Cyclic phosphorus containing flame retardant compounds

A process for the production of compounds having the formula:

• A.sub.3-Y --N--B.sub.Y
• wherein A is ##STR13## R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, halogens, alkyl groups having from 1 to 4 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, aryl and substituted aryl groups having from 6 to 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to 8 carbon atoms, Y is 1 or 2 and each B is independently selected from the group consisting of hydrogen, alkyl groups having from 2 to about 8 carbon atoms, halogenated alkyl groups having from 2 to about 8 carbon atoms, aryl and substituted aryl groups having from 6 to about 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to about 8 carbon atoms, comprising the steps of:
• (a) adding phosphorus trichloride to a mixture of a 1,3-diol derivative and water and an organic solvent at a temperature of from about 10.degree. C. to about 60.degree. C. to produce a 5,5-di-substituted 1,3,2-dioxaphosphorinane-2-oxide having the general formula:
• ##STR14## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, halogens, alkyl groups having from 1 to 4 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, aryl and substituted aryl groups having from 6 to 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to 8 carbon atoms;
• (b) purifying the 5,5-di-substituted 1,3,2-dioxaphosphorinane-2-oxide;
• (c) reacting the 5,5-di-substituted 1,3,2-dioxaphosphorinane-2-oxide, paraformaldehyde and an amine having the general formula:
• B.sub.Y NH.sub.3-Y,
• wherein Y is 1 or 2 and each B is independently selected from the group consisting of hydrogen, alkyl groups having from 2 to about 8 carbon atoms, halogenated alkyl groups having from 2 to about 8 carbon atoms, aryl and substituted aryl groups having from 6 to about 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to about 8 carbon atoms in an organic solvent to produce a (1,3,2-dioxaphosphorinanemethan) amine compound having the general formula:
• A.sub.3-Y --N--B.sub.Y
• wherein A is ##STR15## R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, halogens, alkyl groups having from 1 to 4 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, aryl and substituted aryl groups having from 6 to 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to 8 carbon atoms, Y is 1 or 2 and each B is independently selected from the group consisting of hydrogen, alkyl groups having from 2 to about 8 carbon atoms, halogenated alkyl groups having from 2 to about 8 carbon atoms, aryl and substituted aryl groups having from 6 to about 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to about 8 carbon atoms;
• and
• (f) purifying and drying the (1,3,2-dioxaphosphorinanemethan) amine compound.

A process for the production of compounds having the formula:

• A.sub.3-Y --N--B.sub.Y
• wherein A is ##STR16## Y is 1 or 2 and each B is independently selected from the group consisting of hydrogen, alkyl groups having from 2 to about 8 carbon atoms, halogenated alkyl groups having from 2 to about 8 carbon atoms, aryl and substituted aryl groups having from 6 to about 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to about 8 carbon atoms comprising the steps of:
• (a) adding phosphorus trichloride to a mixture of neopentyl glycol and water and an organic solvent at a temperature of from about 10.degree. C. to about 60.degree. C. to produce a 5,5-dimethyl 1,3,2-dioxaphosphorinane-2-oxide having the general formula:
• ##STR17## (b) purifying the 5,5-dimethyl 1,3,2-dioxaphosphorinane-2-oxide;
• (c) reacting the 5,5-dimethyl 1,3,2-dioxaphosphorinane-2-oxide, paraformaldehyde and an amine having the general formula
• B.sub.Y NH.sub.3-Y,
• wherein Y is 1 or 2 and each B is independently selected from the group consisting of hydrogen, alkyl groups having from 2 to about 8 carbon atoms, halogenated alkyl groups having from 2 to about 8 carbon atoms, aryl and substituted aryl groups having from 6 to about 8 carbon atoms and halogenated aryl and halogenated substituted aryl groups having from 6 to about 8 carbon atoms, in an organic solvent with an acid catalyst to produce a (1,3,2-dioxaphosphorinanemethan) amine compound having the general formula:
• A.sub.3-Y --N--B.sub.Y
• wherein A is ##STR18## Y is 1 or 2 and each B is independently selected from the group consisting of hydrogen, alkyl groups having from 2 to about 8 carbon atoms, halogenated alkyl groups having from 2 to about 8 carbon atoms, aryl and substituted aryl groups having from 6 to about 8 carbon atoms and halogenated aryl and substituted aryl groups having from 6 to about 8 carbon atoms;
• and
• (d) purifying and drying the (1,3,2-dioxaphosphorinanemethan) amine compound.