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Process for making n-butyl esters from butadiene

a technology of butadiene and n-butyl esters, which is applied in the preparation of ester-hydroxy reactions, chemical apparatus and processes, organic chemistry, etc., can solve the problems of increasing capital costs, and achieve the effect of increasing activity and increasing the cost of reaction selectivity

Inactive Publication Date: 2005-11-01
UNIVERSITY OF SOUTHERN MISSISSIPPI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0005]It has now been found that saturated n-butyl esters and secondary butyl esters can be synthesised without resort to either (a) the hydroformylation route from propylene or (b) the use of vinyl acetate or ethylene feedstocks in relatively simple stages.

Problems solved by technology

This method however requires a source of syngas which increases capital costs.
In addition, all these methods rely on the use of either relatively expensive feedstocks such as ethylene and n-butanol or involve multiple reaction stages or expensive catalysts and separation stages.

Method used

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  • Process for making n-butyl esters from butadiene
  • Process for making n-butyl esters from butadiene
  • Process for making n-butyl esters from butadiene

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0069]

sec-Butenyln-ButenylRuntimeacetateacetate4-Vinyl cyclohexeneHighers(Hours)(% w / w)(% w / w)(% w / w)(% w / w)0001.3057.77.591.32.8568.959.371.283.9179.4910.241.254.34810.4911.721.265.072410.9814.210.776.55

[0070]These results illustrate that the reaction proceeds to give predominantly the isomeric C4 acetates and that some loss of selectivity occurs to higher boiling point materials particularly at high reaction times. The reaction product was pale yellow which darkened on standing.

Example 2

Use of Amberlyst 15H® Resin with Pre-conditioning

[0071]The general method was used and the resin washed with ethyl acetate and dried prior to use. The following components were charged to the autoclave:[0072]Amberlyst 15H®—85 g[0073]Acetic acid—3600 g[0074]1,3-Butadiene—700 g[0075]Reaction conditions: 50° C., with stirring at 1200 rpm

example 2

[0076]

sec-Butenyln-ButenylRuntimeacetateacetate4-Vinyl cyclohexeneHighers(Minutes)(% w / w)(% w / w)(% w / w)(% w / w)0001.390301.080.721.310.21601.971.371.340.45902.832.021.350.711504.013.11.311.22105.34.371.261.752706.25.431.192.263306.966.361.192.713907.927.581.23.09

[0077]These results reaffirm the previous results and demonstrate that the sec-butenyl acetate is the kinetic reaction product and that the n-butenyl acetate is the thermodynamic product. The reaction product was initially colourless but darkened on standing to a pale yellow. This illustrates that pre-treatment of the Amberlyst 15H® resin served to reduce the colour of the product.

examples 3 and 4

Effect of Temperature on Reaction Rate

[0078]Two sequential reactions were carried out on the charge of 85 g of Amberlyst 15H® used in example 2 (ethyl acetate pre-washed), the catalyst between runs was washed with acetic acid in situ to remove residual material from the previous run in the sequential reactions. The charge of butadiene was 700 g and acetic acid was 3600 g for all three experiments.

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Abstract

Process for making a butyl ester from butadiene, comprising (a) reacting butadiene with a saturated aliphatic monocarboxylic acid to form a mixture of n-butenyl and secondary butenyl esters, (b) separating the n-butenyl ester from the secondary butenyl ester, and (c) hydrogenating the n-butenyl ester separated in step (b) in the presence of a catalyst to the corresponding n-butyl ester.

Description

[0001]This is a continuation of PCT application No. PCT / GB99 / 03452, filed Oct. 19, 1999, the entire content of which is hereby incorporated by reference in this application.[0002]The present invention relates to a process for making n-butyl esters by reacting butadiene with a carboxylic acid in the presence of a Brønsted or Lewis acid catalyst to form the unsaturated ester which is subsequently hydrogenated to form the saturated ester.BACKGROUND OF THE INVENTION[0003]It is known that n-butyl esters such as n-butyl acetate can be produced by a number of routes. For instance, the hydroformylation of propylene in the presence of acetic acid is a method which gives a mixture of n-butyl acetate and iso-butyl acetate. This method however requires a source of syngas which increases capital costs. An alternative method is to react ethylene with vinyl acetate in the presence of an acid catalyst followed by the hydrogenation of the resultant unsaturated ester. A further method is the reaction...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C67/02C07C67/04C07C67/00C07B61/00C07C67/03C07C67/283C07C69/14
CPCC07C67/04C07C67/283Y02P20/582C07C69/007C07C69/14C07C69/145
Inventor GRACEY, BENJAMIN PATRICKKAMP, NORBERT WALTER JOSEF
Owner UNIVERSITY OF SOUTHERN MISSISSIPPI
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