Rudolph Fittig

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Rudolph Fittig
Rudolph Fittig

Wilhelm Rudolph Fittig (born December 6, 1835 in Hamburg , † November 19, 1910 in Strasbourg ) was a German chemist . Fittig discovered a process for converting halobenzenes to alkylbenzenes. He synthesized the methacrylic acid and of acetone , the pinacol , he clarified the structure of benzoquinone on.

Live and act

Rudolph Fittig was the son of a private school teacher in Hamburg. The living conditions were very modest, so that the young Fittig was already working as a teacher at a private school at the age of 16. Fittig earned the money for studying at the Pestalozzi Foundation. In 1856 Rudolph Fittig began studying natural sciences at the University of Göttingen . On the advice of Traun, he took courses in chemistry with Friedrich Wöhler , in physics, botany and technology. In October 1858 Fittig finished his chemistry studies with a dissertation on some products of the dry distillation of acetic acid salts with Heinrich Limpricht . He worked at Friedrich Wöhler together with Friedrich Konrad Beilstein as an internship assistant. In August 1860 , Fittig completed his habilitation with a lecture on Auguste Laurent and Jean Baptiste Dumas and their influence on theoretical organic chemistry.

Fittig soon wrote the textbooks Grundriß der Organic Chemistry (Berlin 1863), Grundriß der Chemie [Inorganische Chemie, Organic Chemistry (Leipzig 1871, 1873)].

From 1865 Fittig published the Zeitschrift für Chemie together with Beilstein . In 1866 Fittig became a full professor in Göttingen, and in 1870 Fittig went to Tübingen as the successor to Adolph Strecker . In 1876, Fittig succeeded Adolf von Baeyer at the University of Strasbourg . A new chemical laboratory was built here under his aegis. In 1895/1896 Fittig was elected rector of the university. In 1902 Fittig ended his teaching activities and Johannes Thiele accepted the offer to succeed him.

He is a co-developer of the Wurtz-Fittig synthesis for hydrocarbons, named after him and Adolphe Wurtz . His significant discoveries include the molecular formula for fructose and glucose and the chemical substances pinacolin and biphenyl .

In Hamburg he became a member of the Masonic lodge Zur Brudertreue on the Elbe .

Scientific work

In his work on acetone, Fittig treated acetone with sodium and discovered a substance that could crystallize well, which he called "paraacetone". A heated argument broke out between him and the older Georg Städeler about the structures of acetone reduction and condensation products. Städeler proved (him) that this substance contained more hydrogen than acetone and he called the substance "Pinakon" because of its tabular crystals. The newly found substance was pinacol (2,3-dimethylbutanediol) and by-products such as diacetone alcohol , mesityl oxide and pinacolone delayed its identification.

Fittig obtained the previously unknown toluic acid from the oxidation of toluene (contaminated with a little xylene - the oxidation product was detected in the work) with dilute nitric acid .

As a result, Fittig searched for alkyl derivatives of benzene (the structure of which was still unknown at the time). Since the bromine derivatives of benzene were easy to prepare, and the positional isomers were easily distinguished by their chemical properties (boiling points, melting points), it was advantageous to find a reaction that replaces the bromine with an alkyl group (which is clearly detectable in an elemental analysis).

First he tried to react bromobenzene with cyanide - in the hope of getting the benzonitrile. These attempts - unlike with aliphatic bromine compounds - failed.

He then made benzyl chloride and let it act on the bromobenzene together with sodium. He was able to replace the bromine in benzene with a benzyl radical. Together with Bernhard Tollens, Fittig now produced ethylbenzene and butylbenzene with benzyl radicals. This was followed by reactions of bromobenzene with sodium and methyl iodide , ethyl iodide and propyl iodide , they obtained toluene , ethylbenzene and propylbenzene. This reaction is known in textbooks as the Wurtz-Fittig reaction. Fittig was also able to show that the homologous compounds chlorotoluene and benzyl chloride behave quite differently in terms of reactivity (substitution, alkylation).

Also due to an extensive work on homologues of benzene by Fittig, Kekule decided to publish his ideas about the structure of the benzene ring.

Between 1867 and 1870, Fittig and his colleagues converted mono-, di- and tri-bromotoluene into xylene, mesitylene and tetramethylbenzene . A doctoral student in Göttingen, Otto Wallach , discovered that the bromotoluenes differed. One bromotoluene crystallized out in the cold, the others remained in solution. When xylene , there are several positional isomers (ortho, meta, para). Various positional isomers of xylene could be clearly represented by oxidation and carbon dioxide elimination. Positional isomers of xylenes could also be distinguished via oxidation to terephthalic acid and the formation of anhydrides. Based on this knowledge, the positional isomers on the benzene ring (ortho, meta, para) could be assigned.

Another important work by Fittig was the elucidation of the structure of quinone. Initially, Fittig had clarified the structure of anthraquinone at the same time as Zincke . However, the correct structure of benzoquinone proposed by Fittig remained unproven for some time. The arrangement, the position of the two keto groups (ortho, meta- or para) also remained questionable. Only the formation of the oximes by Heinrich Goldschmidt brought a clear clarification.

Together with Paul Bieber, Fittig was able to find out more precisely how the Perkin reaction took place . He showed that first aldol condensation and then elimination of water took place. Also for the coumarin showed Fittig the correct structure and mode of formation on the coumaric. He also successfully used succinic anhydride instead of acetic anhydride in the Perkin reaction .

Fittig and Ostermeier also clarified the structure of phenanthrene and gave this compound its name. Fittig also found fluoranthene .

Fittig and coworkers also discovered the lactones . The addition of hydrogen bromide to cinnamic acid or ethyl crotonic acid led to the release of carbon dioxide when heated. According to the findings of E. Erlenmeyer, the bromine ion is deposited in the β-position and the hydrogen cation in the α-position to the carboxy group. The adjacent carboxy group substitutes the bromine ion and forms a lactone. Fittig also discovered methacrylic acid during this work . G. Kahlbaum soon used this acid to produce flexible glass ( Plexiglas ). Distyrene could be prepared in a similar way from cinnamic acid.

Works (selection)

  • Grundriss der Chemie , from 1963. In 1863, the book Wöhler's Grundriß der Organic Chemistry, expanded and revised by Fittig, was published . This was supplemented by Fittig in 1871 with an outline of inorganic chemistry , so that the outline of chemistry was created in two parts. This was published in several editions, e.g. B. Organic Chemistry in 7th edition in 1868 and in 9th edition in 1874 as well as an English translation in 1873.
  • The Nature and Aims of Chemical Research and Study , 1870
  • About the constitution of the so-called carbohydrates , 1871
  • Contributions to testing the additive behavior of molecular heat, especially organic compounds , Göttingen 1900.

literature

Individual evidence

  1. ^ Biographical data, publications and academic family tree of Wilhelm Rudolph Fittig at academictree.org, accessed on January 1, 2018.
  2. ↑ R. Fittig: About some products of the dry distillation of acetic acid salts . In: Annals of Chemistry and Pharmacy . tape 110 , no. 1 , 1859, p. 17 , doi : 10.1002 / jlac.18591100103 ( archive.org ).
  3. ↑ R. Fittig: About some metamorphoses of the acetone of acetic acid . In: Annals of Chemistry and Pharmacy . tape 110 , no. 1 , 1859, p. 23 , doi : 10.1002 / jlac.18591100104 ( archive.org ).
  4. ↑ R. Fittig: 41. About some derivatives of acetone . In: Annals of Chemistry and Pharmacy . tape 114 , no. 1 , 1860, p. 54 , doi : 10.1002 / jlac.18601140107 ( archive.org ).
  5. ↑ G. Städeler: Investigations on acetone . In: Annals of Chemistry and Pharmacy . tape 111 , no. 3 , 1859, p. 277 , doi : 10.1002 / jlac.18591110303 ( archive.org ).
  6. ↑ Zeitschrift für Chemie, 2 , 36–37.
  7. ↑ Dear. Ann. Chem. 13 , 303 (1864).
  8. ^ News from the Royal Society of Science in Göttingen, 352–359 (1864).
  9. ^ Journal of Chemistry, 5 , 138 (1869).
  10. ↑ Dear. Ann. d. Ch. 156 , 231-245 (1870).
  11. ↑ Ber. German Chem. Ges., 6 , 168 (1873)
  12. ↑ Rudolph Fittig, W. Siepermann: Contributions to the knowledge of the quinones . In: Justus Liebig's Annals of Chemistry . tape 180 , no. 1-2 , 1876, pp. 23 , doi : 10.1002 / jlac.18761800103 .
  13. ↑ Heinrich Goldschmidt: About the nitrosophenols. In: Reports of the German Chemical Society. 17, 1884, pp. 213-217, doi: 10.1002 / cber.18840170165 .
  14. ↑ Dear. Ann. d. Ch. 153 , 358-368 (1870).
  15. ↑ Journal f. Ch., 11 , 595 (1868).
  16. ↑ Ber. German Chem. Ges., 5 , 934 (1872).
  17. ↑ Ber. German Chem. Ges., 200 , 65-74 (1880).
  18. ↑ Rudolph Fittig: Outline of Chemistry . First part. Inorganic chemistry. 1st edition. Duncker & Humblot, Leipzig 1871 ( online in the Internet Archive [accessed October 12, 2019]).
  19. ↑ Rudolph Fittig, Friedrich Wöhler: Wöhler's floor plan of organic chemistry . 7th revised edition. Duncker & Humblot, Leipzig 1868 ( limited preview in Google book search [accessed October 12, 2019]).
  20. ↑ Rudolph Fittig, Friedrich Wöhler: Wöhler's floor plan of organic chemistry . 9th revised edition. Duncker & Humblot, Leipzig 1874 ( limited preview in the Google book search, digitized online at the University of Innsbruck, University and State Library of Tyrol [accessed on October 12, 2019]).
  21. ↑ Rudolph Fittig, Friedrich Wöhler, Ira Remsen: Wöhler's Outlines of Organic Chemistry . Henry C. Lea, Philadelphia 1873, OCLC 908334442 (English, limited preview in Google Book Search, online in the Internet Archive [accessed October 12, 2019]).
  22. ↑ Rudolph Fittig: The essence and goals of chemical research and study of chemistry . Academic inaugural speech. Quandt & Handel, JR Hirschfeld, Leipzig 1870, OCLC 1068274069 ( limited preview in the Google book search [accessed on October 12, 2019] 16 pages): “The task of chemistry is to determine the composition of the body and all when changing this composition to investigate occurring natural phenomena in order to derive the legal connection and the cause of these phenomena, ie the laws of nature which govern the formation and decomposition of the body. "
  23. ↑ Rudolph Fittig: About the constitution of the so-called carbohydrates . For the academic celebration of the birthday of His Majesty the King Karl von Württemberg. Ludwig Friedrich Fues, Tübingen 1871, OCLC 37966234 ( online at the Bavarian State Library BSB [accessed October 12, 2019]).
  24. ↑ Rudolph Fittig: Contributions to the examination of the additive behavior of molecular heat, especially organic compounds . Inaugural dissertation. EA Huth, Göttingen 1900, OCLC 493889618 .
personal data
SURNAME Fittig, Rudolph
ALTERNATIVE NAMES Fittig, Wilhelm Rudolph (full name)
BRIEF DESCRIPTION German chemist
DATE OF BIRTH December 6, 1835
PLACE OF BIRTH Hamburg
DATE OF DEATH November 19, 1910
Place of death Strasbourg