I'm glad it worked for you Ritter and thanks for the props! The write up is excellent, and the commentary worth while. Great job.
That Ultrasonic crap:
From "The Journal of the American Chemical Soceity", yr 1987, Vol 109,
pages 3459-3461
"Hetrogeneous Sonocatalysis with Nickel Powder
We have discovered that ultrasonic irradition of Ni powder increases
it's activity as a hydrogenation catalyst by >10^5. ...
The use of high-intensity ultrasound to initiate or enhance both
homogeneous and hetrogeneous chemical reactions has been under
intense investigation [1-7],...
Simple Ni powder is an extremely inactive catalyst for hydrogenation of
alkenes. Even after 2 X 10^4 min, no alkanes are deteacted with rapid
stirring under 1 atm of H2 at 273 K (i.e., <10 nM/min). In comparison
under the same conditions, if the nickel was first irradiated with
ultrasound [12], 1-nonene is hydrogenated at millimolar per min rates,
as shown on Figure 1. Ultrasonic pretreatment of ~1 h gives optimal
activity, which decreases with longer irradiation. The hydrogenation
activity is quite general and shows little dependance on the choice of
alkene... ; no reduction of ketones or aldehydes was observed.
Other methods of creating active Ni catalysts exsist [13]. The thermal
hydrogenation rates at 1 atm of H2 and 273 K with high surface area Ni
sponge (Raney Ni [13a], Aldrich Chemicals, grade W-2) are comparable
to those obtained eith ultrasoniclly activated Ni powder. Compared to
Raney Ni, however, our activaed Ni powder is more selective
(C-O double bonds are untouched), much easier to produce, and much
simpler to handle (nonpryophoric). Activation of Ni powders by H2 at
150 C and 10 atm will also generate reactive catalysts [13b], which
rapidily lose activity upon exposure to O2.
..."
[1] Adv, Organomet. Chem. 1986, 25, 73. (b) Modern Syth. Methods 1986,
4, 1. (c) Ultrasound: Its Chemical, Physical and Boilogical Effects
1987. (d) J Chem. Ed. 1986, 63, 427. (e) Ultrasonics 1985, 23, 157.
[2] J. Am. Chem. Soc. 1983, 105, 5781. (b) J. Am. Chem. Soc. 1983,
105, 6042. (c) High Energy Processes in Organomettalic Chemistry,
American Chemical Society 1987, p 191.
[3] High Energy Processes in Organomettalic Chemistry, American
Chemical Society 1987, pp 209-222. (b) Organometallics 1986, 5, 1257.
(c) Nachr. Chem. Tech. Lab. 1983, 31, 797. (d) J Org. Chem. 1982,
5030.
[4] Ultrsonics 1987, 25, 40. (b) Tetrahedron Lett. 1986, 27, 3149.
(c) J. Org. Chem. 1985, 50, 910, 5761. (d) J. Amer. Chem. Soc. 1980,
102, 7926.
[5] Angew. Chem., Intl. Ed. Engl. 1983, 22, 728. (b) J. Am. Chem. Soc.
1984, 106, 6856.
[6] Ultrasonics 1987, 25, 45. (b) J. Lab. Pract. 1984, 33, 13 and
references therein.
[7] Tetrahedron Lett. 1986, 27, 415. (b) J. Am. Oil Chem. Soc. 1983,
60, 1257. (c) Chim. Ind. (Milan 1968, 50, 314.
[12] All sonications were performed with a Heat Systems-Ultrasonics
W375 cell disruptor with a titanium immersion horn at acoustic
intensties of ~50 W/cm^2 at 20KHz, as described elesewher in
detail [2]. Irradiation in a low-intenstity ultrasonic cleaning bath
does give hydrogenation, but at greatly reduced rates. Hydrogenation
reactions were carried out at 273 K under 1 atm of H2. In a typical
reaction, 1 g of Ni powder (200 mesh, EM Science, Cherry Hill, NJ
08034) was added to a 10% solution of alkene in octane. ...
[13] Reagents for Organic Synthesis 1967, by Fieser, L. F., Vol. 1,
pp 723-731. (b) Thomas, C. L., Catalytic Porcesses and Proven
Catalysts 1970, pp 126-133. (c) Somorjai, G. A.; Chemistry in Two
Dimensions: Surfaces; 1981, pp 445-447 (d) J. Phys. Chem. 1983, 87,
915. (e) High Energy Process in Organicmetallic Chemistry,
... pp 223-245.
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