Octa-1,3-dien-1-ol → 2,7-Octadien-1-ol

Temperature

130 °C

A one-liter stainless steel autoclave equipped with thermometer, magnetic stirrer, liquid metering and feeding pump, hydrogen gas inlet, off gas flow meter, and liquid outlet was charged with 1.5 g of nickel-on-diatomaceous earth catalyst (Nissan-Girdler's G-69; Ni content 52 percent by weight) and 100 g of n-octanol. After sufficiently replacing the atmosphere with hydrogen gas, the system was heated to 160° C. with stirring. Then, the octadienol mixture obtained by the procedure mentioned above under (iii) was continuously fed to the system at the rate of 70 g per hour at the temperature of 160° C., hydrogen pressure of 10 kg/cm2 (gauge), rate of stirring of 500 rpm and off gas flow rate of 30 liters per hour, with stirring for 7 hours. After effecting the hydrogenation reaction in this manner, octadienol mixture feeding, hydrogen gas introduction and stirring were discontinued, and the reaction mixture was immediately removed from the system via the liquid outlet. After removing the catalyst by filtration, the mixture was analyzed by gas chromatography, whereupon it was revealed that the average conversion of octadienols to octanols was 98.5 percent and that the hydrogenation product contained small amounts of intermediary hydrogenation products, namely octenols. The filtrate obtained upon separation of the catalyst by filtration was charged into the above-mentioned autoclave. The autoclave was connected via the liquid feeding pump to a column hydrogenation reactor (50 mm in inside diameter and 250 mm in column length) packed with a nickel-on-diatomaceous earth (Nissan-Girdler's G-49B; Ni content 55 percent by weight) in the form of cylinders (3/16"×1/8"), containing 123 g of n-octanol, and fitted with a jacket. The autoclave and packed column were heated to 130° C., and hydrogen was introduced to the pressure of 5 kg/cm2 (gauge). The autoclave contents were saturated with hydrogen gas by stirring at the rate of 400 rpm. After the internal temperature and hydrogen pressure respectively became constant, the mixture was continuously fed from the autoclave to the bottom of the packed column hydrogenation reactor at the rate of 450 ml/hr (corresponding to the liquid space velocity of 3 hr-1). The hydrogenated mixture was continuously taken out from the top of the packed column into a one-liter reservoir autoclave by the overflow method. The finishing hydrogenation was carried out under said conditions continuously for 90 minutes. Gas chromatography and ultraviolet absorption spectrometry of the mixture taken out did not reveal the presence of octenols and octanals within the limits of analytical error.

1. stirringwith stirring for 7 hours
2. customthe reaction mixture was immediately removed from the system via the liquid outlet
3. customAfter removing the catalyst
4. filtrationby filtration
5. customThe filtrate obtained upon separation of the catalyst by filtration
6. additionwas charged into the above-mentioned autoclave
7. customfitted with a jacket
8. stirringby stirring at the rate of 400 rpm
9. customcorresponding to the liquid space velocity of 3 hr
10. customcontinuously for 90 minutes
11. customGas chromatography and ultraviolet absorption spectrometry of the mixture

ORD record

ord-ffbb8f5b75f9456c9c66342fa2b2a23f

Source dataset

uspto-grants-1983_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04417079