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Alkylation process using an alkyl halide promoted ionic liquid catalyst

By using a mixture of acidic ionic liquids and alkyl halides as catalysts, the issues of catalyst safety and environmental friendliness in the refining industry are solved, a more efficient and environmentally friendly alkylation reaction is achieved, and a viable alternative to traditional catalysts is achieved .

Active Publication Date: 2009-04-08
CHEVRON USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, to date, no viable alternative to the current method has been brought into practice in industrial refineries

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 prepares fresh 1-butylpyridinium chloroaluminate ionic liquid catalyst A (fresh IL A)

[0041] 1-Butylpyridinium chloroaluminate is a room temperature ionic liquid prepared by mixing pure 1-butylpyridinium chloride (solid) and pure aluminum trichloride solid under an inert atmosphere. The synthesis of butylpyridinium chloride and the corresponding 1-butylpyridinium chloroaluminate is described below.

[0042] In a 2L polytetrafluoroethylene-lined autoclave, 400g (5.05mol) of anhydrous pyridine (99.9% purity, purchased from Aldrich) was mixed with 650g (7mol) 1-chlorobutane (99.5% purity, purchased from Aldrich) mix. The autoclave was sealed and the neat mixture was stirred overnight at 125° C. under autogenous pressure. After the autoclave had cooled, it was opened, and the reaction mixture was diluted and dissolved in chloroform, and transferred to a 3 L round bottom flask. The reaction mixture was concentrated under reduced pressure on a rotary evapora...

Embodiment 2

[0045] Example 2 Alkylation of ethylene and isopentane in the absence of accelerators 40 g of ionic liquid catalyst, 100 g of anhydrous isopentane and 10 g of ethylene were added to a 300 ml autoclave. The reaction was then stirred at about 1200 rpm and heated to 50°C under autogenous pressure. The starting pressure was 288 psi. The reaction was allowed to proceed until the pressure dropped to the single digit range (5 psi in this case after 28 minutes of reaction time). With the reaction proceeding slowly, the reaction was allowed to proceed for 1 hour. At the end of the reaction, the reactor was vented and the gas samples were checked for ethylene concentration by GC. The liquid reaction mixture was allowed to settle into two phases. The organic phase was decanted and analyzed for product distribution by GC analysis. The reaction results are shown in Table 1.

Embodiment 3

[0046] Example 3 Alkylation of Ethylene with Isopentane in the Presence of HCl as Cocatalyst

[0047] Table 1 below shows the results of the alkylation of ethylene with isopentane in the presence of ethyl chloride and in the presence of isopentyl chloride. The alkylation of isopentane with ethylene was carried out according to the following procedure.

[0048] 40 g of ionic liquid catalyst, 100 g of anhydrous isopentane, 10 g of ethylene and 0.35 g of anhydrous HCl were added to a 300 ml autoclave. The reaction was then stirred at about 1200 rpm and heated to 50°C under autogenous pressure. The starting pressure was 320 psi. The reaction was allowed to proceed until the pressure dropped to the single digit range (9 psi in this case after 4 minutes of reaction time). With the reaction proceeding slowly, the reaction was allowed to proceed for 1 hour. At the end of the reaction, the reactor was vented and the gas samples were checked for ethylene concentration by GC. The li...

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Abstract

A process for the production of a high quality gasoline blending components from refinery process streams by the alkylation of light isoparaffins with olefins using an ionic liquid catalyst is disclosed. The alkylation process comprises contacting a hydrocarbon mixture comprising at least one olefin having from 2 to 6 carbon atoms and at least one isoparaffin having from 3 to 6 carbon atoms under alkylation conditions, the catalyst comprising a mixture of at least one acidic ionic liquid and at least one alkyl halide. In one embodiment, the acidic ionic liquid is chloroaluminate ionic liquid prepared by mixing aluminum trichloride (AlCl3) and a hydrocarbyl substituted pyridinium halide, a hydrocarbyl substituted imidazolium halide, trialkylammonium hydrohalide or tetraalkylammonium halide of the general formulas A, B, C and D, respectively, where R-H, methyl, ethyl, propyl, butyl, pentyl or hexyl group and X is a halide and preferably a chloride, and R1 and R2-H, methyl, ethyl, propyl, butyl, pentyl or hexyl group and where R1 and R2 may or may not be the same, and R3, R4, and R5 and R6=methyl, ethyl, propyl, butyl, pentyl or hexyl group and where R3, R4, R5 and R6 may or may not be the same.

Description

field of invention [0001] The present invention relates to a process for the alkylation of light isoparaffins with olefins using a catalyst comprising an ionic liquid and an alkyl halide. Background of the invention [0002] In general, the conversion of light isoparaffins and light olefins into more valuable fractions is highly beneficial to the refining industry. This has been accomplished by the alkylation of paraffins with olefins and by the polymerization of olefins. One of the most widely used methods in this field is the use of sulfuric and hydrofluoric acids with C 3 -C 5 Alkylation of isobutane with olefins to produce high octane gasoline fractions. The method has been used by the oil refining industry since the 1940s. This approach is driven by the increasing need for high-quality and clean-burning high-octane gasoline. [0003] Alkylate gasoline is a high quality and efficiently burning gasoline that makes up about 14% of gasoline stocks. Alkylate gasoline i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/60C07C2/62
CPCC07C2527/11C10G29/205C07C2/60C07C2/62C07C2531/02
Owner CHEVRON USA INC
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