetic Chemistry,” by Clarence J. West and Henry Gilman. The first 17 pages comprise a brief discussion of the various types of reaction in which the Grignard reagent may be used. The bibliography proper contains about 1500 references and is arranged alphabetically by author. This is followed by a sub- ject index by compounds, which contains practically all the compounds prepared by means of this very useful reagent. Up to the present time, interest in the Grignard reaction has been largely scientific. The only apparent reason for this is the fact that the reagent has been considered too unstable for plant use. Recent studies by Gilman indicate that the stability is greater than has been hitherto supposed and this discovery may lead to a more extended industrial use. The wide variety of compounds that can be prepared from this re- agent should make it very valuable for the manufacture of re- search chemicals. Copies of this work may be obtained from the Publication Division, National Research Council, 1701 Massachusetts Ave., Washington, D. C., for $1.50. Chicago Chemists Urge Embargo When the embargo was up in the Senate, fifteen prominent members of the Chicago Section of the AMERICAN CHEMICAL SOCIETY signed the following resolution, which was sent to the senators from Illinois : The Chicago Section of the AMERICAN CHEMICAL SOCIETY is thoroughly convinced that 5~ dye embaigo is absolutely necessary for proper development of the chemical industries and that it is to the decided advantage of American users of chemicals. Before it is too late, we urge you to reopen the matter and do your utmost in action and support for the embargo. A. C. S. Monographs Eight AMERICAN CHEMICAL SOCIETY Monograkhs have been published to date. The first printing of the Chemistry of Enzyme Action,” by Falk, has been exhausted, and it is expected that the accumulation of orders for this volume will warrant a second printing in the near future. Two monographs of the series are now in the hands of the printers and will be published during October, five others are expected to be published during this year, and fifteen are in less advanced stages of preparation. The entire series to date numbers thirty volumes and more will be added from time to time. Record in Gasoline Production All previous records for monthly production of gasoline in the United States were broken in July, when 569,711,415 gal. were produced, according to figures compiled by the Bureau of Mines. Domestic consumption of gasoline for July was also the largest ever recorded in a single month, amounting to 566,000,000 gal. as compared with 457,000,000 gal. for July of last year. The fact that consumption figures showed a larger increase than the production figures accounts for a reduction of stocks of gasoline for the month, amounting to 52,000,000 gal. A daily average of 1,593,000 bbl. of oil was run through the stills of 305 refineries reported to the Bureau of Mines as operat- ing during July. This shows an increase of 2.96 per cent in the amount of oil run and a decrease of 5 in the number of operating refineries as compared with June. Plants operating in July ran an average of 89.55 per cent of their daily indicated capacity. Imports of gasoline for July amounted to 4,840,098 gal., exports were 58,630,402 gal., and shipments to insular possessions were 1,866,789 gal. The increase over July of last year is 150,000,000 gal.

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912

should therefore be very useful to the analyst of azo dyes, since it would enable him to split dyes of unknown composi- tion into their components without the addition of any foreign material.

Fierz and WiessenbachZ2 report that the reduction of 1,5- and 1,8-nitronaphthalenesulfonic acids, and 1,3,6,8-nitro- naphthalenetrisulfonic acid proceeds auite satisfactorilv to the

THE JOURNAL OF INDUSTRIAL AND ENGl NEERING CHEMISTRY Vol. 14, No. 10

country an organic reaction is being conducted electrolyt- ically on a paying commercial scale, lead to a firm optimism that organic electrochemistry will play a very considerable part in the establishment of America’s organic chemical industry.

corresponding amines. The dye-makers would do well to consider seriously the use of this method of reduction in the factory, since it has much to commend it for the manufacture of H-acid. On the other hand, the reductiop of 1,6- and 1,7- nitronaphthalene sulfonic acids produces principally the cor- responding hydroxylamines, which rapidly form tarry sub- stances, a statement that sounds quite plausible t o anyone who has ever made Cleve acid.

A. Lowy reports the results of a study of the electrolytic oxidation of leucomalachite green.2s

The role of electrochemistry in the dyeing industry has been discussed by F. Mollwo PerkhZ4

The possibility of modifying the oxidizing or reducing power of an electrode by altering its potential, and thus ex- ercising control over the products of electrolysis was empha- sized by all the early workers in this field who were apparently unaware that the electrode potential is not easy to control, since it is conditioned by the acidity or alkalinity of the electrolyte, and that this in turn frequently affects the course of the reaction more powerfully than the electrode poten- tial does. Furthermore, specific catalytic action of the electrode material is a greater factor in determining the prod- ucts of electrolysis than over-voltage is. These consider- ations, coupled with the practical difficulty of producing a reversible electrode of organic material, have resulted in a dearth of information on the single electrode potentials of organic reactions. Two researches have been published re- cently on this subject, one establishing the potential of the hydroquinone-quinone electrode26 and the other the oxidizing potential of several anthraquinone-sulfonic acids.26 It is disappointing that the authors of the latter article did not exercise that care in establishing the identity and purity of their materials for which their laboratory is famous.

No strikingly new features are embodied in recent patents of cells for the electrolysis of organic materials. Several- call for a porous electrode through which the organic material may be forced. Others seek to eliminate the diaphragm by em- ploying difference of density to keep the anolyte and catholyte apart, or depend on rotating parts and centrifugal force or an immiscible solvent for this purpose. One particularly interest- ing looking device allows benzene to rise through the electro- lyte to the anode, above which it collects in a layer and is pumped back to the bottom of the cell again. Circulation is maintained until the desired degree of oxidation is accom- plished.

The literature on the electrochemistry of organic materials gives the casual reader a sense of a great deal of disorganized effort. Such is partly the case, but in this field, as in many of the newer fields of chemical investigation, a great many ex- ploratory experiments must be performed before investiga- tors can define and limit the problem before them. The exploratory work is by no means complete, yet out of the chaos there arise a few guiding generalizations. These, coupled with the knowledge that here and there through the

2 2 Helvetica Chzm. Acta, 3 (1920), 305. 23 Trans Am Electrochem. Soc , 1921 (Preprint). x4 J . SOL. Dyers Colour., 36 (1920), 138 26 Biilmann, Ann chim., 16 (1921), 109, Sbrensen and Linderstrom-Lang,

26 Conant, Kahn, Pieser, and Kurtz, J. Am Chem SoC, 44 (19221,

17 U. S Patent 1,322,580 (1919).

Ibsd. , 16 (l920), 283.

1382.

Bibliography of the Grignard Reagent The National Research Council has recently issued, as Re-

print and Circular Series No. 24, a bibliography of the Grig- nard reagent, entitled “Organomagnesium Compounds in Syn- thetic Chemistry,” by Clarence J. West and Henry Gilman. The first 17 pages comprise a brief discussion of the various types of reaction in which the Grignard reagent may be used. The bibliography proper contains about 1500 references and is arranged alphabetically by author. This is followed by a sub- ject index by compounds, which contains practically all the compounds prepared by means of this very useful reagent.

Up to the present time, interest in the Grignard reaction has been largely scientific. The only apparent reason for this is the fact that the reagent has been considered too unstable for plant use. Recent studies by Gilman indicate that the stability is greater than has been hitherto supposed and this discovery may lead to a more extended industrial use. The wide variety of compounds that can be prepared from this re- agent should make it very valuable for the manufacture of re- search chemicals.

Copies of this work may be obtained from the Publication Division, National Research Council, 1701 Massachusetts Ave., Washington, D. C., for $1.50.

Chicago Chemists Urge Embargo When the embargo was up in the Senate, fifteen prominent

members of the Chicago Section of the AMERICAN CHEMICAL SOCIETY signed the following resolution, which was sent to the senators from Illinois :

The Chicago Section of the AMERICAN CHEMICAL SOCIETY is thoroughly convinced that 5~ dye embaigo is absolutely necessary for proper development of the chemical industries and that it is to the decided advantage of American users of chemicals. Before it is too late, we urge you to reopen the matter and do your utmost in action and support for the embargo.

A. C. S. Monographs Eight AMERICAN CHEMICAL SOCIETY Monograkhs have been

published to date. The first printing of the Chemistry of Enzyme Action,” by Falk, has been exhausted, and it is expected that the accumulation of orders for this volume will warrant a second printing in the near future. Two monographs of the series are now in the hands of the printers and will be published during October, five others are expected to be published during this year, and fifteen are in less advanced stages of preparation. The entire series to date numbers thirty volumes and more will be added from time to time.

Record in Gasoline Production All previous records for monthly production of gasoline in

the United States were broken in July, when 569,711,415 gal. were produced, according to figures compiled by the Bureau of Mines.

Domestic consumption of gasoline for July was also the largest ever recorded in a single month, amounting to 566,000,000 gal. as compared with 457,000,000 gal. for July of last year. The fact that consumption figures showed a larger increase than the production figures accounts for a reduction of stocks of gasoline for the month, amounting to 52,000,000 gal.

A daily average of 1,593,000 bbl. of oil was run through the stills of 305 refineries reported to the Bureau of Mines as operat- ing during July. This shows an increase of 2.96 per cent in the amount of oil run and a decrease of 5 in the number of operating refineries as compared with June. Plants operating in July ran an average of 89.55 per cent of their daily indicated capacity.

Imports of gasoline for July amounted to 4,840,098 gal., exports were 58,630,402 gal., and shipments to insular possessions were 1,866,789 gal.

The increase over July of last year is 150,000,000 gal.