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Topic: unsaturation in fatty acids  (Read 3044 times)

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Offline dilip786

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unsaturation in fatty acids
« on: January 25, 2012, 02:14:08 PM »
I m stuck at a problem,which i googled but unable to find solution my problem is
"i want to convert saturated fatty acids into unsaturated fatty acid and i was thinking to use alchoalic KOH since it perfrom elimination reaction but in this case it will give saponifiaction reaction,so i want to know a simple and easy reaction or any regent which i can use to create unstauration in fatty acid-suggestions are welcome
dilip singh

Offline discodermolide

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Re: unsaturation in fatty acids
« Reply #1 on: January 25, 2012, 03:20:51 PM »
I m stuck at a problem,which i googled but unable to find solution my problem is
"i want to convert saturated fatty acids into unsaturated fatty acid and i was thinking to use alchoalic KOH since it perfrom elimination reaction but in this case it will give saponifiaction reaction,so i want to know a simple and easy reaction or any regent which i can use to create unstauration in fatty acid-suggestions are welcome
dilip singh

How many double bonds doe you require. One method that springs to mind is (per)-bromination followed by base elimination of HBR's
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Offline Honclbrif

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Re: unsaturation in fatty acids
« Reply #2 on: January 26, 2012, 10:59:33 AM »
"i want to convert saturated fatty acids into unsaturated fatty acid"

Just creating a double bond (or frankly doing any chemistry at all) in the middle of a saturated alkyl chain with any degree of specificity or selectivity is nearly impossible. Is there a specific site mentioned in the question?

More to the point: are you sure you didn't get the question backwards and is not really "convert an unsaturated fatty acid to a saturated fatty acid" because this is a much more common problem, a much more easily answered problem, and frankly one that makes more sense.
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Offline zaphraud

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Re: unsaturation in fatty acids
« Reply #3 on: January 28, 2012, 01:11:28 AM »
Fats and fatty acids can be brominated, in fact, brominated vegetable oil is still used in soft drinks in the United States. It's in "FANTA", an orange flavored drink that tastes pretty good.

The problem is, even if you brominate the thing and then do an elimination taking care to make sure all of your product is "cis" and not "trans", you're still not going to get the unsaturation in the right spot!! the location of the unsaturation(s) is critically important in the health effects of fatty acids, so unless you are trying to make something for its properties as a material (like a polymer or something) this isn't of much use either.

If you really want to do this right for biological purposes, you're probably going to need to construct a bioreactor of some type and get some little critters to do all the hard work for you.  ;)

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