95-11-4, Adding a certain compound to certain chemical reactions, such as: 95-11-4, name is 5-Norbornene-2-carbonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 95-11-4.
Example 1; Into a 50-ml glass round bottom flask equipped with a stirrer, a thermometer, a nitrogen inlet tube and a condenser were introduced 1.07 g (4.5 mmol) of nickel chloride hexahydrate, 0.60 g (9.2 mmol) of zinc, 8.90 g (28.7 mmol) of TPP containing 0.2 weight % of triphenyl phosphate purified by a known method and 26. 5 g (22.2 mmol) of CNN, and the replacement with nitrogen was surely carried out for the gas phase to obtain a tetrakis(triphenyl phosphite) nickel catalyst. Next, into a 1-L glass flat bottom separable flask equipped with a stirrer, a thermometer, a nitrogen inlet tube, a hydrogen cyanide inlet tube and a condenser were introduced 307.0 g (2.58 mol) of CNN, 90.0 g of toluene and the catalyst synthesis solution obtained as above, and the replacement with nitrogen was fully carried out for the gas phase at room temperature and then the temperature was elevated to 60 degrees centigrade. Then, 69.13 g (2.66 mol) of liquid hydrogen cyanide was supplied over 3.5 hours and hydrogen cyanide reaction was carried out to obtain 480.7 g of a coarse DCN. Nitrogen gas was bubbled in 480.7 g of the resulting coarse DCN at a flow rate of 500 ml/min for 1 hour for degassing, and then insoluble substances were filtered off. To this filtrate was added 1.9 g of 40% sulfuric acid, and the resulting solution was heated at 60 degrees centigrade for 3 hours for carrying out acid decomposition of the catalyst. 5.5 g of 25 weight % sodium hydroxide was further added thereto and the mixture was heated at 40 degrees centigrade for 2 hours and neutralized, and then 449.0 g of toluene was added for extracting DCN to obtain a DCN toluene solution. Then, toluene was removed to obtain 447.6 g of 85 weight % DCN. The resulting DCN was analyzed and as a result, triphenyl phosphate was not contained therein. Next, into a 500-ml autoclave were introduced 287.8 g of DCN obtained above, 32.6 g of 25% ammonia water and 7.9 g of a Raney cobalt catalyst, and the catalytic hydrogenation reaction was carried out at 120 degrees centigrade at hydrogen pressure of 3.5 MPa for 430 minutes. The resulting solution was cooled to room temperature and filtered to remove the Raney cobalt catalyst, and then 0.5 g of 32 weight % caustic soda was added to the filtrate for removing ammonia and toluene contained in DCN at 75 degrees centigrade at 2.6 KPa. Subsequently, the resulting residue was distilled under conditions of 0.1 MPa and a temperature in the flask of 150 to 160 degrees centigrade to obtain 204 g of NBDA. Phenol was analyzed and as a result, NBDA did not contain phenol. Furthermore, the obtained NBDA was sealed with nitrogen and then tightly closed up. The resultant was stored in a light-shielded vessel at room temperature (25 to 35 degrees centigrade) for 1 month and then time-dependent coloring was confirmed and as a result, no time-dependent coloring was found as APHA was not more than 10. The test results are shown in Table 1.; Example 2; The test was conducted in the same manner as in Example 1 using TPP containing 0.6 weight % of triphenyl phosphate. Said TPP was purified by a known method. The resulting DCN was analyzed and as a result, 0.08 weight % of triphenyl phosphate was contained therein. NBDA obtained by using this DCN contained 0.04 weight % of phenol. However, it was stored in a light-shielded vessel at room temperature (25 to 35 degrees centigrade) for 1 month and then time-dependent coloring was confirmed and as a result, no time-dependent coloring was found as APHA was not more than 10. The test results are shown in Table 1.; Comparative Example 1; The test was conducted in the same manner as in Example 1 using TPP containing 1.1 weight % of triphenyl phosphate. The resulting DCN was analyzed and as a result, 0.25 weight % of triphenyl phosphate was contained therein. NBDA obtained by using this DCN contained 0.20 weight % of phenol. It was stored in a light-shielded vessel at room temperature (25 to 35 degrees centigrade) for 1 month and then time-dependent coloring was confirmed and as a result, time-dependent coloring was confirmed as APHA was 30. The test results are shown in Table 1.
According to the analysis of related databases, 95-11-4, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Mitsui Chemicals, Inc.; EP2036883; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts