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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: GinaTageldin on August 06, 2017, 01:30:38 PM

Title: acryloyl chloride problem
Post by: GinaTageldin on August 06, 2017, 01:30:38 PM
from about 2 months i opened acryloyl chloride for the 1st time and i kept it in my locker. Today, i opened it and it turned from liquid to white solid?
Can anyone explain that? Is it a polymerization problem!!! and i would like to know if i have a chance to regain it back since it is difficult to be imported again also it is expensive
Title: Re: acryloyl chloride problem
Post by: chenbeier on August 06, 2017, 02:15:24 PM
Acryl compounds polymerize easily. What you can try is to put it in a round flasked and heat it up and do dry destillation. So you can get some monomer back.
Title: Re: acryloyl chloride problem
Post by: wildfyr on August 07, 2017, 09:15:34 AM
There is also a strong possibility that there is a bunch of acrylic acid in there. Acryloyol chloride hydrolyzes even more easily than it polymerizes.

You should keep it cold to minimize both of these.
Title: Re: acryloyl chloride problem
Post by: GinaTageldin on August 07, 2017, 01:26:25 PM
Acryl compounds polymerize easily. What you can try is to put it in a round flasked and heat it up and do dry destillation. So you can get some monomer back.
Thank you Sir
Does this process need a specific condition? since leakage of acryloyl chloride vapors are very dangerous.
Could you specify the distillation procedure from safety point of view?
How to avoid polymerization again?
Title: Re: acryloyl chloride problem
Post by: GinaTageldin on August 07, 2017, 01:28:43 PM
There is also a strong possibility that there is a bunch of acrylic acid in there. Acryloyol chloride hydrolyzes even more easily than it polymerizes.

You should keep it cold to minimize both of these.
I kept it in the refrigerator but nothing occurs, i think it is a polymer rather than acid as acrylic acid is also a liquid not solid.
Title: Re: acryloyl chloride problem
Post by: wildfyr on August 07, 2017, 02:39:58 PM
Most monomers come with a stabilizer like MEHQ or BHT. I'm a bit surprised, but acryloyl chloride does too according to Sigma's site (I'd expect an acid chloride to react with a phenol). If your monomer did not come with a stabilizer, you should add a small amount. This will prevent polymerization.
Title: Re: acryloyl chloride problem
Post by: GinaTageldin on August 07, 2017, 03:24:56 PM
Most monomers come with a stabilizer like MEHQ or BHT. I'm a bit surprised, but acryloyl chloride does too according to Sigma's site (I'd expect an acid chloride to react with a phenol). If your monomer did not come with a stabilizer, you should add a small amount. This will prevent polymerization.
It came with phenothiazine as a stabilizer