2-(Dimethylamino)ethyl acrylate synthesis
- Product Name:2-(Dimethylamino)ethyl acrylate
- CAS Number:2439-35-2
- Molecular formula:C7H13NO2
- Molecular Weight:143.18
108-01-0
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$10.00/20mg
140-88-5
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$12.00/100ml
2439-35-2
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$11.00/1g
64-17-5
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$10.00/50g
Yield:2439-35-2 76%
Reaction Conditions:
with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;10H-phenothiazine;titanium(IV) tetraethanolate at 85 - 140;Product distribution / selectivity;Heating / reflux;
Steps:
EXAMPLE; In the following example, the flow rates correspond to a “residence time” of 3 hours for 9 compartments of the reactor, under reduced pressure: 91 kPa.A solution of ethyl acrylate (EA) and dimethylamino-ethanol (DMAE) in a molar ratio EA/DMAE=1.56 is prepared and stabilized with 2010 ppm of phenothiazine (PTZ) and 50 ppm of 4-HO TEMPO (tetramethyl-4-hydroxy-l-piperidinyloxy) by successively introducing into a 5 litre tank:1500 g of DMAE2628 g of EA8.3 g of PTZ0.21 g of 4-HO TEMPOThe catalyst used is prepared in the form of a commercial solution at 80% by weight ethyl titanate in previously prepared and ready-to-use dimethylaminoethanol.It is used at a rate of 2.85 g/h.The vacuum pump, the refrigeration system, the bubbling of dry air into the reactor R1, as well as heating the reactors R1 and R2 to 140° C., are set in operation. The mixture EA and DMAE (comprising PTZ and 4-HO TEMPO) is introduced into the reactor R1, with a flow rate of 278 g/h by the pump P1. When R1 is ¾ full (100 ml), R2 is fed from R1. The level of the reactor R1 is maintained constant by the presence of the accelerator pump P2 (flow rate of 694.5 g/h in a steady state).The pump P3 for introduction of the catalyst is actuated with a flow rate of 2.85 g/h.When the temperature at the head of the column is equal to the boiling temperature of the EA/EtOH azeotrope, the column is in a steady state (T=71° C.) and the drawing off can be carried out, with a reflux of 5 to 1 (Fraction F1). After bringing the installation on stream (6 hours), the reaction is carried out for a duration of 6 hours (2 repetitions of “residence time”), by drawing off the EA/EtOH azeotrope in the upper part of each of the 9 compartments. The crude reaction mixture is analyzed by gas chromatography in order to determine the selectivity and the yield of DAMEA (dimethylaminoethyl acrylate), as well as the conversion of DMAE.During this test 606.5 g of crude reaction mixture is recovered and 134.5 g in total of fraction F1 comprising the EA/EtOH azeotrope.In the reactor R2, the temperature has varied from 85° C. in the 1st compartment to 120° C. in the last compartment.Crude Reaction Mixture:DAMEA: 60.34%EA: 28.24%DMAE: 8.9%EtOH: 2.52%i.e. a DAMEA yield of 76% and a DMAE conversion of 82%, or a DAMEA selectivity of 92.7%.
References:
ARKEMA FRANCE US2008/161596, 2008, A1 Location in patent:Page/Page column 3
108-01-0
7 suppliers
$10.00/20mg
140-88-5
511 suppliers
$12.00/100ml
2439-35-2
240 suppliers
$11.00/1g
108-01-0
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$10.00/20mg
814-68-6
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$21.21/5gm:
2439-35-2
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$11.00/1g
108-01-0
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141-32-2
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$18.12/100 mL
2439-35-2
240 suppliers
$11.00/1g