2,4- and 2,6-TOLUENEDIAMINE: METHOD 5516, Issue 2, dated 15 August 1994 - Page 5 of 5
| [12] | Elskamp, C. J., “Benzidine; 3,3’-Dichlorobenzidine; 2,4-Toluenediamine; 2,6-Toluenediamine. Method 65,” OSHA Analytical Laboratory, Salt lake City, Utah (1987). |
| [13] | NIOSH [1988], Registry of Toxic Effects of Chemical Substances, data base: 2,4-Toluenediamine. D.V. Sweet, Ed., U. S. Department of Health and Human Services, Public Health Service, Centers for Disease Control and Prevention, National Institute for Occupational Safety and Health, Division of Standards Development and Technology Transfer. |
| [14] | Ibid., 2,6-Toluenediamine. |
METHOD WRITTEN BY:
James E. Arnold, NIOSH/DPSE and Alexander W. Teass, Ph.D., NIOSH/DBBS.
APPENDIX A: PURIFICATION OF 1-(2-METHOXYPHENYL)PIPERAZINE:
Place 25 g 1-(2-methoxyphenyl)piperazine (yellowish white solid) in a 250-mL beaker. Add ca. 125 mL pentane. Bring to a boil (CAUTION: Pentane is FLAMMABLE) on a water bath and allow to boil until all but a small amount of yellow oil is in solution. The 1-(2-methoxyphenyl)piperazine will melt as it is warmed in the pentane. Decant the solution into a clean beaker, cover with a watchglass, and cool in the freezer for 2 to 3 h. Collect the resulting white needles in a Buchner funnel using suction filtration and dry them in a vacuum desiccator. The crystals are hygroscopic and melt at 26 to 29 °C. Store them in an airtight container in a refrigerator.
APPENDIX B: SYNTHESIS OF 2,4- AND 2,6-BISACETAMIDOTOLUENE:
Place 0.5 g of 2,4- or 2,6-toluenediamine in a 250-mL beaker. Add ca. 100 mL of distilled water and warm to dissolve the compound. Filter the solution, if necessary. Chill the solution in an ice bath, then slowly add 5 mL acetic anhydride and stir. After keeping the mixture at least 1 h in the ice bath, collect the solid product by suction filtration. Recrystallize the product from water by dissolving it in boiling water, filtering the hot solution, chilling the filtrate in a refrigerator, and collecting the precipitate by suction filtration. Dry the precipitate in a vacuum desiccator.
2,4-Bisacetamidotoluene recrystallizes as white needles and melts at 230 °C.
2,6-Bisacetamidotoluene recrystallizes as brownish needles and melts at ca. 318 °C.
NIOSH Manual of Analytical Methods (NMAM), Fourth Edition
