Method for preparing deuterated aromatic compounds
View Patent ↗There is provided a method for deuterating an aromatic compound having aromatic hydrogens. The method includes the steps: (a) providing a liquid composition including deuterium oxide having dissolved or dispersed therein the aromatic compound and a transition metal catalyst; and (b) heating the liquid composition at a temperature of 120° C. or greater, and a pressure of 50 psi or greater, for a period of 24 hours or less, to form a deuterated aromatic compound.
1. A method for deuterating an aromatic compound having aromatic hydrogens, said method comprising:
(a) providing a liquid composition comprising deuterium oxide having dissolved or dispersed therein the aromatic compound and a transition metal catalyst; and
(b) heating the liquid composition at a temperature of 120° C. or greater, and a pressure of 50 psi or greater, for a period of 24 hours or less, to form a deuterated aromatic compound;
wherein (b) is carried out in an air atmosphere.
2. The method of claim 1 , wherein the aromatic compound is a hydrocarbon aromatic compound.
3. The method of claim 2 , wherein the hydrocarbon aromatic compound is selected from the group consisting of naphthalene, anthracene, biphenyl, terphenyl, naphthacene, pentacene, phenanthrene, chrysene, pyrene, fluoranthene, fluorene, benzofluorene, triphenylene, tetrabenzanthracene, and substituted derivatives thereof.
4. The method of claim 1 , wherein the aromatic compound is an N-heteroaryl compound.
5. The method of claim 4 , wherein the N-heteroaryl compound is selected from the group consisting of pyrrole, imidazole, purine, pyrazole, triazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, indoloindole, carbazole, indolocarbazole, benzimidazole, imidazobenzimidazole, indazole, benzotriazole, triazolopyridine, quinoline, isoquinoline, quinazoline, quinoxaline, naphthyridine, phenanthroline, quinolinoquinolines, and substituted derivatives thereof.
6. The method of claim 1 , wherein the transition metal catalyst is selected from the group consisting of Pd, Pt, Ir, Rh, Ru, oxides thereof, complexes thereof, and combinations thereof.
7. The method of claim 6 , wherein the transition metal catalyst is a platinum catalyst selected from the group consisting of finely divided platinum metal, platinum metal on graphitized carbon at loadings of at least 2.5 wt. %, and finely divided platinum oxide.
8. The method of claim 1 , wherein the molar ratio of available hydrogens in the aromatic compound to deuterons is in a range of 1:1.5 to 1:1000.
9. The method of claim 1 , wherein the temperature is between 120° C. and 500° C.
10. The method of claim 1 , wherein the pressure is in the range of 200-800 psi.
11. The method of claim 1 , wherein (b) is carried out for a period of 3-10 hours.
12. The method of claim 1 , wherein the deuterated aromatic compound is at least 50% deuterated.
13. The method of claim 1 , wherein the deuterated aromatic compound is at least 70% deuterated.