Compositions for Improved Production of Acrylic Acid

• US 20190031592A1
• Filed: 06/29/2018
• Published: 01/31/2019
• 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., Sherry, Kyle Evan
• Granted Patent: US 10,781,156 B2
• Time in Patent Office: Days
• CPC Class Codes: B01J 27/232 Carbonates
• CPC Class Codes: B01J 31/0209 Esters of carboxylic or carbonic acids
• CPC Class Codes: B01J 31/0239 Quaternary ammonium compounds
• CPC Class Codes: B01J 31/04 containing carboxylic acids or their salts B01J31/0277 - B01J31/0298 take precedence; multi-metal carboxylate complexes like Pd (II) acetate, i.e. Pd3 (OAc) 6 or Cr(II)acetate, i.e. Cr2(OAc)4 B01J31/2226
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 51/377 by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups C07C51/36 - C07C51/373 take precedence
• CPC Class Codes: C07C 57/04 Acrylic acid; Methacrylic acid

Abstract

The present invention is directed to compositions which may undergo thermolysis to produce a higher purity acrylic acid product. In preferred embodiments of the present invention, the compositions comprise polypropiolactone and one or more active salts. The one or more active salts may catalyze thermolysis of the polypropiolactone so that the polymer depolymerizes into acrylic acid monomers. Certain concentrations of the one or more active salts result in higher purity acrylic acid products of thermolysis. In certain preferred embodiments, the one or more active salts include an acrylate group which may decompose under thermolysis to provide acrylic acid and thus decrease the concentration of undesirable contaminants in the acrylic acid product. In certain preferred embodiment, the one or more active salts comprise sodium acrylate.

Claims

1. A composition for producing a high purity acrylic acid thermolysis product, comprising:

a. polypropiolactone; and

b. one or more active salts for catalyzing thermolysis of said polypropiolactone when said composition undergoes thermolysis at thermolysis conditions.

2. The composition of claim 1, wherein a portion of said active salt is residual from a polymerization reaction producing said polypropiolactone.

3. The composition of claim 1, wherein said composition has a polypropiolactone concentration of at least about 95% by weight.

4. The composition of claim 1, wherein said composition has polypropiolactone concentration of at least about 98% by weight.

5. The composition of claim 1, wherein said polypropiolactone has a number average molecular weight between about 750 g/mol and about 10,000 g/mol.

6. The composition of claim 1, wherein said polypropiolactone has a number average molecular weight of greater than about 10, 000 g/mol.

7. The composition of claim 1, wherein said composition has a concentration of said one or more active salts of at least about 0.01 by weight%

8. The composition of claim 1, wherein said composition has a concentration of said one or more active salts of at least about 1% by weight.

9. The composition of claim 1, wherein said composition has a concentration of said one or more active salts less than about 10% by weight.

10. The composition of claim 1, wherein said composition has one or more active salts chosen from the group including sodium acrylate, potassium acrylate, sodium carbonate, potassium carbonate, and tert-butyl ammonium acrylate.

11. The composition of claim 1, wherein the composition further comprises phenothiazine.

22. The composition of claim 1, wherein said one or more active salts are residual polymerization catalyst from polymerization of said polypropiolactone.

12. A composition for producing a high purity acrylic acid thermolysis product, comprising:

a. polypropiolactone having with a concentration of at least about 95% by weight and a number average molecular weight between about 750g/mol and about 10,000 g/mol; and

b. one or more active salts with a concentration of at least about 0.01% by weight for catalyzing thermolysis of said polypropiolactone when said composition undergoes thermolysis at thermolysis conditions.

13. The composition of claim 12, wherein a portion of said one or more active salts is residual from a polymerization reaction producing said polypropiolactone.

14. The composition of claim 12, wherein said composition has polypropiolactone concentration of at least about 98% by weight.

15. The composition of claim 12, wherein said composition has a concentration of said one or more active salts less than about 10% by weight.

16. The composition of claim 12, wherein said composition has one or more active salts chosen from the group including sodium acrylate, potassium acrylate, sodium carbonate, potassium carbonate, and tert-butyl ammonium acrylate.

23. The composition of claim 12, wherein said one or more active salts are residual polymerization catalyst from polymerization of said polypropiolactone.

17. A composition for producing a high purity acrylic acid thermolysis product, comprising:

a. polypropiolactone with a concentration of at least about 98% by weight and a number average molecular weight greater than about 10,000 g/mol; and

b. one or more active salts with a concentration between about 0.5% and about 1.5% by weight for catalyzing thermolysis of said polypropiolactone when said composition undergoes thermolysis at thermolysis conditions.

18. The composition of claim 17, wherein a portion of said one or more active salts is residual from a polymerization reaction producing said polypropiolactone.

19. The composition of claim 17, wherein said composition has polypropiolactone concentration of at least about 98% by weight.

20. The composition of claim 17, wherein said composition has a concentration of said one or more active salts less than about 10% by weight.

21. The composition of claim 17, wherein said composition has one or more active salts chosen from the group including sodium acrylate, potassium acrylate, sodium carbonate, potassium carbonate, and tert-butyl ammonium acrylate.

24. The composition of claim 17, wherein said one or more active salts are residual polymerization catalyst from polymerization of said polypropiolactone.