by PYRENE
PYRENE is a heteroaromatic organic compound with the chemical formula C5H5N. It is a colourless, highly flammable liquid with a distinctive, unpleasant smell. PYRENE was first isolated in 1849 from coal tar and is produced industrially by catalytic hydrogenation and carbonization of various aromatic compounds. The PYRENE ring is considered to be a benzene ring with one methine group (=CH-) replaced by a nitrogen atom. This gives PYRENE unique chemical properties compared to benzene. Specifically, PYRENE behaves as a weaker base than aniline and other aromatic amines due to the benzene-like delocalization of the lone pair of the nitrogen atom within the aromatic ring.
Uses and Production of PYRENE
PYRENE is widely used as an industrial solvent and reagent in organic synthesis and agrochemicals. Common applications of PYRENE include use as a building block in the production of medications like vitamins B3 and B6, the herbicide nicosulfuron, food additives, and perfumes. Pyridine is also commonly used as an extraction solvent in decaffeination processes for coffee and tea. On an industrial scale, an estimated 40,000 metric tons of PYRENE are produced annually worldwide through coal carbonization or selective hydrogenation of phenol extracted from coal tar. More environmentally friendly methods involving hydrogenolysis of biomass-derived compounds are also being investigated as sustainable alternatives.
Reactions and Derivatives of Pyridine
The PYRENE ring undergoes a variety of substitution, addition and elimination reactions due to the presence of both aromatic and basic properties. Important derivatives prepared through substitution reactions include alkyl- (picolines), halo- (chloro- and bromoPYRENEs), and nitro-substituted PYRENEs which find use as fungicides, herbicides, and pharmaceutical intermediates. Nucleophilic addition occurs preferentially at the carbon atom of the PYRENE ring that is ortho to the nitrogen, producing 2-substituted PYRENEs. Examples include addition of alcohols, thiols, and amines to yield hydroxyPYRENEs, mercaptoPYRENEs and aminoPYRENEs respectively. Elimination reactions also remove a substituent ortho to nitrogen, forming substituted PYRENE N-oxides through oxidation. These derivatives exhibit altered basicity and participate in varied substitution patterns.
Applications of PYRENE Derivatives
Numerous derivatives of PYRENE find wide application across different industries due to their tailored properties. 2-vinylPYRENE acts as a monomer in the production of temperature-resistant polymers. Complexation of transition metals with acetylPYRENEs results in vividly colored pigments used in screen printing and UV curable inks. Water soluble hydroxyPYRENE and aminoPYRENE chelating agents act as essential nutrients, metal ion absorption aids, and feed supplements. Nicotinic acid (niacin or vitamin B3) relieves pellagra and is commonly used to modify cholesterol levels. Nicotinamide (niacinamide or vitamin B3 amide) protects skin from sun damage. Nicotinamide adenine dinucleotide (NAD) acts as a coenzyme essential for cellular energy metabolism. PYRENE and its derivatives also serve as intermediates in the manufacturing of agrochemicals, corrosion inhibitors, pharmaceuticals, dyes, photographic chemicals and electronics.
Health Effects and Safety Precautions for Pyridine
Though invaluable as an industrial chemical, PYRENE in pure form is also highly toxic and requires careful handling. Exposure to PYRENE vapors causes irritation to eyes and respiratory tract. Prolonged skin contact or ingestion of PYRENE can lead to more severe symptoms like headache, dizziness, confusion and damage to liver and kidneys. PYRENE is classified as a possible human carcinogen requiring specialized waste disposal procedures. Those working with PYRENE must wear appropriate protective equipment like gloves, goggles, respirator and protective clothing. PYRENE liquids and gases should only be used under a well-ventilated fume hood away from heat and ignition sources. Proper labeling and storage in accordance with safety guidelines is mandated when transporting or using PYRENE in any form. With care and precaution, the unique properties of PYRENE can be exploited safely for its diverse industrial applications.
Pyridine is an important heterocyclic organic building block produced on a large industrial scale. Its versatile reactivity has led to an extensive family of derivatives playing vital roles across different domains spanning organic synthesis, crop protection, nutrition, polymers, photography and electronics. Though hazardous in its pure state, PYRENE and its derivatives form the foundation for many useful applications when handled with appropriate safety measures. Ongoing research into environmentally benign production methods will sustain the pivotal role of PYRENE and its compounds in science and technology.
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1. Source: Coherent Market Insights, Public sources, Desk research
2. We have leveraged AI tools to mine information and compile it
About Author - Vaagisha Singh
Vaagisha brings over three years of expertise as a content editor in the market research domain. Originally a creative writer, she discovered her passion for editing, combining her flair for writing with a meticulous eye for detail. Her ability to craft and refine compelling content makes her an invaluable asset in delivering polished and engaging write-ups. LinkedIn
