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The Products of the Destructive Distillation of Keratin in the Form of Leather

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The Products of the Destructive Distillation of Keratin in the Form of Leather KU ScholarWorks | The University of Kansas Pre-1923 Dissertations and Theses Collection http://kuscholarworks.ku.edu The Products of the Destructive Distillation of Keratin in the Form of Leather by R. Phillips Rose 1913 Submitted to the Department of Chemistry of the University of Kansas in partial fulfillment of the requirements for the Degree of Master of Science This work was digitized by the Scholarly Communications program staff in the KU Libraries’ Center for Digital Scholarship. DESTRUCTIVE DI< THE PRODUCTS OF THE DESTRUCTIVE DISTILLATION OP KERATIN IN THE FORM OF LEATHER. By R. Phillips Rose Presented to the Faculty of the GRADUATE SCHOOL of the University of Kansas In Partial Fulfillment of the Requirements for the degree of MASTER OF SCIENCE May 15, 1913• R0005S 371t3 INTRODUCTION This research was undertaken for the purpose of finding a method for the commercial utilization of leather scrap from boot factories, (it was done in the Department of Industrial Research of the University of Kansas, under the direction of Dr. Robert Kennedy Duncan). The work will be considered from a theoretical and practical point* Since the commercial application would simply be the application of engineering principles« to the known scientific facts obtained. In the classification of chemical substances, leather comes under the general caption of protein compounds. According to Mann*, protein substances may be divided into three groups: 1* Albumins occurring as * native albumins8* They include the albuminoid substances 2 which form the supporting and connective tissue of the animal organism. 2. Proteins or " Proteids* proper, which are combinations of albumins proper with other organic compounds, containing phosphorus or iron. 3. Derivatives of native albumins and proteins which retain in their chemical configuration the characteristics of albuminus substances, as represented by albumins, peptones, pep• tides as products of digestion or metabolism, either natural or artificial. The decomposition products of the above com• pounds have been a subject of investigation which early attracted the attention of chemists. It was early recognized, that on account of the complex• ity of the albumin molecule, the only methods that would ultimately lead to its structural for• mula would be a study of the products obtained i- • Chemistry of Proteids*, P. 4, First Edition. 3 from its decomposition by various methods. Prom the knowledge thus obtained, it was hoped that the original compounds could be synthesized, and in fact much success along this line has been gained by Emil Fischer of Berlin and his pupils. While no albumin, which could be identified as •native" has as yet been obtained, still complex poly-pep- tides, as Fischer terms them, giving practically all of the special reactions characteristic of al• buminous substances, have bden synthesized. One aim of the various processes used was to preserve the original chain intact, breaking only the imid linking (which linked together the side chains), so that its linking could be identified. The products that result when this reaction takes place are called the primary dissociation products, while those in which the chain is ruptured, are called the secondary dissociation products. In the secondary decomposition, the same products are obtained in general as in the primary decom- position, but a part of the compounds break down into simpler products. This fact applies to the three classes of albuminous substances noted above. The products of both the primary and secondary de• composition are in general the same for the classes, with the exception of a very few of the minor indiv• iduals of each class. There is a wide variation in the ration of the amounts produced for each class and for each individual in the class. The primary dissociation products of album• inous materials are obtained by fermentation or hydrolysis with acids. Acid hydrolysis is consid• ered equivalent to the action of ferments. One of the more common methods is that of Hlasiwetz and Habermann. These experimenters boil the albumin in a solution of hydrochloric acid containing stannous chloride. This reaction breaks the imid grouping (by means of which the chains are kept together) without breaking the chain itself, that !• Liebig's Ann. 159, 204, (1871) 5 is without changing the relative position of the nitrogen atoms. One proof of this is shown by Schylzei, who showed the changes which took place in guanidin,when treated "by the above, to be as follows: -CO-NH-CNH-NH-C- becomes COOH-NH-CNH-NH-C Without going into the details of the isola• tion and estimation of the primary decomposition products, the following list is given according to Cohnheim. A. OPEN-CHAIN AMINO-ACIDS« 1. (a) mono-amino-mono-carboxylic acids 1. amino-acetic CaH6N02 2. amino-propionic C8H7N0S amino-butyric C4H9N02 3. amino-valerianic CsHnNOa 4. amino-iso-butyl-acetic C6HlaN02 (b) mono-amino-mono-carboxylic-hydroxy acids 5. amino-hydroxy-propionic CaH7NOa 6» amino-tetra-hydroxy-caproic CaHiaNOa (c) mono-amino-di-carboxylic acids 7. amino-succinic C^I^NO^ 8» amino-glutaminic C5H9NO4 (d) mono-amino-di-carboxylic-hydroay acids 9. amino-hydroxy-succinic C^lfyNOo NO 10. amino-hydroxy-suberic CeHia c x. Liebig*s Ann. 169, 150 (1879). 6 A. OPEN-CHAIN AMINO-ACIDS• (cont} II. (e) diamino-mono-carboxylic acids 11. diamino-propionic CAH8N0a 12. diamino-caproic C6Hi4NaOa 13. guanidin-amino-valerianic C6Hi4N4Oa 14. histidin C6HfNs0a (f) diamino-mono-carboxylic-hydroxy acids. 15. diamino-trihydroxy-dodecanoic (g) diamino-di-carboxylic acids 16. diamino-glutaric C5HiANa04 17. diamino-adipic C6Hi4Na04 (h) diamino-di-carboxylic-hydroxy acids 18. diamino-di-hydroxy-suberic CsHi6Na06 19. diamino-hydroxy-sebacic Ci0HAON205 20. caseanic acid I?) C9Hi6N206 21. caseinic acid (?) CiAHL6Na0c B. RING-COMPOUNDS. (See Histidin under No.14) (i) pyrrolidin compounds 22. a-pyrrolidin-carboxylic acid CsH^NOjj 23. hydroxy-pyrrolidin-carboxylic acid C8H9N0a (k) aromatic amino-acids 24. phenyl-amino-propionic C9HnN0a 25. phenyl-hydroxy-amino-propionic CQHUNQJ 26. indol-amino-propionic CnHxANaOa C. AMMONIA, (l) ammonia 27 • ammonia NH8 D. THIO-AMINO-ACIDS, (m) diamino-di-thio-dicarboxylic acid 28. cystin C6HiaNa04Sa 7 Since in the experimental work we are dealing only with keratin, a discussion of the above pro• ducts will not be taken up at this time, but those which are derived from keratin will be considered under that heading. The secondary dissociation products are those resulting from the action of reagents upon the primary products. The most common reagents used to produce this class of compounds are boiling alkalies, superheated steam, oxidizing reagents, such as - calcium, barium and potassium permanganates in boiling acid or alkaline solution, hydrogen perox• ide in acid solution, fusion with alkalies and dry distillation. The action of these reagents upon the complex proteins produce a great number of simpler products included in all the divisions of organic chemistry and are too numerous for tabulation in a paper of this kind. 8 Animal hides are made into leather, which is composed principally of the albuminoid keratin com• bined either chemically or coloidally with some other substance, the principal ones of which are tannin and chromic oxide. Tannin is one of the most common precipitants for albuminous solutions and is supposed by many chemists to form a compound with the albumin; others believe it to be a coagulation of the albumin, which carries down most of the tannin. Many examples of this class of reaction are known in colloidal chem• istry and it is also a fact that the solutions of albuminous substances are,for the most part, colloidal in their nature. Chromic acid is another important coagulating reagent and it is by the reduction of chromic acid to chromic oxide in the raw skins that leather is produced. It is a well known fact that all animal tissues are made up of cells which are capable of being 9 differentiated only under the microscope. Leather, when examined under the microscope shows a fibrous structure. From these considerations it is perfect• ly obvious that the cells of the hide, when in the swelled and semi-colloidal condition brought about by the usual tan house treatment, could be conceived as being coagulated into fibers by the tanning mater• ial which is absorbed in great quantities by the cells during coagulation. The subsequent rubbing and oiling which the hide undergoes after the tanning proper, serves further to complete the action,and where oil or leather dressing is used to form around the fibers a protective coating. A well known fact supporting this argument is the coagulation of blood - first into a gelatinous mass and then into fibers. From the above considerations, it seems reason• able to conclude that the decomposition product of leather will be ultimately the same as those of the 10 albuminoid keratin when both are treated under the same conditions* Prom our knowledge of the de• structive distillation of organic substances, the most common of which are coal, wood, bones, peat and lignite, it is reasonable to conclude also that the destructive distillation of keratin in the form of leather will yield a coke or charcoal containing the mineral constituents of the original substance and reduced carbon, a liquid distillate containing the moisture originally in the leather, and the de• composition products of the keratin both primary and secondary, and lastly a gas containing the vol• atile constituents of the decomposition products, together with carbon monoxide and dioxide formed from the hot decomposition products and the oxygen of the air. Since this research was conducted in order to obtain a commercial method for the utilization of leather scrap, the charcoal residue, the nitrogen content of the distillate and the utilization of the gas as fuel, are the factors considered at greater length in this paper. 12 APPARATUS.
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