CN114507125A - Preparation method of pinacolone - Google Patents
Preparation method of pinacolone Download PDFInfo
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- CN114507125A CN114507125A CN202210169991.0A CN202210169991A CN114507125A CN 114507125 A CN114507125 A CN 114507125A CN 202210169991 A CN202210169991 A CN 202210169991A CN 114507125 A CN114507125 A CN 114507125A
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- pinacolone
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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
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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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention discloses a preparation method of pinacolone, which comprises the following specific processes: the prenyl and formaldehyde are catalyzed by a catalyst to generate prins reaction, and a 4,4, 5-trimethyl-1, 3-dioxane intermediate is directionally synthesized; then slowly raising the temperature to enable the 4,4, 5-trimethyl-1, 3-dioxane intermediate to generate ring-opening rearrangement, and synthesizing a crude pinacolone product; rectifying the crude product in a rectifying still to obtain 98% pinacolone, and treating the residual product in a residual still bucket for solid waste treatment; and (3) generating waste acid water with a small amount of tar after the reaction is finished, distilling the acid water out by distillation, barreling the residual kettle residue, adding sulfuric acid and solid formaldehyde into the distilled liquid, and continuously applying the solution to the next batch. The content of the pinacolone prepared by the method can reach 98 percent, and a new route is adopted, so that the polymerization of organic matters is effectively inhibited, the generation of waste acid is reduced, the environmental protection pressure is reduced, and a cleaner and more environment-friendly production process is realized.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of pinacolone.
Background
Pinacolone, i.e. 3, 3-dimethyl-2-butanone, is an important raw material for producing pesticides such as triadimefon and multi-effect wakame and is an intermediate for producing various fine chemical products such as medicines and dyes. The pinacolone is synthesized by a plurality of methods, and the rearrangement method takes pinacol as a raw material and generates pinacolone through dehydration and rearrangement in an acidic environment. The method has the defects that the source of the raw material pinacol is difficult and the reaction conditions are harsh. The oxidation method takes 2, 3-dimethyl-2-butylene as a raw material, takes organic peroxy acid or hydrogen peroxide as an oxidant for oxidation, and then obtains pinacolone through rearrangement. The method has the defects of limited source of the raw material 2, 3-dimethyl-2-butylene, harsh process conditions, long process flow and the like.
The isoamylene method takes isoamylene as a raw material, firstly reacts with hydrochloric acid to generate tertiary amyl chloride, and then reacts with formaldehyde to generate pinacolone. The method has the advantages that the isoamylene raw material is easy to obtain, the yield is high, and the defects that a large amount of inorganic acid is used and a large amount of waste acid containing various impurities is generated are overcome; a large amount of black waste acid is generated in the production process, is difficult to treat and has high treatment cost and can not be recycled.
Disclosure of Invention
The invention aims to provide a preparation method of pinacolone, which aims to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of pinacolone comprises the following steps:
A) the method comprises the following steps of utilizing formaldehyde and isoamylene to preferentially generate prins reaction under the condition of a catalyst to directly synthesize a 4,4, 5-trimethyl-1, 3-dioxane intermediate, wherein the catalyst is concentrated sulfuric acid, and the molar ratio is that of the isoamylene: 37% aqueous formaldehyde solution: concentrated sulfuric acid is 1:1.20:0.1, prins reaction formula:
B) slowly increasing the temperature of the solution from 25 ℃ at a speed of increasing 5 ℃ every 30min to enable the 4,4, 5-trimethyl-1, 3-dioxane intermediate to generate ring-opening rearrangement, synthesizing a crude pinacolone product, and increasing the temperature to rearrange the reaction formula:
C) finally, the qualified pinacolone is obtained by rectification.
Preferably, the used catalyst is concentrated sulfuric acid, and the corrosion of hydrochloric acid to equipment is relatively high, so that the corrosion to the equipment is reduced by using sulfuric acid, and the catalyst has a relatively high advantage in the aspect of design and modification of process equipment; the catalytic amount of sulfuric acid is used for preparing the pinacolone, the finally generated waste acid is reduced by 80 percent, the environmental protection pressure is greatly reduced, and a cleaner, environment-friendly and friendly process is realized.
Preferably, the molar weight of the formaldehyde is 1.0-1.5 times of that of the isoamylene, and if the molar weight of the formaldehyde exceeds 1.5 times through experiments, the yield is not obviously improved, and the more the polymers are, the experimental data are shown in the examples, and the ratio is the optimal ratio.
Preferably, the molar weight of the concentrated sulfuric acid is 0.05 to 0.2 times of that of the isoamylene, and if the ratio is exceeded, the more the concentrated sulfuric acid is, the more decomposition is, and the lower the yield is.
Preferably, the reaction temperature in the step B is controlled to be 70-90 ℃, and when the temperature is lower than 70 ℃, the lower the temperature is, the slower the reaction is, the more decomposition is, and the yield is reduced; at temperatures above 90 ℃, the higher the temperature, the more severe the decomposition and the lower the yield.
Preferably, the temperature rise time in the step B is controlled to be 4-10 hours; if the temperature rise time is controlled to be short, the temperature rise is too fast, the isoamylene reaction is not timely, and large reflux is easily formed, so that the isoamylene is seriously volatilized; if the temperature rise time is controlled to be longer, the temperature rise is too slow, so that more intermediate products are decomposed in the process of rephotography, and the final yield of the pinacolone is influenced.
Preferably, sulfuric acid and solid formaldehyde are added into clean acidic distillate obtained by distilling and dehydrating the waste acid water, and the clean acidic distillate can be continuously applied to the next batch; the lower layer waste acid obtained by layering the waste acid after the reaction is finished is distilled out of acidic distilled water through the traditional kettle type distillation, and then is mixed with solid formaldehyde to prepare a 37% formaldehyde aqueous solution for reuse.
Preferably, the molar weight of the concentrated sulfuric acid is 0.1 time of that of the isoamylene; the more concentrated sulfuric acid, the more decomposition and the lower yield, and 0.1 time is the optimum.
Preferably, the molar amount of the formaldehyde is 1.2 times that of the isoamylene; the more the molar amount of formaldehyde, the less the yield is significantly improved, and the more the polymer, 1.2 times is optimal.
Preferably, the reaction temperature in the step B is controlled at 80 ℃; the lower the temperature, the slower the reaction, the more decomposition, the lower the yield; the higher the temperature, the more violent the decomposition and the lower the yield, 80 ℃ being the optimum temperature.
Preferably, the temperature rise time in the step B is 6 hours; if the temperature rise time is controlled to be short, the temperature rise is too fast, the isoamylene reaction is not timely, and large reflux is easily formed, so that the isoamylene is seriously volatilized; if the temperature rise time is controlled to be longer, the temperature rise is too slow, so that more intermediate products are decomposed in the process of rephotography, the final yield of the pinacolone is influenced, and the optimal yield is 6 hours.
The invention has the technical effects and advantages that:
1. the invention has simple process steps, the obtained pinacolone content can reach 98 percent, the reaction lightens the phenomenon of formaldehyde polymerization, and the yield of the pinacolone is improved from 70 percent of the original process to 95 percent.
2. The invention uses the sulfuric acid to replace the common hydrochloric acid, and the sulfuric acid has higher corrosion to equipment, so the corrosion to the equipment is reduced by using the sulfuric acid, and the invention has greater advantages in the design and modification of process equipment.
3. According to the invention, catalytic amount of sulfuric acid is utilized to enable isoamylene and formaldehyde to preferentially generate prins reaction to obtain a 4,4, 5-trimethyl-1, 3-dioxane intermediate, then the temperature is directly raised to carry out ring opening rearrangement, and the process for acid water distillation and reuse in the later period is combined, so that the final waste acid is reduced by 80%, the environment-friendly pressure is greatly reduced, and a cleaner, environment-friendly and friendly process is realized.
Drawings
FIG. 1 is a flow chart of the invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
taking 139g of 37% formaldehyde aqueous solution, adding the aqueous solution into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 146g of crude pinacolone, transferring the crude pinacolone into a rectification flask, starting rectification, taking 138.3g of pinacolone with the content of 98.1 percent, the total yield of 95 percent and 7.7g of rectification kettle residue; the waste acid was separated and distilled to give 87.6g of acidic distillate and 19.4g of acidic pot residue.
Example 2:
adding 93g of formaldehyde water solution with the content of 37% into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 126g of crude pinacolone, transferring the crude pinacolone into a rectification flask to start rectification, taking 99.0g of pinacolone with the content of 98.1 percent, the total yield of 68 percent and 27.0g of rectification kettle residue; the waste acid was distilled to give 58.6g of acidic distillate and 22.4g of acidic pot residue.
Example 3:
taking 116g of formaldehyde water solution with the content of 37%, adding the formaldehyde water solution into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 136g of crude pinacolone, transferring the crude pinacolone into a rectification flask, starting rectification, taking 118.1g of pinacolone with the content of 98.01 percent, the total yield of 81 percent and 17.9g of rectification kettle residue; the waste acid was distilled to give 73.1g of acidic distillate and 20.9g of acidic pot residue.
Example 4:
adding 174g of formaldehyde water solution with the content of 37% into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 150g of crude pinacolone, transferring the crude pinacolone into a rectification flask, starting rectification, taking 136.1g of pinacolone with the content of 98.1 percent, the total yield of 93 percent and 13.9g of rectification kettle residue; the waste acid was distilled to give 109.6g of acidic distillate and 28.4g of acidic still residue.
Example 5:
taking 139g of formaldehyde water solution with the content of 37%, adding into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time for 2 hours, having a large reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 143g of crude pinacolone, transferring the crude pinacolone into a rectification flask to start rectification, taking 112.2g of pinacolone with the content of 98.0 percent, the total yield of 77 percent and 30.8g of rectification kettle residue; the waste acid was separated and distilled to obtain 87.6g of acidic distillate and 22.4g of acidic still residue.
Example 6:
taking 139g of formaldehyde water solution with the content of 37%, adding into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time for 8 hours, basically having no reflux, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 140g of crude pinacolone, transferring the crude pinacolone into a rectification flask to start rectification, taking 120.1g of pinacolone with the content of 98.0 percent, the total yield of 82 percent and the rectification kettle residue of 19.9 g; the waste acid was separated and distilled to give 87.6g of acidic distillate and 25.4g of acidic still residue.
Example 7:
taking 139g of formaldehyde water solution with the content of 37%, adding into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 60 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 133g of crude pinacolone, transferring the crude pinacolone into a rectification flask to start rectification, taking 110.1g of pinacolone with the content of 98.0 percent, the total yield of 76 percent and the rectification kettle residue of 22.9 g; the waste acid was distilled to give 87.6g of acidic distillate and 32.4g of acidic pot residue.
Example 8:
taking 139g of formaldehyde water solution with the content of 37%, adding into a flask, adding 28g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 140g of crude pinacolone, transferring the crude pinacolone into a rectification flask to start rectification, taking 130.2g of pinacolone with the content of 98.0 percent, the total yield of 89 percent and 9.8g of rectification kettle residue; the waste acid was separated and distilled to give 87.6g of acidic distillate and 39.4g of acidic pot residue.
Example 9:
taking 139g of formaldehyde water solution with the content of 37%, adding 5g of concentrated sulfuric acid into a flask, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after feeding, and stirring for 3 hours; continuing to heat to 80 ℃, controlling the heating time to be 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 133g of crude pinacolone, transferring the crude pinacolone into a rectification flask, starting rectification, taking 88.0g of pinacolone with the content of 98.0 percent, the total yield of 60 percent and 45.0g of rectification kettle residue; the waste acid was separated and distilled to give 87.6g of acidic distillate and 23.4g of acidic pot residue.
Example 10:
taking 139g of formaldehyde water solution with the content of 37%, adding into a flask, adding 14g of concentrated sulfuric acid, cooling to 5-10 ℃, slowly pouring 100g of isoamylene, slowly heating to 25 ℃ after the feeding is finished, and stirring for 3 hours; continuing to heat to 90 ℃, controlling the heating time for 6 hours, causing a weak reflux phenomenon, finishing heat preservation, cooling to 20 ℃, standing for layering, taking 144g of crude pinacolone, transferring the crude pinacolone into a rectification flask, starting rectification, taking 133.2g of pinacolone with the content of 98.1 percent, the total yield of 91 percent and the rectification kettle residue of 10.8 g; the waste acid was separated and distilled to obtain 87.6g of acidic distillate and 21.4g of acidic still residue.
The above 10 groups of data are organized as follows:
1) summary of the Experimental conditions
| Serial number | Isoamylene/g | 37% aqueous Formaldehyde solution/g | Formaldehyde equivalent | Concentrated sulfuric acid/g | Temperature rise Final temperature/. degree.C | Time of temperature rise/h |
| 1 | 100 | 139 | 1.20 | 14 | 80 | 6 |
| 2 | 100 | 93 | 0.80 | 14 | 80 | 6 |
| 3 | 100 | 116 | 1.00 | 14 | 80 | 6 |
| 4 | 100 | 174 | 1.50 | 14 | 80 | 6 |
| 5 | 100 | 139 | 1.20 | 14 | 80 | 2 |
| 6 | 100 | 139 | 1.20 | 14 | 80 | 8 |
| 7 | 100 | 139 | 1.20 | 14 | 60 | 6 |
| 8 | 100 | 139 | 1.20 | 28 | 80 | 6 |
| 9 | 100 | 139 | 1.20 | 5 | 80 | 6 |
| 10 | 100 | 139 | 1.20 | 14 | 90 | 6 |
2) Product data analysis
| Serial number | Pinacolone/g | Distillation still residue/g | Content/% | Yield/% | Distilled water/g | Acid still residue/g |
| 1 | 138.3 | 7.7 | 98.1 | 95 | 87.6 | 19.4 |
| 2 | 99.0 | 27.0 | 98.1 | 68 | 58.6 | 22.4 |
| 3 | 118.1 | 17.9 | 98.0 | 81 | 73.1 | 20.9 |
| 4 | 136.1 | 13.9 | 98.1 | 93 | 109.6 | 28.4 |
| 5 | 112.2 | 30.8 | 98.0 | 77 | 87.6 | 22.4 |
| 6 | 120.1 | 19.9 | 98.0 | 82 | 87.6 | 25.4 |
| 7 | 110.1 | 22.9 | 98.0 | 76 | 87.6 | 32.4 |
| 8 | 130.2 | 9.8 | 98.0 | 89 | 87.6 | 39.4 |
| 9 | 88.0 | 45.0 | 98.0 | 60 | 87.6 | 23.4 |
| 10 | 133.2 | 10.8 | 98.1 | 91 | 87.6 | 21.4 |
The above data were analyzed as follows:
1) as can be seen from examples 1, 2,3 and 4, the molar weight of formaldehyde is 1.2 times that of isoamylene, and the yield is highest;
2) as can be seen from examples 1, 5 and 6, the yield is highest when the temperature rise value is 80 ℃ and the yield is controlled within 6 hours;
3) as can be seen from examples 1, 7 and 10, the final reaction temperature is 80 ℃ and the yield is highest;
4) as can be seen from examples 1, 8 and 9, the amount of sulfuric acid used was 10% of the molar amount of isoamylene, and the yield was the highest.
The invention greatly reduces the consumption of sulfuric acid and the output of waste acid by optimizing reaction conditions, basically ensures that no waste acid is generated in the process by combining the distillation of subsequent waste acid water, simultaneously lightens the phenomenon of formaldehyde polymerization, improves the yield of pinacolone and improves the yield from 70 percent of the original process to 95 percent.
The applicant further states that the present invention is described in the above embodiments to explain the implementation method and device structure of the present invention, but the present invention is not limited to the above embodiments, i.e. it is not meant to imply that the present invention must rely on the above methods and structures to implement the present invention. It should be understood by those skilled in the art that any modifications to the present invention, the implementation of alternative equivalent substitutions and additions of steps, the selection of specific modes, etc., are within the scope and disclosure of the present invention.
The present invention is not limited to the above embodiments, and all the ways of achieving the objects of the present invention by using the structure and the method similar to the present invention are within the protection scope of the present invention.
Claims (12)
1. A preparation method of pinacolone is characterized by comprising the following steps: the method comprises the following steps:
A) the method comprises the following steps of (1) utilizing formaldehyde and isoamylene to preferentially generate prins reaction under the condition of a catalyst, and directly synthesizing a 4,4, 5-trimethyl-1, 3-dioxane intermediate;
B) the solution temperature is slowly increased to lead the 4,4, 5-trimethyl-1, 3-dioxane intermediate to generate ring-opening rearrangement, and a crude pinacolone is synthesized;
C) finally, the qualified pinacolone is obtained by rectification.
2. The method for preparing pinacolone according to claim 1, characterized in that: the catalyst used in the step A is concentrated sulfuric acid.
3. The method for preparing pinacolone according to claim 1, characterized in that: the molar weight of the formaldehyde is 1.0-1.5 times of that of the isoamylene.
4. The method for preparing pinacolone according to claim 1, characterized in that: the molar weight of the concentrated sulfuric acid is 0.05-0.1 time of that of the isoamylene.
5. The method for preparing pinacolone according to claim 1, characterized in that: and in the step B, the reaction temperature is controlled to be 70-80 ℃.
6. The method for preparing pinacolone according to claim 1, characterized in that: and C, controlling the temperature rise time in the step B to be 6-8 hours.
7. The method for preparing pinacolone according to claim 1, characterized in that: the whole reaction is carried out in the same set of reaction kettle.
8. The method for preparing pinacolone according to claim 1, characterized in that: and adding sulfuric acid and solid formaldehyde into clean acidic distillate obtained by distilling and dehydrating the waste acid water, and continuously applying the sulfuric acid and the solid formaldehyde to the next batch, wherein the residual acidic tar is subjected to kettle residue treatment.
9. The method for preparing pinacolone according to claim 4, wherein: the molar weight of the concentrated sulfuric acid is 0.1 time of that of the isoamylene.
10. The method for preparing pinacolone according to claim 3, characterized in that: the molar weight of the formaldehyde is 1.2 times that of the isoamylene.
11. The method for preparing pinacolone according to claim 5, wherein: the reaction temperature in step B was controlled at 80 ℃.
12. The method for preparing pinacolone according to claim 6, wherein: the temperature rise time in step B was 6 hours.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE714488C (en) * | 1938-08-18 | 1941-12-01 | Ig Farbenindustrie Ag | Manufacture of pinacolin |
| US4057583A (en) * | 1974-12-27 | 1977-11-08 | Bayer Aktiengesellschaft | Process for the preparation of pinacolone |
| US4059634A (en) * | 1975-12-15 | 1977-11-22 | Mobay Chemical Corporation | Production of pinacolone |
| JPS5479217A (en) * | 1977-12-02 | 1979-06-25 | Kuraray Co Ltd | Preparation of pinacolone |
| US4224252A (en) * | 1978-05-15 | 1980-09-23 | Kuraray Co., Ltd. | Production of pinacolone |
| CN1286242A (en) * | 1999-08-30 | 2001-03-07 | 姜堰市鸿泰化工厂 | Process for synthesizing pinacolone |
-
2022
- 2022-02-24 CN CN202210169991.0A patent/CN114507125A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE714488C (en) * | 1938-08-18 | 1941-12-01 | Ig Farbenindustrie Ag | Manufacture of pinacolin |
| US4057583A (en) * | 1974-12-27 | 1977-11-08 | Bayer Aktiengesellschaft | Process for the preparation of pinacolone |
| US4059634A (en) * | 1975-12-15 | 1977-11-22 | Mobay Chemical Corporation | Production of pinacolone |
| JPS5479217A (en) * | 1977-12-02 | 1979-06-25 | Kuraray Co Ltd | Preparation of pinacolone |
| US4224252A (en) * | 1978-05-15 | 1980-09-23 | Kuraray Co., Ltd. | Production of pinacolone |
| CN1286242A (en) * | 1999-08-30 | 2001-03-07 | 姜堰市鸿泰化工厂 | Process for synthesizing pinacolone |
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