Bio-based terephthalic acid (bio-TPA), bio-based dimethyl terephthalate (bio-DMT), and bio-based polyesters, which are produced from a biomass containing a terpene or terpenoid, such as limonene are described, as well as the process of making these products. The bio-based polyesters include poly(alk
Bio-based terephthalic acid (bio-TPA), bio-based dimethyl terephthalate (bio-DMT), and bio-based polyesters, which are produced from a biomass containing a terpene or terpenoid, such as limonene are described, as well as the process of making these products. The bio-based polyesters include poly(alkylene terephthalate)s such as bio-based poly(ethylene terephthalate) (bio-PET), bio-based poly(trimethylene terephthalate) (bio-PTT), bio-based poly(butylene terephthalate) (bio-PBT), and bio-based poly(cyclohexylene dimethyl terephthalate) (bio-PCT).
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1. A process of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at le
1. A process of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at least 85% by oxidation in a two-step oxidation comprising: (i) a first step using a mineral acid, and(ii) a second step using a transition metal oxidant;the oxidation being performed substantially in the absence of chromium oxide;(d) converting the bio-based terephthalic acid with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof to provide bio-based dimethyl terephthalate;wherein the bio-based terephthalic acid has a mean bio-based content of at least 95%; andwherein the biomass is a biological material which excludes organic material that has been transformed by geological processes into a member selected from the group consisting of petroleum, petrochemicals, and combinations thereof; and(e) converting the bio-based dimethyl terephthalate of Formula II to a bio-based poly(alkylene terephthalate) of Formula III by reacting the bio-based dimethyl terephthalate with a diol of the formula: HO—R1—OHwherein R1 is selected from the group consisting of alkyl, cycloalkyl, cycloalkylene alkyl, and cycloalkylene dialkyl groups having from two to ten carbons,n is an integer between about 50 and about 130; andwherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 5%. 2. A process according to claim 1 wherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 33%. 3. A process according to claim 1 wherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 80%. 4. A process according to claim 1 wherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 90%. 5. A process according to claim 1 wherein the diol of the formula: HO—R1—OH is at least in part a bio-based diol, the diol having a mean bio-based content of at least 80%. 6. A process of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at least 85% by oxidation in a two-step oxidation comprising: (i) a first step using a mineral acid, and(ii) a second step using a transition metal oxidant;the oxidation being performed substantially in the absence of chromium oxide;(d) converting the bio-based terephthalic acid with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof to provide bio-based dimethyl terephthalate;wherein the bio-based terephthalic acid has a mean bio-based content of at least 95%; andwherein the biomass is a biological material which excludes organic material that has been transformed by geological processes into a member selected from the group consisting of petroleum, petrochemicals, and combinations thereof; and(e) converting the bio-based dimethyl terephthalate to bio-based poly(butylene terephthalate) of Formula IV: by reacting the bio-based dimethyl terephthalate with 1,4-butane diol, wherein n is an integer between about 50 and about 130; andwherein the bio-based poly(butylene terephthalate) has a mean bio-based content of at least 5%. 7. A process according to claim 6 wherein the bio-based poly(butylene terephthalate) has a mean bio-based content of at least 60%. 8. A process according to claim 6 wherein the bio-based poly(butylene terephthalate) has a mean bio-based content of at least 80%. 9. A process according to claim 6 wherein the bio-based poly(butylene terephthalate) has a mean bio-based content of at least 90%. 10. A process according to claim 6 wherein the 1,4-butane diol is selected from the group consisting of petroleum based 1,4-butane diol, bio-based 1,4-butane diol, and combinations thereof. 11. A process according to claim 6 wherein the 1,4-butane diol is at least in part bio-based 1,4-butane diol. 12. A process of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at least 85% by oxidation in a two-step oxidation comprising: (i) a first step using a mineral acid, and(ii) a second step using a transition metal oxidant;the oxidation being performed substantially in the absence of chromium oxide;(d) converting the bio-based terephthalic acid with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof to provide bio-based dimethyl terephthalate;wherein the bio-based terephthalic acid has a mean bio-based content of at least 95%; and wherein the biomass is a biological material which excludes organic material that has been transformed by geological processes into a member selected from the group consisting of petroleum, petrochemicals, and combinations thereof; and (e) converting the bio-based dimethyl terephthalate to bio-based poly(trimethylene terephthalate) of Formula V: by reacting the bio-based dimethyl terephthalate with 1,3-propane diol, wherein n is an integer between about 50 and 130, andwherein the bio-based poly(trimethylene terephthalate) has a mean bio-based content of at least 5%. 13. A process according to claim 12 wherein the bio-based poly(trimethylene terephthalate) has a mean bio-based content of at least 50%. 14. A process according to claim 12 wherein the bio-based poly(trimethylene terephthalate) has a mean bio-based content of at least 80%. 15. A process according to claim 12 wherein the bio-based poly(trimethylene terephthalate) has a mean bio-based content of at least 90%. 16. A process according to claim 12 wherein the 1,3-propane diol is selected from the group consisting of petroleum based 1,3-propane diol, bio-based 1,3-propane diol, and combinations thereof. 17. A process according to claim 12 wherein the 1,3-propane diol is at least in part bio-based 1,3-propane diol. 18. A process according to claim 12 wherein the 1,3-propane diol is at least in part bio-based 1,3-propane diol, the 1,3-propane diol having a mean bio-based content of at least 80%. 19. A process of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at least 85% by oxidation in a two-step oxidation comprising: (i) a first step using a mineral acid, and(ii) a second step using a transition metal oxidant;the oxidation being performed substantially in the absence of chromium oxide;(d) converting the bio-based terephthalic acid with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof to provide bio-based dimethyl terephthalate;wherein the bio-based terephthalic acid has a mean bio-based content of at least 95%; andwherein the biomass is a biological material which excludes organic material that has been transformed by geological processes into a member selected from the group consisting of petroleum, petrochemicals, and combinations thereof; and(e) converting the bio-based dimethyl terephthalate to bio-based poly(ethylene terephthalate) of Formula VI: by reacting the bio-based dimethyl terephthalate with ethylene glycol, wherein n is an integer between about 50 and 130; andwherein the bio-based poly(ethylene terephthalate) has a mean bio-based content of at least 5%. 20. A process according to claim 19 wherein the bio-based poly(ethylene terephthalate) has a mean bio-based content of at least 70%. 21. A process according to claim 19 wherein the bio-based poly(ethylene terephthalate) has a mean bio-based content of at least 80%. 22. A process according to claim 19 wherein the bio-based poly(ethylene terephthalate) has a mean bio-based content of at least 90%. 23. A process according to claim 19 wherein the ethylene glycol is selected from the group consisting of petroleum based ethylene glycol, bio-based ethylene glycol, and combinations thereof. 24. A process according to claim 19 wherein the ethylene glycol is at least in part bio-based ethylene glycol. 25. A process according to claim 19 wherein the ethylene glycol is at least in part bio-based ethylene glycol, the ethylene glycol having a mean bio-based content of at least 80%. 26. A of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at least 85% by oxidation in a two-step oxidation comprising: (i) a first step using a mineral acid, and(ii) a second step using a transition metal oxidant;the oxidation being performed substantially in the absence of chromium oxide;(d) converting the bio-based terephthalic acid with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof to provide bio-based dimethyl terephthalate;wherein the bio-based terephthalic acid has a mean bio-based content of at least 95%; andwherein the biomass is a biological material which excludes organic material that has been transformed by geological processes into a member selected from the group consisting of petroleum, petrochemicals, and combinations thereof; and(e) converting the bio-based dimethyl terephthalate to bio-based poly(cyclohexylene dimethylene terephthalate) of Formula VIII: by reacting the bio-based dimethyl terephthalate with 1,4-cyclohexane dimethanol, wherein n is an integer between about 50 and 130, andwherein the bio-based poly(1,4-cyclohexylene dimethylene terephthalate) has a mean bio-based content of at least 5%. 27. A process according to claim 26 wherein the bio-based poly(1,4-cyclohexylene dimethylene terephthalate) has a mean bio-based content of at least 50%. 28. A process according to claim 26 wherein the bio-based poly(1,4-cyclohexylene dimethylene terephthalate) has a mean bio-based content of at least 80%. 29. A process according to claim 26 wherein the bio-based poly(1,4-cyclohexylene dimethylene terephthalate) has a mean bio-based content of at least 90%. 30. A process according to claim 26 wherein the 1,4-cyclohexane dimethanol is selected from the group consisting of petroleum based 1,4-cyclohexane dimethanol, bio-based 1,4-cyclohexane dimethanol, and combinations thereof. 31. A process according to claim 26 wherein the 1,4-cyclohexane dimethanol is at least in part bio-based 1,4-cyclohexane dimethanol. 32. A process according to claim 26 wherein the 1,4-cyclohexane dimethanol is at least in part bio-based 1,4-cyclohexane dimethanol, the 1,4-cyclohexane having a mean bio-based content of at least 80%. 33. A process of making a polymer from a bio-based terephthalic acid composition, the process comprising: (a) providing a biomass comprising limonene;(b) converting the limonene to para-cymene at a yield of at least 95%; and(c) converting the para-cymene to terephthalic acid at a total yield of at least 85% by oxidation in a two-step oxidation comprising: (i) a first step using a mineral acid, and(ii) a second step using a transition metal oxidant;the oxidation being performed substantially in the absence of chromium oxide;(d) converting the bio-based terephthalic acid with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof to provide bio-based dimethyl terephthalate;wherein the bio-based terephthalic acid has a mean bio-based content of at least 95%; andwherein the biomass is a biological material which excludes organic material that has been transformed by geological processes into a member selected from the group consisting of petroleum, petrochemicals, and combinations thereof; and(d) converting the bio-based terephthalic acid to a poly(alkylene terephthalate) of Formula III: by reacting the bio-based terephthalic acid with a diol of the formula: HO—R1—OHwherein R1 is selected from the group consisting of alkyl, cycloalkyl, cycloalkylene alkyl, and cycloalkylene dialkyl groups having from two to ten carbons,n is an integer between about 50 and about 130; andwherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 40%. 34. A process according to claim 33 wherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 33%. 35. A process according to claim 33 wherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 80%. 36. A process according to claim 33 wherein the bio-based poly(alkylene terephthalate) has a mean bio-based content of at least 90%. 37. A process according to claim 33 wherein the diol of the formula: HO—R1—OH is at least partially bio-based, the diol having a mean bio-based content of at least 80%. 38. The process of claim 37 wherein the diol comprises a component of both bio-based diols and petrochemically-derived diols.
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