P,P'-DDD synthesis
- Product Name:P,P'-DDD
- CAS Number:72-54-8
- Molecular formula:C14H10Cl4
- Molecular Weight:320.04
50-29-3
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1022-22-6
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101-76-8
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72-55-9
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72-54-8
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90-98-2
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Yield:-
Reaction Conditions:
in benzene at 20; for 12 h;
Steps:
14 Example 14: Dehalogenation of Chlorinated Pesticides Reaction of 4,4′-dichlorodiphenyltrichloroethane (DDT) with 1,3-di-tert-butyl-imidazolidine to provide 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane (DDD), 1,1-dichloro-2, 2-bis(4-chlorophenyl)ethene (DDE), 1-chloro-2,2-bis(4-chlorophenyl)ethene (DDMU), 4,4′-dichlorobenzophenone (DBP), and 1,1-bis(4-chlorophenyl)methane (DDM)
Example 14: Dehalogenation of Chlorinated Pesticides Reaction of 4,4′-dichlorodiphenyltrichloroethane (DDT) with 1,3-di-tert-butyl-imidazolidine to provide 1,1-dichloro-2,2-bis(4-chlorophenyl)ethane (DDD), 1,1-dichloro-2, 2-bis(4-chlorophenyl)ethene (DDE), 1-chloro-2,2-bis(4-chlorophenyl)ethene (DDMU), 4,4′-dichlorobenzophenone (DBP), and 1,1-bis(4-chlorophenyl)methane (DDM) (0176) (0177) DDT (2.8 g, 7.8 mmol), benzene (20 mL), and imidazolidine (5.5 eqiv., R=Me, tBu, or Ph) were added to a 50 mL round bottom flask and stirred magnetically at room temperature. After 12 hours, GC-MS showed the complete conversion of DDT to DDD, DDE, DDMU, DBP, and DDM. After 24 hours, GC-MS showed complete conversion to DDMU, DBP, and DDM. Retention times for all products were compared to those of the blank analytical standards. DDD: GC-MS: tr=15.77 min, m/z (rel. in %): 319(1)[M+], 235(100), 165(55), 88(5). DDE: GC-MS: tr=14.95 min, m/z (rel. in %): 317(85)[M+], 246(100), 210(15), 176(33), 105(12), 87(9). DDMU: GC-MS: tr=14.36 min, m/z (rel. in %): 282(80)[M+], 247(21), 212(100), 176(44), 123(11), 105(10), 88(18), 75(16). DBP: GC-MS: tr=13.61 min, m/z (rel. in %): 250(34)[M+], 215(12), 139(100), 111(38), 75(28). DDM: GC-MS: tr=12.81 min, m/z (rel. in %): 236(49)[M+], 201(100), 165(78), 125(13), 89(15), 82(11).
References:
UNIVERSITY OF GUELPH;Denk, Michael K.;Milutinovic, Nicholas;Marczenko, Katherine US9744392, 2017, B1 Location in patent:Page/Page column 20-21
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![1-chloro-4-[1-(4-chlorophenyl)ethyl]benzene](/CAS/GIF/3547-04-4.gif)
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