Acrylonitrile derivatives from epoxide and carbon monoxide reagents

• US 10,676,426 B2
• Filed: 06/29/2018
• Issued: 06/09/2020
• Est. Priority Date: 06/30/2017
• Status: Active Grant

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: Sookraj, Sadesh H.
• Primary Examiner(s): Kosack, Joseph R
• Application Number:
  US16/023,136
• Publication Number:
  US 20190002400A1
• Time in Patent Office: 711 Days
• CPC Class Codes: C07C 253/26 containing carbon-to-carbon multiple bonds, e.g. unsaturated aldehydes
• CPC Class Codes: C07C 255/08 Acrylonitrile; Methacrylonitrile
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 51/347 by reactions not involving formation of carboxyl groups
• CPC Class Codes: C07C 57/04 Acrylic acid; Methacrylic acid
• CPC Class Codes: C07C 57/08 Crotonic acid
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

Abstract

The present invention is directed to reactor systems and processes for producing acrylonitrile and acrylonitrile derivatives. In preferred embodiments of the present invention, the processes comprise the following steps: introducing an epoxide reagent and carbon monoxide reagent to at least one reaction vessel through at least one feed stream inlet; contacting the epoxide reagent and carbon monoxide reagent with a carbonylation catalyst to produce a beta-lactone intermediate; polymerizing the beta-lactone intermediate with an initiator in the presence of a metal cation to produce a polylactone product; heating the polylactone product under thermolysis conditions to produce an organic acid product; optionally esterifying the organic acid product to produce one or more ester products; and reacting the organic acid product and/or ester product with an ammonia reagent under ammoxidation conditions to produce an acrylonitrile product.

Claims

1. A process for producing an acrylonitrile product, comprising:

introducing an epoxide reagent and a carbon monoxide reagent to at least one reaction vessel through at least one feed stream inlet;

contacting the epoxide reagent and the carbon monoxide reagent with a carbonylation catalyst in the at least one reaction vessel to produce a beta-lactone intermediate;

converting the beta-lactone intermediate to an organic acid intermediate; and

reacting the organic acid intermediate with an ammonia reagent under ammoxidation conditions in the at least one reaction vessel to produce the acrylonitrile product.

2. The process of claim 1, wherein the converting of the beta-lactone intermediate to the organic acid intermediate comprises:

polymerizing the beta-lactone intermediate with a polymerization initiator in the at least one reaction vessel to produce a polylactone product; and

heating the polylactone product under thermolysis conditions in the at least one reaction vessel to produce the organic acid intermediate.

3. The process of claim 1, wherein the carbonylation catalyst comprises one or more metal carbonyl-Lewis acid catalysts.

4. The process of claim 1, wherein the carbonylation catalyst is introduced to the at least one reaction vessel under a carbon monoxide blanket.

5. The process of claim 1, wherein the carbonylation catalyst comprises a neutral metal carbonyl compound.

6. The process of claim 2, wherein the polymerization initiator has the general formula of M″

X, where M″

is cationic and X is anionic.

7. The process of claim 2, wherein the polymerization initiator comprises a carboxylate salt.

8. The process of claim 2, wherein the polylactone product undergoes thermolysis continuously.

9. The process of claim 1, wherein the converting of the beta-lactone intermediate to the organic acid intermediate comprises:

contacting the beta-lactone intermediate with a heterogenous catalyst to directly produce the organic acid intermediate.