Process for the production of furfural using a water immiscible organic solvent

a technology of immiscible organic solvent and production process, applied in the field of furan derivative production, can solve the problems of affecting heat transfer characteristics and affecting the fouling of exposed reactor surfaces

Inactive Publication Date: 2021-03-11
DUPONT IND BIOSCIENCES USA LLC
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This approach reduces reactor fouling, enhances furan derivative yields, and allows for more efficient separation and purification of products, thereby improving the overall process efficiency and product quality.

Problems solved by technology

A major difficulty with known methods for dehydration of sugars is the formation of undesirable resinous material called humins that not only leads to yield loss but can also lead to the fouling of exposed reactor surfaces and negatively impact heat transfer characteristics.

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
  • Process for the production of furfural using a water immiscible organic solvent
  • Process for the production of furfural using a water immiscible organic solvent
  • Process for the production of furfural using a water immiscible organic solvent

Examples

Experimental program
Comparison scheme
Effect test

examples

[0072]Unless otherwise specified, all the reagents are available from the Sigma-Aldrich Chemical Co (St. Louis, Mo.) and / or Alfa Aesar (Ward Hill, Mass.).[0073]In the examples, the following abbreviations are used:[0074]MN—1-methyl naphthalene[0075]2TBP—2-tert-butyl phenol[0076]2SBP—2-sec-butyl phenol[0077]NP—p-nonyl phenol

example a

[0078]Determination of the stability of the water immiscible solvent at reaction temperatures.

[0079]Three organic solutions were prepared by combining 1-methylnaphthalene (MN) with the desired alkyl phenol. 1 weight percent of tert-butylbenzene and sulfolane were added as dual internal standards to the organic solutions (only tert-butylbenzene was needed for quantitative analysis), making these solutions 74 weight percent 1-methylnaphthalene, 24 weight percent of the alkyl phenol and 2 weight percent internal standard. The desired alkyl phenols were 2-tertbutylphenol (2TBP), 2-sec-butylphenol (2SBP) and p-nonylphenol (NP). 1 milliliter of each solution was added to 8 different metal tube reactors. To each tube reactor was added 10 microliters (1 volume percent) of an aqueous acidic solution containing between 25 and 80 weight, percent sulfuric acid.

[0080]The metal tubes were sealed and were then put into a hot oil bath (initially set at 170° C., this cooled to about 150° C. upon loa...

example b

[0085]Water uptake in a water immiscible organic solvent

[0086]An excess of water (greater than 20 wt %) was added to the organic solvents and the mixtures were vigorously agitated for several minutes. The samples were allowed to sit overnight before being separated by centrifugation at 4000 rpm for 5 min. The water content, of the organic solvent samples was then measured by adding a known mass of the solvent sample to a Mettler Toledo DL31 Karl Fischer Titrator. The titrator used AQUASTARO CombiTitrant 5 titrant and HYDRANALO Methanol Dry solvent. Samples were run in sets of four, and the average value of the four runs is reported in TABLE 2.

TABLE 2Water inAromaticorganicPhenolhydrocarbonAromaticsolventExample(wt %)Phenol(wt %)hydrocarbon(wt %)25 52TBP95MN0.126 102TBP90MN0.227 252TBP75MN0.428 502TBP50MN1.0Comparative1002TBP 04.0AComparative1002TBP 04.2B

[0087]The results in TABLE 2 show that the water immiscible organic solvent of the disclosure absorbs a significantly less amount o...

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

The disclosure relates to an efficient process for the production of a furan derivative from C5 and / or C6 sugars. The process utilizes a water immiscible organic solvent system comprising at least one alkyl phenol and at least one alkylated naphthalene.

Description

[0001]FIELD OF THE DISCLOSURE[0002]The present disclosure is directed towards the production of furan derivatives, especially, furfural, 5-hydroxymethylfurfural, and furfuryl alcohol from C5 and C6 sugars.CROSS-REFERENCE TO RELATED APPLICATION[0003]This application is a continuation of U.S. patent application Ser. No. 16 / 818645, filed Mar. 13, 2020 which is a continuation of U.S. patent application Ser. No. 16 / 303005, filed Nov. 19, 2018 which is a 371 of International Patent Application No. PCT / US17 / 35626, filed on Jun. 2, 2017 which claims the benefit of U.S. Provisional Application No. 62 / 345031, filed Jun. 3, 2016, the entire disclosure of which is incorporated herein by reference.[0004]BACKGROUND OF THE DISCLOSURE[0005]Furfural and related compounds, such as 5-hydroxymethyl furfural (HMF), are useful precursors and starting materials for industrial chemicals for use as pharmaceuticals, herbicides, stabilizers, fuels, fuel additives and polymers. The current furfural manufacturi...

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
Patent Type & AuthorityApplications(United States)
IPC IPC(8): C07D307/50C07D307/48
CPCC07D307/50C07D307/48C07D307/46
InventorHUTCHENSON, KEITH W.CARLSON, TORREN RYANDICKINSON, JACOB G.DREW, DAVID WILLIAMFAGAN, PAUL JOSEPHGALLAGHER, FRANCIS G.LIBERIS, ISABELMERSMAN, KENNETHSUNSHINE, GREGG
OwnerDUPONT IND BIOSCIENCES USA LLC