# US 11,306,256 B2 · Transfer hydrogenation of heavy hydrocarbons with hydrogen-donor solvents

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- Number: US 11,306,256 B2
- Document ID: US11306256B2
- Status: Granted
- Kind: B2
- Application number: 16/631,106
- Filed: 2018-07-13
- Published: 2020-08-27
- Granted: 2022-04-19
- Earliest claimed: 2017-07-14
- Assignees: Battelle Memorial Institute
- Applicants: Battelle Memorial Institute
- Inventors: Satya P. Chauhan; Daniel B. Garbark
- Web page: https://patentgrep.com/patent/US11306256B2

## CPC

- C10G 1/065: {in the presence of a solvent}
- C08H 6/00: {Macromolecular compounds derived from lignin, e.g. tannins, humic acids}
- C08L 97/005: {Lignin}
- C10G 1/002: {in combination with oil conversion- or refining processes}
- C10G 1/02: by distillation
- C10G 1/042: {by the use of hydrogen-donor solvents}
- C10G 1/045: {Separation of insoluble materials}
- C10G 3/50: {in the presence of hydrogen, hydrogen donors or hydrogen generating compounds}
- C10G 45/32: Selective hydrogenation of the diolefin or acetylene compounds
- C10G 45/44: Hydrogenation of the aromatic hydrocarbons
- C10G 47/00: Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions (C10G15/00 takes precedence; destructive hydrogenation of non-melting solid carbonaceous or similar materials C10G1/06)
- C10G 49/007: {in the presence of hydrogen from a special source or of a special composition or having been purified by a special treatment}
- C10G 69/06: including at least one step of thermal cracking in the absence of hydrogen
- C10G 2300/1011: Biomass
- C10G 2300/107: Atmospheric residues having a boiling point of at least about 538 °C
- C10G 2300/42: Hydrogen of special source or of special composition
- C10G 2300/44: Solvents
- Y02P 30/00: Technologies relating to oil refining and petrochemical industry
- Y02P 30/20: using bio-feedstock
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C08H: DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS (polysaccharides C08B; natural rubber C08C; natural resins or their derivatives C09F; bituminous materials C10)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Processes for treating highly viscous hydrocarbons, such as bitumen from oil sands or petroleum residues, with hydrogen-donor solvents are described. The hydrogen-donor solvent is prepared. A mixture of the hydrocarbon and the hydrogen-donor solvent is heated, and the product is cooled to produce a low viscosity and mildly upgraded hydrocarbon. The hydrogen-donor solvent can be modified to improve its solvent usefulness.

## Claims

### Claim 1

A process of thermally treating a highly viscous, heavy hydrocarbon comprising:
preparing a hydrogen-donor solvent capable of dehydrogenation;
mixing the heavy hydrocarbon and the hydrogen-donor solvent to form a slurry;
heating the slurry such that the heavy hydrocarbon depolymerizes to form smaller fragments and wherein the hydrogen-donor solvent transfers hydrogen to the smaller fragments to prevent repolymerization of the smaller fragments; and
cooling the product wherein the product comprises a hydrocarbon having a lower viscosity than a viscosity of the heavy hydrocarbon;
wherein the heavy hydrocarbon is treated without using molecular hydrogen and an added catalyst.

### Claim 2 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent comprises a mixture of hydrogen-donor solvents.

### Claim 3 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent is partially or exclusively derived from a biomass feedstock.

### Claim 4 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent is derived from petroleum refinery streams rich in hydroaromatics.

### Claim 5 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent is derived from coal by liquefying the coal and selectively hydrotreating the liquefied coal.

### Claim 6 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent is derived from lignin, by liquefying the lignin and selectively hydrotreating the liquefied lignin.

### Claim 7 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent has a cyclic ring with one or more double bonds on the ring without being fully aromatized.

### Claim 8

The process of claim I wherein the hydrogen-donor solvent contains compounds that can dehydrogenate during hydrocarbon treatment.

### Claim 9 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent is prepared by conjugating double bonds in multiply unsaturated fatty acids.

### Claim 10 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent comprises a dimer acid.

### Claim 11 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent comprises a material produced from pine tree processing.

### Claim 12 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent comprises an oil produced by catalytic hydrothennolysis.

### Claim 13 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent has been chemically converted to improve its solvent usefulness before heating the mixture.

### Claim 14 (depends on 1)

The process of claim 1 wherein the hydrogen-donor solvent has been chemically converted by one or more of the following processes:
esterification, hydrothermolysis, Diels-Alder reactions, dimerization, pyrolysis, hydrotreatment, or bodying.

### Claim 15 (depends on 1)

The process of claim 1 wherein the hydrocarbon is bitumen from oil sands.

### Claim 16 (depends on 1)

The process of claim 1 wherein the hydrocarbon is a petroleum residue.
