US 11,814,360 B2
Isocyanates, derivatives, and processes for producing the same
Oleg Kulikov, Rochester, NY (US); Sadesh H. Sookraj, Cambridge, MA (US); Utpal Mahendra Vakil, West Henrietta, NY (US); and Matthew Goodrich, Rochester, NY (US)
Assigned to Novomer, Inc., Rochester, NY (US)
Appl. No. 16/753,591
Filed by Novomer, Inc., Rochester, NY (US)
PCT Filed Oct. 4, 2018, PCT No. PCT/US2018/054375
§ 371(c)(1), (2) Date Apr. 3, 2020,
PCT Pub. No. WO2019/070981, PCT Pub. Date Apr. 11, 2019.
Claims priority of provisional application 62/661,951, filed on Apr. 24, 2018.
Claims priority of provisional application 62/568,511, filed on Oct. 5, 2017.
Prior Publication US 2020/0331876 A1, Oct. 22, 2020
Int. Cl. C07D 305/12 (2006.01); C07D 305/08 (2006.01); C07D 305/14 (2006.01); C07D 307/20 (2006.01); C07D 407/12 (2006.01); C08G 18/09 (2006.01); C08L 75/04 (2006.01); C07C 263/12 (2006.01); C08G 18/44 (2006.01); C08G 18/48 (2006.01); C07C 263/00 (2006.01); C07C 265/00 (2006.01)
CPC C07D 305/12 (2013.01) [C07C 263/00 (2013.01); C07C 263/12 (2013.01); C07C 265/00 (2013.01); C07D 305/08 (2013.01); C07D 305/14 (2013.01); C07D 307/20 (2013.01); C07D 407/12 (2013.01); C08G 18/09 (2013.01); C08G 18/44 (2013.01); C08G 18/48 (2013.01); C08L 75/04 (2013.01)] 20 Claims
 
1. 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. combining the beta-lactone intermediate with a nucleophile to produce an amide ring-opened intermediate or to produce an hydroxamic acid ring-opened intermediate; and
c. contacting an amide ring-opened intermediate with a caustic base reagent in the presence of a halogen reagent to produce the isocyanate product or rearranging the hydroxamic acid ring-opened intermediate to produce the isocyanate product.