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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: iyc on November 25, 2004, 05:58:53 AM

Title: Making Nylon 6.6
Post by: iyc on November 25, 2004, 05:58:53 AM

In manufacturing Nyon 6.6, a solution of hexane-1,6-diamine(in NaOH_(aq)) is added to a solution of hexanedioyl dichloride (in 1,1,1-trichloromethane).

- What is the use of aqueous sodium hydroxide and 1,1,1-trichloromethane ???
- If replace the aqueous sodium hydroxide with 1,1,1-trichloromethane, what will happen ???
- If replace the aqueous sodium hydroxide with water, what will happen ???

Title: Re:Making Nylon 6.6
Post by: AWK on November 25, 2004, 08:31:46 AM

Chloroform is just a solvent for organic compounds. You have water in solution of NaOH.
In classic Schotten-Baumann reaction other basic compounds can be used, eg: Na2CO3, CaO, BaO, MgO, NaHCO3 or CH3COONa.

Title: Re:Question about Making Nylon 6.6 reply
Post by: iyc on November 25, 2004, 10:10:21 AM

Excuse me. I would like to ask one more question.
Is it possible that NaOH(aq) is used to provide a alkaline medium to prevent the amine from dissociate( I don't know whether it is described as dissociate) resulting into no raw material for the reaction?

Title: Re:Making Nylon 6.6
Post by: AWK on November 26, 2004, 01:11:59 AM

Any base in this reaction is used for removing of HCl. otherway you should use more amine (it is also basic) and amine hydrochloride is formed.

Title: Re:Making Nylon 6.6
Post by: iyc on November 26, 2004, 07:15:36 AM

But, what is the aim to remove the HCl molecules?

Title: Re:Making Nylon 6.6
Post by: Donaldson Tan on November 26, 2004, 10:20:51 AM

nylon with traces of hydrochloric acid isn't safe to handle. it's corrosive.

Title: Re:Making Nylon 6.6
Post by: movies on November 26, 2004, 03:23:28 PM

As AWK alluded to, if you didn't use another base then you would need at least 2 equivalents of amine since the HCl formed in the reaction would protonate any free amine and make it unreactive in the polymerization reaction.