Granted Patent B2

US 12,516,006 · App. 17/755,638 · Granted Jan 6, 2026

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)

Assignee: ExxonMobil Product Solutions Company

C07C29/141C07C29/88C10G1/002C10G9/00C10G2400/20

Abstract

Claims (68)

1 . A method of making a recycle content propanol composition (“r-C3OH”), said method comprising

(a) subjecting a cracker feed stream to steam cracking, wherein said cracker feed stream comprises (i) at least 1 and not more than 40 weight percent of a recycle pyoil composition (r-pyoil), along with (ii) at least 60 weight percent of a non-recycle cracker feed chosen from propane, ethane, and/or natural gasoline, based on the total weight of said stream, to provide an olefin stream comprising r-ethylene; followed by

(b) hydroformylation to provide r-propanal (r-PA); followed by

(c) hydrogenation, to provide r-C3OH;

wherein said r-pyoil is prepared from recycled plastic waste comprising not more than 5 weight percent of polyethylene terephthalate.

2 . A method of making propanol, said method comprising:

a. a propanol manufacturer obtaining a propionaldehyde composition from a supplier and either:

i. from said supplier, also obtaining a pyrolysis recycle content allotment or

ii. from any person or entity, obtaining a pyrolysis recycle content allotment without a supply of a propionaldehyde composition from said person or entity transferring said pyrolysis recycle content allotment; and

b. said propanol manufacturer making a propanol composition (“C3OH”) from any propionaldehyde composition obtained from any source; and

c. either:

i. applying said pyrolysis recycle content allotment to C3OH made by the supply of propionaldehyde obtained in step (a); or

ii. applying said pyrolysis recycle content allotment to C3OH not made by the supply of propionaldehyde obtained in step (a), or

iii. depositing said pyrolysis recycle content allotment into a recycle inventory from which is deducted a recycle content value and applying at least a portion of said value to:

1. C3OH to thereby obtain r-C3OH, or

2. To a compound or composition other than C3OH, or

3. both;

whether or not the recycle content value is obtained from a pyrolysis recycle content allotment obtained in step a (i) or step a (ii).

3 . A method of making a recycle content propanol composition (“r-C3OH”), said method comprising:

a. reacting any propionaldehyde composition in a synthetic process to make a propanol composition (“C3OH”); and

b. applying a recycle content value to at least a portion of said C3OH to thereby obtain a recycle content propanol composition (“r-C3OH”); and

c. optionally, obtaining said recycle content value by deducting at least a portion of said recycle content value from a recycle inventory, further optionally said recycle inventory also containing a pyrolysis recycle content allotment or a pyrolysis recycle content allotment deposit having been made into the recycle inventory prior to the deduction; and

d. optionally communicating to a third party that said r-C3OH has recycle content or is obtained or derived from recycled waste.

4 . The method according to claim 3 , said method further comprising:

a. pyrolyzing a pyrolysis feed comprising a recycled waste material to thereby form a pyrolysis effluent comprising recycle pyoil (r-pyoil) and/or a recycle pygas (“r-pygas”);

b. optionally cracking a cracker feed comprising at least a portion of the r-pyoil to thereby produce a cracker effluent comprising r-olefins; or optionally cracking a cracker feed without r-pyoil to make olefins and applying a recycle content value to the olefins so made by deducting a recycle content value from a recycle inventory and applying it to the olefins to make r-olefins; and

c. reacting any olefin volume in a synthetic process to make a propionaldehyde composition; and

d. reacting at least a portion of any propionaldehyde composition in a synthetic process to make a propanol composition; and

e. applying a recycle content value to at least a portion of said propanol composition based on:

i. feeding a pyrolysis recycle content propionaldehyde composition (“pr-PA”) as a feedstock or

ii. depositing at least a portion of an allotment obtained from any one or more of steps a) or b) into a recycle inventory and deducting from said inventory a recycle content value and applying at least a portion of said value to C30H to thereby obtain said r-C30H.

5 . A recycle content propanol composition (“r-C3OH”) obtained by the method according to claim 3 .

6 . The method according to claim 3 , wherein said recycle content value is derived directly or indirectly from cracking r-pyoil or obtained from r-pygas.

7 . The method according to claim 3 , wherein said recycle content value is derived directly or indirectly from cracking r-pyoil in a gas fed cracker furnace.

8 . The method according to claim 3 , wherein the propionaldehyde composition is fed to a reaction vessel and said cellulose reactant composition does not contain recycle content.

9 . The method according to claim 3 , wherein the propanol is made by a propanol manufacturer and the recycle content is apportioned among products made by a propanol manufacturer or the products made by any one entity or a combinations of entities among the Family of Entities of which the propanol manufacturer is a part, and wherein the method of apportioning is an asymmetric distribution of recycle content values among their product(s), and optionally at least one of the products is propanol.

10 . The method according to claim 3 , wherein the propanol is made by a propanol manufacturer and the recycle content is apportioned among products made by a C3OH manufacturer or the products made by any one entity or a combinations of entities among the Family of Entities of which the C30H manufacturer is a part, and wherein the method of apportioning is applied symmetrically or asymmetrically across a combination of C3OH and other products made at the second Site.

11 . The method according to claim 3 , wherein the PA is supplied by an PA supplier that transfers a recycle content allotment to the C30H manufacturer and a supply of PA to the C3OH manufacturer.

12 . The method according to claim 3 , wherein the recycle content allotment is not associated with the PA supplied.

13 . The method according to claim 3 , wherein the PA is supplied by an PA supplier that transfers a recycle content allotment to the C30H manufacturer and a supply of PA to the C3OH manufacturer, and the recycle content allotment is associated with PA made by the supplier.

14 . The method according to claim 3 , wherein the PA supplied is r-PA and at least a portion of the recycle content allotment being transferred is the recycle content in the r-PA supplied.

15 . The method according to claim 3 , wherein the recycle content value applied to C3OH is drawn from a recycle inventory that is derived directly or indirectly from the pyrolysis of recycled waste.

16 . The method according to claim 3 , wherein a C3OH manufacturer or a person or entity among its Family of Entities obtains a supply of PA and an allotment, and at least a portion of the allotment is either:

a. applied to C3OH made from the PA supplied;

b. applied to C3OH not made by the supply of PA; or

c. deposited into a recycle inventory from which is deducted a recycle content value and applying at least a portion of the recycle content value to:

i. C3OH to thereby obtain r-C3OH, or

ii. to a compound or composition other than C3OH, or

iii. both; or

d. deposited into a recycle inventory and stored.

17 . The method according to claim 3 , wherein:

a. an olefin supplier either:

i. cracks a cracker feedstock comprising recycle pyoil to make an olefin composition at least a portion of which is obtained by cracking said recycle pyoil (r-olefin), or

ii. makes a pygas at least a portion of which is obtained by pyrolyzing a recycled waste stream (r-pygas), or

iii. both; and

b. a propanol manufacturer:

i. obtaining an allotment derived directly or indirectly with said r-olefin or said r-pygas from the supplier or a third-party transferring said allotment,

ii. making propanol from propionaldehyde, and

iii. associating at least a portion of the allotment with at least a portion of the propanol, whether or not the propionaldehyde used to make the propanol contains r-propionaldehyde.

18 . The method according to claim 3 , comprising:

a. making a r-olefin by either cracking the r-pyoil or separating an olefin from the r-pygas; and

b. converting at least a portion of the r-olefin in a synthetic process to make propionaldehyde, and

c. converting at least a portion of any or said propionaldehyde to propanol; and

d. applying a recycle content value to said propanol to make a r-C3OH; and

e. optionally, also making a r-pyoil or r-pygas or both by pyrolyzing a recycle feedstock.

19 . The method according to claim 3 , comprising:

a. propanol (“C3OH”), and

b. an identifier associated with said propanol, said identifier being a representation that said propanol has recycle content or is made from a source having recycle content.

Assignments (2)

Continuity (2)

References Cited (400)