Granted Patent B2

US 12,338,211 · App. 17/597,822 · Granted Jun 24, 2025

Inventors: David Eugene Slivensky (Tatum, TX); Kenny Randolph Parker (Afton, TN); William Lewis Trapp (Kingsport, TN); Daryl Bitting (Longview, TX); Michael Gary Polasek (Longview, TX); Xianchun Wu (Longview, TX)

Assignee: Eastman Chemical Company

C07C45/505

Abstract

Claims (43)

1. A method of making recycle (C 4 )alkanal (r-(C 4 )alkanal), said method comprising hydroformylating a recycle propylene composition (r-propylene) to thereby produce a hydroformylation effluent comprising (C 4 )alkanal, wherein said r-propylene is derived directly or indirectly from cracking a cracker feed stream comprising (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; wherein said r-pyoil has a C 8 + content of at least 35 weight percent, based on the total weight of said r-pyoil; and wherein said r-pyoil comprises not more than about 30 weight percent total aromatics, based on the total weight of said r-pyoil.

2. A method of obtaining a recycle content in (C 4 )alkanal comprising:

a. obtaining a propylene composition designated as having recycle content, and

b. feeding said propylene to a reactor under conditions effective to make (C 4 )alkanal, and

wherein, whether or not the designation so indicates, at least a portion of said propylene composition is derived directly or indirectly from cracking a cracker feed stream comprising (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; wherein said r-pyoil has a C 8 + content of at least 35 weight percent, based on the total weight of said r-pyoil; and wherein said r-pyoil comprises not more than about 30 weight percent total aromatics, based on the total weight of said r-pyoil.

3. An integrated process for making an (C 4 )alkanal comprising:

a. providing a propylene manufacturing facility and making a propylene composition (r-propylene) at least a portion of which is obtained from cracking recycle pyoil (r-pyoil), and

b. providing an (C 4 )alkanal manufacturing facility comprising a reactor that accepts propylene; and

c. feeding the r-propylene from the propylene manufacturing facility to the (C 4 )alkanal manufacturing facility through a system that is in fluid communication between said facilities; wherein said r-pyoil has a C 8 + content of at least 35 weight percent, based on the total weight of said r-pyoil; and

wherein said r-pyoil comprises not more than about 30 weight percent total aromatics, based on the total weight of said r-pyoil.

4. The process of claim 3 , wherein the r-propylene is directly or indirectly derived from cracking r-pyoil in a split furnace or a thermal steam gas furnace.

5. The method of claim 1 , wherein a cracker facility in which the r-propylene made is in fluid communication, continuously or intermittently, with an (C 4 )alkanal formation facility.

6. The method of claim 4 , wherein the manufacturer of (C 4 )alkanal certifies, represents to its customers or the public, or advertises that its (C 4 )alkanal contains recycle content or is obtained from feedstock containing or obtained from recycle content, where such recycle content claim is based in whole or in part on a propylene feedstock associated with an allotment from propylene made from cracking r-pyoil.

7. The method of claim 6 , wherein the manufacturer of the (C 4 )alkanal has acquired:

a. a propylene volume made from r-pyoil under a certification, representation, or as advertised, or

b. has transferred credits with the supply of propylene to the manufacturer of the (C 4 )alkanal sufficient to allow the manufacturer of the (C 4 )alkanal to satisfy the certification requirements or to make its representations or advertisements, or

c. the propylene has allocated to it a recycle content where such allocation was obtained, through one or more intermediary entities, from a cracked propylene volume at least part of which is obtained by cracking r-pyoil.

8. The method of claim 7 , wherein the r-pyoil is obtained from waste material comprising plastics, rubber, textiles, wood, biowaste, modified celluloses, wet laid products, industrial sludge, oils, recovered lube oil, or vegetable oil or animal oil, or waste streams from industrial plants, or a combination of any of the foregoing.

9. The method of claim 8 , wherein the r-pyoil is a liquid at 25° C. and 1 atm., and predominantly comprises C 5 to C 25 hydrocarbons.

10. The method of claim 9 , wherein the r-pyoil comprises:

(1) C 4 -C 12 aliphatic compounds and C 13 -C 22 aliphatic compounds in a weight ratio of more than 1:1, each by weight and based on the weight of the r-pyoil;

(2) C 13 -C 22 aliphatic compounds (branched or unbranched alkanes and alkenes including diolefins, and alicyclics) and C 4 -C 12 aliphatic compounds in a weight ratio of more than 1:1, each by weight and based on the weight of the r-pyoil;

(3) paraffins in an amount of 5 to 25, or 5 to 20 wt. % based on the weight of the r-pyoil;

(4) naphthenes or cyclic aliphatic hydrocarbons in amount of 0-35, in each case as wt. % based on the weight of the r-pyoil composition;

(5) not more than 30 weight percent of aromatics, based on the total weight of the r-pyoil;

(6) olefins present in an amount ranging from 40-85, in each case as wt. % based on the weight of the r-pyoil; or

(7) oxygenated compounds or polymers in amount ranging from 0-20, in each case as wt. % based on the weight of the r-pyoil; wherein said r-pyoil has a C 8 + content of at least 35 weight percent, based on the total weight of said r-pyoil; and

wherein said r-pyoil comprises not more than about 30 weight percent total aromatics, based on the total weight of said r-pyoil.

11. The method of claim 10 , wherein the two aliphatic hydrocarbons having the highest concentration in the r-pyoil are in a range of C 5 -C 16 , or C 5 -C 14 , or C 5 -C 10 , or C 5 -C 8 , inclusive.

12. The method of claim 11 , wherein:

1. the amount of oxygen atoms in the r-pyoil is from 0-8, in each case as wt. % based on the weight of the r-pyoil;

2. the amount of heteroatoms in the r-pyoil is not more than 5, in each case wt. %, based on the weight of the r-pyoil; or

3. the sulfur content of the r-pyoil does not exceed 2.5 wt, in each case wt. % based on the weight of the r-pyoil.

13. The method of claim 12 , wherein the solubility of water in the r-pyoil at 1 atm and 25° C. is less than 2 wt. %, water, in each case wt. % water based on the weight of the r-pyoil.

14. The method of claim 13 , wherein the r-pyoil can have the following compositional content:

(i) carbon atom content of at least 75 wt, in each case wt. % and/or

(ii) hydrogen atom content of at least 10 wt, in each case wt. %, or

(iii) an oxygen atom content not to exceed 10, in each case wt. %,

in each case based on the weight of the r-pyoil.

15. The method of claim 14 , wherein the weight ratio of paraffin to naphthene can be at least 1:1, based on the weight of the r-pyoil.

16. The method of claim 15 , wherein the r-pyoil the 90% boiling point of the cracker feed stream or composition to a cracker furnace is not more than 350° C.

17. The method of claim 16 , comprising 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 method of claim 17 , wherein the r-pyoil is fed to at least one coil in a furnace which receives at the inlet of the coil at the entrance to a convection zone in the furnace, a predominately vapor-phase feed (more than 50% of the weight of the feed is vapor) (“gas coil”).

Assignments (2)

Continuity (2)

References Cited (400)