# US 11,898,114 B2 · Reactions and methods for producing fuels

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- Number: US 11,898,114 B2
- Document ID: US11898114B2
- Status: Granted
- Kind: B2
- Application number: 17/546,170
- Filed: 2021-12-09
- Published: 2022-06-23
- Granted: 2024-02-13
- Earliest claimed: 2020-12-11
- Assignees: Alliance for Sustainable Energy, LLC
- Applicants: Alliance for Sustainable Energy, LLC
- Inventors: Daniel Ruddy; Thomas Dwight Foust; Trenton John Wilke; Anh The To; Andrew Wolf Bartling; Martha Arellano-Trevino
- Web page: https://patentgrep.com/patent/US11898114B2

## CPC

- C10L 1/1852: {Ethers; Acetals; Ketals; Orthoesters}
- C07C 41/14: by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
- C07C 41/48: Preparation of compounds having [IMAGE cpc-sch-C07C-0958.gif] groups
- C07C 43/30: Compounds having [IMAGE cpc-sch-C07C-0958.gif] groups
- C10L 1/1985: {polyethers, e.g. di- polygylcols and derivatives; ethers - esters}
- C10L 10/12: for improving the cetane number
- C10L 10/06: for facilitating soot removal
- C10L 2200/0446: Diesel
- C10L 2270/026: for diesel engines, e.g. automobiles, stationary, marine
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present disclosure relates to a composition that includes a compound having the structure R1O—(CH2O)n—R2 and a cetane number between about 65 and about 100, where n is between 1 and 10, inclusively, R1 includes a first alkyl group, and R2 includes a second alkyl group.

## Claims

### Claim 1

A fuel composition comprising:
CH3O(CH2O)nBu′,
Bu″O(CH2O)mBu′″, and
CH3O(CH2O)zCH3, 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 2)

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

### Claim 4 (depends on 3)

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

### Claim 5 (depends on 4)

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

### Claim 6 (depends on 1)

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

### Claim 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 CH3O(CH2O)zCH3,
the fuel mixture comprises CH3O(CH2O)mR and RO(CH2O)nR,
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.

### Claim 8 (depends on 1)

The fuel composition of claim 1, further comprising at least one of CH3O(CH2O)nPe′ or Pe″O(CH2O)mPe′″, 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.

### Claim 9 (depends on 7)

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.

### Claim 10 (depends on 7)

The method of claim 7, wherein, when the reacting is started, the alcohol and CH3O(CH2O)zCH3 are provided at a ratio between about 1:1 and about 50:1 (alcohol:CH3O(CH2O)zCH3).

### Claim 11 (depends on 7)

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

### Claim 12 (depends on 7)

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

### Claim 13 (depends on 7)

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

### Claim 14 (depends on 7)

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.