Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for the preparation of alkyl levulinates

A technology of alkyl levulinate and alkyl, which is applied in the field of preparing alkyl levulinate, can solve problems such as loss of catalytic activity, achieve good safety, avoid equipment corrosion, and avoid the effects of by-product formation

Inactive Publication Date: 2012-04-04
SEGETIS
View PDF9 Cites 19 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this prior art, a significant loss of catalytic activity is lost due to the conversion of the second alcohol to the alkyl halide

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for the preparation of alkyl levulinates
  • Method for the preparation of alkyl levulinates
  • Method for the preparation of alkyl levulinates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] A 250 mL 3-necked flask equipped with a magnetic stirring bar, a thermocouple, a condenser and a rubber septum was charged with 100 mL of ethyl levulinate (obtained from Langfang Triple Well Chemicals Company, Ltd., Langfang, Hebei Province, China) and 5 mL of ethanol (100% , obtained from Sigma-Aldrich, St. Louis, MO). The flask was heated to reflux using a heating mantle. The boiling point stabilized at 154.2°C within 25 minutes. At 10 minute intervals, three consecutive 5 mL aliquots of ethanol were added to the flask through a rubber septum using a syringe and the boiling point was recorded. Finally, 1 mL of deionized water was added to the flask through the rubber. The boiling point was recorded after 10 minutes. Table 1 shows the recorded boiling points of the mixtures.

[0108]

[0109] Table 1. Boiling points of ethanol / ethyl levulinate mixture diaphragms.

Embodiment 2

[0111] A 500mL 3-necked flask was equipped with a magnetic stirring bar, dropping funnel, condenser and thermocouple. The flask was charged with 100.06g (0.694mol) ethyl levulinate (from Langfang Triple Well Chemicals Company, Ltd., Langfang City, Hebei Province, China) 11.48g (0.249mol) ethanol (99.5+%, from Acros Organics of Geel, Belgium) and sulfuric acid solution (prepared by mixing 0.575 mL concentrated sulfuric acid in 1.463 mL deionized water). The mixture was stirred and heated to reflux at 107.0°C in a 120°C oil bath. A mixture of 49.23 g (0.497 mol) furfuryl alcohol (99%, from Acros Organics) and 31.50 g (0.684 mol) ethanol was added dropwise to the reaction mixture over 108 minutes. After the addition was complete, the reaction was refluxed for another 1 h. The reaction flask was removed from the oil bath and allowed to cool to ambient temperature.

[0112] A sample of the crude reaction mixture was removed for analysis. The crude reaction product was dissolved...

Embodiment 3

[0115] A 500 mL 3-neck flask equipped with a magnetic stirring bar, dropping funnel, condenser and thermocouple was charged with 100.21 g (0.695 mol) ethyl levulinate (obtained from Langfang Triple Well Chemicals Company, Ltd., Langfang, Hebei Province, China) , 7.60 g (0.165 mol) of ethanol (99.5+%, from Acros Organics of Geel, Belgium) and sulfuric acid solution (prepared by mixing 0.575 mL of concentrated sulfuric acid in 1.463 mL of deionized water). The mixture was stirred and heated to reflux at 116.3°C in a 135°C oil bath. A mixture of 49.12 g (0.496 mol) furfuryl alcohol (99%, from Acros Organics) and 28.72 g (0.624 mol) ethanol was added dropwise to the reaction mixture over 115 minutes. After the addition was complete, the reaction was refluxed for another 1 h. The reaction flask was then removed from the oil bath and allowed to cool to room temperature.

[0116] About 50.445 g of the reaction mixture was transferred to a 250 mL flask and distillation was performed...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Provided is a process for the conversion of furfuryl alcohol into levulinate esters in a single step reaction comprising addition of the product levulinate ester to the reaction mixture of an alkanol and furfuryl alcohol in the presence of a strong protic acid catalyst, wherein high yield of the levulinate ester is accompanied by low amounts of tarry residue that do not precipitate or solidify in the reaction mixture.

Description

[0001] The application was filed on March 5, 2010 as a PCT International Patent Application in the name of a U.S. domestic enterprise, Segetis, Inc., and the applicant designates all countries except the United States, as well as Feng Jing, a citizen of the People's Republic of China, and Steven Donen, a citizen of the United States , Sergey Selifonov, US Citizen, and Brian Mullen, US Citizen, applicants designating the United States only, and claiming priority to US Patent Application Serial No. 61 / 157,746, filed March 5, 2009, entitled "Method For The Preparation Of Alkyl Levulinates" , which is incorporated herein by reference. technical field [0002] The present disclosure relates to a process for the preparation of levulinate from furfuryl alcohol. Background technique [0003] It is known to prepare levulinic acid and esters of levulinic acid from furfuryl alcohol. [0004] US Patent No. 2,738,367 discloses a method for preparing levulinic acid comprising heating an ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C51/00C07C59/185
CPCC07C67/00Y02P20/582
Inventor F・荆S・多南S・萨利富诺B・木兰
Owner SEGETIS
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com