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ChemicalBook CAS DataBase List P,P'-DDD
72-54-8

P,P'-DDD synthesis

10synthesis methods
-

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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