	US 11,912,648 B2
	Method for preparing C-H acidic (meth)acrylates
Marcel Treskow, Darmstadt (DE); Maik Caspari, Alsbach-Haehnlein (DE); Thorben Schütz, Alsbach-Hähnlein (DE); and Steffen Krill, Mühltal (DE)
Assigned to Evonik Operations GmbH, Essen (DE)
Appl. No. 17/260,226
Filed by EVONIK OPERATIONS GMBH, Essen (DE)
PCT Filed Jul. 10, 2019, PCT No. PCT/EP2019/068485 § 371(c)(1), (2) Date Jan. 14, 2021, PCT Pub. No. WO2020/016071, PCT Pub. Date Jan. 23, 2020.
Claims priority of application No. 18183907 (EP), filed on Jul. 17, 2018.
Prior Publication US 2021/0269393 A1, Sep. 2, 2021
Int. Cl. C07C 253/30 (2006.01); C07C 253/34 (2006.01)

CPC C07C 253/30 (2013.01) [C07C 253/34 (2013.01)]

12 Claims

1. A method for preparing C—H acidic (meth)acrylates of formula (I):

CH₂═CR¹—CO—NH—R²—NH—CO—CH²—CN (I)

(P)

wherein:

R¹is H or methyl;

R²is C_nH_mO_xN_y;

wherein:

n=2-15;

m=4-30;

x=0-4; and

y=0-4;

wherein said method comprises:

a) reacting an ester of cyanoacetic acid (A) with a diamine (B) in excess;

b) removing unreacted diamine (B) from the reaction solution to obtain the intermediate product (IP), an amino-functionalized cyanoacetamide;

c) obtaining product (P) by reacting intermediate product (IP) obtained in step b) with either:

c1) (meth)acrylic acid esters (MAD); or

c2) (meth)acrylic anhydride (MAD) or (meth)acryloyl halide (MAD);

d) optionally isolating (P) by extraction or crystallization.