Granted Patent B2

US 12,577,188 · App. 17/755,637 · Granted Mar 17, 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

C07C45/505C07C29/141C07C45/51

Abstract

Claims (84)

1 . A method of making a recycle content 2,2 substituted 1,3-propane diol composition (“r-OG”), said method comprising hydroformylating a recycle content olefin composition at least a portion of which is derived directly or indirectly from pyrolyzing a recycled waste with syngas to form a recycle content aldehyde (r-AD) and then reacting at least a portion of the r-AD in the presence of a catalyst to produce a glycol effluent comprising (“r-OG”) m , the method 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. cracking a cracker feed comprising at least a portion of the r-pyoil to thereby produce a cracker effluent comprising r-olefins;

c. reacting the r-olefin volume in a synthetic process to make the recycle content aldehyde (r-AD);

d. reacting at least a portion of the recycle content aldehyde (r-AD) in a synthetic process to make the recycle content 2,2 substituted 1,3-propane diol composition; and

e. applying a recycle content value to at least a portion of said 2,2 substituted 1,3-propane dio composition based on feeding a pyrolysis recycle content oilefin (“pr-olefin”) or recycle aldehyde composition (“pr-AD”) as a feedstock.

2 . The method according to claim 1 , wherein the glycol effluent is produced by hydrogenating at least a portion of the r-AD to produce a glycol effluent comprising (“r-OG”).

3 . A method of making oxo glycol, said method comprising:

a. an oxo glycol manufacturer obtaining an olefin or an aldehyde 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 an olefin or aldehyde composition from said person or entity transferring said pyrolysis recycle content allotment; and

b. said oxo glycol manufacturer making an oxo glycol composition (“OG”) from any olefin or aldehyde composition obtained from any source; and

c. either:

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

ii. applying said pyrolysis recycle content allotment to OG not made by the supply of olefin or aldehyde 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. OG to thereby obtain r-OG, or

2. to a compound or composition other than OG, or

3. both, wherein the pyrolysis recycle content allotment is a pyrolysis recycle content value that is an allocation or a credit;

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

4 . A method of making a recycle content oxo glycol composition (“r-OG”), said method comprising:

a. reacting any olefin or aldehyde composition in a synthetic process to make an oxo glycol composition (“OG”); and

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

c. 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, wherein the pyrolysis recycle content allotment is a pyrolysis recycle content value that is an allocation or a credit; and

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

5 . The method according to claim 4 , 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 an aldehyde composition; and

d. reacting at least a portion of any aldehyde composition in a synthetic process to make an oxo glycol composition; and

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

i. feeding a pyrolysis recycle content olefin (“pr-olefin”) or recycle aldehyde composition (“pr-AD”) 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 OG to thereby obtain said r-OG.

6 . A recycle content oxo glycol composition (“r-OG”) obtained by the method according to claim 4 .

7 . The method according to claim 4 , wherein said recycle content value is derived directly or indirectly from cracking r-pyoil or obtained from r-pygas.

8 . The method according to claim 4 , wherein said recycle content value is derived directly or indirectly from cracking r-pyoil in a gas fed cracker furnace.

9 . The method according to claim 4 , wherein the olefin or aldehyde composition is fed to a reaction vessel and said olefin or aldehyde composition does not contain recycle content.

10 . The method according to claim 4 , wherein the oxo glycol is made by an oxo glycol manufacturer and the recycle content is apportioned among products made by a oxo glycol manufacturer or the products made by any one entity or a combinations of entities among the Family of Entities of which the oxo glycol manufacturer is a part, and wherein the method for apportioning is an asymmetric distribution of recycle content values among their product(s), and optionally at least one of the products is oxo glycol.

11 . The method according to claim 4 , wherein the oxo glycol is made by an oxo glycol manufacturer and the recycle content is apportioned among products made by a OG manufacturer or the products made by any one entity or a combinations of entities among the Family of Entities of which the OG manufacturer is a part, and wherein the method for apportioning is applied symmetrically or asymmetrically across a combination of OG and other products.

12 . The method according to claim 4 , wherein the AD is supplied by an AD supplier that transfers a recycle content allotment to the OG manufacturer and a supply of AD to the OG manufacturer.

13 . The method according to claim 4 , wherein the recycle content allotment is not associated with the AD supplied.

14 . The method according to claim 4 , wherein the AD is supplied by an AD supplier that transfers a recycle content allotment to the OG manufacturer and a supply of AD to the OG manufacturer, and the recycle content allotment is associated with AD made by the supplier.

15 . The method according to claim 4 , wherein the AD supplied is r-AD and at least a portion of the recycle content allotment being transferred is the recycle content in the r-AD supplied.

16 . The method according to claim 4 , wherein the recycle content value applied to OG is drawn from a recycle inventory that is derived directly or indirectly from the pyrolysis of recycled waste.

17 . The method according to claim 4 , 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. an oxo glycol manufacturer:

i. obtains 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. makes oxo glycol from olefin or aldehyde, and

iii. associates at least a portion of the allotment with at least a portion of the oxo glycol, whether or not the olefin or aldehyde used to make the oxo glycol contains r-olefin or r-aldehyde.

18 . The method according to claim 4 , comprising:

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

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

c. converting at least a portion of any or said olefin or aldehyde to oxo glycol; and

d. applying a recycle content value to said oxo glycol to make a r-OG; and

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

19 . The method according to claim 4 , comprising:

a. oxo glycol (“OG”), and

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

20 . The method of claim 1 , wherein a minimum amount of r-AD reacted with the catalyst to produce r-OG is calculated as:

P

=

(

%

⁢

D

100

)

×

(

Pm

Rm

)

×

(

100

Y

)

×

100

where P is the minimum amount of r-AD, % D is a percentage of recycle content declared in r-OG, P m is a molecular weight of r-OG, R m is a molecular weight of reactant olefin or aldehyde as a moiety in r-OG, Y is a percent yield of the r-OG determined as an average annual yield.

Assignments (2)

Continuity (2)

References Cited (180)