Decomposition of 2-bromophenol in NaOH solution at high temperature. 2003

Miho Uchida, and Masaaki Furusawa, and Akitsugu Okuwaki
Department of Applied Chemistry, Graduate School of Engineering, Tohoku University, Aoba 07, Aramaki, Aoba-ku, 980-8579, Sendai, Japan. miho@env.che.tohoku.ac.jp

2-Bromophenol was reacted in aqueous sodium hydroxide at 200-250 degrees C. The decomposition rate was remarkably faster at 250 degrees C than at 225 or 200 degrees C, and the percentage debromination reached almost 100% in 1M NaOH at 250 degrees C for 4h. The percentage increased with NaOH concentration over the range 0.1-1M. Aliphatic compounds, such as 2,2-dimethoxypropane and 4-hydroxy-4-methyl-2-pentanone, and aromatic compounds, such as phenol and cresol, were formed as decomposition products. The formation of carboxylic acids, such as formic, acetic, and propionic acids, in the presence of oxygen was also confirmed. Under a nitrogen atmosphere, the oxidation caused by oxygen in solution was suppressed and hydrolysis became the dominant reaction in the decomposition of 2-bromophenol.

UI MeSH Term Description Entries
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D010636 Phenols Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D002424 Caustics Strong alkaline chemicals that destroy soft body tissues resulting in a deep, penetrating type of burn, in contrast to corrosives, that result in a more superficial type of damage via chemical means or inflammation. Caustics are usually hydroxides of light metals. SODIUM HYDROXIDE and potassium hydroxide are the most widely used caustic agents in industry. Medically, they have been used externally to remove diseased or dead tissues and destroy warts and small tumors. The accidental ingestion of products (household and industrial) containing caustic ingredients results in thousands of injuries per year. Caustic,Corrosive,Corrosives
D004785 Environmental Pollutants Substances or energies, for example heat or light, which when introduced into the air, water, or land threaten life or health of individuals or ECOSYSTEMS. Environmental Pollutant,Pollutant,Pollutants,Pollutants, Environmental,Pollutant, Environmental
D005411 Flame Retardants Materials applied to fabrics, bedding, furniture, plastics, etc. to retard their burning; many may leach out and cause allergies or other harm. Fire Retardant,Fire Retardants,Fireproofing Agent,Fireproofing Agents,Flame Retardant,Agent, Fireproofing,Agents, Fireproofing,Retardant, Fire,Retardant, Flame,Retardants, Fire,Retardants, Flame
D012972 Sodium Hydroxide A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed) Caustic Soda,Hydroxide, Sodium,Soda, Caustic
D013696 Temperature The property of objects that determines the direction of heat flow when they are placed in direct thermal contact. The temperature is the energy of microscopic motions (vibrational and translational) of the particles of atoms. Temperatures

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