Claims
- 1. A product produced according to the process of reacting isobutyraldehyde with acetone in the presence of a catalyst selected from the group consisting of an alkali metal hydroxide, an alkaline earth metal hydroxide, aluminum chloride, sulfuric acid and pyrrolidinium acetate in the presence of an inert solvent thereby forming a mixture of compounds defined according to the structure: ##STR132## wherein in the mixture one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond; then dimerizing the resulting mixture of ketones to form a mixture of cyclic dimers at a temperature in the range of from about 25.degree. C. up to 120.degree. C. atmospheric pressure in the presence of:
- (a) a solvent selected from the group consisting of hydrocarbons and inert alkanols and a catalyst selected from the group consisting of alkali metal hydroxides, aluminum chloride, alkaline earth metal hydroxides and pyrrolidinium acetate, the mole ratio of isobutyraldehyde:acetone varying from about 1.5:0.5 up to 0.5:1.5 isobutyraldehyde:acetone, the reaction temperature for the reaction of isobutyraldehyde with acetone varying from about 25.degree. C. up to about 120.degree. C.; and then
- (b) reacting the resulting unsaturated ketone mixture with hydrogen in the presence of a hydrogenation catalyst selected from the group consisting of palladium, palladium on a carbon support, palladium on a calcium carbonate support or palladium on a barium sulfate support at a hydrogen pressure of from 50 psig up to 10 atmospheres, the mole ratio of hydrogen:ketone dimer reactant being in the range of from 1:1 hydrogen:ketone up to about 3:1 hydrogen:ketone, the reaction being carried out in an inert solvent and the reaction temperature varying from about 20.degree. C. up to about 100.degree. C.
- 2. A product produced according to the process comprising the steps of:
- (a) reacting acetone with isobutyraldehyde in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, aluminum chloride, sulfuric acid and pyrrolidinum acetate in the presence of an inert solvent, the mole ratio of isobutyraldehyde:acetone varying from 1.5:0.5 up to 0.5:1.5 isobutyraldehyde:acetone the temperature of reaction varying from about 25.degree. C. up to about 120.degree. C. and the concentration of catalyst in the reaction mass varying from about 50 grams per liter up to about 400 grams per liter whereby a mixture of compounds is formed defined according to the structure: ##STR133## wherein in the mixture in each of the compounds, one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond; and then
- (b) dimerizing the resulting product to form a cyclic ketone dimer, said dimerization reaction being carried out at a temperature in the range of from about 25.degree. C. up to about 120.degree. C. at atmospheric pressure in the presence of a hydrocarbon solvent or an inert alkanol solvent and in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, aluminum chloride and pyrrolidinium acetate; and then
- (c) reacting the resulting ketone dimer with an alkali metal borohydride whereby the ketone moiety is reduced to a carbinol moiety in the presence of a lower alkanol solvent which is inert in the reaction mass, the concentration of alkali metal borohydride in the reaction mass varying from about 20 grams per liter of reaction mass up to about 50 grams per liter of reaction mass, the concentration of ketone dimer in the mixture varying from 200 grams per liter up to about 800 grams per liter and the reaction temperature being in the range of from 40.degree. C. up to 70.degree. C.
- 3. A product produced according to the process comprising the steps of:
- (a) reacting acetone with isobutyraldehyde in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, aluminum chloride, sulfuric acid and pyrrolidinum acetate in the presence of an inert solvent, the mole ratio of isobutyraldehyde:acetone varying from 1.5:0.5 up to 0.5:1.5 isobutyraldehyde:acetone the temperature of reaction varying from about 25.degree. C. up to about 120.degree. C. and the concentration of catalyst in the reaction mass varying from about 50 grams per liter up to about 400 grams per liter whereby a mixture of compounds is formed defined according to the structure: ##STR134## wherein in the mixture in each of the compounds, one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond;
- (b) dimerizing the resulting product to form a cyclic ketone dimer, said dimerization reaction being carried out at a temperature in the range of from about 25.degree. C. up to about 120.degree. C. at atmospheric pressure in the presence of a hydrocarbon solvent or an inert alkanol solvent and in the presence of a catalyst selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, aluminum chloride and pyrrolidinium acetate;
- (c) reacting the resulting ketone dimer with an alkali metal borohydride whereby the ketone moiety is reduced to a carbinol moiety in the presence of a lower alkanol solvent which is inert in the reaction mass, the concentration of alkali metal borohydride in the reaction mass varying from about 20 grams per liter of reaction mass up to about 50 grams per liter of reaction mass, the concentration of ketone dimer in the mixture varying from 200 grams per liter up to about 800 grams per liter and the reaction temperature being in the range of from 40.degree. C. up to 70.degree. C.; and then
- (d) reacting the resultant carbinol mixture with acetic anhydride at a temperature in the range of from 90.degree. C. up to about 120.degree. C., the mole ratio of acetic anhydride:alcohol reactant mixture varying from about 1:0.5 up to about 2:1 alcohol:acetic anhydride.
Parent Case Info
This is a divisional of application Ser. No. 343,571, filed Apr. 26, 1982, now U.S. Pat. No. 4,451,403.
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Number |
Name |
Date |
Kind |
3996296 |
Moakbeyie et al. |
Dec 1976 |
|
4147727 |
Sprecker et al. |
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|
4250332 |
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|
4277618 |
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4326996 |
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Non-Patent Literature Citations (3)
Entry |
Wiemann et al., Ann Chim, 1972, T7 #6, pp. 399-409. |
Hickinbotton, "Reactions of Organic Compounds", pp. 118-125 (1957). |
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Divisions (1)
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Number |
Date |
Country |
Parent |
343571 |
Apr 1982 |
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