Fundamental Processes of Dye Chemistry

f f FUNDAMENTAL PROCESSES OF DYE CHEMISTRY By HANS EDUARD FIERZ-DAVID and Louis BLANGEY Eidgenossische Technische Hochschule, Zurich Translated from the Fifth Austrian Edition By PAUL W. VITTUM Eastman Kodak Company, Rochester, New York Published and distributed in the public interest with the consent of the Attorney-General under License No. A-1360 1949 INTERSCIENCE PUBLISHERS, INC., NEW YORK INTERSCIENCE PUBLISHERS LTD., LONDON Translated from Grundlegende Operationen der Farbenchemie, Siebente Unveranderte Auflage, Springer-Verlag, Wien, 1947. The sixth (1946) and seventh (1947) Austrian editions are unchanged reprints of the fifth (1943) Austrian edition. Copyright, 1922, Springer-Verlag OHG., Berlin. Copyright, 1938, 1943, Springer-Verlag OHG., Vienna. Copyright vest ed in the Alien Property Custodian, 1944, pursuant to law. Copyright, 1949, Interscience Publishers, Inc. ALL RIGHTS RESERVED This translation or any part thereof must not be reproduced without permission of the pub lishers in writing. This applies specifically to photdstatic and microfilm reproductions. INTERSCIENCE PUBLISHERS, INC. 215 Fourth Avenue, New York 3, N. Y. For Great Britain and Northern Ireland: INTERSCIENCE PUBLISHERS LTD. 2a Southampton Row, London, W. C. 1 PRINTED IN THE UNITED STATES OF AMERICA OFFSET BY NEW YORK LITHOGRAPHING CORP., NEW YORK COMPOSED BY GRAPHIC PRODUCTION CORP., NEW YORK Preface to the Fifth Austrian Edition This fifth edition of Grundlegende Operationen der Farbenchemie constitutes an expansion of the fourth edition. Since the appearance of the first edition in 1920, so many new processes of dye chemistry have been discovered that it appeared necessary to rework or enlarge various sections. In particular, the preparation of several important intermedi ates has been resurveyed. The book is intended principally to introduce to the beginner the methods of dye chemistry, and not merely to present a collection of recipes. To this end, the chapter on the practical work in the organic industrial laboratory has been reworked and enlarged in order to clarify all the important points. The chapter on analysis of dyes has been re vised so that the student may gain some insight into this difficult field. Also, the section on the determination of light fastness has been re written, and we are grateful to Dr. Ris (Basel) for his contributions to this subject. These additions have increased the scope of the book. We hope that they have also increased its usefulness. H. E. Fierz-David Louis Blangey Zurich, November 3, 1942 Chem.-Techn. Laboratorium der Eidgenossischen Technischen Hochschule v Preface to the Translation Twenty-eight years have elapsed since the publication of the first edition of Grundlegende Operationen der Farbenchemie. In the mean time the technology of dyestuff intermediates and the dyes obtained from them has developed widely, and the processes described in 1920 are very well known today. Editions subsequent to the first (up to the seventh edition, published in Vienna in 1947) were expanded considerably in collaboration with L. Blangey. The main aim was always to explain the fundamental prin ciples of dye chemistry to the student; and, since it was the endeavor of the authors to write a laboratory book and not an encyclopedia, in general only simple examples were given in this work. The preface to the first edition indicated that the processes described were perhaps not the best, but that by following the instructions exactly the results stated would be obtained. In dye chemistry, as is well known, many roads lead to the same goal. The present edition is not intended to compete with more compre hensive books such as that of P. H. Groggins, Unit Processes in Organic Synthesis (1947). The latter is a textbook, while Grundlegende Opera- tionen der Farbencherhie, like Gattermann's book Praxis des Organ- ischen Chemikers, is primarily a laboratory manual. The reprinting of the fifth Austrian edition in the United States — without the consent of the authors — indicated recognition of the need for such a volume. It seems apropriate, however, to publish a new, American edition in which several reactions are described that have not appeared in pre vious editions and which corrects minor errors discovered in the Aus trian edition on which the translation is based. These are the only changes considered necessary. After the present translation had been printed, the allied reports on German and Japanese industry were made public. The authors noted to their satisfaction that the processes they described corresponded closely in many cases with those of the German dye factories. Certain large-scale industrial reactions can be reproduced only with difficulty in the laboratory with the small amounts of material at the chemist's disposal. In our opinion, for example, it is practically impossible in the Vll viii PREFACE TO THE TRANSLATION laboratory to fractionate and crystallize out at low temperatures the mixtures of chlorotoluenes as described in BIOS Final Report No. 1145. On the other hand, we would like to point out here that 1-naphthyl- amine-3-sulfonic acid can be separated easily from the mixture of the 1,6-, 1,7-, and 1,8- acids by precipitating carefully with acid, according to FIAT Final Report No. 1016. The other processes correspond so closely with those we present that there is no need for further amend ments. We want to thank Dr. Paul W. Vittum for a translation that corre sponds so well with the sense of the original German. We hope that this American edition will fulfill its purpose and be cordially received. H. E. Fierz-David Louis Blangey Zurich, December 1, 1948 Swiss Federal Institute of Technology CONTENTS Preface to the Austrian edition v Preface to the translation vii Index of reactions xix List of figures xxvii List of tables xxix The foundations of the dye industry 1 I. INTERMEDIATES General discussion 3 The various operations of intermediate chemistry 6 Sulfonation 6 Nitration 6 Reduction 7 Introduction of the hydroxyl group 7 Introduction of amino and alkoxy groups 8 Oxidation methods 8 Introduction of halogen 9 Practical work in the industrial organic laboratory 10 General 10 Proportions and weighing 13 Laboratory journals and reports 14 Apparatus 14 Stirring apparatus 15 Filtration 18 Distillation 21 Distillation under ordinary pressure 21 Vacuum distillation 25 Steam distillation 25 Separation of reaction products 27 Rasic substances 27 Acidic substances 30 Purification of products 34 Testing the product for purity 40 Orientation rules 50 Orientation in the benzene series 50 Orientation in the naphthalene series 53 Orientation in the anthraquinone series 56 Orientation in the carbazole series 60 ix X CONTENTS A. Compounds of the benzene series 62 Chlorobenzene 62 Halogenation in general 65 Nitrobenzene 68 Nitration in general 69 The Lunge nitrometer 72 Aniline from nitrobenzene 75 Reduction in general 77 Benzenesulfonic acid 80 Sulfonation in general 82 Phenol 86 Alkali fusion in general 88 Derivatives of chlorobenzene 90 o- and p-Nitrochlorobenzene 90 p- and 0-Nitroaniline from p- and o-nitrochlorobenzene 92 p-Nitrophenyloxamic acid and p-aminophenyloxamic acid 93 p-Nitrophenylhydrazine 95 o-Nitroanisole from o-nitrochlorobenzene 97 p-Nitrochlorobenzene-o-sulfonic acid and p-nitroaniline- o-sulfonic acid from p-nitrochlorobenzene 99 Diaminodiphenylaminesulfonic acid 99 Aminodiphenylaminesulfonic acid (III), and aminophenyltolylaminesulfonic acid 100 2,4-Dinitrochlorobenzene from chlorobenzene 101 m-Phenylenediaminesulfonic acid from 2,4-dinitrochlorobenzene 103 Aniline-2,5-disulfonic acid from chlorobenzene 104 2-Nitrochlorobenzene-4-sulfonic acid from chlorobenzene 104 Nitrobenzene-2,5-disulfonic acid 106 Aniline-2,5-disulfonic acid 106 4-Chloro-2-aminophenol from p-dichlorobenzene .... 108 Nitro-p-dichlorobenzene from p-dichlorobenzene . 108 4-Chloro-2-nitrophenol from nitro-p-dichlorobenzene 109 4-Chloro-2-aminophenol from 4-chloro-2-nitrophenol 110 Derivatives of nitrobenzene Ill m-Dinitrobenzene from nitrobenzene Ill m-Nitroaniline from m-dinitrobenzene 113 Partial reductions in general 114 m-Phenylenediamine from m-dinitrobenzene 115 m-Chloronitrobenzene from nitrobenzene 116 2-Chloro-4-dimethylaminobenzaldehyde 118 p-Tolyhydroxylaminesulfonic acid 118 2-Chloro-4-dimethylaminobenzaldehyde 119 m-Nitrobenzenesulfonic acid and metanilic acid from nitrobenzene 120 2,2'-Benzidinedisulfonic acid from nitrobenzene 123 Benzidine from nitrobenzene 124 CONTENTS xi Derivatives of aniline 126 Sulfanilic acid from aniline (baking process) 126 The baking process in general 127 1- (p-Sulfophenyl) -3-methyl-5-pyrazolone from sulfanilic acid 128 Phenylhydrazine-p-sulfonic acid 128 p-Sulfophenyl-3-methyl-5-pyrazolone 129 p-Aminoacetanilide from aniline 129 Acetanilide from aniline 130 p-Nitroacetanilide from acetanilide 131 p-Aminoacetanilide from p-nitroacetanilide 132 Dimethylaniline (diethyl-and ethylbenzylanilines) . 133 Ethylbenzylanilinesulfonic acid 136 Tetramethyl-p,p'-diaminodiphenylmethane from dimethylaniline and formaldehyde 137 Tetramethyl-p,p'-diaminobenzohydrol (Michler hydrol) 138 Tetramethyl-p,p'-diaminobenzophenone (Michler ketone) 139 Diphenylamine from aniline and aniline salt 140 Acetoacetanilide 142 Derivatives of benzenesulfonic acid 143 Benzene-m-disulfonic acid 143 Resorcinol 144 Derivatives of phenol 145 o- and p-Chlorophenol from phenol 145 Chloranil 146 o- and p-Nitrophenols and their ethers 147 Alkylation of nitrophenols 148 Trinitrophenol (picric acid) 150 Picramic

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