2-(2,3-EPOXYPROPYL)PHENOL COMPOSITION AND METHOD OF MAKING
Disclosed herein is a method of making a 2-(2,3-epoxypropyl)phenol by reacting a 2-allylphenol with an oxidant in the presence of a catalyst. A 3-chromanol can be formed as a by-product. The method can be used to make 2-(2,3-epoxypropyl)-6-methylphenol. Transition metal catalysts and peroxide oxidants can be used. Also disclosed is a composition comprising 1 to 90 weight percent of a 2-(2,3-epoxypropylphenol, 5 to 90 weight percent of a 2-allylphenol, and 0 to 40 weight percent of a 3-chroman-ol, and in particular, a composition comprising 1 to 90 weight percent 2-(2,3-epoxypropyl)-6-methylphenol, 5 to 90 weight percent 2-allyl-6-methylphenol, and 0 to 40 weight percent 8-methyl-3-chromanol.
1 . A method of making 2-(2,3-epoxypropyl)-6-methylphenol, comprising reacting 2-allyl-6-methylphenol with an oxidant in the presence of a catalyst.
2 . (canceled)
3 . The method of claim 1 , wherein the catalyst is a transition metal catalyst comprising molybdenum, vanadium, tungsten, titanium, manganese, niobium, or combination thereof.
4 . The method of claim 1 , wherein the catalyst comprises bis(acetylacetonato)dioxomolybdenum (VI), molybdenum dichloride dioxide, tungstic acid, tungsten hexacarbonyl, or combination thereof.
5 . The method of claim 1 , wherein the oxidant comprises hydrogen peroxide, an alkyl peroxide, an alkyl hydroperoxide, a ketone peroxide, a diacyl peroxide, a diperoxy ketal, a peroxyester, a peroxydicarbonate, a peroxy acid, a perbenzoic acid, or combination thereof.
6 . The method of claim 1 , wherein the oxidant comprises m-chloroperbenzoic acid.
7 . The method of claim 1 , wherein the oxidant comprises hydrogen peroxide.
8 . The method of claim 1 , wherein reaction temperature is −10 to 50° C., and reaction time is 10 minutes to 6 hours.
9 . The method of claim 1 , wherein there is 50 to 100% conversion of the 2-allyl-6-methylphenol in 10 minutes to 6 hours at a reaction temperature of −10 to 50° C.
10 . The method of claim 1 , wherein there is 50 to 100% selectivity for 2-(2,3-epoxypropyl)-6-methylphenol.
11 . The method of claim 1 , wherein 8-methyl-3-chromanol is made along with 2-(2,3-epoxypropyl)-6-methylphenol.
12 . The method of claim 1 , wherein: the oxidant comprises m-chloroperbenzoic acid and the catalyst comprises bis(acetylacetonate)dioxomolybdenum (VI), tungstic acid, tungsten hexacarbonyl, or combination thereof.
13 . A composition comprising:
1 to 90 weight percent of 2-(2,3-epoxypropyl)-6-methylphenol
5 to 90 weight percent of 2-allyl-6-methylphenol
0 to 40 weight percent of 8-methyl-3-chromanol
wherein all weight percents are based on the total weight of the 2-(2,3-epoxypropyl)-6-methylphenol, 2-allyl-6-methylphenol, and 8-methyl-3-chromanol.
14 - 16 . (canceled)
17 . A thermoset polymer made by reacting a 2-allylphenol of structure
wherein each occurrence of Z is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms,
with an oxidant in the presence of a catalyst.
18 . The thermoset polymer of claim 17 , wherein the 2-allylphenol comprises 2-allyl-6-methylphenol, and the thermoset polymer has a glass transition temperature of 235 to 245° C.
19 . A method of making a 2-(2,3-epoxypropyl)phenol, comprising reacting a 2-allylphenol with an oxidant in the presence of a catalyst;
wherein the 2-allylphenol comprises
and the 2-(2,3-epoxypropyl)phenol comprises
and
wherein each occurrence of Z is independently hydrogen, halogen, unsubstituted or substituted C 1 -C 12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; and
wherein the oxidant comprises m-chloroperbenzoic or hydrogen peroxide, and/or the catalyst comprises bis(acetylacetonato)dioxomolybdenum (VI), molybdenum dichloride dioxide, tungstic acid, tungsten hexacarbonyl, or combination thereof.