Diphenylmethane is an organic compound with the formula (C 6 H 5 ) 2 CH 2 (often abbreviated CH 2 Ph 2 ). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups . It is a white solid.
5-410: The bisphenols ( / ˈ b ɪ s f ɪ n ɒ l / ) are a group of industrial chemical compounds related to diphenylmethane ; commonly used in the creation of plastics and epoxy resins. Most are based on two hydroxyphenyl functional groups linked by a methylene bridge . Exceptions include bisphenol S, P, and M. "Bisphenol" is a common name ; the letter following denotes the variant, which depends on
10-480: A variety of environmental matrices, even though it has a fairly short half-life . Diphenylmethane Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as benzhydryl . It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride : The methylene group in diphenylmethane
15-559: Is mildly acidic with a p K a of 32.2, and so can be deprotonated with sodium amide . The resulting carbanion can be alkylated. For example, treatment with n -bromobutane produces 1,1-diphenylpentane in 92% yield. Alkylation of various benzhydryl compounds has been demonstrated using the corresponding alkyl halides, both primary ( benzyl chloride , β-phenylethyl chloride , and n-octyl bromide) and secondary ( benzhydryl chloride , α-phenylethyl chloride , and isopropyl chloride ), in yields between 86 and 99%. The acidity of
20-480: The additional substituents. Bisphenol A is the most popular representative of the group, with millions of metric tons produced globally in the past decade, often simply called "bisphenol". Bisphenols A (BPA), F (BPF) and S (BPS) have been shown to be endocrine disruptors , potentially relating to adverse health effects. Due to its high production volumes, BPA has been characterised as a "pseudo-persistent" chemical, leading to its spreading and potential accumulation in
25-472: The methylene group in diphenylmethane is due to the weakness of the (C 6 H 5 ) 2 CH–H bond, which has a bond dissociation energy of 82 kcal mol (340 kJ mol ). This is well below the published bond dissociation energies for comparable C–H bonds in propane , where BDE((CH 3 ) 2 CH–H)=98.6 kcal mol , and toluene , where BDE(C 6 H 5 CH 2 –H)=89.7 kcal mol . This article about
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