# US 8,465,560 B1 · Gasoline deposit control additive composition

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- Number: US 8,465,560 B1
- Document ID: US8465560B1
- Status: Granted
- Kind: B1
- Application number: 12/697,590
- Filed: 2010-02-01
- Granted: 2013-06-18
- Earliest claimed: 2009-02-05
- Assignees: Butamax Advanced Biofuels LLC
- Applicants: Leslie R. Wolf
- Inventors: Leslie R. Wolf
- Web page: https://patentgrep.com/patent/US8465560B1

## CPC

- C10L 1/22: containing nitrogen
- C07C 249/02: of compounds containing imino groups
- C10L 1/026: {for compression ignition}
- C10L 1/1824: {mono-hydroxy}
- C10L 1/221: {compounds of uncertain formula; reaction products where mixtures of compounds are obtained}
- C10L 1/2222: {(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates (C10L1/221 takes precedence)}
- C10L 1/224: Amides; Imides {carboxylic acid amides, imides (C10L1/221, C10L1/2227 take precedence)}
- C10L 1/226: containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines {(C10L1/221 takes precedence)}
- C10L 1/228: containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles {(C10L1/221, C10L1/226 take precedence)}
- C10L 1/2283: {containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine (C10L1/221, C10L1/226 take precedence)}
- C10L 1/232: containing nitrogen in a heterocyclic ring {(C10L1/221 takes precedence)}
- C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)}
- C10L 1/2383: Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)}
- C10L 1/2387: Polyoxyalkyleneamines {(poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)}
- C10L 10/18: use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
- 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

A gasoline deposit control additive composition for use in a fuel comprising from about 70 to about 95 volume percent of hydrocarbons in the gasoline boiling range and from about 5 to about 30 volume percent of at least one alcohol, comprising the imine or tertiary amine product of the reaction between (a) at least one aldehyde or ketone or mixture thereof having the formula R16 CHO, R16 CH2 CHO, R17 (C=0) R18 or R17 CH2 (C=0) R18, wherein R16, R17, and R18 are the same or different and are each independently a straight or branched chain hydrocarbyl or aryl group that contains from 1 to 18 carbon atoms, and (b) a primary or secondary amine functionality.

## Claims

### Claim 1

A liquid automotive fuel comprising from about 70 to about 95 volume percent of hydrocarbons boiling in the gasoline range, from about 5 to about 30 volume percent of at least one alcohol, and an imine or tertiary amine product of the reaction between
(a) at least one aldehyde having the formula R16 CHO or R16 CH2 CHO, wherein R16 is a straight or branched chain hydrocarbyl or aryl group that contains from 1 to 18 carbon atoms, and
(b) a primary or secondary amine functionality of the formula:
wherein: R4 is nitro or —(CH2)n—NR9R10, wherein R9 and R10 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms and n is 0 or 1; R5 is hydrogen, hydroxy, nitro or —NR11 R12, wherein R11 and R12 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R6 and R7, are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; and R8 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000.

### Claim 2 (depends on 1)

The liquid automotive fuel of claim 1 wherein R16 of the aldehyde contains from 1 to 8 carbon atoms.

### Claim 3 (depends on 1)

The liquid automotive fuel of claim 1 wherein R16 contains from 1 to 12 atoms.

### Claim 4 (depends on 1)

The liquid automotive fuel claim 1 wherein the liquid automotive fuel comprises about 2 to about 30 volume percent of the at least one alcohol.

### Claim 5 (depends on 1)

The liquid automotive fuel of claim 1 wherein the at least one alcohol comprises ethanol or a butanol or both.

### Claim 6 (depends on 5)

The liquid automotive fuel of claim 5 wherein the at least one alcohol comprises a butanol isomer.

### Claim 7 (depends on 6)

The liquid automotive fuel of claim 6 wherein the at least one alcohol comprises isobutanol.

### Claim 8 (depends on 1)

The liquid automotive fuel of claim 1 comprising the imine or tertiary amine product of the reaction between the aldehyde and a primary amine functionality.

### Claim 9 (depends on 1)

The liquid automotive fuel of claim 1 comprising from about 50 to about 4000 parts per million by volume of the imine or tertiary amine.

### Claim 10 (depends on 9)

The liquid automotive fuel of claim 9 wherein the imine or tertiary amine is at a level of from about 100 to about 2000 parts per million by volume.

### Claim 11 (depends on 10)

The liquid automotive fuel of claim 10 wherein the imine or tertiary amine is at a level of from about 100 to about 1000 parts per million by volume.