Systems and Processes for Producing Organic Acids Direct from Beta-Lactones

a technology of organic acids and betalactones, which is applied in the field of reactor systems and processes for producing organic acids directly from betalactones, can solve the problems of high reaction rate, capital intensive process, additional equipment and operating costs, etc., and achieves economic benefits and high purity

Inactive Publication Date: 2018-10-25
NOVOMER INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent discusses the need for better and more efficient ways to make higher purity organic acid products from beta-lactone reagents. The invention provides methods to achieve this goal and the benefits of using beta-lactone reagents in organic acid production are discussed. The technical effect is that economically viable and high purity organic acid products can be produced using these reagents.

Problems solved by technology

Due to corrosiveness of phosphoric acid and slow reaction rate this process is capital intensive.
This leads to the need to separate water from the produced acrylic acid resulting in additional equipment and operating costs.
This process capital intensive and has high operating costs as highly exothermic polymerization reaction is followed by highly endothermic thermolysis reaction.

Method used

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  • Systems and Processes for Producing Organic Acids Direct from Beta-Lactones
  • Systems and Processes for Producing Organic Acids Direct from Beta-Lactones
  • Systems and Processes for Producing Organic Acids Direct from Beta-Lactones

Examples

Experimental program
Comparison scheme
Effect test

example 1

n of β-methyl-β-propiolactone to trans-2-butenoic acid Using a Zeolite

[0072]This Example demonstrates the production of trans-2-butenoic acid from bPL derivative using a zeolite.

[0073]A mixture of β-methyl-β-propiolactone (3.0 g) and phenothiazine (9.0 mg) is added using a needle valve to a mixture of sulfolane (40.0 g) and Zeolite Y hydrogen (20.0 g) at about 165° C. with 50 psi of carbon monoxide. Zeolite Y hydrogen (80:1 mole ratio SiO2 / Al2O3, powder S.A. 780 m2 / g) is dried under vacuum at about 100° C. for one day before use. Phenothiazine is the polymerization inhibitor used. Sulfolane is the solvent used, and is dried over 3 Å molecular sieves prior to use. β-methyl-β-propiolactone is added slowly using the needle valve over about 8.6 minutes. The reaction mixture is heated to about 170° C. to produce trans-2-butenoic acid.

[0074]The reaction is monitored by infrared spectroscopy (IR). The reaction is observed to be completed after about 3 hours, when no β-methyl-β-propiolacton...

example 2

se Conversion of β-methyl-β-propiolactone to trans-2-butenoic acid Using an H-ZSM-5

[0076]Vapor phase conversion of β-methyl-β-propiolactone to trans-2-butenoic acid is performed in packed-bed reactor using H-ZSM-5 (ACS Materials LLC, Si:Al=38, diameter 2 mm, surface area >=250 m2 / g) as a catalyst. 11 grams of H-ZSM-5 catalyst is loaded into jacketed stainless steel 316 pipe reactor (ID 0.5 inch), the catalyst is supported between glass beads columns (stainless steel wool is placed below and above glass beads). Multi-point thermocouple is inserted through the center of the reactor and hot oil is circulated through the reactor jacket to maintain the desired reactor temperature. β-methyl-β-propiolactone is fed to the reactor by means of saturator: N2 at the rate of 28 g / hr is flown into the bottom of the vessel containing liquid β-methyl-β-propiolactone at a=94° C., this results in β-methyl-1-propiolactone feed rate of 5 g / hr. The pressure of reactor and saturator is maintained at 9.5 ...

example 3

n of 3-methyloxetan-2-one to Methacrylic Acid Using a Zeolite

[0077]This Example demonstrates the production of methacrylic acid from 3-methyloxetan-2-one using a zeolite.

[0078]A mixture of 3-methyloxetan-2-one (3.0 g) and phenothiazine (9.0 mg) is added using a needle valve to a mixture of sulfolane (40.0 g) and Zeolite Y hydrogen (20.0 g) at 165° C. with 50 psi of carbon monoxide. Zeolite Y hydrogen (80:1 mole ratio SiO2 / Al2O3, powder S.A. 780 m2 / g) is dried under vacuum at 100° C. for one day before use. Phenothiazine is the polymerization inhibitor used. Sulfolane is the solvent used, and is dried over 3 Å molecular sieves prior to use. 3-methyloxetan-2-one is added slowly using the needle valve over about 8.6 minutes. The reaction mixture is heated to 170° C. to produce methacrylic acid.

[0079]The reaction is monitored by infrared spectroscopy (IR). The reaction is observed to be completed after about 3 hours, when no 3-methyloxetan-2-one is detectable by IR.

[0080]The zeolite is ...

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Abstract

Provided herein are reactor systems and processes for producing organic acids directly from beta-lactones. Such reactor systems and processes involve the use of a heterogeneous catalyst, such as a zeolite at vapor phase conditions. The reactor systems and processes may use a fixed bed, moving bed or fluidized contacting zone as reactor configurations.

Description

CROSS-REFERENCES[0001]The present application claims benefit from U.S. application Ser. No. 15 / 640,197 filed Jun. 30, 2017, which claims benefit from U.S. application Ser. No. 15 / 464,346, filed Mar. 21, 2017, which claims benefit from U.S. Provisional Application No. 62 / 311,262, filed Mar. 21, 2016, which are hereby incorporated by reference in their entireties as if fully restated herein.FIELD OF THE INVENTION[0002]This invention generally relates to reactor systems and processes for producing organic acids directly form beta-lactones.BACKGROUND OF THE INVENTION[0003]The production and use of organic acids such as acrylic acid (AA) has grown significantly in recent decades as the demand for polyorganic acids such as polyacrylic acid-based superabsorbent polymers (SAPs) has grown. SAPs are used extensively for the manufacture of diapers, adult incontinence products, and feminine hygiene products, as well as in agricultural applications.[0004]Currently, commercial acrylic acid is typ...

Claims

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Application Information

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IPC IPC(8): C07C51/09C07C309/22C07F7/18C07D307/54C07D317/30C07C231/12
CPCC07C51/09C07C309/22C07F7/1892C07D307/54C07D317/30C07C231/12B01J3/006B01J8/067B01J2219/0004C07C67/28C07F7/1804Y02P20/582C07C57/08C07C57/04C07C57/52C07C59/58C07C59/68C07C59/62C07C59/42C07C57/13C07C69/145C07C69/78C07C69/54C07C69/593
Inventor SOOKRAJ, SADESH H.
Owner NOVOMER INC
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