Английская Википедия:Acenaphthene

Материал из Онлайн справочника
Перейти к навигацииПерейти к поиску

Шаблон:Distinguish Шаблон:Chembox Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.[1]

Production and reactions

Acenaphthene was prepared the first time from coal tar by Marcellin Berthelot.[2] Later Berthelot and Bardy synthesized the compound by cyclization of α-ethylnaphthalene. Industrially, it is still obtained from coal tar together with its derivative acenaphthylene (and many other compounds).

Like other arenes, acenaphthene forms complexes with low valent metal centers. One example is (η6-acenaphthene)Mn(CO)3]+.[3]

Uses

It is used on a large scale to prepare naphthalene dicarboxylic anhydride, which is a precursor to dyes and optical brighteners.[1] Naphthalene dicarboxylic anhydride is the precursor to perylenetetracarboxylic dianhydride, precursor to several commercial pigments and dyes.[4][5]

Файл:Pig29route.png

References

Шаблон:Reflist

Шаблон:PAHs Шаблон:Authority control

  1. 1,0 1,1 Шаблон:Ullmann
  2. Шаблон:Cite book
  3. S. B. Kim, S. Lotz, S. Sun, Y. K. Chung, R. D. Pike, D. A. Sweigart "Manganese Tricarbonyl Transfer (MTT) Agents" Inorganic Syntheses, 2010, Vol. 35, 109–128. Шаблон:Doi
  4. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. Шаблон:Doi
  5. Greene, M. "Perylene Pigments" in High Performance Pigments, 2009, Wiley-VCH, Weinheim. pp. 261-274.Шаблон:Doi