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Use of quaternised alkyl amines as additives in fuels and lubricants

A technology of fuel additive and quaternization reagent, applied in the field of decontamination additive and monocarboxylic acid, can solve the problems of no residue burning, excessive quaternization reagent, incomplete quaternization reaction conditions and the like

Active Publication Date: 2014-10-22
BASF AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, the quaternizing agents used preferably in WO 2006 / 135881 have serious disadvantages such as: toxicity or carcinogenicity (e.g. in the case of dimethyl sulfate and benzyl halides), no residue-free combustion (e.g. in the case of dimethyl sulfate and alkyl halides), and insufficient activity, which can lead to incomplete quaternization or uneconomical reaction conditions (long reaction time, high reaction temperature, excess of quaternizing agent; e.g. in case of methyl ester)

Method used

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  • Use of quaternised alkyl amines as additives in fuels and lubricants
  • Use of quaternised alkyl amines as additives in fuels and lubricants
  • Use of quaternised alkyl amines as additives in fuels and lubricants

Examples

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preparation example Construction

[0107] A5) preparation of additive of the present invention:

[0108] a) Quaternization

[0109] The quaternization is carried out in a manner known per se.

[0110] (1) For quaternization, a tertiary amine is mixed with at least one compound of formula 1 or 2 above, especially in a stoichiometric amount to achieve the desired quaternization. For example, 0.1 to 5.0, 0.2 to 3.0, or 0.5 to 2.5 equivalents of quaternizing agent may be used per equivalent of quaternizable tertiary nitrogen atoms. More specifically, however, in order to completely quaternize the tertiary amine groups, about 1 to 2 equivalents of the quaternizing agent are used relative to the amount of tertiary amine.

[0111] Typical operating temperatures here are in the range of 50 to 180°C, eg 90 to 160°C, or 100 to 140°C. The reaction time can be several minutes or several hours, for example about 10 minutes up to about 24 hours. The reaction can be carried out at a pressure of about 0.1 to 20 bar, for ex...

preparation example 1

[0293] Preparation Example 1: Synthesis of N,N-dimethyl-N,N-ditallowyl ammonium oxalate methyl ester based on EP 2 033 945

[0294] N-Methyl-N,N-ditallowylamine (90 g) was mixed with dimethyl oxalate (90 g) and lauric acid (1.8 g). The reaction mixture was heated to 120 °C and stirred at this temperature for 4 h. Subsequently, excess dimethyl oxalate was removed under reduced pressure at 130° C. by means of a rotary evaporator. 110.8 g of a white waxy product are obtained. 1 H NMR (CDCl 3 ) confirms the quaternization reaction.

preparation example 2

[0295] Preparation Example 2: N,N-Dimethyl-N,N-Ditallow Ammonium Salicylate

[0296] N-Methyl-N,N-ditallowylamine (80 g) was mixed with methyl salicylate (45.4 g) and 3,5,5-trimethylhexanoic acid (0.8 g). The reaction mixture was heated to 160 °C and stirred at this temperature for 4 h. After cooling to room temperature, 124 g of a white waxy product are obtained. 1 H NMR (CDCl 3 ) confirms the quaternization reaction.

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Abstract

Fuel- or lubricant composition comprises at least one reaction product comprising a quaternized nitrogen compound, or its partial fraction, which contains the quaternized nitrogen compound, and is obtained from the reaction product by purification, in a fuel or a lubricant. The reaction product is obtainable by reacting a quaternizable alkylamine containing at least one quaternizable tertiary amino group, with a quaternizing agent comprising e.g. an aliphatic polycarboxylic acid, preferably a dicarboxylic acid, which converts the tertiary amino group into a quaternary ammonium group. Fuel- or lubricant composition comprises at least one reaction product comprising a quaternized nitrogen compound, or its partial fraction, which contains the quaternized nitrogen compound, and is obtained from the reaction product by purification, in a fuel or a lubricant. The reaction product is obtainable by reacting a quaternizable alkylamine containing at least one quaternizable tertiary amino group, with a quaternizing agent comprising (a) an alkyl ester of a cyclo-aromatic or cycloaliphatic mono- or polycarboxylic acid, preferably a mono- or dicarboxylic acid, (b) an aliphatic polycarboxylic acid, preferably a dicarboxylic acid, (c) a hydrocarbyl epoxide optionally in combination with a free acid, or (d) a dialkyl carbonate, which converts the tertiary amino group into a quaternary ammonium group. Independent claims are also included for: (1) the quaternized nitrogen compound; (2) preparing the quaternized nitrogen compound, comprising reacting the quaternizable alkylamine with the quaternizing agent including (a)-(c); and (3) an additive concentrate comprising the quaternized nitrogen compound in combination with further diesel or gasoline fuel additives or lubricant additives.

Description

[0001] The present invention relates to the use of quaternized alkylamine nitrogen compounds as fuel additives and lubricant additives, such as, in particular, as decontamination additives; for reducing or preventing injection systems, especially common rail injection, of direct injection diesel engines Deposits in systems for reducing the fuel consumption of direct-injection diesel engines, especially diesel engines with common rail injection systems, and for increasing the performance of direct-injection diesel engines, especially diesel engines with common rail injection systems loss minimization; and as an additive for the operation of gasoline fuels, especially for DISI engines. Background technique [0002] In a direct-injection diesel engine, the fuel is injected through a multi-hole injection nozzle and distributed (atomized) in an ultra-fine form, which reaches the engine's combustion chamber directly, rather than being introduced into the pre-combustion chamber as in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C10M133/02C10M133/06C10M133/54C07C209/20C07C211/63C10L1/22C10L10/04C10L10/06C10N40/25C10N30/04C10N70/00
CPCC10L10/04C10M2215/04C07C211/63C10N2230/04C10M2215/02C10L1/2222C10M133/06C10L1/2225C10L10/06C10M133/54C10L1/14C10M2215/26C10N2270/02C10M2215/042C10L1/22C10L2270/026C07C209/20C10L10/18C10N2240/104C10L2270/023C10M133/02C10N2240/102C10N2230/54C10N2030/04C10N2030/54C10N2040/252C10N2040/255C10N2070/02Y02T10/12
Inventor M·汉施H·博恩克L·沃尔凯尔W·格雷巴斯J·斯特里特马特
Owner BASF AG