Dimethylaminoethyl acrylate
Names | |
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Preferred IUPAC name
2-(Dimethylamino)ethyl prop-2-enoate | |
Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.017.691 |
EC Number |
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PubChem CID
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UNII | |
UN number | 3302 |
CompTox Dashboard (EPA)
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Properties | |
C7H13NO2 | |
Molar mass | 143.19 g·mol−1 |
Appearance | yellowish liquid with a pungent, amine-like odor[1] |
soluble in water (240 g/L[1]) upon hydrolysis, miscible with organic solvents[2] | |
Hazards | |
GHS labelling: | |
Danger | |
H226, H302, H311, H314, H317, H330, H400, H412 | |
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P333+P313, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethylaminoethyl acrylate (2-dimethylaminoethyl acrylate) or DMAEA is an unsaturated
Preparation
2-Dimethylaminoethyl acrylate is prepared via
During the reaction,
Properties
Dimethylaminoethyl acrylate is a clear, colorless to slightly yellowish liquid with a pungent amine-like odor. It is miscible with water, reacts bases and hydrolyzes rapidly to acrylic acid and
Use
Dimethylaminoethyl acrylate is an acrylic acid ester carrying a
As a reactive monomer, 2-dimethylaminoethyl acrylate forms homopolymers and copolymers with acrylic acid and acrylic acid salts, amides and esters, as well as
The most significant use for DMAEA is the quaternization with alkylating agents (for example chloromethane, dimethyl sulfate or benzyl chloride) to the quaternary ammonium salt.[9]
The most important compound is the reaction product with methyl chloride, trimethylammonium ethyl acrylate chloride.[10] It has the most pronounced cationic properties of all acrylates and is traded as an 80% aqueous solution. Copolymerization of trimethylammoniumethyl acrylate chloride with acrylamide leads to high molecular weight cationic polyacrylamides, which are widely used as coagulants and flocculants[11] in waste water purification and as retention and dewatering agents in papermaking.
References
- ^ a b c Record of 2-(Dimethylamino)ethylacrylat in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 1 February 2016.
- ^ Sicherheitsdatenblatt DIMETHYLAMINOETHYLACRYLAT, BASF AG, überarbeitet 13 December 2010.
- .
- ^ US 6437173, P. Hurtel et al., "Process for the continuous manufacturing of dialkylaminoalkyl (meth)acrylates having a critical order of steps", issued 2002-08-20, assigned to Elf Atochem S.A.
- ^ EP 1299345, J. Houben et al., "Verfahren zur Herstellung von Aminoalkyl(meth)acrylaten", issued 2003-04-09, assigned to Stockhausen GmbH
- ^ Deutsche Offenlegungsschrift DE 10127939 A1, Verfahren zur Herstellung von (Meth)acrylsäureestern, invent1: M. Geissendörfer et al., assign1: BASF AG, offengelegt 29 May 2002.
- ^ US 4851568, P. Hurtel et al., "Process for the manufacture of dialkylaminoalkyl (meth)acrylates", issued 1985-07-25, assigned to Elf Atochem S.A.
- ^ Technical Data Sheet, Ethyl Acrylate, BASF AG, June 2002.
- ^ EP 0604844, I. Bartholomae et al., "Verfahren zur Herstellung von Trialkylammoniumalkyl(meth)acryl-Verbindungen", issued 1994-07-06, assigned to Röhm GmbH
- ^ Arkema S.A.: 2-dimethylaminoethyl acrylate Archived 2016-07-31 at the Wayback Machine, retrieved 6 December 2016.
- ^ SNF Floerger, Water Treatment