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Author Topic: 1,2-dichloroethane synthesis ?  (Read 160 times)

NaBH4

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1,2-dichloroethane synthesis ?
« on: February 01, 2011, 03:14:46 PM »
Hi,

What do you think about that :

1) Absolute Ethanol + H2SO4 conc. (heat) ==> Ethylene
2) Immediately perform a clorination with Chlorine in aqueous saturated solution. (heat) ==> 1,2-dichloroethane/ene.


That is for the Phenmetrazine synthesis (PPA + Dichloroethane in catalytic conditions).  :D
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Wizard X

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Re: 1,2-dichloroethane synthesis ?
« Reply #1 on: February 01, 2011, 11:38:21 PM »
1,2-Dichloroethane production. http://en.wikipedia.org/wiki/1,2-Dichloroethane#Production

Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethene (ethylene) and chlorine.

1,2-Dichloroethene. http://en.wikipedia.org/wiki/1,2-Dichloroethene

MSDS: http://www.chemicalbook.com/ChemicalProductProperty_EN_CB4674238.htm
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jon

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Re: 1,2-dichloroethane synthesis ?
« Reply #2 on: February 02, 2011, 08:41:14 PM »
there are'nt any published procedures for phenmetrazine using dichloroethane.
the consensus is that you will get stringy nitrogeneous polymers and nitrogen mustards but, no o-alkylation.
« Last Edit: February 02, 2011, 08:43:08 PM by jon »

Sedit

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Re: 1,2-dichloroethane synthesis ?
« Reply #3 on: February 03, 2011, 02:34:30 AM »
Ethylene Glycol can be halogenated using standard alcohol SN2 reactions and while Cl- does not normally produce the yeilds that other halogens do one could halogenate Ethylene glycol using HCl and a catalyst such as Zinc chloride. I would suggest forming Dibromoethane using Phosphoric acid and NaBr simular to the process I outlined here for the formation of Bromoethane from Ethanol.

In this case however assure that there is an excess of HBr avalible to make sure you don't get Bromoethanol as a side product. I will in the future outline my synthesis for Dibromoethane in the future sometime but its been on the back burner for a while. I need it for Ethylene Diamine synthesis.
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Wizard X

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Re: 1,2-dichloroethane synthesis ?
« Reply #4 on: February 04, 2011, 12:15:09 AM »
Quote from: Sedit on February 03, 2011, 02:34:30 AM
Ethylene Glycol can be halogenated using standard alcohol SN2 reactions and while Cl- does not normally produce the yeilds that other halogens do one could halogenate Ethylene glycol using HCl and a catalyst such as Zinc chloride. I would suggest forming Dibromoethane using Phosphoric acid and NaBr simular to the process I outlined here for the formation of Bromoethane from Ethanol.

In this case however assure that there is an excess of HBr avalible to make sure you don't get Bromoethanol as a side product. I will in the future outline my synthesis for Dibromoethane in the future sometime but its been on the back burner for a while. I need it for Ethylene Diamine synthesis.

Ethylene Glycol is a primary alcohol. Primary alcohols do not react appreciably with Lucas reagent at room temperature.

Lucas' reagent. http://en.wikipedia.org/wiki/Lucas'_reagent The reaction is SN1 with secondary & tertiary alcohols
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Sedit

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Re: 1,2-dichloroethane synthesis ?
« Reply #5 on: February 04, 2011, 03:54:19 AM »
Zinc chloride was used to produce the only successful Ethylchloride experiment over at science madness even though the yeilds where shitty(<35% IIRC)they where higher then using only HCl alone. At elevated temperatures the reaction does proceed from what I understand but im all ears for a better catalyst to perform this chlorination on primary alcohols.

Thats why I suggest for the thread starter to use NaBr and H2SO4 to generate HBr insitu in order to brominate the diethylene glycol in order to form Dibromoethane. As long as the concentration of the H2SO4 is lower then 70% then the oxidative effects of Sulfuric acid will not form very much Br2 and the reaction should proceed nicely.
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atara

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Re: 1,2-dichloroethane synthesis ?
« Reply #6 on: February 04, 2011, 05:12:27 AM »
Furthermore dibromoethane is less volatile and less flammable, a better target in all respects IMO.

lugh

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Dichloroethane from Acetylene
« Reply #7 on: November 23, 2011, 02:25:51 AM »
Two patents in which acetylene is chlorinated to form dichloroethane are attached  8)
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