# US 2010/0168461 A1 · Bio-Based Terephthalate Polyesters

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- Number: US 2010/0168461 A1
- Document ID: US20100168461A1
- Status: Published application
- Kind: A1
- Application number: 12/347,221
- Filed: 2008-12-31
- Published: 2010-07-01
- Earliest claimed: 2008-12-31
- Inventors: Corrado Berti; Enrico Binassi; Martino Colonna; Maurizio Fiorini; Ganesh Kannan; Sreepadaraj Karanam; Marzia Mazzacurati; Ihab Odeh
- Web page: https://patentgrep.com/patent/US20100168461A1

## CPC

- C07C 51/09: from carboxylic acid esters or lactones
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 69/82: Terephthalic acid esters
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

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).

## Claims

### Claim 1

A compound comprising bio-based terephthalic acid of Formula I:
wherein the bio-based terephthalic acid has a mean bio-based content of at least 5%.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein the bio-based terephthalic acid has a mean bio-based content of at least 80%.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein the bio-based terephthalic acid has a mean bio-based content of at least 90%.

### Claim 4

A compound comprising bio-based terephthalic acid of Formula I:
wherein the bio-based terephthalic acid has a mean bio-based content of at least 5%; and
wherein the bio-based terephthalic acid of Formula I is prepared by a process comprising:
(a) providing a biomass;
(b) converting the biomass to terephthalic acid, the biomass being converted to terephthalic acid substantially in the absence of chromium oxide,
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.

### Claim 5

A compound comprising bio-based dimethyl terephthalate of Formula II:
wherein the bio-based dimethyl terephthalate has a mean bio-based content of at least 5%.

### Claim 6 (depends on 5)

A compound according to claim 5 wherein the bio-based dimethyl terephthalate has a mean bio-based content at least 80%.

### Claim 7 (depends on 5)

A compound according to claim 5 wherein the bio-based dimethyl terephthalate has a mean bio-based content of at least 90%.

### Claim 8 (depends on 5)

A compound according to claim 5 wherein the compound of Formula II is made by a process comprising converting bio-based terephthalic acid to bio-based dimethyl terephthalate by esterification of the bio-based terephthalic acid.

### Claim 9

A compound comprising bio-based dimethyl terephthalate of Formula II:
wherein the bio-based dimethyl terephthalate has a mean bio-based content of at least 5%; and
wherein the bio-based dimethyl terephthalate of Formula II is prepared by a process comprising:
(a) providing a biomass;
(b) converting the biomass to bio-based terephthalic acid of Formula I:
the biomass being converted to the terephthalic acid of Formula I substantially in the absence of chromium oxide; and
(c) converting the bio-based terephthalic acid to the bio-based dimethyl terephthalate of Formula II,
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.

### Claim 10 (depends on 9)

A compound according to claim 9 wherein in process step (c), the bio-based terephthalic acid is converted to bio-based dimethyl terephthalate of Formula II with methanol selected from the group consisting of bio-based methanol, petroleum based methanol, and combinations thereof.

### Claim 11 (depends on 9)

A compound according to claim 9 wherein in process step (c), the bio-based terephthalic acid is converted to bio-based dimethyl terephthalate of Formula II with bio-based methanol, the bio-based methanol having a mean bio-based content of at least 90%.

### Claim 12 (depends on 9)

A compound according to claim 9 wherein in process step (c) the biomass is converted to the terephthalic acid of Formula I substantially in the absence of chromium.