Recycle content cyclobutane diol polyester

Patent metadata

Field	Value
Publication number	US-12534590-B2
Application number	US-202017597726-A
Country	US
Kind code	B2
Filing date	Jul 29, 2020
Priority date	Jul 29, 2019
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

Described is a process for preparing a recycle content polyester, the process comprising obtaining a recycled propylene composition derived from cracking a recycle content pyrolysis oil composition made from a waste plastic-containing stream, using the recycled propylene as a feedstock in a reaction scheme to produce a polyester reactant, and reacting the polyester reactant to prepare at least one polyester.

First claim

What we claim is:

1 . A process for preparing a recycle polyester (r-polyester) comprising: (1) obtaining a recycled propylene composition (r-propylene) derived directly or indirectly from cracking a recycle content pyrolysis oil composition (r-pyoil); (2) using the r-propylene as a feedstock in a reaction scheme to produce at least one polyester reactant for preparing a polyester; and (3) reacting said at least one polyester reactant to prepare at least one polyester; wherein the r-pyoil is made from a waste plastic-containing stream that comprises at least 30 wt % waste plastic; and wherein the at least one polyester reactant is TMCD and the at least one polyester is chosen from TMCD modified PCT, TMCD modified PET, or combinations thereof.

2 . The process according to claim 1 , wherein the reaction scheme to produce at least one polyester reactant comprises one or more of the following reactions: (1) converting said r-propylene to a recycle isobutyraldehyde composition (r-isobutyraldehyde); (2) converting said r-propylene to a first recycle content isobutyric acid (r-isobutyric acid); (3) converting said r-isobutyraldehyde to a second recycle content isobutyric acid (r-isobutyric acid); (4) converting said first and/or second r-isobutyric acid to a recycle content isobutyric anhydride (r-isobutyric anhydride); and (5) converting said r-isobutyric anhydride in a reaction scheme to a recycle content TMCD (r-TMCD).

3 . The process according to claim 2 , wherein the reaction scheme to produce at least one polyester reactant comprises: all of reactions (1) through (5).

4 . An article comprising the polyester composition made according to claim 3 .

5 . A method of obtaining a recycle content in polyester comprising:
a. obtaining a TMCD composition designated as having recycle content, and b. feeding the TMCD and one or more dicarboxylic acids (or derivative thereof) and (optionally) one or more other diols to a reactor under conditions effective to make polyester, and wherein, whether or not the designation so indicates, at least a portion of said TMCD composition is derived directly or indirectly from cracking a recycle pyoil composition (r-pyoil); wherein the r-pyoil is made from a waste plastic-containing stream that comprises at least 30 wt % waste plastic.

6 . The process according to claim 1 , wherein the process is an integrated process for making a polyester composition comprising:
a. providing a TMCD manufacturing facility and making a recycle content TMCD composition (r-TMCD) from a feed composition at least a portion of which is obtained by a reaction scheme starting from the r-propylene, and b. providing a polyester manufacturing facility comprising a reactor containing one or more dicarboxylic acids (or derivative thereof) and (optionally) one or more other diols that accepts TMCD; and c. feeding the r-TMCD from the TMCD manufacturing facility to the polyester manufacturing facility through a system that is in fluid communication between said facilities.

7 . The method of claim 5 , wherein the method comprises introducing or establishing a recycle content in polyester by:
a. obtaining a recycle propylene composition (r-propylene) allocation or credit, b. converting propylene in a synthetic process to make isobutyric acid and/or to isobutyraldehyde and then convert the isobutyraldehyde to isobutyric acid, c. optionally converting isobutyric acid in a synthetic process to make isobutyric anhydride, d. converting isobutyric anhydride and/or isobutyric acid in a synthetic process to make dimethyl ketene, e. converting dimethyl ketene in a synthetic process scheme to make TMCD, f. converting TMCD in a synthetic process to make polyester, g. designating at least a portion of the polyester as corresponding to at least a portion of the r-propylene allocation or credit, and optionally h. offering to sell or selling the polyester as containing or obtained with recycle content corresponding with such designation.

8 . The process according to claim 1 , wherein step (1) comprises:
a. making a recycle pyoil composition by pyrolyzing a recycle feedstock (r-pyoil); and b. cracking the r-pyoil to make a first recycle propylene composition at least a portion of which is obtained from cracking the r-pyoil (r-propylene); and wherein step (2) comprises: a. converting at least a portion of said r-propylene in a synthetic process to make isobutyric acid and/or to make isobutyraldehyde and convert said isobutyraldehyde to make isobutyric acid, and b. optionally converting at least a portion of said isobutyric acid in a synthetic process to make isobutyric anhydride, c. converting at least a portion of the isobutyric anhydride and/or isobutyric acid in a synthetic process to make dimethyl ketene, d. converting dimethyl ketene in a synthetic process scheme to make TMCD, and wherein step (3) comprises: a. reacting the TMCD in a synthetic process with a dicarboxylic acid (or a derivative thereof) to make polyester.

9 . A polyester composition obtained by the method according to claim 1 .

10 . The process according to claim 1 , wherein the r-propylene is directly or indirectly derived from cracking r-pyoil in a gas furnace.

11 . The process according to claim 1 , wherein the r-propylene is directly or indirectly derived from cracking r-pyoil in a split furnace.

12 . The process according to claim 1 , wherein the r-propylene is directly or indirectly derived from cracking r-pyoil in a thermal steam gas furnace.

13 . The process according to claim 1 , wherein the r-pyoil comprises not more than 30 weight percent of aromatics, based on the total weight of the r-pyoil.

14 . The process according to claim 1 , wherein the r-pyoil comprises olefins present in an amount ranging from 40-85, as wt. % based on the weight of the r-pyoil.

15 . The process according to claim 1 , wherein the weight ratio of paraffin and naphthene combined to aromatics in the r-pyoil is in a range of from 1:1-7:1.

16 . The process according to claim 1 , wherein the cracking is performed by feeding a cracker feed stream or composition to a cracker furnace, wherein the cracker feed stream or composition comprises the r-pyoil and the 90% boiling point of the cracker feed stream or composition fed to the cracker furnace is not more than 350° C.

17 . The process according to claim 1 , comprising feeding a cracker feed stream comprising r-pyoil to a furnace, said cracker feed stream comprising a majority of a C 2 to C 4 hydrocarbon containing composition.

18 . The process according to claim 1 , comprising feeding a cracker feed stream comprising r-pyoil to a furnace, wherein the furnace comprises a gas coil that receives a feedstock that comprises a majority of C 2 -C 4 hydrocarbons.

19 . The process according to claim 10 , wherein the gas furnace has more than one gas coil.

Assignees

• Eastman Chem Co

Inventors

• Slivensky David Eugene
• Parker Kenny Randolph
• Trapp William Lewis
• Bitting Daryl
• Polasek Michael Gary
• Wu Xianchun

Classifications

• C08J2323/12

  Polypropene · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08G63/199 Primary

  Acids or hydroxy compounds containing cycloaliphatic rings · CPC title

• C08G63/183 Primary

  Terephthalic acids · CPC title

• C08J11/12 Primary

  by dry-heat treatment only · CPC title