Related Products of 1835-49-0, A common heterocyclic compound, 1835-49-0, name is Tetrafluoroterephthalonitrile, molecular formula is C8F4N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Water-wet tetrafluoroterephthalonitrile 56. 69 G (10% water content, 98% pure, 50.0 g in terms of tetrafluoroterephthalonitrile), water-wet 5% Pd/C 1.18 g (58% water content, 0.5 g in terms of Pd), and toluene 200.0 g were introduced into a 500 ml three-necked glass flask equipped with a stirrer, a thermometer, a Claisen tube and a cooling tube. The contents were heated to distill away toluene and water together in an amount of 187.5 g. After cooling, toluene 187.5 g was added and the water content was measured to be 150 ppm. The resultant reaction solution was introduced into a 500 ml stainless steel autoclave (NU-4 model produced by Nitto Koatu Co., Ltd. ), and further Zeolite 5A powder 45 g (Molecular Sieve 5A produced by Union Showa K. K. ) was added thereto. Then the autoclave was purged with nitrogen. THEREAFTER THE CONTENTS WERE HEATED TO 160C under stirring, and hydrogen pressurized at a pressure higher than that in the autoclave at the above temperature by 0.1 MPa was supplied to initiate hydrogenolysis. The rate of hydrogen absorption lowered in approximately 5 hours and 30 minutes of reaction time, and the supply of hydrogen was terminated to end the reaction. The hydrogen absorption was 116 MOL% (based on the mol of tetrafluoroterephthalonitrile under standard conditions). Cooled to room temperature, the reaction slurry was filtered, and the filtrate was analyzed with the gas chromatography analyzer. The analysis gave a conversion of 97. 8% and a reaction yield of 84.4 % (product: 2,3, 5,6-tetrafluorobenzonitrile). Example 5 Reaction was conducted basically in the same manner as in Example 4 except that the amount of 5% Pd/C was altered to 2.38 g (58% water content, 1.0 g in terms of Pd) and that the amount of the Zeolite 5A powder was altered to 37.5 g (Molecular Sieve 5A produced by Union Showa K. K. ). The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 114%. The analysis gave a conversion of 98. 2% and a reaction yield of 87. 5% (product: 2,3, 5, 6-tetrafluorobenzonitrile).Example 6 Reaction was conducted basically in the same manner as in Example 4 except that the amount of 5% Pd/C was altered to 1.43 g (58% water content, 0.6 g in terms of Pd). The results were that the hydrogenolysis reaction was completed in 5 hours and 20 minutes and the hydrogen absorption was 121%. The analysis gave a conversion of 99.4% and a reaction yield of 86. 2% (product: 2,3, 5, 6-tetrafluorobenzonitrile). Example 7 Reaction was conducted basically in the same manner as in Example 4 except that the hydrogenolysis temperature was altered to 170C. The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 111%. The analysis gave a conversion of 99. 3% and a reaction yield of 87. 5% (product: 2,3, 5,6-tetrafluorobenzonitrile). Example 8 Reaction was conducted basically in the same manner as in Example 4 except that the hydrogenolysis temperature was altered to 180C. The results were that the hydrogenolysis reaction was completed in 5 hours and 10 minutes and the hydrogen absorption was 114%. The analysis gave a conversion of 99. 3% and a reaction yield of 89. 1% (product: 2,3, 5, 6-tetrafluorobenzonitrile). Example 9 Reaction was conducted basically in the same manner as in Example 4 except that the additional toluene was used in an amount of 147.5 g. The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 112%. The analysis gave a conversion of 98. 9% and a reaction yield of 87. 0% (product: 2,3, 5,6-tetrafluorobenzonitrile). Example 10 Reaction was conducted basically in the same manner as in Example 4 except that the additional toluene was used in an amount of 107.5 g. The results were that the hydrogenolysis reaction was completed in 5 hours and 30 minutes and the hydrogen absorption was 108%. The analysis gave a conversion of 98.7% and a reaction yield of 86.5% (product: 2,3, 5,6-tetrafluorobenzonitrile).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; SHOWA DENKO K.K.; WO2004/9535; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts