Method and apparatus for preparing monofunctional aromatic chloroformates suitable for use as chainstopping agents

A continuous process for the preparation of an MAC product having the structure (I)

• wherein n is an integer from 1 to 5, and R1 represents hydrogen, a branched or unbranched alkyl group having from 1–15 carbon atoms, an aryl group which may be substituted or unsubstituted, a cycloaliphatic group which may be substituted or unsubstituted, or an arylalkyl group which may be substituted or unsubstituted, the method comprising the steps of
• a) providing a reaction system comprising a reactor consisting essentially of a tubular reactor and a means for conveying fluids through the reactor;
• the tubular reactor having an input at the upstream end and an outlet at the downstream end;
• b) introducing into the tubular reactor at the input of the upstream end a feed stream comprising an inert organic solvent and a monofunctional hydroxyaromatic compound;
• c) introducing into the tubular reactor a carbonyl chloride;
• d) introducing into the tubular reactor an aqueous caustic solution;
• e) effecting contact between the carbonyl chloride, the monofunctional hydroxyaromatic compound and the aqueous caustic solution for a time period and at conditions sufficient to yield the MAC product.

A continuous process for the preparation of paracumyl phenyl chloroformate comprising the steps of:

• a) providing a reaction system comprising a reactor consisting essentially of a tubular reactor and a means for conveying fluids through the reactor;
• the tubular reactor having an input at the upstream end and an outlet at the downstream end;
• b) introducing into the tubular reactor at the input of the upstream end a feed stream comprising methylene chloride and paracumyl phenol;
• c) introducing phosgene into the tubular reactor;
• d) introducing an aqueous caustic solution into the tubular reactor;
• e) effecting contact between the phosgene, the paracumyl phenol and the aqueous caustic solution for a time period and at conditions sufficient to yield paracumyl phenyl chloroformate.

A continuous process for the preparation of monofunctional aromatic haloformate having the structure V

• wherein n is an integer from 1 to 5, and R1 represents hydrogen, a branched or unbranched alkyl group having from 1–15 carbon atoms, an aryl group which may be substituted or unsubstituted, a cycloaliphatic group which may be substituted or unsubstituted, or an arylalkyl group which may be substituted or unsubstituted, and X represents bromine, fluorine, iodine or chlorine;
• the method comprising the steps of
• a) introducing
• 1) an aqueous caustic solution;
• 2) a carbonyl halide;
• 3) at least one monofunctional hydroxyaromatic compound;
• and
• 4) at least one inert organic solvent into a continuous reaction system;
• and
• b) effecting contact between 1), 2), 3) and 4) for a time and at conditions sufficient to produce a MAC of structure (I).