IP Library Granted Patent US 10,538,464
Granted Patent B1
US 10,538,464 · App. 16/165,198 · Granted Jan 21, 2020

Process for enhanced production of desired hydrocarbons from biologically-derived compounds and bio-oils containing cyclic compounds by opening of aromatics and naphthenic ring-containing compounds

Inventors: Vanessa Dagle (Richland, WA); Karl O. Albrecht (Richland, WA); Robert A. Dagle (Richland, WA)
Assignee: BATTELLE MEMORIAL INSTITUTE
C07C4/06B01J19/245C10G11/04C07C2521/04C07C2523/46C07C2529/74C10G2300/1014
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Quick Facts
Patent No.
US 10,538,464
App. No.
16/165,198
Granted
Jan 21, 2020
Kind
B1
Abstract

A system and process for processing biologically-derived compounds or a complex bio-oil by converting cyclic compounds in a complex bio-oil or biologically-derived compounds to desired materials such as high molecular weight paraffins with minimal carbon loss by using a ring-contraction catalyst to selectively produce C 5 ring containing compounds; and then reacting the C 5 ring containing compounds with a C 5 ring opening catalyst in a second reactor to minimize carbon loss via cracking reactions.

Claims (19)

1. A process for converting cyclic compounds having at least six carbons, the process comprising the steps of:

providing a bio-oil feedstock containing C-6 or greater cyclic compounds, the bio-oil feedstock having complex microemulsions of aqueous and non-aqueous phases containing different organic and inorganic compounds including esters, acids, aldehydes, alcohols, ketones, sugars, and various phenol derivatives;

reacting the bio-oil feedstock containing C-6 or greater cyclic compounds in a first reactor with an acidic ring-contraction catalyst containing at least one metal to open and reduce the C-6 or greater cyclic compounds and selectively produce C-5 ring containing compounds from the C-6 or greater cyclic compounds; and

reacting the C-5 ring containing compounds with a C-5 ring opening catalyst in a second reactor to yield a higher molecular weight material comprising paraffins,

wherein the step of reacting the bio-oil feedstock occurs under a first set of operating conditions comprising a temperature 320° C. and a pressure 20 bars and the step of reacting the C-5 ring containing compounds operates under a second set of conditions comprising a temperature 280° C. and a pressure 20 bars.

2. The process of claim 1 wherein the first reactor is loaded with the acidic ring-contraction catalyst and operates at a temperature 320° C. and a pressure 20 bars and the second reactor is loaded with the C-5 ring opening catalyst and operates at a temperature 280° C. and a pressure 20 bars.

3. The process of claim 1 wherein the acidic ring-contraction catalyst in the first reactor is an acid catalyst containing Pt.

4. The process of claim 1 wherein the acidic ring-contraction catalyst in the first reactor is an acid catalyst containing Pd.

5. The process of claim 1 wherein the C-5 ring opening catalyst in the second reactor is a metal catalyst.

6. The process of claim 5 wherein the C-5 ring opening catalyst comprises Ir.

7. The process of claim 1 wherein the higher molecular weight material is paraffins.

8. A process for converting cyclic compounds from a bio-oil feedstock into higher molecular weight materials comprising paraffins, the process comprising the steps of:

providing a bio-oil feedstock containing C-6 or greater cyclic compounds, the bio-oil feedstock having complex microemulsions of aqueous and non-aqueous phases containing different organic and inorganic compounds including esters, acids, aldehydes, alcohols, ketones, sugars, and various phenol derivatives;

reacting the bio-oil feedstock containing C-6 or greater cyclic compounds in a first a reactor with a ring-contraction catalyst comprising 1 wt % Pt/HZSM-22 thereby selectively producing C 5 ring containing compounds; and

reacting the C 5 ring containing compounds with a C 5 ring opening metal catalyst comprising 1 wt % Ir/Al 2 O 3 in a second reactor to yield a higher molecular weight material comprising paraffins,

wherein the first reactor operates at a temperature 320° C. and a pressure 20 bars and the second reactor operates at a temperature 280° C. and a pressure 20 bars.

9. The process of claim 8 wherein the higher molecular weight material is paraffins.

10. The process of claim 8 wherein the ring-contraction catalyst is 1 wt % Pt/HZSM-22.

11. The process of claim 8 wherein the C 5 ring opening metal catalyst is 1 wt % Ir/Al 2 O 3.

Assignments (2)
CONFIRMATORY LICENSE Recorded Nov 29, 2018
From: BATTELLE MEMORIAL INSTITUTE, PACIFIC NORTHWEST DIVISION
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 047675/0677 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2018
From: DAGLE, VANESSA; ALBRECHT, KARL O.; DAGLE, ROBERT A.
To: BATTELLE MEMORIAL INSTITUTE
Reel/Frame 047355/0681 →