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Synthesis method of ethyl tetrahydrofurfuryl ether

A technology of tetrahydrofurfuryl alcohol and a synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of insecurity, low ETFE separation efficiency, low dehydration efficiency, etc., and achieve the effects of easy production control, easy process control, and high dehydration efficiency.

Pending Publication Date: 2022-01-07
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In 2008, Beijing University of Chemical Technology used tetrahydrofurfuryl alcohol, caustic soda, ethyl bromide, sodium metal and hydrocarbon solvents as raw materials to prepare ETFE, and obtained ETFE with a mass fraction greater than 98%, but the preparation and refining process contained excessive amounts of unstable Sodium metal, causing trouble in handling and uncontinuous and unsafe industrial production
[0007] In summary, in the prior art, tetrahydrofurfuryl alcohol is used as the benchmark to synthesize ETFE, and the technology has long reaction time for alkoxide production and low dehydration efficiency, and the synthesized THFA salt is muddy, and condenses with ethyl halide Poor mass transfer and heat transfer effects, difficult production control, and low separation efficiency of ETFE from THFA, or the defects of ETFE after distillation and purification can not meet the standard of activation regulator for anionic polymerization
[0008] At the same time up to now, there is no literature to report a complete high-efficiency method for preparing high-purity ETFE based on tetrahydrofurfuryl alcohol

Method used

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  • Synthesis method of ethyl tetrahydrofurfuryl ether
  • Synthesis method of ethyl tetrahydrofurfuryl ether
  • Synthesis method of ethyl tetrahydrofurfuryl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Add 1028g of THFA, 450g of caustic soda of 99.0%, 1200mL of benzyl alcohol of 98.6% and 99 % of 40mL toluene, stirred and heated to 100-125°C for dehydration reaction, when no obvious water escaped from the azeotropic toluene in the water separator, the dehydration reaction time was 8.5h.

[0048] Then the dehydrated reactant is pressed into a condensation (or coupling) reactor with a cooling system, and the material is lowered to 0-10°C with -5°C brine, and the alkoxide presents a yellow viscous resinous fluid. Add 755g of 99.3% ethyl chloride into the condensation reaction kettle at a constant speed within 2 hours to carry out the condensation reaction, and at the same time remove the heat of reaction with brine, control the condensation reaction temperature not higher than 20°C, and the reaction pressure not higher than 0.2MPa, After the addition of ethyl chloride, the reaction was continued for another 2 hours. At this time, the pressure in the kettle dropped to zer...

Embodiment 2

[0054] The relevant process conditions and operating methods in Example 1 were kept unchanged, and only relevant parameters were adjusted in each unit.

[0055] For example, in the dehydration reaction unit, it is set to add 2000mL of phenylethyl alcohol with a mass fraction of 98.2%, 50mL of xylene, and 460g of caustic soda, and the dehydration reaction temperature is 120-135°C. flowing liquid;

[0056] For example, in the condensation reaction unit, 1253 g of ethyl bromide with a mass content of 99.6% is used instead, and the reaction pressure is not higher than 0.1 MPa.

[0057] Results After filtering the salt-containing crude product at room temperature to remove sodium chloride, 3243 g of the filtrate of the salt-free crude product was obtained. The yield of ETFE was 95.15%.

[0058] Table 2

[0059]

[0060] Put the filtrate in a three-necked flask equipped with a silver-plated glass rectification column with high-efficiency packing about 45 plates for rectificati...

Embodiment 3

[0062] The relevant process conditions and operating methods in Example 1 remained unchanged, and only relevant adjustments were made in each unit.

[0063] For example, in the dehydration reaction unit, it is set to add 500g of caustic soda, 1500mL of ditetrahydrofurfurylpropane and 50mL of xylene, and the dehydration reaction temperature is 130-140°C. After a reaction time of 9 hours, the alkoxide presents a dark yellow and easy-flowing fluid;

[0064] For example, in the condensation reaction unit, the reaction temperature is 10-15°C, and the reaction pressure is not higher than 0.2MPa.

[0065] Results After the salt-containing crude product was filtered at room temperature to remove sodium chloride, 2714 g of the filtrate of the salt-free crude product was obtained. The yield of ETFE was 94.48%.

[0066] table 3

[0067]

[0068] The filtrate is placed in a three-necked flask equipped with a silver-plated glass rectification column with high-efficiency packing of abo...

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Abstract

The invention discloses a synthesis method of ethyl tetrahydrofurfuryl ether, which comprises the following steps of: performing dehydration reaction on THFA and alkali metal hydroxide in an alkoxide solvent system containing a water-carrying agent, and separating water generated by the dehydration reaction to obtain an alkoxide product; wherein the alkoxide solvent is aryl alcohol or furan ether of C7 to C12; cooling the alkoxide product, and carrying out condensation reaction on the alkoxide product and halogenated ethane to obtain a salt-containing crude ETFE product; filtering the salt-containing crude ETFE product to remove chlorine salt, and rectifying to collect ETFE fractions; wherein the mass content of the obtained ETFE fractions is higher than 98.0% of ETFE, the total reaction yield is higher than 95%, and the rectifying still liquid solvent can be recycled.

Description

technical field [0001] The invention relates to a synthesis method of tetrahydrofurfuryl alcohol ethyl ether, in particular to a method for synthesizing tetrahydrofurfuryl alcohol ethyl ether by an improved Williamson synthesis method, and belongs to the field of organic synthesis. Background technique [0002] Tetrahydrofurfuryl alcohol ethyl ether (ETFE) is a derivative fine chemical based on furan, which is not only used as a solvent, but also as an activator for anionic polymerization and a microstructure regulator for conjugated diene monomers, such as butane For the production of diene-styrene polymers SBS, SSBR, SEBS and other products, the content of ETFE as anionic polymerization is required to reach 98-99%, and the lower the content of alcohols and polar organic impurities, the better. The reason for the early development of this product by American Painner Chemical Company is that ETFE is cheap and used to replace the high-priced ditetrahydrofurfuryl propane. At ...

Claims

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Application Information

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IPC IPC(8): C07D307/12
CPCC07D307/12
Inventor 姚琼张建国蒋文英付为金
Owner CHINA PETROLEUM & CHEM CORP
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