THE publication of this series of pamphlets has been undertaken
to make available in a permanent form complete detailed directions
for the preparation of various organic chemical reagents.
In announcing this purpose it may be well to mention at the outset
some of the difficulties in the way of the research chemist, which it
is hoped this series will be able to overcome. The cost of chemicals
is prohibitive to the majority of chemists; this was true before
the war when Kahlbaum's complete supply was available, and to-day
with our dependence on domestic stocks, this cost has increased.
The delay in obtaining chemicals, especially from abroad,
even if the expense need not be considered, is an important factor.
These difficulties have therefore thrown the research chemist on his
own resources. The preparation of materials for research, always time
consuming and annoying, is made increasingly so by the inexactness
of the published information which so often omits essential details.
Because of this, much needless experimentation is necessary
in order to obtain the results given in the published reports.
As the additional information thus acquired is seldom published,
duplication of such experiments occurs again and again,--
a waste of time and material. It is hoped these difficulties
may be remedied by the publication of this series of pamphlets.
In other words, the authors hope to make this a clearing house
for the exchange of information as to methods of preparation of some
of the most needed organic chemical reagents.
On account of the impossibility of obtaining the less common
organic chemicals in the United States during the past few years,
university laboratories have had no option but to prepare their
own supplies. At the University of Illinois, for instance,
a special study has been made of this field, and methods for
the production of various substances have been investigated.
As a result, reliable methods and directions have been developed
for producing the materials in one-half to five pound lots.
Such work as Illinois has done is now being given an even more extensive
scope at the Research Laboratory of the Eastman Kodak Company. It is
felt that the results from these various laboratories should be
available to all chemists and it is hoped that they eventually
will be completely incorporated in these pamphlets.
The organic chemicals herein discussed have been quite
arbitrarily chosen, being those which have been needed in various
research laboratories in the last years and for which the directions
happen now to be ready for publication. The methods are in only
a few cases new ones; they are in general the most satisfactory
to be found in the literature. Only such details have been added
as will enable a man with a reasonable amount of experience
in organic chemistry to duplicate the results without difficulty.
To be absolutely sure that each set of directions can be repeated,
every experiment has been carried out in at least two laboratories.
Only after exact duplication of the results in both laboratories
are the directions considered ready for publication.
The names of the chemists who have studied the various experiments
are given so that further information concerning any obscure point
can be obtained if any question arises in using these directions.
And finally, in describing the experiments, special attention has
been given to the explanation of why it is necessary to follow
the directions carefully, and what will happen if these directions
are not followed.
Although the main object in this series is to give the most convenient
laboratory methods for preparing various substances in one-half
to five pound lots, an attempt has also been made to have these
processes as far as possible adaptable to large scale development.
For example, extractions have been avoided wherever possible,
cheap solvents have been sub-stituted for expensive ones,
and mechanical agitation, a procedure extremely important in the
success of many commercial processes, has usually been specified.
The apparatus used is always carefully described and wherever necessary
an illustration is given. Accompanying each preparation there will
be found a bibliography containing references to all the methods
for the production of the substance described in the literature.
This is given in order to aid any future investigator who
may wish to study or improve the methods of preparation.
It is not claimed that the methods are, in every case,
completely perfect, but only that the yields are very satisfactory
and allow the production of the substances at a reasonable cost.
It is hoped therefore that the pamphlets will benefit not only
the scientific research man of the university, but also the
technical chemist who desires to develop the preparation of one
of these substances to a large scale process of manufacture.
The editors trust also that this work may be used to advantage
as a preparation manual in intermediate or advanced courses in
organic chemistry in university laboratories, and that it will aid
small colleges in the production of necessary reagents which they
are often financially unable to purchase.
The pamphlets are to be edited by the following committee:
Roger Adams, University of Illinois, Urbana, Illinois; J. B. Conant,
Harvard University, Cambridge, Massachusetts; H. T. Clarke, Eastman
Kodak Company, Rochester, New York; Oliver Kamm, Parke, Davis Company,
Detroit, Michigan; each to act for one year as editor-in-chief
and the other three to assist him as associate editors. A new number
of the series will appear annually, and every five years the data will
be rearranged, revised, corrected, and then published in book form.
The number of preparations to be completed yearly is not fixed.
There will be, it is certain, about twenty; and it is hoped,
as the interest is stimulated in this work, that this number may
increase considerably. The editors especially desire to solicit
contributions from other chemists, not only in this country but abroad.
Whenever a compound is thoroughly and extensively studied in
connection with some research, it is hoped that complete directions
for its preparation will be assembled and sent to the editor.
He will then have them checked and published in a subsequent number.
Directions for the preparation of substances already on the market
are needed to make this work complete and will be gladly accepted.
It will, of course, be recognized that an occasional mistake or omission
will inevitably be found in such a pamphlet as this which contains
so many references and formulae. The committee on publication will
therefore deem it a favor if they are notified when any such error
is discovered. It is hoped also that if any chemist knows a better
method for the preparation of any of the compounds considered,
or if anyone discovers any improvements in the methods, he will
furnish the authors with such information. Any points which may arise
in regard to the various preparations will be gladly discussed.
In conclusion, the editors are ready to do all they can to make this.
work successful, and welcome suggestions of any kind.
They feel that the success of the series will undoubtedly depend
upon the cooperation of others, and as its success promises to be
important to research chemists, the editors urge all interested
to assist. THE EDITORS
TABLE OF CONTENTS
PAGE
I. BENZALACETOPHENONE...........................1
II. BENZYL BENZOATE.............................5
III. BENZYL CYANIDE.............................9
IV. a, g-DICHLOROACETONE..............13
V. _p_-DIMETHYLAMINOBENZALDEHYDE..................17
VI. ETHYL OXALATE...............................23
VII. ETHYL PHENYLACETATE........................27
VIII. GLYCEROL a, g-DICHLOROHYDRIN....29
IX. GLYCEROL a-MONOCHLORORYDRIN............33
X. HYDRAZINE SULFATE............................37
XI. MESITYLENE..................................41
XII. METHYL RED.................................47
XIII. _p_-NITROBENZOIC ACID.......................53
XIV. _p_-NITROBENZYL CYAI~DE......................57
XV. _p_-NITROPHENYLACETIC ACID....................59
XVI. NITROSO-b-NAPHTHOL....................61
XVII. PHENYLACETIC ACID.........................63
XVIII. PHENYLACETYLENE..........................67
XIX. PHENYLHYDRAZINE............................71
XX. PHTHALIMIDE.................................75
XXI. QUINOLINE..................................79
XXII. QUINONE...................................85
XXIII. SODIUM _p_-TOLUENESULFINATE................89
XXIV. 1,3,5-TRINTROBENZENE......................93
XXV. 2,4,6-TRINTROBENZOIC ACID..................95
INDEX.....................................99