C07D305/12

PROCESS FOR PRODUCTION OF ACRYLATES FROM EPOXIDES

In one aspect, the present invention encompasses integrated processes for the conversion of epoxides to acrylic acid derivatives and polyesters. In certain embodiments, the methods of the present invention comprise the steps of: providing a feedstock stream comprising an epoxide and carbon monoxide; contacting the feedstock stream with a metal carbonyl in a first reaction zone to effect conversion of at least a portion of the provided epoxide to a beta lactone; directing the effluent from the first reaction zone to a second reaction zone where the beta lactone is subjected to conditions that convert it to a compound selected from the group consisting of: an alpha beta unsaturated acid, an alpha beta unsaturated ester, an alpha beta unsaturated amide, and an optionally substituted polypropiolactone polymer; and isolating a final product comprising the alpha-beta unsaturated carboxylic acid, the alpha-beta unsaturated ester, the alpha-beta unsaturated amide or the polypropiolactone.

LIGAND-ENABLED BETA-C(sp3)-H LACTONIZATION FOR BETA-C-H FUNCTIONALIZATIONS
20220306595 · 2022-09-29 ·

Provided herein is a method of forming a beta-lactone from a carboxylic acid having a beta-carbon with a hydrogen atom disposed thereon. The method comprises contacting a carboxylic acid of formula (1) as described herein with an effective amount of a palladium(I) catalyst, an effective amount of an N-protected aminoacid ligand, and t-butylhydroperoxide in a solvent comprising hexafluoroisopropanol (HFIP), at about 60° C. to provide a beta-lactone of formula (2) as described herein.

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LIGAND-ENABLED BETA-C(sp3)-H LACTONIZATION FOR BETA-C-H FUNCTIONALIZATIONS
20220306595 · 2022-09-29 ·

Provided herein is a method of forming a beta-lactone from a carboxylic acid having a beta-carbon with a hydrogen atom disposed thereon. The method comprises contacting a carboxylic acid of formula (1) as described herein with an effective amount of a palladium(I) catalyst, an effective amount of an N-protected aminoacid ligand, and t-butylhydroperoxide in a solvent comprising hexafluoroisopropanol (HFIP), at about 60° C. to provide a beta-lactone of formula (2) as described herein.

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ACRYLIC ACID PRODUCTION PROCESS

Provided herein are methods of producing acrylic acid from bPL. Such methods involve the use of a heterogeneous catalyst, such as a zeolite at vapor phase conditions. The method may use a fixed bed, moving bed or fluidized contacting zone as the reactor configurations.

INTEGRATED METHODS FOR CHEMICAL SYNTHESIS
20210403446 · 2021-12-30 ·

The integrated processes herein provide improved carbon efficiency for processes based on coal or biomass gasification or steam methane reforming. Provided are also ethylene oxide carbonylation products such as beta-propiolactone and succinic anhydride having a bio-based content between 0% and 100%, and methods for producing and analyzing the same.

INTEGRATED METHODS FOR CHEMICAL SYNTHESIS
20210403446 · 2021-12-30 ·

The integrated processes herein provide improved carbon efficiency for processes based on coal or biomass gasification or steam methane reforming. Provided are also ethylene oxide carbonylation products such as beta-propiolactone and succinic anhydride having a bio-based content between 0% and 100%, and methods for producing and analyzing the same.

Proteasome inhibitors

The disclosure provides proteasome inhibitors that can be used to halt cell division of rapidly dividing cells by preventing the degradation of cell cycle-regulating proteins, such as cyclins, cyclin-dependent kinase inhibitors, and p53. The proteasome inhibitor compounds can be used to inhibit the proliferation of cancer cells.

Proteasome inhibitors

The disclosure provides proteasome inhibitors that can be used to halt cell division of rapidly dividing cells by preventing the degradation of cell cycle-regulating proteins, such as cyclins, cyclin-dependent kinase inhibitors, and p53. The proteasome inhibitor compounds can be used to inhibit the proliferation of cancer cells.

SYSTEMS AND METHODS FOR REGIOSELECTIVE CARBONYLATION OF 2,2-DISUBSTITUTED EPOXIDES
20210403445 · 2021-12-30 ·

Provided are methods of carbonylating cyclic substrates to produce carbonylated cyclic products. The cyclic substrates may be 2, 2-di substituted epoxides and the cyclic products may be β,β-di substituted lactones. The method may be carried out by forming and pressurizing a reaction mixture of the cyclic substrate, a solvent, carbon monoxide, and a [LA.sup.+][CO(CO)4.sup.−] catalyst, where [LA.sup.+] is a Lewis acid capable of coordinating to the cyclic substrate. The method may proceed with a regio selectivity of 90:10 or greater. The resulting carbonylated cyclic products may be converted to ketone aldol products that retain the stereochemistry and enantiomeric ratio of the carbonylated cyclic products.

SYSTEMS AND METHODS FOR REGIOSELECTIVE CARBONYLATION OF 2,2-DISUBSTITUTED EPOXIDES
20210403445 · 2021-12-30 ·

Provided are methods of carbonylating cyclic substrates to produce carbonylated cyclic products. The cyclic substrates may be 2, 2-di substituted epoxides and the cyclic products may be β,β-di substituted lactones. The method may be carried out by forming and pressurizing a reaction mixture of the cyclic substrate, a solvent, carbon monoxide, and a [LA.sup.+][CO(CO)4.sup.−] catalyst, where [LA.sup.+] is a Lewis acid capable of coordinating to the cyclic substrate. The method may proceed with a regio selectivity of 90:10 or greater. The resulting carbonylated cyclic products may be converted to ketone aldol products that retain the stereochemistry and enantiomeric ratio of the carbonylated cyclic products.