CN112592262A - Preparation method of adamantanone - Google Patents
Preparation method of adamantanone Download PDFInfo
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- CN112592262A CN112592262A CN202011474116.0A CN202011474116A CN112592262A CN 112592262 A CN112592262 A CN 112592262A CN 202011474116 A CN202011474116 A CN 202011474116A CN 112592262 A CN112592262 A CN 112592262A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Abstract
The invention discloses a preparation method of adamantanone, relating to the technical field of synthesis of adamantanone; the method aims to solve the problems of long reaction time and complicated operation process; the method specifically comprises the following steps: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 30 ℃; heating to 50 ℃, and introducing nitrogen into the batching kettle; pressing the mixed materials into a reaction tube, and staying for 1 minute; pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9; extraction was performed with 3 times the weight of adamantane in toluene. The method comprises the steps of mixing and heating raw materials, introducing nitrogen, carrying out oxidation reaction, controlling the residence time and temperature of reaction liquid in a reaction tube during the derivation period, extracting by toluene and NaOH aqueous solution, carrying out reduced pressure distillation concentration, cooling, separation and drying on extract liquor to obtain a final product, wherein the operation process is relatively simple, the reaction is controllable and the reaction time is short.
Description
Technical Field
The invention relates to the technical field of adamantanone synthesis, in particular to a preparation method of adamantanone.
Background
Adamantane is a derivative of adamantane, and from the viewpoint of effective utilization of carbon resources, a technique for converting a hydrocarbon compound into an alcohol or a ketone by oxidation is industrially very important, and as a technique for selectively producing adamantanone which is an important intermediate for various pharmaceutical and agricultural chemicals or industrial raw materials, a method for producing adamantanone in concentrated sulfuric acid is known, wherein adamantanone is produced industrially by a direct oxidation method using adamantane or 1-adamantanol as a starting material and concentrated sulfuric acid, and when adamantanone is selectively produced using sulfuric acid, heavy components as by-products are produced at a high reaction rate, the yield is low, or the reaction time is extremely long although the yield is high, and the productivity is low.
Through search, the chinese patent application No. CN201010605609.3 discloses a method for producing 2-adamantanone, based on the principle of oxidizing adamantane with concentrated sulfuric acid to prepare 2-adamantanone, the oxidation reaction occurs between the phase interface of non-polar organic phase and inorganic phase which are insoluble each other, and then the esterification product is extracted from the inorganic phase by the polar organic solvent to perform the next hydrolysis process. The production method of 2-adamantanone in the above patent has the following disadvantages: the total reaction time is 16-27 hours, multiple two-phase reaction and extraction operations are adopted, and the operation process is complicated.
Disclosure of Invention
The invention aims to solve the defects in the prior art and provides a preparation method of adamantanone.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing adamantanone, comprising the steps of:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 30 ℃;
s2: heating to 50 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 1 minute;
s4: pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 63%, and then carrying out cooling, separation and drying treatment to obtain the product.
Preferably: the ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 1: 6: 2, the concentration of the sulfuric acid is more than or equal to 98 percent.
Preferably: the preparation method of the adamantane in the S1 comprises the following steps:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 220 ℃ for reacting for 6 hours;
s23: then stirring the mixture in a recrystallization kettle for 9.5 hours at the temperature of 5 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
Preferably: the catalyst consists of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio of the molybdenum pentachloride to the manganese chloride to the anhydrous iridium chloride is 6: 2: 2.
preferably: and after introducing nitrogen into the S2, controlling the pressure in the kettle to be 0.06 Mpa.
Preferably: the temperature of the heating medium outside the reaction tube in the S3 is 80-120 ℃.
Preferably: and the reaction tube in the S3 is a titanium steel thin round tube.
The invention has the beneficial effects that:
1. mixing and heating the raw materials, introducing nitrogen, carrying out oxidation reaction, controlling the residence time and temperature of reaction liquid in a reaction tube during the derivation period, extracting by toluene and NaOH aqueous solution, carrying out reduced pressure distillation concentration, cooling, separation and drying on extract liquor to obtain a final product, wherein the operation process is relatively simple, the reaction is controllable and the time is short.
2. The retention time in the reaction tube is short, so that the efficiency of the material reaction for generating the 2-adamantanol sulfate is high, the side reaction is effectively inhibited, the polymerized colloid is not easy to generate, and the yield of the adamantanone is improved.
3. The adamantane and concentrated sulfuric acid are stirred and mixed, so that the solid particle raw material is dispersed in sulfuric acid solution, and the yield of the prepared adamantane reaches over 60 percent.
Drawings
FIG. 1 is a schematic flow chart of examples 1, 3 and 5 of a preparation method of adamantanone provided by the invention;
fig. 2 is a schematic flow chart of example 2 and example 4 of a preparation method of adamantanone provided by the invention.
Detailed Description
The technical solution of the present patent will be described in further detail with reference to the following embodiments.
Reference will now be made in detail to embodiments of the present patent, examples of which are illustrated in the accompanying drawings, wherein like or similar reference numerals refer to the same or similar elements or elements having the same or similar function throughout. The embodiments described below with reference to the drawings are exemplary only for the purpose of explaining the present patent and are not to be construed as limiting the present patent.
In the description of this patent, it is to be understood that the terms "center," "upper," "lower," "front," "rear," "left," "right," "vertical," "horizontal," "top," "bottom," "inner," "outer," and the like are used in the orientations and positional relationships indicated in the drawings for the convenience of describing the patent and for the simplicity of description, and are not intended to indicate or imply that the referenced devices or elements must have a particular orientation, be constructed and operated in a particular orientation, and are not to be considered limiting of the patent.
In the description of this patent, it is noted that unless otherwise specifically stated or limited, the terms "mounted," "connected," and "disposed" are to be construed broadly and can include, for example, fixedly connected, disposed, detachably connected, disposed, or integrally connected and disposed. The specific meaning of the above terms in this patent may be understood by those of ordinary skill in the art as appropriate.
Example 1:
a method for preparing adamantanone, as shown in FIG. 1, comprises the following steps:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 30 ℃;
s2: heating to 50 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 1 minute;
s4: pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 63%, and then carrying out cooling, separation and drying treatment to obtain the product.
The ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 1: 6: 2, the concentration of the sulfuric acid is more than or equal to 98 percent.
The preparation method of the adamantane in the S1 comprises the following steps:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 220 ℃ for reacting for 6 hours;
s23: then stirring the mixture in a recrystallization kettle for 9.5 hours at the temperature of 5 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
Further, the catalyst consists of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio of the molybdenum pentachloride to the manganese chloride to the anhydrous iridium chloride is 6: 2: 2.
and after introducing nitrogen into the S2, controlling the pressure in the kettle to be 0.06 Mpa.
The temperature of the heating medium outside the reaction tube in the S3 is 80-120 ℃.
And the reaction tube in the S3 is a titanium steel thin round tube.
When the method is used, the raw materials are mixed and heated, oxidation reaction is carried out after nitrogen is introduced, the residence time and temperature of reaction liquid in a reaction tube are controlled during derivation, the residence time in the reaction tube is short, the efficiency of generating 2-adamantanol sulfate through material reaction is high, side reactions are effectively inhibited, polymerized colloid is not easy to generate, the adamantanone yield is improved, the reaction liquid is extracted by toluene and NaOH aqueous solution, the extract liquid is subjected to reduced pressure distillation concentration, cooling, separation and drying treatment to obtain a final product, the operation is simple, the reaction is controllable, the time is short, adamantane and concentrated sulfuric acid are stirred and mixed, solid particle raw materials are dispersed in sulfuric acid liquid, and the prepared adamantane yield reaches more than 60%.
Example 2:
a method for preparing adamantanone, as shown in fig. 2, comprising the steps of:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 35 ℃;
s2: heating to 35 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 40 s;
s4: pouring the reaction solution into 500g of ice water, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 62%, and then carrying out cooling, separation and drying treatment to obtain the product.
The ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 1: 6: 2, the concentration of the sulfuric acid is more than or equal to 98 percent.
The preparation method of the adamantane in the S1 comprises the following steps:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 220 ℃ for reacting for 6 hours;
s23: then stirring the mixture in a recrystallization kettle for 9.5 hours at the temperature of 5 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
Further, the catalyst consists of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio of the molybdenum pentachloride to the manganese chloride to the anhydrous iridium chloride is 6: 2: 2.
and after introducing nitrogen into the S2, controlling the pressure in the kettle to be 0.06 Mpa.
The temperature of the heating medium outside the reaction tube in the S3 is 80-120 ℃.
And the reaction tube in the S3 is a titanium steel thin round tube.
Example 3:
a method for preparing adamantanone, as shown in FIG. 1, comprises the following steps:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 30 ℃;
s2: heating to 50 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 1 minute;
s4: pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 63%, and then carrying out cooling, separation and drying treatment to obtain the product.
The ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 1: 6: 3, the concentration of the sulfuric acid is more than or equal to 98 percent.
The preparation method of the adamantane in the S1 comprises the following steps:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 200 ℃ for reaction for 7 hours;
s23: then stirring the mixture in a recrystallization kettle for 9.5 hours at the temperature of 5 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
Further, the catalyst consists of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio of the molybdenum pentachloride to the manganese chloride to the anhydrous iridium chloride is 6: 2: 2.
and after introducing nitrogen into the S2, controlling the pressure in the kettle to be 0.05 Mpa.
The temperature of the heating medium outside the reaction tube in the S3 is 80-120 ℃.
And the reaction tube in the S3 is a titanium steel thin round tube.
Example 4:
a method for preparing adamantanone, as shown in fig. 2, comprising the steps of:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 35 ℃;
s2: heating to 35 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 40 s;
s4: pouring the reaction solution into 500g of ice water, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 62%, and then carrying out cooling, separation and drying treatment to obtain the product.
The ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 1: 6: 3, the concentration of the sulfuric acid is more than or equal to 98 percent.
The preparation method of the adamantane in the S1 comprises the following steps:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 210 ℃ for reacting for 6 hours;
s23: then stirring the mixture for 9 hours in a recrystallization kettle at the temperature of 4 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
Further, the catalyst consists of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio of the molybdenum pentachloride to the manganese chloride to the anhydrous iridium chloride is 6: 2: 2.
and after introducing nitrogen into the S2, controlling the pressure in the kettle to be 0.03 Mpa.
The temperature of the heating medium outside the reaction tube in the S3 is 80-120 ℃.
And the reaction tube in the S3 is a titanium steel thin round tube.
Example 5:
a method for preparing adamantanone, as shown in FIG. 1, comprises the following steps:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 30 ℃;
s2: heating to 50 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 1 minute;
s4: pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 63%, and then carrying out cooling, separation and drying treatment to obtain the product.
The mixture ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 2: 6: 2, the concentration of the sulfuric acid is more than or equal to 98 percent.
The preparation method of the adamantane in the S1 comprises the following steps:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 190 ℃ for reacting for 6.5 hours;
s23: then stirring the mixture in a recrystallization kettle for 9.5 hours at the temperature of 5 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
Further, the catalyst consists of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio of the molybdenum pentachloride to the manganese chloride to the anhydrous iridium chloride is 6: 2: 2.
and after introducing nitrogen into the S2, controlling the pressure in the kettle to be 0.07 Mpa.
The temperature of the heating medium outside the reaction tube in the S3 is 80-120 ℃.
And the reaction tube in the S3 is a titanium steel thin round tube.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (7)
1. A method for producing adamantanone, characterized by comprising the steps of:
s1: putting raw materials of adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at the temperature of 30 ℃;
s2: heating to 50 ℃, and introducing nitrogen into the batching kettle;
s3: pressing the mixed materials into a reaction tube, and staying for 1 minute;
s4: pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution with the weight 7 times that of the adamantane during cooling, and adjusting the pH to 9;
s5: extracting with toluene 3 times the weight of adamantane, and analyzing the extractive solution by gas chromatography;
s6: and (3) carrying out reduced pressure distillation and concentration on the extract liquor to 63%, and then carrying out cooling, separation and drying treatment to obtain the product.
2. A method for preparing adamantanone according to claim 1, where in the ratio of adamantane, sulfuric acid and trifluoroacetic acid in S1 is 1: 6: 2, the concentration of the sulfuric acid is more than or equal to 98 percent.
3. A method of producing adamantane according to claim 2, wherein the method of producing adamantane in S1 includes the steps of:
s21: adding dicyclopentadiene and a nickel catalyst into a reaction kettle, replacing gas in the kettle with nitrogen, and introducing hydrogen for reaction to obtain tetrahydrodicyclopentadiene;
s22: mixing and dissolving 0.5g of catalyst, 5g of phosphorus trichloride and 450g of triethyl phosphate, adding 95g of tetrahydrodicyclopentadiene, and heating to 220 ℃ for reacting for 6 hours;
s23: then stirring the mixture in a recrystallization kettle for 9.5 hours at the temperature of 5 ℃, and washing the mixture by using a small amount of acetone;
s24: filtering and drying to obtain the finished product.
4. A preparation method of adamantanone according to claim 3, wherein the catalyst is composed of molybdenum pentachloride, manganese chloride and anhydrous iridium chloride, and the mass ratio is 6: 2: 2.
5. a process for producing adamantanone and claimed in claim 1, wherein the pressure in the reaction vessel after introducing nitrogen gas into S2 is controlled to 0.06 MPa.
6. A method for preparing adamantanone according to claim 5 and wherein the temperature of the heating medium outside the reaction tube in S3 is 80-120 ℃.
7. A method for preparing adamantanone and use according to any one of claims 1 to 6, where in S3 the reaction tube is a titanium steel thin round tube.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114507124A (en) * | 2022-01-28 | 2022-05-17 | 浙江荣耀生物科技股份有限公司 | Separation method of 2-adamantanone |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114507124A (en) * | 2022-01-28 | 2022-05-17 | 浙江荣耀生物科技股份有限公司 | Separation method of 2-adamantanone |
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