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Topic: Reduction of a Carboxylic Acid Without Standard Reagents  (Read 4385 times)

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Offline neilcopes

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Reduction of a Carboxylic Acid Without Standard Reagents
« on: July 30, 2008, 03:53:44 PM »
Okay, I’ve been thinking on this one for days.  I have a carboxylic acid and I need to make a primary alcohol, but I don’t have borane (of any kind) or lithium aluminum hydride (or even sodium borohydride for that matter).  All I have are more common, less toxic reagents.  I’m guessing that this problem involves a multistep solution.  Any ideas?

Offline neilcopes

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Re: Reduction of a Carboxylic Acid Without Standard Reagents
« Reply #1 on: July 30, 2008, 06:05:07 PM »
By the way, I’m a biology student.  This problem concerns the production of dodecanol from lauric acid.  Dodecanol is one of the products necessary for the generation of sodium dodecyl sulfate, which is used extensively in biotechnology (and shampoo).  Alternatively, because lauric acid begins as a triglyceride (an ester), the problem could be viewed in terms of going from an ester to a primary alcohol.  However, I don’t know if that would make things simpler.  Also, since this is primarily an organic chemistry question, I assumed this problem belongs here more than in the chemical biology forum.

Offline macman104

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Re: Reduction of a Carboxylic Acid Without Standard Reagents
« Reply #2 on: July 30, 2008, 06:20:01 PM »
By the way, I’m a biology student.  This problem concerns the production of dodecanol from lauric acid.  Dodecanol is one of the products necessary for the generation of sodium dodecyl sulfate, which is used extensively in biotechnology (and shampoo).  Alternatively, because lauric acid begins as a triglyceride (an ester), the problem could be viewed in terms of going from an ester to a primary alcohol.  However, I don’t know if that would make things simpler.  Also, since this is primarily an organic chemistry question, I assumed this problem belongs here more than in the chemical biology forum.
Why do you say lauric acid begins as a triglyceride?  It is an acid, no ester.  Also, if you don't have access to standard reducing agents, I'm not sure how you would go about accomplishing this.  What is your end goal?  Are you trying to make sodium dodecyl sulfate?  Dodecanol is not very expensive to purchase, neither are the standard reducing agents for that matter.

I guess more importantly, what do you have access to...

Offline neilcopes

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Re: Reduction of a Carboxylic Acid Without Standard Reagents
« Reply #3 on: July 30, 2008, 07:43:53 PM »
Essentially, I’m looking at the problem of starting with a raw ingredient - coconut oil - and transforming it into sodium dodecyl sulfate.  Coconut oil is composed of triglycerides, which are simply fatty acids connected to glycerol by ester bonds.  When the oil is ingested,  the body naturally hydrolyzes the ester bonds, releasing the free fatty acids.  Lauric acid is the primary fatty acid found in coconut oil (44.6%).  The lauric acid from coconut oil is also the standard starting material in the production of sodium dodecyl sulfate (also referred to as sodium lauryl sulfate).  In the standard manufacturing process, lauric acid is reduced to dodecanol, which is then esterified with sulfuric acid and neutralized with sodium carbonate.  Sure, I could just buy dodecanol, but that takes all of the fun out of it.  As for what I have access to: pretty much anything except the reducing agents mentioned above, and any type of hydrogenation process that involves high pressure.  Okay, so I suppose that I could just buy some lithium aluminum hydride, but once again … the fun!  That would remove the fun!

Offline nj_bartel

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Re: Reduction of a Carboxylic Acid Without Standard Reagents
« Reply #4 on: July 30, 2008, 08:10:43 PM »
And the fun is in having other people tell you what to do?   ???

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