IP Library › Granted Patent US 12,497,467
Granted Patent B2
US 12,497,467 · App. 17/595,565 · Granted Dec 16, 2025

Recycle content cellulose ester

Inventors: David Eugene Slivensky (Tatum, TX); Daryl Bitting (Longview, TX); Kenny Randolph Parker (Afton, TN); Michael Gary Polasek (Longview, TX); William Lewis Trapp (Kingsport, TN); Xianchun Wu (Longview, TX); Wenlai Feng (Johnson City, TN); Thomas Joseph Pecorini (Kingsport, TN); Michael Eugene Donelson (Kingsport, TN); Haining An (San Jose, CA)
Assignee: Exxon Mobil Product Solutions Company
C08B16/00C07C4/04C08B3/08
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Quick Facts
Patent No.
US 12,497,467
App. No.
17/595,565
Granted
Dec 16, 2025
Kind
B2
Abstract

A process for preparing a recycle content cellulose ester and a recycle content cellulose ester composition comprising at least one cellulose ester having at least one substituent on an anhydroglucose unit (AU) derived from a recycle ethylene composition are provided.

Claims (39)

1 . A process for preparing a recycle cellulose ester (cellulose ester) comprising: (1) obtaining a recycled ethylene composition (r-ethylene) derived directly or indirectly from cracking a recycle content pyrolysis oil composition (r-pyoil), wherein the pyrolysis oil composition is not subjected to hydrogenation; (2) using the r-ethylene as a feedstock in a reaction scheme to produce at least one cellulose reactant for preparing a cellulose ester; and (3) reacting said at least one cellulose reactant to prepare at least one cellulose ester; 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 30 wt % waste plastic comprises not more than 5 wt % of polyvinyl chloride.

2 . The process according to claim 1 , wherein at least one cellulose reactant is chosen from propionic acid, propionic anhydride, and combinations thereof; and wherein at least one cellulose ester is chosen from cellulose propionate (CP), cellulose tri-propionate (CTP), cellulose acetate propionate (CAP), cellulose propionate butyrate (CPB), or combinations thereof.

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

4 . The process according to claim 3 , wherein the reaction scheme to produce at least one cellulose reactant comprises: all of reactions (1) through (4); or reactions (1), (3) and (4); or reactions (2) and (4).

5 . The process according to claim 1 , wherein the process is an integrated process for making a cellulose ester composition and at least one cellulose reactant is propionic anhydride, said integrated process comprising:

a. providing a propionic anhydride manufacturing facility and making a recycle content propionic anhydride composition (r-propionic anhydride) from a feed composition at least a portion of which is obtained by a reaction scheme starting from the r-ethylene, and

b. providing a cellulose ester manufacturing facility comprising a reactor for making cellulose ester that accepts propionic anhydride; and

c. feeding the r-propionic anhydride from the propionic anhydride manufacturing facility to the cellulose ester manufacturing facility through a system that is in fluid communication between said facilities.

6 . A method of obtaining a recycle content in cellulose ester comprising:

a. obtaining a propionic acid composition and/or a propionic anhydride composition designated as having recycle content, and

b. feeding said propionic acid and/or propionic anhydride to a reactor under conditions effective to make cellulose ester, and

wherein, whether or not the designation so indicates, at least a portion of said propionic acid and/or propionic anhydride 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 wherein the method further comprises introducing or establishing a recycle content in cellulose ester by:

c. obtaining a recycle ethylene composition (r-ethylene) allocation or credit,

d. converting ethylene in a synthetic process to make propionic acid and/or to propionaldehyde and then convert the propionaldehyde to propionic acid,

e. converting propionic acid in a synthetic process to make propionic anhydride,

f. reacting propionic anhydride and/or propionic acid in a synthetic process to make cellulose ester,

g. designating at least a portion of the cellulose ester as corresponding to at least a portion of the r-ethylene allocation or credit, and optionally

h. offering to sell or selling the cellulose ester as containing or obtained with recycle content corresponding with such designation.

7 . The process according to claim 1 , wherein step (1) comprises:

a. making a recycle pyoil composition by pyrolyzing a waste plastic-containing stream that comprises at least 30 wt % waste plastic (r-pyoil); and

b. cracking the r-pyoil to make a first recycle ethylene composition at least a portion of which is obtained from cracking the r-pyoil (r-ethylene); and

wherein step (2) comprises:

a. converting at least a portion of said r-ethylene in a synthetic process to make propionic acid and/or to make propionaldehyde and convert said propionaldehyde to make propionic acid, and

b. converting at least a portion of said propionic acid in a synthetic process to make propionic anhydride, and

wherein step (3) comprises:

reacting at least a portion of said propionic acid and/or said propionic anhydride in a synthetic process to make said cellulose ester.

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

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

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

11 . The process according to claim 1 , wherein the r-pyoil is a liquid at 25° C. and 1 atm, and predominantly comprises C 5 to C 25 hydrocarbons.

12 . The process according to claim 1 , wherein the r-pyoil comprises C 4 -C 12 aliphatic compounds and C 13 -C 22 aliphatic compounds in a weight ratio of at least 1.25:1, based on the weight of the r-pyoil.

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 cracker feed stream or composition to a cracker furnace comprises r-pyoil and the 90% boiling point of the cracker feed stream or composition to the cracker furnace is not more than 350° C.

17 . The process according to claim 1 , wherein the r-pyoil subjected to cracking is present in an amount of not more than 40 weight percent based on the total weight of a combined stream with a non-recycle cracker feed stream; or

wherein said cracking comprises feeding a cracker feed stream to a furnace comprising r-pyoil, said cracker feed stream comprising a predominantly C 2 to C 4 hydrocarbon containing composition.

18 . The process according to claim 1 , wherein the r-pyoil is cracked in a split furnace, and

wherein the cracking comprises feeding a cracker wherein a liquid coil receives a predominately C 6 -C 22 feedstock, or a predominately a C 7 -C 16 feedstock to the inlet of the coil in the convection section, or alternatively, having at least one coil receiving more than 50 wt. % naphtha, and/or more than 50% natural gasoline, and/or more than 50% diesel, and/or more than JP-4, and/or more than 50% Stoddard Solvent, and/or more than 50% kerosene, and/or more than 50% fresh creosote, and/or more than 50% JP-8 or Jet-A, and/or more than 50% heating oil, and/or more than 50% heavy fuel oil, and/or more than 50% bunker C, and/or more than 50% lubricating oil, based on the weight of the cracker feed to the liquid coil, or alternatively based on the weight of the cracker feed to the convection zone.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2025
From: EASTMAN CHEMICAL COMPANY
To: EXXONMOBIL PRODUCT SOLUTIONS COMPANY
Reel/Frame 073142/0954 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2022
From: SLIVENSKY, DAVID EUGENE; BITTING, DARYL; PARKER, KENNY RANDOLPH; POLASEK, MICHAEL GARY; TRAPP, WILLIAM LEWIS; WU, XIANCHUN; FENG, WENLAI; PECORINI, THOMAS JOSEPH; DONELSON, MICHAEL EUGENE; AN, HAINING
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 058735/0948 →
Continuity (2)
Provisional Application 62852394 · May 24, 2019
Related Publication 20220227892A1 · Jul 21, 2022
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