IP Library Granted Patent US 11,898,114
Granted Patent B2
US 11,898,114 · App. 17/546,170 · Granted Feb 13, 2024

Reactions and methods for producing fuels

Inventors: Daniel Ruddy (Arvada, CO); Thomas Dwight Foust (Evergreen, CO); Trenton John Wilke (Seattle, WA); Anh The To (Denver, CO); Andrew Wolf Bartling (Golden, CO); Martha Arellano-Trevino (Golden, CO)
Assignee: Alliance for Sustainable Energy, LLC
C10L1/1852C07C41/14C10L10/12C10L10/06C10L2200/0446
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Quick Facts
Patent No.
US 11,898,114
App. No.
17/546,170
Granted
Feb 13, 2024
Kind
B2
Abstract

The present disclosure relates to a composition that includes a compound having the structure R 1 O—(CH 2 O) n —R 2 and a cetane number between about 65 and about 100, where n is between 1 and 10, inclusively, R 1 includes a first alkyl group, and R 2 includes a second alkyl group.

Claims (36)

1. A fuel composition comprising:

CH 3 O(CH 2 O) n Bu′,

Bu″O(CH 2 O) m Bu′″, and

CH 3 O(CH 2 O) z CH 3 , and

a boiling point between 160° C. and 300° C., wherein:

n is between 1 and 6, inclusively,

m is between 1 and 6, inclusively, and

z is between 1 and 6, inclusively, and

each of Bu′, Bu″, and Bu′″ is independently selected from the group consisting of an n-butyl group, an iso-butyl group, and a sec-butyl group.

2. The fuel composition of claim 1 , further comprising a lower heating value (LHV) between about 30 MJ/kg and about 34 MJ/kg.

3. The fuel composition of claim 2 , further comprising a flash point temperature between about 62° C. and about 69° C.

4. The fuel composition of claim 3 , further comprising a cloud point temperature between about −58° C. and about 10° C.

5. The fuel composition of claim 4 , further comprising a yield sooting index (YSI) between about 37 and about 45.

6. The fuel composition of claim 1 , further comprising a water solubility between about 0.3 g/L and about 14 g/L.

7. A method comprising:

reacting a first mixture with an alcohol, R—OH, to form a first fuel mixture, wherein:

the reacting comprises an acid catalyzed trans-acetalization reaction,

the first mixture comprises CH 3 O(CH 2 O) z CH 3 ,

the fuel mixture comprises CH 3 O(CH 2 O) m R and RO(CH 2 O) n R,

the fuel mixture has a boiling point between 160° C. and 300° C.,

m is between 1 and 6, inclusively,

n is between 1 and 6, inclusively,

z is between 1 and 6 inclusively, and

R comprises a first alkyl group.

8. The fuel composition of claim 1 , further comprising at least one of CH 3 O(CH 2 O) n Pe′ or Pe″O(CH 2 O) m Pe′″, wherein:

each of Pe′, Pe″, and Pe′″ is independently selected from the group consisting of an n-pentyl group, an iso-pentyl group, and a neo-pentyl group.

9. The method of claim 7 , wherein R comprises at least one of an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an iso-butyl group, a sec-butyl group, an iso-propyl group, a 1-methylpropyl group, a 2-methylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a iso-pentyl group, or a neo-pentyl group.

10. The method of claim 7 , wherein, when the reacting is started, the alcohol and CH 3 O(CH 2 O) z CH 3 are provided at a ratio between about 1:1 and about 50:1 (alcohol:CH 3 O(CH 2 O) z CH 3 ).

11. The method of claim 7 , wherein the reaction is catalyzed using an ion exchange resin.

12. The method of claim 7 , wherein the reacting is performed at a temperature between about 20° C. and about 100° C.

13. The method of claim 7 , wherein the reacting is performed at a pressure between about 1 atm and 2 atm (gauge).

14. The method of claim 7 , further comprising:

after the reacting, treating the first fuel mixture, wherein:

the treating separates the first fuel mixture into a second fuel mixture and a third fuel mixture,

the second fuel mixture comprises molecules having a boiling point in a range between about 160° C. and about 338° C., and

the third fuel mixture comprises molecules having a boiling point outside the range.

Assignments (3)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
CONFIRMATORY LICENSE Recorded May 18, 2022
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 059948/0505 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2022
From: RUDDY, DANIEL; FOUST, THOMAS DWIGHT; WILKE, TRENTON JOHN; TO, ANH THE; BARTLING, ANDREW WOLF; ARELLANO-TREVINO, MARTHA
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 058632/0930 →