Low molecular weight amide/ester containing quaternary ammonium salts

a technology of quaternary ammonium salts and ester, which is applied in the direction of liquid carbonaceous fuels, lubricant compositions, fuels, etc., can solve the problems of poor efficacy of materials in modern engines, power loss and misfiring, and incomplete diesel combustion, so as to improve water shedding or demulsification performance, and enhance fuel economy

Inactive Publication Date: 2017-05-04
THE LUBRIZOL CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0014]Embodiments of the present technology may provide the use of amide / ester quat for at least one of antiwear performance, friction modification (particularly for enhancing fuel economy), detergent performance (particularly deposit control or varnish control), dispersancy (particularly soot control or sludge control), or corrosion control.
[0015]One embodiment of the present technology provides a method of improving water shedding, or demulsification, performance of a fuel composition. The method includes employing in a fuel, which is liquid at room temperature, a composition containing an amide / ester quat as described herein.
[0016]Also provided is the use of a composition containing an amide / ester quat as described herein, to provide improved water shedding or demulsification performance in a fuel that is liquid at room temperature.

Problems solved by technology

Deposit formation in diesel fuel injector nozzles is highly problematic, resulting in incomplete diesel combustion, and therefore power loss and misfiring.
Traditionally, polyisobutylene succinimide detergents have been used to inhibit injector fouling, but these materials have shown poor efficacy in modern engines.
The entrainment of water in, for example, crude oil or downstream fuel pipelines, and during product transfer, can result in the formation of stable emulsions and suspended matter in the crude or fuel.
Such emulsions can plug filters or otherwise make such emulsion containing fuels unacceptable.
This could also result in corrosion issues downstream.

Method used

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  • Low molecular weight amide/ester containing quaternary ammonium salts
  • Low molecular weight amide/ester containing quaternary ammonium salts
  • Low molecular weight amide/ester containing quaternary ammonium salts

Examples

Experimental program
Comparison scheme
Effect test

example 1

of 550 Mn Polyisobutylene Succinic Anhydride (PIBSA)

[0234]A 550 number average molecular weight (Mn) polyisobutylene (PIB) (2840 g., 5.163 moles, mid-vinylidene PIB available from Daelim) having greater than 20% vinylidene groups is charged to a 5-liter flange flask equipped with overhead stirrer, air condenser, nitrogen inlet, thermocouple and Eurotherm™ temperature controller (reaction kit).

[0235]Maleic anhydride (632.2 g 6.449 moles) is then charged to the reaction vessel. The batch is agitated under a nitrogen blanket and slowly heated to 203° C. over a 90 minute period. The batch is maintained at 203° C. for 24 hours.

[0236]The reaction kit is then reconfigured for vacuum stripping. The batch is stripped at 203° C. and 0.05 bar to remove unreacted maleic anhydride. The batch comprising the formed PIBSA is then cooled back to 50° C. and decanted into a storage vessel.

example 2

of Quaternizable Compound—550 Mn PIBSA and 2-Dimethylaminoethanol

[0237]The 550 Mn PIBSA (1041.6 g, 1.50 moles) (product of Example 1) is charged to a 2-liter flask equipped with a water condenser, a thermocouple, a dropping funnel, an overhead stirrer and Nitrogen inlet and heated to 90° C.

[0238]2-Dimethylaminoethanol (133.71 g, 1.50 moles) is added to the flask via the dropping funnel over 60 minutes. The batch temperature is kept below 120° C. while adding the 2-dimethylaminoethanol.

[0239]Once all the 2-dimethylaminoethanol is added, the reaction maintained at 120° C. for 2 hours. The resulting product is a 550 Mn PIBSA / 2-dimethylaminoethanol quaternizable compound.

example 3 (

Prophetic)—Formation of a 550 Mn PIBSA / 2-Dimethylaminoethanol Quaternary Ammonium Salt Using Dimethyl Sulfate (an Ester / Dimethyl Sulfate Quat)

[0240]The 550 Mn PIBSA / 2-dimethylaminoethanol (595.5 g 0.76 moles) (product of Example 2) is charged to a 2 liter flask equipped with a water condenser, a thermocouple, a dropping funnel, an overhead stirrer and a nitrogen inlet.

[0241]Diluent oil (1046.6 g), such as mineral oil of type SN 100-SN 150, is added to the flask and the flask is heated to 60° C. under agitation and nitrogen atmosphere.

[0242]Dimethyl sulfate (86.6 g, 0.69 moles) is then added drop wise to the flask. An exotherm of 29° C. is noted taking the batch temperature from 60° C. to 89° C. The batch is then maintained at 90° C. for two hours before cooling back to 50° C. and decanting the ester / dimethyl sulfate quat into storage vessel.

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Abstract

The present technology is related to amide or ester containing quaternary ammonium salts having a hydrocarbyl substituent of number average molecular weight ranging from 300 to 750, and the use of such quaternary ammonium salts in fuel compositions to improve the water shedding performance of the fuel composition.

Description

FIELD OF THE INVENTION[0001]The present technology is related to amide or ester containing quaternary ammonium salts having a hydrocarbyl substituent of number average molecular weight of 300 to 750, and the use of such quaternary ammonium salts in fuel and lubricant compositions to improve the water shedding performance of the compositions. The invention further relates to a method of lubricating an internal combustion engine with the lubricant composition for at least one of antiwear, friction, detergency, dispersancy, and / or corrosion control performance.BACKGROUND OF THE INVENTION[0002]Deposit formation in diesel fuel injector nozzles is highly problematic, resulting in incomplete diesel combustion, and therefore power loss and misfiring. Traditionally, polyisobutylene succinimide detergents have been used to inhibit injector fouling, but these materials have shown poor efficacy in modern engines. A new class of compounds based on quaternized polyisobutylene succinimides has bee...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C10M159/12C10L10/04C10L10/18C10L1/18C10L1/22
CPCC10M159/12C10L2270/026C10L1/22C10L10/18C10L10/04C10M2207/127C10M2217/043C10N2240/10C10N2220/021C10N2230/12C10L1/1883C10L1/221C10L1/232C10L2200/0259C10L2200/0423C10L2200/0446C10L2270/023C10L1/18C10L1/2383C10M133/56C10M2215/28C10M2215/042C10M2215/04C10M2215/02C10L1/238C10N2020/04C10N2040/253C10N2040/26C10N2040/252C10N2040/255C10N2040/25C10L1/2437C10N2070/00C10N2030/12
Inventor MORETON, DAVID J.STEVENSON, PAUL R.GREENFIELD, HANNAHARTERS, DAVID C.BUSH, JAMES H.ADAMS, PAUL E.
Owner THE LUBRIZOL CORP
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