Isocyanates, derivatives, and processes for producing the same

A process for producing an isocyanate product comprising the steps:

• a. carbonylation of an epoxide reagent with a carbon monoxide reagent to produce a beta-lactone intermediate;
• b. contacting the beta-lactone intermediate with a catalyst to produce an organic acid intermediate;
• c. reacting the organic acid intermediate with an azide reagent to produce an acyl azide intermediate;
• and
• d. thermally decomposing the acyl azide intermediate to produce the isocyanate product.

A process for producing a diisocyanate product comprising the steps:

• a. carbonylation of an epoxide reagent with a carbon monoxide reagent to produce a beta-lactone intermediate;
• b. carbonylation of the beta-lactone intermediate with a carbon monoxide reagent to produce a succinic anhydride intermediate;
• c. combining the succinic anhydride intermediate with a nucleophile to produce an amide intermediate;
• and
• d. rearranging the amide intermediate in the presence of a halogen reagent with a caustic base reagent to produce the diisocyanate product.

A process for producing an aromatic isocyanate product comprising the steps:

• a. carbonylation of an epoxide reagent with a carbon monoxide reagent to produce a beta-lactone intermediate;
• b. carbonylation of the beta-lactone intermediate with a carbon monoxide reagent to produce a succinic anhydride intermediate;
• c. oxidizing the succinic anhydride intermediate to provide an unsaturated four carbon intermediate;
• d. contacting the unsaturated four carbon intermediate with furan to provide a cyclohexene ring intermediate;
• e. combining the cyclohexene ring intermediate with a nucleophile to produce an amide intermediate;
• and
• f. rearranging the amide intermediate in the presence of a halogen reagent with a caustic base reagent to produce the aromatic isocyanate product.

A process for producing an aromatic isocyanate product comprising the steps:

• a. carbonylation of an epoxide reagent with a carbon monoxide reagent to produce a beta-lactone intermediate;
• and
• i b. reacting said beta-lactone intermediate with a furan reagent to produce an aromatic dicarboxylic acid intermediate;
• i c. reacting said aromatic dicarboxylic acid intermediate with an acyl chloride to produce a chlorocarbonyl intermediate;
• i d. reacting said chlorocarbonyl intermediate with a hydroxylamine to produce an aromatic hydroxamic acid intermediate;
• and
• i e. rearranging said aromatic hydrocamic acid intermediate to produce the aromatic isocyanate product, or
• ii b. rearranging said beta-lactone intermediate to produce an acrylic acid intermediate;
• ii c. reacting said acrylic acid intermediate with an isoprene intermediate to produce a cyclohexene-carboxylic acid intermediate;
• ii d. dehydro-aromatization of said cyclohexene-carboxylic acid intermediate to produce an aromatic dicarboxylic acid intermediate;
• ii e. reacting said aromatic dicarboxylic acid intermediate with an acyl chloride to produce a chlorocarbonyl intermediate;
• ii f. reacting said chlorocarbonyl intermediate with a hydroxylamine to produce an aromatic hydroxamic acid intermediate;
• and
• ii g. rearranging said aromatic hydrocamic acid intermediate to produce the aromatic isocyanate product.