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Process for producing dihydric alcohol butyl ether

A technology for glycol ether and n-butenyl glycol ether, which is applied in the field of producing glycol butyl ether, and can solve the problems of loss and separation complexity, unfavorable method economy, influence and the like

Inactive Publication Date: 2004-07-28
UNIVERSITY OF SOUTHERN MISSISSIPPI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The loss of selectivity and the resulting separation complexity adversely affects the economics of the method

Method used

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  • Process for producing dihydric alcohol butyl ether
  • Process for producing dihydric alcohol butyl ether
  • Process for producing dihydric alcohol butyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1 Addition of butadiene on ethylene glycol

[0075] Into a 10 liter stainless steel autoclave, 85 grams of washed Amberlyst  15H ion exchange resin was added to a stainless steel "tea bag" mounted around the impeller shaft. For test BS1, ethylene glycol (3600 grams, ex Aldrich) was added and butadiene (750 grams) was added after purging the system with nitrogen and heating to 90°C. In the case of test BS2, the above procedure was repeated except that water (78 g) was added together with ethylene glycol. The progress of the reaction was monitored by GC. A typical GC plot for this reaction is shown below:

[0076]

[0077] test ed

[0078] From the above it can be seen that the addition of water increases the reaction selectivity (reduction of higher oligomers relative to C4 products) while decreasing the reaction rate. The reaction selectivities of the two C4 glycol ethers are BS1=73%, BS2=83.2%+

Embodiment 2

[0079] Embodiment 2 The isomerization of C4 glycol ether isomers

[0080] A sample of the autoclave final product from the direct addition reaction of butadiene and ethylene glycol prepared as described above in BS1 was rotary evaporated at 9 mbar and 80 °C to concentrate the lower boiling butenyl glycols ether. A sample of this distillation was then further distilled (4 mbar, 55° C.) in a packed column to concentrate the sec-butenyl glycol ether isomer in the distillate and the crotyl glycol ether isomer in the kettle.

[0081] in Amberlyst  A mixture of concentrated sample (100 g), ethyl acetate (184 g) and decane (1.2637 g - internal standard) was heated to 50°C for 5 hours in the presence of 15 resin (15 g). Samples of initial and final product were analyzed by gas chromatography.

[0082] See attached chromatogram for results using crotyl glycol ether enriched samples. The upper graph represents a crotyl glycol ether rich starting mixture (retention time -8.35 minute...

Embodiment 3

[0091] Embodiment 3 The hydrogenation of crotyl glycol ether

[0092] The hydrogenation was carried out in a batch, stirred autoclave (500 ml zirconium metal) starting with:

[0093] Concentrated crotyl glycol ether fraction 60g

[0094] 240 g toluene

[0095] Decane 2.99 g

[0096] Catalyst (Raney nickel supported on Ni / C Harshaw, ground to 60 mesh) 6 g

[0097] The autoclave was charged and purged with nitrogen, pressure tested and subsequently pressurized to 30 bar with hydrogen. The reaction mixture was heated to 100°C and stirred at 1000 rpm for 16 hours. An air-packed vessel was used to maintain an autoclave pressure of 30 bar. Analysis of the final reaction mixture by GC determined that 100% of the crotyl glycol ether had been converted to obtain a high yield (estimated >95%) of n-butyl glycol ether.

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Abstract

Processes are described for the preparation of glycol butyl ethers involving reaction of butadiene with saturated aliphatic glycols, separating the thus formed n- and sec-butenyl glycol ethers and hydrogenating the n-butenyl glycol ethers. Additional features are the use in the first step of heterogeneous catalyst modified by alkylpyridinium quaternary ammonium, quaternary arsonium quaternary phosphonium counterions and / or the conversion of sec-butenyl glycol ethers to butadiene and saturated aliphatic glycols.

Description

[0001] This application is a divisional application of the invention patent application whose application number is 99815102.5, the application date is October 21, 1999, and the invention title is "method for producing glycol butyl ether". technical field [0002] The present invention relates to a process for the preparation of glycol butyl ethers by hydrogenation of the corresponding butenyl ethers. They can be prepared by reaction of butadiene with diols in the presence of Bronsted acid or Lewis acid catalysts. Background technique [0003] n-Butyl glycol ethers are useful chemicals. These glycol ethers have previously been prepared by reacting n-butanol with alkylene oxides such as ethylene oxide. However, the selectivity of this process is limited by the formation of large amounts of unwanted by-products such as diethylene glycol ethers and triethylene glycol ethers. The presence of these by-products increases the difficulty of isolating the desired n-butyl monoglycol...

Claims

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Application Information

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IPC IPC(8): C07C41/06
CPCC07C41/42C07C41/06Y02P20/582C07C43/178
Inventor B·P·格雷西
Owner UNIVERSITY OF SOUTHERN MISSISSIPPI
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