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Author: Subject: formyl isocyanate
dragonfly
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smile.gif posted on 21-9-2006 at 09:51
formyl isocyanate


Hi all

Does anyone have a suggestion on how to go about preparing formyl isocyanate.

As yet ?I have been unable to find any refrences to a procedure. I imagine one would begin with formamide. What then? carbon dioxide, pressure and a catalyst such as raney nickle?

[Edited on 21-9-2006 by dragonfly]
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Nicodem
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[*] posted on 21-9-2006 at 11:26


Are you sure it exists?

I can only find references to theoretical studies, DFT and spectroscopy calculations but nothing on that species as a compound. Perhaps it does not exist as a stable compound (like formyl chloride, for example).

PS: From formamide it could utmost form by the reaction with phosgene (or triphosgene) in pyridine, but certainly not with CO2.




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[*] posted on 21-9-2006 at 11:53


Experimental Investigation of the Reaction between Nitric Oxide and Ketenyl Radicals (HCCO + NO): Rate Coefficient at T = 290-670 K and Product Distribution at 700 K
Werner Boullart, Minb Tho Nguyen, and Jozef Peefed
J. Phys. Chem. 1994,98, 8036-8043


Abstract
The HCCO + NO reaction (r5) was investigated in C2H2/0/NO systems at a pressure of 2 Torr (He bath gas) using discharge flow-molecular beam mass spectrometry techniques (DF-MBMS). The first rate coefficient
data at temperatures > 300 K are presented. The coefficient was measured relative to the known k(HCCO+O) from the changeof steady-state HCCO signals upon adding increasing amounts of NO. Thus, in the temperature
range from 290 to 670 K, the k(HCCO+NO) coefficient was found to exhibit a slight but significant temperature dependence: k(T) = (1.0 f 0.3) X 10-lo e-(350*150)/(TIcQm 3 molecule-’ (T = 290-670 K). The product
distribution was determined at 700 K. The experiments relied on the fact that all reaction pathways yield either CO or C02. Ketenyl radicals, generated by quantitative reaction of a known amount of 0 atoms with C2H2
in high excess, were reacted with a large excess of NO, ensuring quantitative conversion into the products C02 and CO. The product distribution was essentially deduced from the ratios [CO2]fomd/[O]input and [CO]for,d/
[O]inPut. Formation of CO together with CHz(3B1) in a minor (25 f 15%) channel of the C2H2 + 0 reaction was taken into account. Small corrections for secondary reactions such as HCCO + 0 - H + 2 CO were made
by kinetic modeling.
Thus, the following yields were obtained: for HCCO + NO - (CHNO) + CO, 77 f
9%; for HCCO + NO - (CHN) + C02, 23 f 9%. Strong product signals were also observed at m/e = 43 and m/e = 27, confirming that CHNO isomers and CHN isomers are formed along with CO and COz, respectively. Theoretical predictions regarding the CO/CO2 yield ratio, presented in a companion paper in this issue, can be reconciled with the experimental product distribution only when an as yet unidentified entrance pathway to the formyl isocyanate intermediate is assumed to exist and to be thermally accessible.

Attachment: Experimental Investigation of the Reaction between Nitric Oxide and Ketenyl Radicals .pdf (917kB)
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dragonfly
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[*] posted on 26-9-2006 at 03:33


Hi Nicodem and Solo

Thank you for your responses. This is clearly an impractical approach to a new project

The idea behind this question originates from a request I recieved. I was asked to prepare a methylenemethanamine type polymer. I fiqured the formyl isocyanate would be the best place to start. Any ideas ?

I thought that if I was to react the formylisocyanate with methyldiamine the polymer would at the very least be interesting- Expect to have electrical, optical and perhaps some elastomer type properties.

What are your thoughts?
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