Bio-derived olefin synthesis

J.P.M. Sanders (Inventor), J. van Haveren (Inventor), E.L. Scott (Inventor), D.S. van Es (Inventor), J.E.L. le Notre (Inventor)

Research output: PatentOther research output

Abstract

Disclosed is a method for the combined synthesis of at least two vinylic monomers, at least one of which being an acrylic compound, comprising subjecting a monoconjgated alkene-1-carboxylic compound to reaction with a C2-C4 alkene under conditions of olefin cross-metathesis. The invention is particularly useful for extracting value from protein side streams. Upon protein hydrolysis, suitable amino acids (preferably phenylalanine or tyrosine) are subjected to reductive amination so as to form the corresponding alkene-1-carboxylic acid. Preferably after esterification and separation, this is used in cross-metathesis for the concomitant production of styrene resp. hydroxy styrene, and acrylates. The invention is applicable more widely, to the synthesis of olefins on the basis of carbohydrates, naturally occurring phenolic components, natural protein resources, or amino acids obtained from fermentations.
Original languageEnglish
Patent numberWO2011002284
Priority date2/07/09
Publication statusPublished - 6 Jan 2011

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Alkenes
Styrene
Patents and inventions
Acrylates
Amination
Amino Acids
Proteins
Esterification
Carboxylic Acids
Phenylalanine
Fermentation
Acrylics
Tyrosine
Hydrolysis
Monomers
Carbohydrates

Cite this

Sanders, J. P. M., van Haveren, J., Scott, E. L., van Es, D. S., & le Notre, J. E. L. (2011). Bio-derived olefin synthesis. (Patent No. WO2011002284).
Sanders, J.P.M. (Inventor) ; van Haveren, J. (Inventor) ; Scott, E.L. (Inventor) ; van Es, D.S. (Inventor) ; le Notre, J.E.L. (Inventor). / Bio-derived olefin synthesis. Patent No.: WO2011002284.
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abstract = "Disclosed is a method for the combined synthesis of at least two vinylic monomers, at least one of which being an acrylic compound, comprising subjecting a monoconjgated alkene-1-carboxylic compound to reaction with a C2-C4 alkene under conditions of olefin cross-metathesis. The invention is particularly useful for extracting value from protein side streams. Upon protein hydrolysis, suitable amino acids (preferably phenylalanine or tyrosine) are subjected to reductive amination so as to form the corresponding alkene-1-carboxylic acid. Preferably after esterification and separation, this is used in cross-metathesis for the concomitant production of styrene resp. hydroxy styrene, and acrylates. The invention is applicable more widely, to the synthesis of olefins on the basis of carbohydrates, naturally occurring phenolic components, natural protein resources, or amino acids obtained from fermentations.",
author = "J.P.M. Sanders and {van Haveren}, J. and E.L. Scott and {van Es}, D.S. and {le Notre}, J.E.L.",
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Sanders, JPM, van Haveren, J, Scott, EL, van Es, DS & le Notre, JEL 2011, Bio-derived olefin synthesis, Patent No. WO2011002284.

Bio-derived olefin synthesis. / Sanders, J.P.M. (Inventor); van Haveren, J. (Inventor); Scott, E.L. (Inventor); van Es, D.S. (Inventor); le Notre, J.E.L. (Inventor).

Patent No.: WO2011002284.

Research output: PatentOther research output

TY - PAT

T1 - Bio-derived olefin synthesis

AU - Sanders, J.P.M.

AU - van Haveren, J.

AU - Scott, E.L.

AU - van Es, D.S.

AU - le Notre, J.E.L.

PY - 2011/1/6

Y1 - 2011/1/6

N2 - Disclosed is a method for the combined synthesis of at least two vinylic monomers, at least one of which being an acrylic compound, comprising subjecting a monoconjgated alkene-1-carboxylic compound to reaction with a C2-C4 alkene under conditions of olefin cross-metathesis. The invention is particularly useful for extracting value from protein side streams. Upon protein hydrolysis, suitable amino acids (preferably phenylalanine or tyrosine) are subjected to reductive amination so as to form the corresponding alkene-1-carboxylic acid. Preferably after esterification and separation, this is used in cross-metathesis for the concomitant production of styrene resp. hydroxy styrene, and acrylates. The invention is applicable more widely, to the synthesis of olefins on the basis of carbohydrates, naturally occurring phenolic components, natural protein resources, or amino acids obtained from fermentations.

AB - Disclosed is a method for the combined synthesis of at least two vinylic monomers, at least one of which being an acrylic compound, comprising subjecting a monoconjgated alkene-1-carboxylic compound to reaction with a C2-C4 alkene under conditions of olefin cross-metathesis. The invention is particularly useful for extracting value from protein side streams. Upon protein hydrolysis, suitable amino acids (preferably phenylalanine or tyrosine) are subjected to reductive amination so as to form the corresponding alkene-1-carboxylic acid. Preferably after esterification and separation, this is used in cross-metathesis for the concomitant production of styrene resp. hydroxy styrene, and acrylates. The invention is applicable more widely, to the synthesis of olefins on the basis of carbohydrates, naturally occurring phenolic components, natural protein resources, or amino acids obtained from fermentations.

M3 - Patent

M1 - WO2011002284

ER -

Sanders JPM, van Haveren J, Scott EL, van Es DS, le Notre JEL, inventors. Bio-derived olefin synthesis. WO2011002284. 2011 Jan 6.