Dimethylaminoethyl acrylate

Structural formula
General
Surname	Dimethylaminoethyl acrylate
other names	2- (dimethylamino) ethyl acrylate; 2-propenoic acid 2- (dimethylamino) ethyl ester; DMAEA; ADAME;
Molecular formula	C 7 H 13 NO 2
Brief description	yellowish liquid with a pungent, amine-like odor
External identifiers / databases
EC number	219-460-0
ECHA InfoCard	100.017.691
PubChem	17111
Wikidata	Q15632909
properties
Molar mass	143.19 g mol −1
Physical state	liquid
density	0.938 g cm −3 (20 ° C )
Melting point	−61 ° C
boiling point	172.8 ° C
Vapor pressure	68 Pa (20 ° C)
solubility	soluble in water (240 g / l) with hydrolysis, miscible with organic solvents
Refractive index	1.4368 (20 ° C)
safety instructions
H and P phrases	H: 226-302-311-330-314-317-400
	P: 210-280-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338-370 + 378
MAK	20 mg m −3
Toxicological data	455 mg kg −1 ( LD 50 , rat , oral ) ; 0.066 mg l −1 4 l −1 ( LC 50 , rat , inh. ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Dimethylaminoethyl acrylate (2-dimethylaminoethyl acrylate) or DMAEA is a functional unsaturated carboxylic acid ester with a tertiary amine group . It is a colorless to yellowish chemical compound that is miscible with water under hydrolysis, is liquid at room temperature and has a pungent, amine-like odor. DMAEA is an important acrylic monomer that gives copolymers basic properties.

presentation

The preparation of 2-dimethylaminoethyl acrylate is carried out by transesterification of Acrylsäureestern as methyl acrylate (R = -CH ₃ ) or ethyl acrylate (R = -CH ₂ -CH ₃ ) with 2- dimethylaminoethanol (z. B. stannoxanes) under basic catalysis with tin or Titanium compounds (e.g. tetraisopropyl orthotitanate ) with product yields over 95% of theory. be achieved.

Because of the high tendency of the starting material and product to polymerize, inhibitors, such as. B. phenothiazine , are added. The ethanol formed when ethyl acrylate is used forms an azeotrope with the ethyl acrylate of the composition ethanol / ethyl acrylate 72.7%: 26.3%, which boils at 77.5 ° C. under normal pressure and distills from the reaction mixture to achieve a high reaction yield becomes. The product is purified by vacuum distillation and stabilized with approx. 1,000ppm 4-methoxyphenol ( MEHQ ).

properties

Dimethylaminoethyl acrylate is a clear, colorless to slightly yellowish liquid with a pungent amine-like odor. It is miscible with water, has a basic reaction in it and quickly hydrolyzes to acrylic acid and dimethylaminoethanol (DMAE). In air it forms ignitable mixtures. DMAEA tends to polymerize spontaneously at elevated temperatures, when exposed to radiation and in the presence of radical initiators. It must therefore be sufficiently stabilized, stored in a dry place with exclusion of light in tightly closed containers in a cool place (<25 ° C). DMAEA is a T + substance because of its high inhalation toxicity.

use

Dimethylaminoethyl acrylate is a functional acrylic acid ester with basic properties and, as an α, β-unsaturated carbonyl compound, therefore adds nucleophiles in a Michael addition .

As a reactive monomer, DMAEA forms homopolymers and copolymers with acrylic acid and acrylic acid salts, amides and esters, as well as with methacrylates, acrylonitrile , maleic acid esters, vinyl acetate , vinyl chloride , vinylidene chloride , styrene , 1,3-butadiene , unsaturated polyesters and drying oils. In copolymers, DMAEA improves their nucleophilicity, basicity, water solubility and adhesion to polar negatively charged substrates, as well as the dyeability of acrylic fibers with anionic dyes. Such copolymers are used as resins and varnishes, coatings and adhesives, and as hair setting agents.

The most important use for DMAEA is quaternization with alkylating agents, e.g. B. methyl chloride , dimethyl sulfate , benzyl chloride , to the quaternary ammonium salt.

The most important representative is the reaction product with methyl chloride, trimethylammoniumethyl acrylate chloride (also called acryloxyethyltrimethylammonium chloride or ADQUAT or MADAME), which has the most pronounced cationic properties of all acrylates and is traded as an 80% aqueous solution. Copolymerization of ADQUAT with acrylamide leads to high molecular weight cationic polyacrylamides , which are widely used as coagulants and flocculants in ( waste ) water purification and as retention and drainage aids in paper production .

Individual evidence

↑ ^a ^b Arkema SA: 2-dimethylaminoethyl acrylate , accessed on December 6, 2016.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2- (dimethylamino) ethyl acrylate in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ SIDS Initial Assessment Report For SIAM 16, May 27-30, 2003, Paris, France: 2-DIMETHYLAMINOETHYL ACRYLATE (PDF; 2.4 MB)
↑ Safety data sheet DIMETHYLAMINOETHYL ACRYLATE, BASF AG, revised on December 13, 2010.
↑ Technical Information, Dimethylaminoethylacrylate, BASF AG
↑ P. Jiang et al., A new catalytic transesterification for the synthesis of N, N-dimethylaminoethyl acrylate with organotin catalyst , Catalysis Letters, vol. 110, 101, August 2006, doi : 10.1007 / s10562-006-0091-1 .
↑ Patent US6437173 : Process for the continuous manufacturing of dialkylaminoalkyl (meth) acrylates having a critical order of steps. Published on August 20, 2002 , Applicant: Elf Atochem SA, inventor P. Hurtel et al ..
↑ Patent EP1299345 : Process for the preparation of aminoalkyl (meth) acrylates. Published on April 9, 2003 , Applicant: Stockhausen GmbH, inventors J. Houben et al ..
↑ German Offenlegungsschrift DE 10127939 A1, process for the production of (meth) acrylic acid esters , inventor: M. Geissendörfer et al., Applicant: BASF AG, published May 29, 2002.
↑ Patent US4851568 : Process for the manufacture of dialkylaminoalkyl (meth) acrylates. Published on July 25 , Applicant: Elf Atochem SA, inventor P. Hurtel et al ..
↑ Technical Data Sheet, Ethyl Acrylate , BASF AG, June 2002.
↑ Patent EP0604844 : Process for the preparation of trialkylammonium alkyl (meth) acrylic compounds. Published on July 6, 1994 , Applicant: Rohm GmbH, inventor I. Bartholomae et al ..
↑ SNF Floerger , Water Treatment

[Arkema-1] Arkema SA: 2-dimethylaminoethyl acrylate , accessed on December 6, 2016.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2- (dimethylamino) ethyl acrylate in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[SIDS-3] SIDS Initial Assessment Report For SIAM 16, May 27-30, 2003, Paris, France: 2-DIMETHYLAMINOETHYL ACRYLATE (PDF; 2.4 MB)

[SIDAT_BASF-4] Safety data sheet DIMETHYLAMINOETHYL ACRYLATE, BASF AG, revised on December 13, 2010.

[5] Technical Information, Dimethylaminoethylacrylate, BASF AG

[6] P. Jiang et al., A new catalytic transesterification for the synthesis of N, N-dimethylaminoethyl acrylate with organotin catalyst , Catalysis Letters, vol. 110, 101, August 2006, doi : 10.1007 / s10562-006-0091-1 .

[7] Patent US6437173 : Process for the continuous manufacturing of dialkylaminoalkyl (meth) acrylates having a critical order of steps. Published on August 20, 2002 , Applicant: Elf Atochem SA, inventor P. Hurtel et al ..

[8] Patent EP1299345 : Process for the preparation of aminoalkyl (meth) acrylates. Published on April 9, 2003 , Applicant: Stockhausen GmbH, inventors J. Houben et al ..

[9] German Offenlegungsschrift DE 10127939 A1, process for the production of (meth) acrylic acid esters , inventor: M. Geissendörfer et al., Applicant: BASF AG, published May 29, 2002.

[10] Patent US4851568 : Process for the manufacture of dialkylaminoalkyl (meth) acrylates. Published on July 25 , Applicant: Elf Atochem SA, inventor P. Hurtel et al ..

[11] Technical Data Sheet, Ethyl Acrylate , BASF AG, June 2002.

[12] Patent EP0604844 : Process for the preparation of trialkylammonium alkyl (meth) acrylic compounds. Published on July 6, 1994 , Applicant: Rohm GmbH, inventor I. Bartholomae et al ..

[13] SNF Floerger , Water Treatment