| Wt. of boat | 2.8402 | 2.8402 |
| Wt. of boat and resin | 3.0500 | 3.0250 |
| Wt. of resin | .2098 | .1848 |
| Wt. of H2SO4 tube | 78.0250 | 78.1415 |
| Wt. of tube plus water | 78.1520 | 78.2550 |
| Wt. of water | .1270 | .1135 |
| Hydrogen equiv. | .0143 | .0126 |
| Wt. of KOH bulb | 48.8140 | 51.7095 |
| Wt. of bulb plus CO2 | 49.3800 | 52.2085 |
| Wt. of CO2 | .5660 | .4990 |
| Carbon equiv. | .1543 | .1361 |
| Percent Hydrogen | 78.5% | 73.6% |
| Percent Carbon | 6.8% | 6.8% |
| Percent Oxygen | 19.7% | 19.6% |
An attempt was made to make the potassium salts of the barium acids by saponification with alcoholic potash. A small quantity of the acid was treated with an excess of ten percent alcoholic potash and heated to eighty degrees Centigrade to complete the saponification. Instead of the formation of the potassium salts, a thick dark brown solid, gummy mass separated. On cooling it solidified to a brittle solid which had all the physical properties of a true resin. This solid is soluble in ether, chloroform and benzol, slightly soluble in alcohol and insoluble in petroleum ether and water. It burns without the formation of an ash. Evidently, this brittle material is a condensation product of the original barium acid.
OXIDATION PRODUCTS OF THE BARIUM ACIDS.
A small amount of the Barium acids was sealed with concentrated nitric acid in a hard glass tube and heated in a bomb furnace for an hour and a half at 115 to 120 degrees Centigrade. On cooling a yellow solid separated. Qualitative tests showed that this oxidation product contained no nitrogen, combined with sodium hydroxide readily, is soluble in hot water, slightly soluble in cold water, easily soluble in ether, alcohol and benzol and slightly soluble in carbon tetrachloride. It decolorizes alkaline permanganate but does not decolorize bromine water.
That there are a number of intermediate products formed and that nitration also takes place during the formation of these intermediate products is shown by the following. A small quantity of the acids were placed in a test tube and covered with concentrated nitric acid. This was suspended in an H2SO4 bath and a thermometer inserted so as to observe the temperature. On being gently warmed the nitric acid and the resin began to react with a rapid evolution of carbon dioxide and oxides of nitrogen. As soon as the reaction had modified and before the temperature rose above one hundred degrees Centigrade, a small amount was removed and added to water. Some of the solid acid was formed and also a number of globules of oil and there was a strong persistent odor of nitrobenzene. The original test tube was heated to about one hundred and twenty degrees centigrade and a small portion again removed. There was more of the solid material formed and the odor was similar to vanillin or coumarin or cinnamic aldehyde. The test tube was again tested when the temperature had reached one hundred and thirty five degrees Centigrade. There was no aromatic odor and a large amount of the solid formed. When viewed under the microscope the substance had the appearance of curled threads.
When the barium acids were treated with the standard nitrating mixture, a solid was obtained which showed the presence of nitrogen when the standard test was applied.
After the preliminary tests were made, the following method of preparation was used. Two or three grams of the barium acids were introduced into a hard glass tube of about thirty centimeters in length and fifteen or twenty cubic centimeters of concentrated nitric acid added. The reaction which is very vigorous at first was regulated by keeping the tube under running water. After this vigorous action was over the tube was placed in a sulphuric acid bath, and the temperature gradually increased until it had reached one hundred and twenty five degrees Centigrade, at which temperature it was kept for about five hours. It was necessary to add a small quantities of nitric acid from time to time to make up the loss by evaporation. When the oxidation was completed the product was poured into water and then heated to boiling. The resulting solution was filtered and the filtrate allowed to cool. On standing a quantity of a pale yellow substance separated. The following data gives the percent yield of this oxidation product.
| Wt. of container | 6.7220 |
| Wt. of container and substance | 7.5920 |
| Wt. of substance | .8700 |
| Wt. of oxidation product | .1240 |
| Percent yield | 14% |
The oxidation product was dried by placing it in a vacuum over sulphuric acid for several days. The neutralization equivalent of this crude oxidation product was 157.
| Wt. of substance used | .0502 |
| Number Cc. of NaOH N/10 | 3.2 cc. |
| Neutralization equivalent | 157 |