Methods for preparing materials from polyaromatic heavy feedstocks

Patent metadata

Field	Value
Publication number	US-11059941-B2
Application number	US-201916362984-A
Country	US
Kind code	B2
Filing date	Mar 25, 2019
Priority date	Apr 12, 2018
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

The present disclosure relates to methods for preparing materials from heavy feedstocks. In particular, the disclosure provides a chemical process to convert heavy feedstocks with predominant polyaromatic hydrocarbon molecules or species, including the residues of petrochemical refining or extraction, into thermoset or thermoplastic materials that can be used alone or as a component in a composite material.

First claim

The invention claimed is:

1. A method of making a thermoset material from a heavy feedstock comprising polyaromatic hydrocarbon molecules, the method comprising:
contacting a linker agent and a catalyst with the heavy feedstock, a weight of the linker agent comprising 60% w/w or more of a total weight of the heavy feedstock;
reacting the linker agent with molecules in the heavy feedstock under mixing to form a reaction mixture; and
curing the reaction mixture to form a thermoset material,
wherein the catalyst is selected from a group consisting of inorganic acids, organic acids, or Lewis acids, and
wherein the linker agent contains at least two functional groups that can react with the molecules in the heavy feedstock and has the structure of Formula 1:

wherein FG (functional group) is aldehyde, vinyl, halogen, alcohol, acyl halides, tosylate, mesylate, carboxylic acids, carboxylic anhydrides or a combination thereof;
X is a covalent bond, alkyl, cycloalkyl, or an aryl; and
n is an integer in the range of 1 to 5.

2. The method according to claim 1 , wherein the linker contains a diene functional group.

3. The method according to claim 1 further comprising oxidizing the molecules in the heavy feedstock.

4. The method according to claim 3 , wherein the molecules in the heavy feedstock are oxidized to increase molecular weight or functionality.

5. The method according to claim 3 , wherein the molecules in the heavy feedstock are oxidized under concentrated H 2 SO 4 and hydrogen peroxide conditions.

6. The method according to claim 1 , wherein the linker contains a naphthalene, a pyrene, or a biphenyl molecule that is connected to more than one functional groups selected from a group consisting of aldehyde, vinyl, halogen, alcohol, acyl halides, tosylate, mesylate, carboxylic acids, carboxylic anhydrides or a combination thereof.

7. The method according to claim 1 , wherein the catalyst is selected from a group consisting of aluminium chloride, trifluoromethanesulfonic acid, p-toluenesulfonic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, and solid acids.

8. The method according to claim 1 , wherein the linker is in the amount of 60% to 80% w/w of the total weight of the heavy feedstock.

9. The method according to claim 1 , wherein the catalyst is in the amount of 0.1% to 10% w/w of the total weight of the linker and the heavy feedstock.

10. The method according to claim 1 , wherein no solvent is used.

11. The method according to claim 1 , wherein a solvent is used and the solvent is selected from a group consisting of chlorobenzene, dichlorobenzene, trichlorobenzene, other halogenated aromatics, or combination thereof.

12. The method according to claim 1 , wherein the linker agent and molecules in the heavy feedstock are reacted at a temperature between room temperature and 400° C.

13. The method according to claim 1 , wherein the linker agent and molecules in the heavy feedstock are reacted at a temperature between 80° C. and 200° C.

Assignees

• Exxonmobil Res & Eng Co

Inventors

• Zhou Huaxing
• Lustiger Arnold
• Deflorio Victor
• Rajagopalan Srinivasan
• Shaffer Timothy D
• Schulz Donald N

Classifications

• C08G2261/1452

  containing sulfonyl or sulfonate-groups · CPC title

• C10G50/00

  Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C10G2300/1044

  Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C · CPC title

• C08G2261/148

  Side-chains having aromatic units · CPC title