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morsagh
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[*] posted on 28-11-2015 at 11:53
CO in organic chemistry


What are conditions of reaction carbon monoxide and methanol to produce acetic acid? Does it need high pressure or temperature? Any other reaction with CO in organic chemistry?
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[*] posted on 28-11-2015 at 12:15


Depends on the catalyst used. If rhodium catalysts are used, ~50atm and ~175°C are necessary, most certainly not amenable to an amateur environment. As for other uses in organic chemistry, the Gatterman-Koch and Koch-Haaf reactions come to mind. Typically though, it is not terribly useful in organic reactions.



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shivam
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[*] posted on 28-11-2015 at 12:24


I think reaction of CO and CH3OH to produce Acetic acid is not possible in regular lab conditions, or at least, not very easy. It requires catalysts as well as a pressure of 30–60 atm and a temperature of 150–200 °C (source: Wikipedia)
Link: https://en.wikipedia.org/wiki/Monsanto_process

As far as your second question is concerned, as of now, I don't really recall any particular use of it in regular lab setup as most of the organic reactions with CO take place at high temperature and pressures. Although, there has to be a few interesting reactions worth performing that I'm not currently aware about...
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[*] posted on 28-11-2015 at 18:04


Yeah the carbonylation of methanol is pretty tough without high pressures.

However CO insertion is a very researched topic, and it occurs in many reactions. There are a lot of important examples in the lit, the insertion of CO into pentacarbonylmethylmanganese is a particularly famous one.

Inorg. Chem., 1962, 1 (1), pp 30–36
DOI: 10.1021/ic50001a008
Publication Date: February 1962
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annaandherdad
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[*] posted on 28-11-2015 at 19:45


And CO reacts readily with hemoglobin (hence its toxicity).



Any other SF Bay chemists?
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[*] posted on 29-11-2015 at 05:02


There's this reaction too
https://en.wikipedia.org/wiki/Organoboron_chemistry#Rearrang...
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quantumcorespacealchemyst
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[*] posted on 1-4-2016 at 14:37


also, Acetyl_chloride.
"it can also be synthesized from the catalytic carbonylation of methyl chloride.[4]", https://en.wikipedia.org/wiki/Acetyl_chloride
[4] = US 4352761, Production of acetyl chloride , http://worldwide.espacenet.com/publicationDetails/biblio?CC=...

also, "Oxalyl Chloride as a Practical Carbon Monoxide Source for Carbonylation Reactions"
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b01252

"Abstract
"A method for generation of high-quality carbon monoxide by decomposition of oxalyl chloride in an aqueous hydroxide solution is described. The usefulness of the method is demonstrated in the synthesis of heterocycles and for hydroxy-, alkoxy-, amino-, and reductive carbonylation reactions, in several cases under milder conditions than previously reported."
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