Improved methods for converting cannabidiol into delta8-tetrahydrocannabinol

Abstract

Disclosed herein a method for converting (cannabidiol) CBD into a composition comprising Δ8-tetrahydrocannabinol (Δ8-THC) and Δ9-tetrahydrocannabinol (Δ9-THC), in which the composition has a Δ8-THC:Δ9-THC ratio that is greater than 1.0:1.0. The method comprises contacting the CBD with a Lewis-acidic heterogeneous reagent under protic, aprotic, or neat reaction conditions comprising: (i) a reaction temperature that is greater than a threshold reaction temperature for the Lewis-acidic heterogeneous reagent and the solvent system; and (ii) a reaction time that is greater than a threshold reaction time for the Lewis-acidic heterogeneous reagent, the solvent system, and the reaction temperature.

1 .- 48 . (canceled) 
     
     
         49 . A method for converting cannabidiol (CBD) into Δ 8 -tetrahydrocannabinol (Δ 8 -THC), the method comprising contacting the CBD with a Lewis-acidic heterogeneous reagent, optionally in an aprotic-solvent system, wherein the Lewis-acidic heterogeneous reagent is an ion-exchange resin other than Amberlyst-15 or Nafion-SAC-13. 
     
     
         50 . The method of  claim 49 , wherein ion-exchange resin is an Amberlyst polymeric resin which is Amberlyst-16, 31, 33, 35, 36, 39, 46, 70, CH10, CH28, CH43 or M-31, or a H +  or Na +  form thereof, or any combination thereof. 
     
     
         51 . The method of  claim 49 , wherein the ion-exchange resin is a Nafion polymeric resin which is Nafion-NR50, N115, N117, N324, N424 or N1110, or a H +  or Na +  form thereof, or any combination thereof. 
     
     
         52 . The method of  claim 49 , wherein the aprotic-solvent system is present. 
     
     
         53 . The method of  claim 52 , wherein the aprotic-solvent system comprises dimethyl sulfoxide, ethyl acetate, dichloromethane, chloroform, toluene, pentane, heptane, hexane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, anisole, butyl acetate, cumene, ethyl formate, isobutyl acetate, isopropyl acetate, methyl acetate, methylethylketone, methylisobutylketone, propyl acetate, cyclohexane, para-xylene, meta-xylene, ortho-xylene, 1,2-dichloroethane, or any combination thereof. 
     
     
         54 . The method of  claim 52 , wherein the aprotic-solvent system is heptane. 
     
     
         55 . The method of  claim 49 , wherein the Δ 8 -THC is a component of a composition that further comprises Δ 9 -tetrahydrocannabinol (Δ 9 -THC), and wherein the composition has a Δ 8 -THC:Δ 9 -THC ratio that is greater than 1.0:1.0. 
     
     
         56 . A method for converting cannabidiol (CBD) into Δ 8 -tetrahydrocannabinol (Δ 8 -THC), the method comprising contacting the CBD with a Lewis-acidic heterogeneous reagent, optionally in an aprotic-solvent system,
 wherein the Lewis-acidic heterogeneous reagent is a microporous silicate, and 
 wherein the Δ 8 -THC is a component of a composition that further comprises Δ 9 -tetrahydrocannabinol (Δ 9 -THC), and wherein the composition has a Δ 8 -THC:Δ 9 -THC ratio that is greater than 1.0:1.0. 
 
     
     
         57 . The method of  claim 56 , wherein the microporous silicate other than Zeolite Y, Zeolite Beta, SAPO-11 or SAPO-11. 
     
     
         58 . The method of  claim 56 , wherein the microporous silicate is a zeolite which is ZSM-5, ZSM-11, ZSM-22, ZSM-23, ZSM-35, SAPO-34, SSZ-13, TS-1, X-type, Linde type A, Linde type L, Linde type X, or Linde type Y, or a H+ or Na+ form thereof, or any combination thereof. 
     
     
         59 . The method of  claim 56 , wherein the aprotic-solvent system is present. 
     
     
         60 . The method of  claim 59 , wherein the aprotic-solvent system comprises dimethyl sulfoxide, ethyl acetate, dichloromethane, chloroform, toluene, pentane, heptane, hexane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, anisole, butyl acetate, cumene, ethyl formate, isobutyl acetate, isopropyl acetate, methyl acetate, methylethylketone, methylisobutylketone, propyl acetate, cyclohexane, para-xylene, meta-xylene, ortho-xylene, 1,2-dichloroethane, or any combination thereof. 
     
     
         61 . The method of  claim 59 , wherein the aprotic-solvent system is heptane. 
     
     
         62 . A method for converting cannabidiol (CBD) into Δ 8 -tetrahydrocannabinol (Δ 8 -THC), the method comprising contacting the CBD with a Lewis-acidic heterogeneous reagent, optionally in an aprotic-solvent system, wherein the Lewis-acidic heterogeneous reagent is a mesoporous silicate or a phyllosilicate. 
     
     
         63 . The method of  claim 62 , wherein the Lewis-acidic heterogeneous reagent is the mesoporous silicate, and the mesoporous silicate is Al-MCM-41, MCM-41, MCM-48, SBA-15, SBA-16, KIT-5, KIT-6, FDU-12, or any combination thereof. 
     
     
         64 . The method of  claim 62 , wherein the Lewis-acidic heterogeneous reagent is the phyllosilicate, and the phyllosilicate is Faujasite, Mordenite, Ferrierite, Montmorillonite K10, Montmorillonite K20, Montmorillonite K30, Montmorillonite KSF, Clayzic, or bentonite, or any combination thereof. 
     
     
         65 . The method of  claim 64 , wherein the phyllosilicate is Montmorillonite K10, Montmorillonite K20, Montmorillonite K30 or Montmorillonite KSF. 
     
     
         66 . The method of  claim 62 , wherein the aprotic-solvent system is present. 
     
     
         67 . The method of  claim 66 , wherein the aprotic-solvent system comprises dimethyl sulfoxide, ethyl acetate, dichloromethane, chloroform, toluene, pentane, heptane, hexane, diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, anisole, butyl acetate, cumene, ethyl formate, isobutyl acetate, isopropyl acetate, methyl acetate, methylethylketone, methylisobutylketone, propyl acetate, cyclohexane, para-xylene, meta-xylene, ortho-xylene, 1,2-dichloroethane, or any combination thereof. 
     
     
         68 . The method of  claim 66 , wherein the aprotic-solvent system is heptane. 
     
     
         69 . The method of  claim 62 , wherein the Δ 8 -THC is a component of a composition that further comprises Δ 9 -tetrahydrocannabinol (Δ 9 -THC), and wherein the composition has a Δ 8 -THC:Δ 9 -THC ratio that is greater than 1.0:1.0.