METHODS FOR CONVERTING THC-RICH CANNABINOID MIXTURES INTO CBN-RICH CANNABINOID MIXTURES
Disclosed herein is a method of converting a THC-rich cannabinoid mixture that comprises at least about 20% THC into a CBN-rich cannabinoid mixture that comprises at least about 2.0% CBN. The method comprises contacting the cannabinoid mixture with a benzoquinone reagent under reaction conditions comprising: (i) a reaction temperature that is within a target reaction-temperature range; and (ii) a reaction time that is within a target reaction-time range, such that at least a portion of the of the THC in the THC-rich cannabinoid mixture is converted into CBN.
1 . A method of converting a tetrahydrocannabinol (THC)-rich cannabinoid mixture that comprises at least 20 wt. % THC into a cannabinol (CBN)-rich cannabinoid mixture that comprises at least 2.0 wt. % CBN, the method comprising reacting the cannabinoid mixture with a benzoquinone reagent, wherein the benzoquinone reagent comprises a compound as defined in formula (I):
wherein X 1 , X 2 , X 3 , and X 4 are each independently: H; a halide; a C 1-12 -hydrocarbyl; a C 3-12 -heteroaryl; a C 3-12 -heteroaralkyl; a C 3-12 -heteroaralkenyl; hydroxyl; a C 1-12 -alkoxy; a C 0-12 -amino; a C 1-12 -acyl; a C 1-12 -amide; a C 2-12 -ester; or a C 2-12 -ketone, provided that the benzoquinone reagent is not chloranil.
2 . The method of claim 1 , wherein the THC-rich cannabinoid mixture comprises at least about 80 wt. % THC.
3 . The method of claim 1 , wherein the THC-rich cannabinoid mixture comprises at least about 95 wt. % THC.
4 . The method of claim 1 , wherein the THC-rich cannabinoid mixture is derived from a marijuana biomass.
5 . The method of claim 1 , wherein the THC-rich cannabinoid mixture is a cannabis distillate, a cannabis resin, a cannabis extract, or a combination thereof.
6 . The method of claim 1 , wherein the benzoquinone reagent comprises:
or a combination thereof.
7 . The method of claim 1 , wherein the reacting of the THC-rich cannabinoid mixture with the benzoquinone reagent is at a benzoquinone:THC ratio of between 1.0:1.0 and 10.0:1.0 on a molar basis.
8 . The method of claim 1 , wherein the reacting of the THC-rich cannabinoid mixture with the benzoquinone reagent is at a benzoquinone:THC ratio of between 2.0:1.0 and 7.0:1.0 on a molar basis.
9 . The method of claim 1 , wherein the reacting of the THC-rich cannabinoid mixture with the benzoquinone reagent is at a temperature of between about 20° C. and about 190° C.
10 . The method of claim 1 , wherein the reacting of the THC-rich cannabinoid mixture with the benzoquinone reagent is at a temperature of between about 80° C. and about 120° C.
11 . The method of claim 1 , wherein the reacting of the THC-rich cannabinoid mixture with the benzoquinone reagent is in the presence of a solvent.
12 . The method of claim 11 , wherein the solvent is pentane, hexane, heptane, methanol, ethanol, isopropanol, dimethyl sulfoxide, acetone, ethyl acetate, diethyl ether, tert-butyl methyl ether, water, acetic acid, anisole, 1-butanol, 2-butanol, butane, butyl acetate, ethyl formate, formic acid, isobutyl acetate, isopropyl acetate, methyl acetate, 3-methyl-1-butanol, methylethyl ketone, 2-methyl-1-propanol, 1-pentanol, 1-propanol, propane, propyl acetate, trimethylamine, or a combination thereof.
13 . The method of claim 1 , wherein the CBN-rich cannabinoid mixture comprises at least about 60 wt. % CBN.
14 . The method of claim 1 , wherein the CBN-rich cannabinoid mixture comprises at least about 90 wt. % CBN.
15 . The method of claim 1 , wherein the benzoquinone reagent comprises:
a compound as defined in formula (I) where X 1 =H, X 2 =H, X 3 =H, and X 4 =H,
a compound as defined in formula (I) where X 1 =CN, X 2 =CN, X 3 =Cl, and X 4 =Cl, or
a compound as defined in formula (I) where X 1 =H, X 2 =OH, X 3 =H, and X 4 =H.
16 . A method of converting tetrahydrocannabinol (THC) into cannabinol (CBN), the method comprising:
reacting the THC with a benzoquinone reagent that is a compound as defined in formula (I):
where X 1 , X 2 , X 3 and X 4 are as defined as in any one of 1 to 133:
X 1
X 2
X 3
X 4
1
H
H
H
H
2
C 6 H 5
H
H
H
3
CH 3
H
H
H
4
C(CH 3 ) 3
H
H
H
5
OCH 3
H
H
H
6
N(CH 3 ) 2
H
H
H
7
NH 2
H
H
H
8
CH 2 CH 3
H
H
H
9
OH
H
H
H
10
OCH 2 CH 3
H
H
H
11
F
H
H
H
12
Cl
H
H
H
13
Br
H
H
H
14
SH
H
H
H
15
SiH 3
H
H
H
16
CHO
H
H
H
17
COOCH 3
H
H
H
18
CF 3
H
H
H
19
CN
H
H
H
20
COOH
H
H
H
21
SO 3 −
H
H
H
22
NO 2
H
H
H
23
COCH 3
H
H
H
24
C 6 H 5
C 6 H 5
H
H
25
CH 3
CH 3
H
H
26
C(CH 3 ) 3
C(CH 3 ) 3
H
H
27
OCH 3
OCH 3
H
H
28
N(CH 3 ) 2
N(CH 3 ) 2
H
H
29
NH 2
NH 2
H
H
30
CH 2 CH 3
CH 2 CH 3
H
H
31
OH
OH
H
H
32
OCH 2 CH 3
OCH 2 CH 3
H
H
33
F
F
H
H
34
Cl
Cl
H
H
35
Br
Br
H
H
36
SH
SH
H
H
37
SiH 3
SiH 3
H
H
38
CHO
CHO
H
H
39
COOCH 3
COOCH 3
H
H
40
CF 3
CF 3
H
H
41
CN
CN
H
H
42
COOH
COOH
H
H
43
SO 3 −
SO 3 −
H
H
44
NO 2
NO 2
H
H
45
COCH 3
COCH 3
H
H
46
C 6 H 5
H
C 6 H 5
H
47
CH 3
H
CH 3
H
48
C(CH 3 ) 3
H
C(CH 3 ) 3
H
49
OCH 3
H
OCH 3
H
50
N(CH 3 ) 2
H
N(CH 3 ) 2
H
51
NH 2
H
NH 2
H
52
CH 2 CH 3
H
CH 2 CH 3
H
53
OH
H
OH
H
54
OCH 2 CH 3
H
OCH 2 CH 3
H
55
F
H
F
H
56
Cl
H
Cl
H
57
Br
H
Br
H
58
SH
H
SH
H
59
SiH 3
H
SiH 3
H
60
CHO
H
CHO
H
61
COOCH 3
H
COOCH 3
H
62
CF 3
H
CF 3
H
63
CN
H
CN
H
64
COOH
H
COOH
H
65
SO 3 −
H
SO 3 −
H
66
NO 2
H
NO 2
H
67
COCH 3
H
COCH 3
H
68
C 6 H 5
H
H
C 6 H 5
69
CH 3
H
H
CH 3
70
C(CH 3 ) 3
H
H
C(CH 3 ) 3
71
OCH 3
H
H
OCH 3
72
N(CH 3 ) 2
H
H
N(CH 3 ) 2
73
NH 2
H
H
NH 2
74
CH 2 CH 3
H
H
CH 2 CH 3
75
OH
H
H
OH
76
OCH 2 CH 3
H
H
OCH 2 CH 3
77
F
H
H
F
78
Cl
H
H
Cl
79
Br
H
H
Br
80
SH
H
H
SH
81
SiH 3
H
H
SiH 3
82
CHO
H
H
CHO
83
COOCH 3
H
H
COOCH 3
84
CF 3
H
H
CF 3
85
CN
H
H
CN
86
COOH
H
H
COOH
87
SO 3 −
H
H
SO 3 −
88
NO 2
H
H
NO 2
89
COCH 3
H
H
COCH 3
90
C 6 H 5
C 6 H 5
C 6 H 5
H
91
CH 3
CH 3
CH 3
H
92
C(CH 3 ) 3
C(CH 3 ) 3
C(CH 3 ) 3
H
93
OCH 3
OCH 3
OCH 3
H
94
N(CH 3 ) 2
N(CH 3 ) 2
N(CH 3 ) 2
H
95
NH 2
NH 2
NH 2
H
96
CH 2 CH 3
CH 2 CH 3
CH 2 CH 3
H
97
OH
OH
OH
H
98
OCH 2 CH 3
OCH 2 CH 3
OCH 2 CH 3
H
99
F
F
F
H
100
Cl
Cl
Cl
H
101
Br
Br
Br
H
102
SH
SH
SH
H
103
SiH 3
SiH 3
SiH 3
H
104
CHO
CHO
CHO
H
105
COOCH 3
COOCH 3
COOCH 3
H
106
CF 3
CF 3
CF 3
H
107
CN
CN
CN
H
108
COOH
COOH
COOH
H
109
SO 3 −
SO 3 −
SO 3 −
H
110
NO 2
NO 2
NO 2
H
111
COCH 3
COCH 3
COCH 3
H
112
C 6 H 5
C 6 H 5
C 6 H 5
C 6 H 5
113
CH 3
CH 3
CH 3
CH 3
114
C(CH 3 ) 3
C(CH 3 ) 3
C(CH 3 ) 3
C(CH 3 ) 3
115
OCH 3
OCH 3
OCH 3
OCH 3
116
N(CH 3 ) 2
N(CH 3 ) 2
N(CH 3 ) 2
N(CH 3 ) 2
117
NH 2
NH 2
NH 2
NH 2
118
CH 2 CH 3
CH 2 CH 3
CH 2 CH 3
CH 2 CH 3
119
OH
OH
OH
OH
120
OCH 2 CH 3
OCH 2 CH 3
OCH 2 CH 3
OCH 2 CH 3
121
F
F
F
F
122
Br
Br
Br
Br
123
SH
SH
SH
SH
124
SiH 3
SiH 3
SiH 3
SiH 3
125
CHO
CHO
CHO
CHO
126
COOCH 3
COOCH 3
COOCH 3
COOCH 3
127
CF 3
CF 3
CF 3
CF 3
128
CN
CN
CN
CN
129
COOH
COOH
COOH
COOH
130
SO 3 −
SO 3 −
SO 3 −
SO 3 −
131
NO 2
NO 2
NO 2
NO 2
132
COCH 3
COCH 3
COCH 3
COCH 3
133
CN
CN
Cl
Cl
17 . A method of converting tetrahydrocannabinol (THC) into cannabinol (CBN), the method comprising:
reacting the THC with a benzoquinone reagent that is a compound as defined in formula (I):
wherein X 1 , X 2 , X 3 , and X 4 are each independently: H; a halide; a C 1-12 -hydrocarbyl; a C 3-12 -heteroaryl; a C 3-12 -heteroaralkyl; a C 3-12 -heteroaralkenyl; hydroxyl; a C 1-12 -alkoxy; a C 0-12 -amino; a C 1-12 -acyl; a C 1-12 -amide; a C 2-12 -ester; or a C 2-12 -ketone,
provided that the benzoquinone reagent is not chloranil.
18 . The method of claim 17 , wherein the benzoquinone reagent comprises:
or a combination thereof.
19 . The method of claim 17 , wherein the reacting of the THC with the benzoquinone reagent is in the presence of a solvent.
20 . The method of claim 19 , wherein the solvent is pentane, hexane, heptane, methanol, ethanol, isopropanol, dimethyl sulfoxide, acetone, ethyl acetate, diethyl ether, tert-butyl methyl ether, water, acetic acid, anisole, 1-butanol, 2-butanol, butane, butyl acetate, ethyl formate, formic acid, isobutyl acetate, isopropyl acetate, methyl acetate, 3-methyl-1-butanol, methylethyl ketone, 2-methyl-1-propanol, 1-pentanol, 1-propanol, propane, propyl acetate, trimethylamine, or a combination thereof.