Chemical Properties
faintly yellow crystalline powder
Uses
It is used as pharmaceutical intermediates. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuffs.
Application
4,4'-Dichlorobenzophenone can be used to synthesize polyether-polyketones, as well as reduce polymer costs. Furthermore, it is a metabolic product resulting from the degredation of DDT.
Definition
ChEBI: 4-4-Dichlorobenzophenone is a member of benzophenones.
Preparation
4,4'-Dichlorobenzophenone is prepared by the acylation of chlorobenzene with 4-chlorobenzoyl chloride. The conversion is typically conducted in the presence of an aluminium chloride catalyst in a petroleum ether solvent.
ClC6H5C(O)Cl + C6H5Cl → (ClC6H4)2CO + HCl
General Description
4,4′-Dichlorobenzophenone (DBP) is a metabolite obtained when one strain of ectomycorrhizal fungi, Xerocomus chrysenteron, degrades 1,1,1-trichloro-2,2-bis(4-chlorophe-nyl) ethane (DDT).
Purification Methods
Recrystallise it from EtOH [Wagner et al. J Am Chem Soc 108 7727 1986]. The semicarbazone has m 192-193o (from H2O). [Beilstein 7 H 420, 7 I 228, 7 II 359, 7 III 2076, 7 IV 1376.]
References
[1] C. VENKATESAN. Liquid Phase Selective Benzoylation of Chlorobenzene to 4,4′-Dichlorobenzophenone over Zeolite H-Beta[J]. Catalysis Letters, 2001, 75 1-2: 119-123. DOI:10.1023/A:1016771719956.
[2] K. YONEYAMA F. M. Reductive metabolism of heptachlor, parathion, 4,4′-dichlorobenzophenone, and carbophenothion by rat liver systems[J]. Pesticide Biochemistry and Physiology, 1981, 15 3: Pages 213-221. DOI:10.1016/0048-3575(81)90003-1.
[3] YI HUANG Jie W. Degradation and mineralization of DDT by the ectomycorrhizal fungi, Xerocomus chrysenteron[J]. Chemosphere, 2013, 92 7: Pages 760-764. DOI:10.1016/j.chemosphere.2013.04.002.
[4] HONGXIN ZHOU. Synthesis and characterization of phthalazinone‐based poly(aryl ether ketone) derived from 4,4′‐dichlorobenzophenone[J]. Polymers for Advanced Technologies, 2012, 23 1: 742-747. DOI:10.1002/PAT.1950.
