ISOCYANAT ES, TOTA L (MAP): METHO D 5525, Issue 1, dated 15 March 2003 - Page 16 of 17
APPENDIX C: SYNTHESIS OF M AP DERIVATIVES Chem ical
MW
EQ. W T.
MAP Derivative MW
MAP Derivative EQ. W T.
MAP: 1-(9-Anthracenylmethyl)piperazine
276 .4
276 .4
HD I: Hex am ethylene diisocyanate
168 .2
84.1
721 .0
360 .5
TDI: Tolylene diisocyanate (toluene diisocyanate)
174 .2
87.1
727 .0
363 .5
MDI: 4,4'-Methylenebis(phenyl isocyanate)
250 .3
125 .2
803 .1
401 .6
HMD I: 4,4'-Methylenebis(cyclohexyl isocyanate)
262 .4
131 .2
815 .2
407 .6
MDI Trimer (MDI Triiso)
381 .4
127 .1
121 0.6
403 .5
IPD I: Isoph oron e diisocyanate
222 .3
111 .2
775 .1
387 .5
PhICN : Phe nyl isocyanate
119 .1
119 .1
395 .5
395 .5
BuICN : Butyl isoc yanate
99.1
99.1
375 .5
375 .5
318 .4
318 .4
AcMAP: Acetylated MAP
2 MAP + 1 diisocyanate yields 1 MAP-diisocyanate derivative 1. 2. 3. 4. 5. 6. 7. 8. 9. 10.
Theoretical yield 1 meq: range from 360-408 m g. W eigh 1 m eq of d iisocyanate to fou r de cim al places. Dissolve in 10 m L of toluene. W eigh 1.2 meq of MAP (20% excess) to four decimal places. Dissolve in 20 mL of toluene. W hile stirring the M AP solution, add the diisocyanate solution dropw ise ov er a 1 0 to 15 m inute p eriod. Continue to stir for at least one ho ur. Tightly cover the solution and store overnight in the freezer to promote maximum precipitation. Us ing a B uec hne r funnel with filter pap er, filter the solution to collect the prec ipitate. W ash several times with small amounts of cold toluene to remove any remaining MAP. W ash several tim es with sm all am ounts of c old hexane to displace the toluene. Continu e to pull air throu gh the so lid for se vera l minutes to dry. Trans fer the solid derivative into a preweighed vial with T eflon cap. Using the vacuum pum p, apply vacuum until a stable weight is obtained.
NIOSH Manual of Analytical Methods (NMAM), Fourth Edition
