Schmieroel

1,170,612. Amine salts of phosphorus esters; halogen-containing norbinene derivatives. ESSO RESEARCH & ENG. CO. 20 Oct., 1967 [8 Nov., 1966], No. 49979/66. Heading C2C. [Also in Division C5] Amine salts are formed by reacting primary C 12 -C 24 alkyl amines, secondary amines having two C 6 -C 12 alkyl groups, tertiary amines such as tributylamine and trihexylamine, or alkylene diamines and their mono- or di-N-alkyl substituted derivatives with compounds of the formula wherein X 1 to X 10 are hydrogen or halogen atoms or hydrocarbyl groups, Y 1 to Y 4 are oxygen or sulphur atoms, and either (a) the free bonds 1 and 2 are joined to the free bonds 3 and 4 respectively; or (b) the bonds 1 and 2 from part of one, two or more fused carbocyclic rings, which are non substituted or substituted by halogen atoms and/or hydrocarbyl groups, and the bonds 3 and 4 are linked to adjacent carbon atoms in one of said fused rings. 1,4,5,6,7,7- hexachloro - 5 - norbornene 2,3 - dimethanol is prepared by heating cis-2-butene-1,4-diol with hexachlorocyclopentadiene in dioxon, distilling off the dioxan and unconverted starting materials under vacuum, and crystallizing the residue from chloroform. 3-Thiono-3-thiolo- 6,7,8,9,10,10 - hexachloro - 1,5,5a,6,9,9a - hexahydro - 6,9 - methano - 2,4,3 - benzodioxaphosphepin is prepared by refluxing the hexachloronorbornene-dimethanol with P 2 S 5 in a mixture of dioxon and xylene, filtering off unreacted P 2 S 5 and distilling off the solvents under vacuum. The hydroxy dioxa phosphepin-oxide and the hydroxy dithio phosphepin-oxide can be prepared by reacting the halogenated norbornene diol and dithiol respectively with P 2 O 5 or P 2 O 3 . 3 - Hydroxy - 6,7,8,9,10,10- hexachloro 1,5,5a,6,9,9a - hexahydro - 6,9 methano - 2,4,3 - benzodithiaphosphepin and the corresponding benzodithiaphosphepin - 3- oxide can be prepared by reacting halogenated norbornene dithiols with dichloro thiophosphoric acid and dichloro phosphoric acid respectively.