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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Aseelia on May 05, 2015, 05:36:25 AM

Title: thionyl chloride and phosphorus chloride in formation of ester
Post by: Aseelia on May 05, 2015, 05:36:25 AM

whats more safe & easy in use socl2 or pcl5 in formation of acid chloride & ester ??
(I put acid + alcohol+ socl2 or pcl5) ....my acid suspended in alcohol 
and what precaution i can take to use both... I know that socl2 need percautions due to so2 but if the pcl5 give me the ester with good yeild and less hazard I'm ok with it ...  :)
last question i cant do fraction distillation to the side reactions...so I was thinking after finish reaction using sodium bi carbonate to neutralization... any idea for this problem too??!! how i get pure ester

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Hunter2 on May 05, 2015, 06:58:26 AM

Which ester you want to produce?

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Aseelia on May 05, 2015, 07:23:57 AM

I want to produce ethyl ester or methyl one with any aromatic acid
does it make difference?? I mean the type of ester?!

Thanks for thoughts

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Hunter2 on May 05, 2015, 07:40:06 AM

Thionycloride is better choice., because you have gas evaporation. Phosphrouschloride produce phosphorous acid, not easy to remove.

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Aseelia on May 05, 2015, 07:47:06 AM

Quote from: Hunter2 on May 05, 2015, 07:40:06 AM

Thionycloride is better choice., because you have gas evaporation. Phosphrouschloride produce phosphorous acid, not easy to remove.

and what about neutralization with sod.bicarbonate???
and if i use socl2 whats the best method (procedure  if i cant do fraction distillation..)

thanks for consideration, :)

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Hunter2 on May 05, 2015, 08:04:39 AM

You can use neutralization, but then you have to remove the sodium salts. Question is: is the ester soluble in water or better in an solvent and you can extract it.

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Aseelia on May 05, 2015, 08:24:00 AM

Quote from: Hunter2 on May 05, 2015, 08:04:39 AM

You can use neutralization, but then you have to remove the sodium salts. Question is: is the ester soluble in water or better in an solvent and you can extract it.

bingo ;D

thats helpful , now i can use pcl5 with DMF as catalyst ,, but do you think the order of addition may affect the reaction ??
i put acid + alcohol then pcl5 drp wise with stirring then left it to reflux

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Hunter2 on May 05, 2015, 08:31:23 AM

Better is to have the acid and the chloride first to create the acidchloride. This can react later with the alcohol.

Title: Re: thionyl chloride and phosphorus chloride in formation of ester
Post by: Aseelia on May 05, 2015, 08:36:21 AM

thanks.. Hunter2 for your thoughts,
I will work on it & I will see my results  8)