Process for production of an ester and diol from reclaimed carpet material

1. A process for producing an ester comprising:

(a) providing reclaimed carpet material comprising a polyester component comprising a terephthalic unit; and

(b) reacting the polyester component with an alcohol having from 6 to 20 carbon atoms and under conditions effective to produce a terephthalate ester; wherein the reclaimed carpet material comprises one or more additional components that remain unreacted after reacting the polyester component with the alcohol;

(c) separating the unreacted components from the produced terephthalate ester; and

(d) combusting the separated unreacted components to form an ash component.

2. The process of claim 1 , wherein the reclaimed carpet material further comprises at least one of a face fiber, a mineral filler, a backing material, an adhesive composition, a contaminant, or any combinations thereof.

3. The process of claim 2 , wherein the mineral filler comprises calcium carbonate.

4. The process of claim 2 , wherein the backing material comprises a polyolefin, polyurethane, polyester, polyvinyl chloride or any combinations thereof.

5. The process of claim 2 , wherein the adhesive composition comprises at least one homogeneously branched ethylene polymer comprising interpolymer of ethylene with at least one C 3 -C 20 α-olefin.

6. The process of claim 2 , wherein the adhesive composition comprises a crosslinked styrene-butadiene copolymer, a crosslinked ethylene vinyl acetate copolymer, or a combination thereof.

7. The process of claim 1 , wherein the polyester component comprises polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, copolymers thereof, or any combinations thereof.

8. The process of claim 1 , wherein the polyester component is present in at least one of a carpet face fiber, a backing material, or an adhesive composition.

9. The process of claim 1 , wherein the alcohol comprises a straight chain, branched, cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group.

10. The process of claim 1 , wherein the alcohol comprises hexanol, 2-ethyl-1-hexanol, isonanol, isodecanol, isoeicosanol, octanol, decanol, tricadenol, pentadecanol, or any combinations thereof.

11. The process of claim 1 , wherein the conditions effective to produce the terephthalate ester comprise the presence of a catalyst.

12. The process of claim 11 , wherein the catalyst is present in an ash component.

13. The process of claim 12 , wherein the ash component contains CaO.

14. The process of claim 11 , wherein the catalyst is not acidic.

15. The process of claim 1 , wherein the conditions effective to produce the terephthalate ester further comprise a temperature in the range of from about 160° C. to about 260° C.

16. The process of claim 1 , wherein the conditions effective to produce the terephthalate ester further comprise a period of about 0.5 hours to about 12 hours.

17. The process of claim 1 , wherein the produced ester comprises a terephthalate ester having a general formula (I):

wherein R and R′ are the same or different and comprise a straight chain, branched or cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group, each group having from 6 to 20 carbon atoms.

18. The process of claim 17 , wherein R and R′ are the same or different and comprise a straight chain or a branched alkyl group having from 6 to 20 carbon atoms.

19. The process of claim 17 , wherein at least 90% by weight of the produced terephthalate ester is

20. The process of claim 17 , wherein about 10% or less by weight of the produced ester is:

or a combination thereof.

21. The process of claim 17 , wherein the terephthalate ester having a general formula (I) comprises di-n-hexyl terephthalate, dioctyl terephthalate, diisononyl terephthalate, diisodecyl terephthalate, di-n-octyl n-decyl terephthalate, di-n-tridecyl n-pentadecyl terephthalate, or diisoeicosyl terephthalate.

22. The process of claim 1 , wherein reacting under the conditions effective to produce the terephthalate ester further produces a diol.

23. The process of claim 22 , wherein the diol comprises at least one of ethylene glycol, 1,3-propnediol, or 1,4-butanediol.

24. The process of claim 1 , wherein the separated unreacted components are combusted at a temperature of at least about 800° C. for at least 0.5-3.0 hours to form an ash component.

25. The process of claim 24 , wherein the ash component is suitable for use as a reaction catalyst in a transesterification reaction.

26. A process for recycling a reclaimed carpet material comprising:

reacting a reclaimed carpet material comprising a polyester component comprising a terephthalic unit with an alcohol having from 6 to 20 carbon atoms in the presence of a catalyst at a temperature from about 160° C. to about 260° C. to form a reaction mixture, and wherein the reaction mixture comprises:

(a) a terephthalate ester derived from the reclaimed carpet material;

(b) a diol, wherein substantially all of the diol is derived from the polyester component present in the reclaimed carpet material; and

(c) unreacted products; and

(d) separating the unreacted components from the reaction mixture and combusting the separated unreacted components to form an ash component.

27. The process of claim 26 , wherein the polyester component comprises polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, copolymers thereof, or any combinations thereof.

28. The process of claim 26 , wherein the polyester component is present in at least one of a carpet face fiber, a backing material, or an adhesive composition.

29. The process of claim 26 , wherein the alcohol comprises a straight chain, branched, cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group.

30. The process of claim 26 , wherein the alcohol comprises hexanol, 2-ethyl-1-hexanol, isonanol, isodecanol, isoeicosanol, octanol, decanol, tricadenol, pentadecanol, or any combinations thereof.

31. The process of claim 26 , further comprising separating the terephthalate ester, and diol from the reaction mixture.

32. The process of claim 31 , wherein the separated terephthalate ester comprises a terephthalate ester having a general formula (I):

wherein R and R′ are the same or different and comprise a straight chain, branched or cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group, each group having from 6 to 20 carbon atoms.

33. The process of claim 32 , wherein R and R′ are the same or different and comprises a straight chain or a branched alkyl group having from 6 to 20 carbon atoms.

34. The process of claim 32 , wherein at least 90% by weight of the separated terephthalate ester is

35. The process of claim 32 , wherein about 10% or less by weight of the separated terephthalate ester is:

or a combination thereof.

36. The process of claim 26 , wherein the separated terephthalate ester comprises di-n-hexyl terephthalate, dioctyl terephthalate, diisononyl terephthalate, diisodecyl terephthalate, di-n-octyl n-decyl terephthalate, di-n-tridecyl n-pentadecyl terephthalate, or diisoeicosyl terephthalate.

37. The process of claim 26 , wherein the diol comprises at least one of ethylene glycol, 1,3-propanediol, or 1,4-butanediol.

38. A process for producing a diol comprising:

(a) providing reclaimed carpet material comprising a polyester component comprising a terephthalic unit; and

(b) reacting the polyester component with an alcohol having from 6 to 20 carbon atoms under conditions effective to produce a diol, wherein the reclaimed carpet material comprises one or more additional components that remain unreacted after the reaction of the polyester component with the alcohol;

(c) separating unreacted components from the diol; and

(d) combusting the separated unreacted components to form an ash component;

wherein substantially all of the produced diol is derived from the polyester component present in the reclaimed carpet material.

39. The process of claim 38 , wherein the polyester component comprises polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, or any combinations thereof.

40. The process of claim 38 , wherein the polyester component is present in at least one of a carpet face fiber, a backing material, or an adhesive composition.

41. The process of claim 38 , wherein the alcohol comprises a straight chain, branched, cyclic aliphatic group, an aromatic group, an alkaryl group or an aralkyl group.

42. The process of claim 38 , wherein the alcohol comprises hexanol, 2-ethyl-1-hexanol, isonanol, isodecanol, isoeicosanol, octanol, decanol, tricadenol, pentadecanol, or any combinations thereof.

43. The process of claim 38 , wherein the diol comprises at least one of ethylene glycol, 1,3-propanediol, or 1,4-butanediol.

44. The process of claim 1 , wherein about 15-40% of the mass of the terephthalate ester based on a ratio of molecular weights is derived from the polyester component present in the reclaimed carpet material.

45. The process of claim 26 , wherein about 15-40% of the mass of the terephthalate ester based on a ratio of molecular weights is derived from the polyester present in the reclaimed carpet material.

46. The process of claim 26 , wherein the step of combusting the separated unreacted components is at a temperature of at least about 800° C. for at least 0.5-3.0 hours.

47. The process of claim 38 , wherein the step of combusting the separated unreacted components is at a temperature of at least about 800° C. for at least 0.5-3.0 hours.