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Method of producing lower alcohols from glycerol

a technology of glycerol and alcohol, which is applied in the preparation of carbonyl compounds, oxygen-containing compounds, and preparations by oh group elimination, etc., can solve the problems of excessive high temperature and pressure, increase the capital cost of implementing these processes, and degrade reaction products, etc., and achieves the effect of higher catalyst loading

Inactive Publication Date: 2010-01-28
UNIVERSITY OF MISSOURI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes a process for converting glycerol to acetol with high purity and yield. The process involves using a catalyst to hydrogenate glycerol, resulting in the formation of a reaction mixture. By controlling the reaction conditions, including temperature, pressure, and water content, the process can produce exceptional yields of acetol with high purity. The patent also describes the use of a stripper gas to remove the reaction product from the reaction mixture. The gas can be reactive with the acetol reaction product, resulting in the formation of propylene glycol. The process can be carried out in a slurry phase or in a gas phase, with different reaction times depending on the desired outcome. Overall, the patent provides a valuable tool for producing high-quality acetol and related products from glycerol.

Problems solved by technology

Existing processes for the hydrogenation of glycerol to form other products are generally characterized by requirements for excessively high temperatures and pressures.
For example, high temperatures may degrade the reaction products.
Working pressures of several hundred bar create safety concerns and increase the capital costs of implementing these processes.
Most of such processes yield substantial impurities that may necessitate costly purification steps to isolate the desired reaction products.
None of the processes shown by these patents provide a direct reaction product mixture that is suitable for use as antifreeze.
None provide process conditions and reactions that suitably optimize the resultant reaction product mixture for direct use as antifreeze.
None address the use of unrefined crude natural glycerol feed stock, and none of these processes are based on reactive distillation.
The reaction may be performed at temperatures of up to 270° C., 280° C. or even 290° C. or 300° C.; however, the use of these increased temperature results in thermal degradation of the reaction product together with die-reactions, and so is not recommended for applications where high purity of the reaction product is required.

Method used

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  • Method of producing lower alcohols from glycerol
  • Method of producing lower alcohols from glycerol
  • Method of producing lower alcohols from glycerol

Examples

Experimental program
Comparison scheme
Effect test

example 1

Confirmation of Reaction Mechanism

[0059]An experiment was performed to validate the reaction mechanism 200. Reactions were conducted in two steps, namely, Steps 1 and 2. In step 1, relatively pure acetol was isolated from glycerol. Temperature ranged from 150° C. to 250° C. and more specifically from 180° C. to 220° C. There was an absence of hydrogen. Pressure ranged from 1 to 14 psi (6.9 MPa to 96 MPa) more specifically from 5 to 10 psi (34 MPa to 69 MPa). A copper-chromite catalyst was present. In Step 2, the acetol formed in Step 1 was further reacted in presence of hydrogen to form propylene glycol at a temperature ranging from 150° C. to 250° C. and more preferably between 180 to 220° C. Excess hydrogen was added at a hydrogen over pressure between 1 to 25 bars using the same catalyst.

[0060]It was observed in the Step 2 of converting acetol to propylene glycol that lactaldehyde was formed. Propylene glycol is also formed by the hydrogenation 208 of lactaldehyde 302, as illustr...

example 2

Simultaneous Dehydration and Hydrogenation Using Various Catalysts and Reagent Mixtures

[0063]A variety of reaction procedures were performed to show that reaction efficiency may be optimized at any process conditions, such as reaction time, temperature, pressure and flash condition by the selection or choice of catalyst for a given polyhydric feedstock.

[0064]Table 1 reports the results of reacting glycerol in the presence of hydrogen and catalyst to form a mixture containing propylene glycol. The reaction vessel contained 80 grams of refined glycerol, 20 grams of water, 10 grams of catalyst, and a hydrogen overpressure of 200 psig. The reactor was a closed reactor that was topped off with excess hydrogen. The reaction occurred for 24 hours at a temperature of 200° C. All catalysts used in this Example were purchased on commercial order and used in the condition in which they arrived.

TABLE 1Summary of catalyst performances based on 80 grams ofglycerol reported on a 100 grams basis.Ca...

example 3

Packed-Bed Reactor Embodiments

[0084]One method of preparing acetol and propylene glycol from glycerol includes a gas phase reaction at a temperature ranging from 150° to 280° C. in a packed-bed reactor. In some embodiments this temperature is more preferably from 180° C. to 240° C. or 250° C. to avoid thermal degradation of reaction products. The reactions described herein occurred in a packed-bed reactor. The pressures in the reaction vessel are preferably from 0.02 to 25 bars and in some embodiments this pressure is more-preferably between 0.02 and 10 bars. Most preferably, the reaction pressure exists within a range from 0.2 and 1.2 bars.

[0085]FIG. 4 provides a block flow diagram of process equipment 400 including an evaporator 426 for creating a vapor reaction mixture 427. Non-volatile components 428 in the polyhydric feed 104 are removed from the evaporator 426 in a continuous or semi-batch mode. The evaporator 426 is particularly effective for processing crude glycerol that co...

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Abstract

A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 2000 C, at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 2500 C at pressures from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium.

Description

RELATED APPLICATIONS[0001]This application is a continuation-in-part of U.S. application Ser. No. 11 / 510,992 filed Aug. 28, 2006 claiming benefit of priority to U.S. provisional application Ser. No. 60 / 731,673 filed Oct. 31, 2005, and is a continuation-in-part of U.S. application Ser. No. 11 / 088,603 filed Mar. 24, 2005, which claims benefit of priority to U.S. provisional patent application Ser. No. 60 / 556,334 filed Mar. 25, 2004 and is a continuation-in-part of U.S. patent application Ser. No. 10 / 420,047 filed Apr. 21, 2004, which claims benefit of priority to U.S. provisional patent application Ser. Nos. 60 / 374,292, filed Apr. 22, 2002 and 60 / 4103,24, filed Sep. 13, 2002, all of which are incorporated by reference herein.BACKGROUND[0002]1. Field of The Invention[0003]This invention relates generally to a process for value-added processing of fats and oils to yield glycerol and glycerol derivatives. More particularly, the process converts glycerol to acetol and / or propylene glycol,...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09K5/00C07C31/20B01J19/00
CPCC07C29/145C07C29/60C07C45/52C09K5/20C12C11/02C07C31/205C07C49/17
Inventor SUPPES, GALEN J.SUTTERLIN, WILLIAM RUSTY
Owner UNIVERSITY OF MISSOURI
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