CN114702434A - Continuous synthesis method of tetramethyl piperidinol - Google Patents
Continuous synthesis method of tetramethyl piperidinol Download PDFInfo
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- CN114702434A CN114702434A CN202210508974.5A CN202210508974A CN114702434A CN 114702434 A CN114702434 A CN 114702434A CN 202210508974 A CN202210508974 A CN 202210508974A CN 114702434 A CN114702434 A CN 114702434A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention relates to a continuous synthesis method of tetramethyl piperidinol, which comprises the following steps: 1) preparing triacetonamine solution with a certain concentration by using an alcohol solvent as a raw material; 2) continuously feeding triacetonamine solution and hydrogen into a fixed bed reactor loaded with a catalyst at a proper temperature, and carrying out hydrogenation reduction under a certain hydrogen pressure to prepare tetramethyl piperidinol hydrogenation liquid; 3) carrying out desolventizing, cooling and crystallizing on the obtained tetramethylpiperidinol hydrogenation liquid to obtain a finished product tetramethylpiperidinol; the technical scheme adopts the fixed bed reactor to carry out continuous hydrogenation reaction, overcomes the defects of the prior art, and provides a safer and more convenient continuous production approach; the synthetic method is simple and efficient, particularly utilizes a fixed bed reactor to combine with a specific catalyst, is simple and convenient to operate, is green and environment-friendly, has less industrial three wastes, and is a sustainable green synthetic method.
Description
Technical Field
The invention belongs to the field of synthesis of tetramethyl piperidinol, and particularly relates to a continuous synthesis method of tetramethyl piperidinamine.
Background
At present, the synthesis method of tetramethyl piperidinol is mainly intermittent hydrogenation reduction method preparation. The method comprises the steps of taking low-carbon alcohol as a solvent in a high-pressure reaction kettle, introducing hydrogen, and carrying out hydrogenation reduction in the presence of catalysts such as nickel, palladium and the like to obtain the tetramethyl piperidinol with the content of 88-90%; the method for preparing the tetramethyl piperidine alcohol has poor reaction selectivity, wherein the proportion of main by-product tetramethyl piperidine is high, so that finished product crystals are small, the quantity of entrained solvents is large, the recovery process of post-treatment solvents is complex, the production period is prolonged, the cost is increased, and the proportion of organic solvents is too high, so that the yield of each batch is reduced. At present, the quality of products is influenced to a certain extent by the batch hydrogenation reduction method, and the whole operation process is relatively complicated, so that a new scheme is urgently needed to solve the technical problems.
Disclosure of Invention
In order to solve the problems, the invention discloses a continuous synthesis method of tetramethylpiperidinol, the technical scheme adopts a fixed bed to prepare the tetramethylpiperidinol by continuous hydrogenation, overcomes the defects of the prior art, and provides a production way which is safer, more convenient and higher in automation degree.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a continuous synthesis method of tetramethyl piperidinol comprises the following steps:
1) preparing triacetonamine solution with a certain concentration by using an alcohol solvent as a raw material;
2) continuously feeding triacetonamine solution and hydrogen into a fixed bed reactor loaded with a catalyst at a proper temperature, and carrying out hydrogenation reduction under hydrogen pressure to prepare tetramethyl piperidinol hydrogenation liquid;
3) and carrying out desolventizing, cooling and crystallizing on the obtained tetramethyl piperidinol hydrogenation liquid to obtain the finished product tetramethyl piperidinol.
Further, the mass ratio of triacetonamine to the alcohol solvent in the step (1) is 1: 1-1: 5; preferably 1:1.5 to 1: 3.
Further, the alcoholic solvent in step (1) is one or more of methanol, ethanol, propanol, isopropanol, butanol, 2-butanol, tert-butanol, pentanol and hexanol; preferably one or more of ethanol, propanol, isopropanol and butanol; further preferably one or more of propanol, isopropanol and butanol; more preferably isopropanol.
Further, the continuous feeding temperature of the triacetonamine solution and the hydrogen in the step (2) is 120-150 ℃; preferably 140-.
Further, the hydrogen pressure in the step (2) is 1.0-5.0 MPa; preferably 1.5-2.5 MPa.
Further, the catalyst in the step (2) comprises a carrier, an active metal component and an auxiliary metal.
Further, the mass fraction of the active metal component is 15-25%, more preferably 15-20% by weight of the final catalyst; the sum of the mass fractions of the auxiliary metal is 1-10% or no auxiliary metal is added, preferably 1-6%; the balance is carrier.
Further, the carrier is silica of 30-40 meshes.
Furthermore, the carrier is silicon oxide, the active metal component is nickel, and the auxiliary metal is one or two of iron and zinc.
Further, the preparation method of the catalyst comprises the following steps: according to the composition ratio of an active metal component and an auxiliary metal in the catalyst, respectively preparing a metal salt containing the active metal component and a metal salt containing the auxiliary metal into aqueous solutions, weighing silicon oxide, mixing, soaking at room temperature, evaporating to dryness, drying at 120 ℃, and finally placing in a tubular furnace, reducing at 450 ℃, wherein the gas flow rate is 200 mL/min; the metal salt of the active metal component is Ni (NO)3)2·6H2O、Fe(NO3)3·9H2O or Zn (NO)3)2·6H2O; the concentration of the metal salt aqueous solution containing the promoter metal is Ni (NO)3)2·6H2The concentration of O solution is 0.01mol/L, Fe (NO)3)3·9H2O or Zn (NO)3)2·6H2The concentration of the O solution is 0.03 mol/L.
The invention has the beneficial effects that:
the method is green and environment-friendly, low in cost, high in automation degree, simple in operation, long in catalyst service life, high in yield, high in product yield and the like.
Drawings
FIG. 1 is an SEM photograph of the catalyst prepared in example 1;
FIG. 2 is an SEM image of the catalyst prepared in example 3.
Detailed Description
The present invention will be further illustrated with reference to the accompanying drawings and specific embodiments, which are to be understood as merely illustrative of the invention and not as limiting the scope of the invention.
Example 1
Weighing 3407mLNi (NO)3)2·6H2O aqueous solution (0.01mol/L) and 179.2mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 51mLZn (NO)3)2·6H2O aqueous solution (0.03mol/L) and 7.6g of silica were mixed uniformly, immersed at room temperature for 12 hours, and then evaporated to dryness. Then dried at 120 ℃ for 12h, finally placed in a tube furnace and reduced at 450 ℃ for 5h with a gas flow rate of 200mL/min to obtain a silica supported metallic nickel-iron-zinc catalyst with a loading of 20 wt% nickel, 3 wt% iron and 1 wt% zinc, wherein the silica particles are of 40 mesh and the SEM image of the prepared catalyst is shown in FIG. 1.
Triacetonamine and isopropanol were mixed as follows 1:3, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 500mL/h, the raw material feeding flow rate is 500mL/h, the reaction temperature is 140-145 ℃, the reaction hydrogen pressure is 1.5-2.0Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation liquid is 94.2%, and the finished product is obtained by cooling crystallization extraction, wherein the molar yield of the tetramethylpiperidinol is 90.5%.
Example 2
Weighing 3105mLNi (NO)3)2·6H2O water solubleLiquid (0.01mol/L) and 179.2mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 153mLZn (NO)3)2·6H2An aqueous O solution (0.03mol/L) and 7.4g of silica were mixed uniformly, immersed at room temperature for 12 hours, and evaporated to dryness. Then drying at 120 ℃ for 12h, finally placing the mixture in a tubular furnace, reducing at 450 ℃ for 5h with the gas flow rate of 200mL/min to obtain the silicon oxide supported metal nickel-iron-zinc catalyst with the loading of 18 wt% of nickel, 3 wt% of iron and 3 wt% of zinc, wherein the silicon oxide particles are 40 meshes.
Amounts of triacetonamine and isopropanol were measured as 1:1.5, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 800mL/h, the raw material feeding flow rate is 600mL/h, the reaction temperature is 140-145 ℃, the reaction hydrogen pressure is 2.0-2.5Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation solution is 95.8%, and the finished product is obtained through cooling, crystallization and purification, wherein the molar yield of the tetramethylpiperidinol is 93.2%.
Example 3
Weighing 2554mLNi (NO)3)2·6H2O aqueous solution (0.01mol/L) and 358.4mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 153mLZn (NO)3)2·6H2O aqueous solution (0.03mol/L) and 7.4g of silica were mixed uniformly, immersed at room temperature for 12 hours, and then evaporated to dryness. Then dried at 120 ℃ for 12h, finally placed in a tube furnace and reduced at 450 ℃ for 5h with a gas flow rate of 200mL/min to obtain a silica supported metallic nickel-iron-zinc catalyst with a loading of 15 wt% nickel, 6 wt% iron and 3 wt% zinc, wherein the silica particles are of 30 mesh and the SEM image of the prepared catalyst is shown in FIG. 2).
Amounts of triacetonamine and isopropanol were measured as 1:3, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 700mL/h, the raw material feeding flow rate is 800mL/h, the reaction temperature is 140-145 ℃, the reaction hydrogen pressure is 2.0-2.5Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation liquid is 95.2%, and the finished product is obtained through cooling, crystallization and purification, wherein the molar yield of the tetramethylpiperidinol is 93.1%.
Example 4
Weighing 2760mLNi (NO)3)2·6H2O aqueous solution (0.01mol/L) and 179.4mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 306.5mLZn (NO)3)2·6H2O aqueous solution (0.03mol/L) and 7.4g of silica were mixed uniformly, immersed at room temperature for 12 hours, and then evaporated to dryness. Then dried at 120 ℃ for 12h, finally placed in a tube furnace and reduced at 450 ℃ for 5h with a gas flow rate of 200mL/min to obtain 10g of a silica supported metallic nickel-iron-zinc catalyst with a loading of 17 wt% nickel, 3 wt% iron and 6 wt% zinc, wherein the silica particles are 30 mesh.
Amounts of triacetonamine and isopropanol were measured as 1: 2.5, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 750mL/h, the raw material feeding flow rate is 600mL/h, the reaction temperature is 145-150 ℃, the reaction hydrogen pressure is 1.5-2.0Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation solution is 96.5%, and the finished product is obtained by cooling and crystallization, wherein the molar yield of the tetramethylpiperidinol is 94.8%.
Example 5
Weighing 2554mLNi (NO)3)2·6H2O aqueous solution (0.01mol/L) and 179.4mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 306.5mLZn (NO)3)2·6H2O aqueous solution (0.03mol/L) and 7.4g of silica were mixed uniformly, immersed at room temperature for 12 hours, and then evaporated to dryness. Then drying for 12h at 120 ℃, finally placing the product in a tube furnace, reducing for 5h at 450 ℃ at a gas flow rate of 200mL/min to obtain a silicon oxide supported metallic nickel-iron-zinc catalyst with the loading of 15 wt% of nickel, 3 wt% of iron and 6 wt% of zinc, wherein the silicon oxide particles are 40 meshes.
Amounts of triacetonamine and isopropanol were measured as 1: 1.8, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 800mL/h, the raw material feeding flow rate is 600mL/h, the reaction temperature is 145-150 ℃, the reaction hydrogen pressure is 2.0-2.5Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation solution is 97.6%, and the finished product is obtained by cooling and crystallization, wherein the molar yield of the tetramethylpiperidinol is 95.3%.
Example 6
Weighing 2554mLNi (NO)3)2·6H2O aqueous solution (0.01mol/L) and 120mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 306.5mLZn (NO)3)2·6H2O aqueous solution (0.03mol/L) and 7.0g of silica were mixed uniformly, immersed at room temperature for 12 hours, and then evaporated to dryness. Then drying for 12h at 120 ℃, finally placing the product in a tube furnace, reducing for 5h at 450 ℃ at a gas flow rate of 200mL/min to obtain a silicon oxide supported metallic nickel-iron-zinc catalyst with the loading of 15 wt% of nickel, 2 wt% of iron and 6 wt% of zinc, wherein the silicon oxide particles are 30 meshes.
Amounts of triacetonamine and isopropanol were measured as 1:3, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 600mL/h, the raw material feeding flow rate is 600mL/h, the reaction temperature is 145-150 ℃, the reaction hydrogen pressure is 1.5-2.0Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation liquid is 96.2%, and the finished product is obtained by cooling and crystallization, wherein the molar yield of the tetramethylpiperidinol is 95.0%.
Example 7
Weighing 2554mLNi (NO)3)2·6H2O aqueous solution (0.01mol/L) and 60mL Fe (NO)3)3·9H2O aqueous solution (0.03mol/L), 51mLZn (NO)3)2·6H2An aqueous O solution (0.03mol/L) and 7.4g of silica were mixed uniformly, immersed at room temperature for 12 hours, and evaporated to dryness. Then drying at 120 ℃ for 12h, finally placing the mixture in a tubular furnace, reducing at 450 ℃ for 5h with the gas flow rate of 200mL/min to obtain the silicon oxide supported metal nickel-iron-zinc catalyst with the loading of 15 wt% of nickel, 1 wt% of iron and 1 wt% of zinc, wherein the silicon oxide particles are 40 meshes.
Amounts of triacetonamine and isopropanol were measured as 1:1, carrying out continuous hydrogenation by a fixed bed loaded with 10g of catalyst, wherein the introduced hydrogen flow is 800mL/h, the raw material feeding flow rate is 600mL/h, the reaction temperature is 145-150 ℃, the reaction hydrogen pressure is 2.0-2.5Mpa, the continuous operation is 240h, the catalyst is not obviously inactivated, the content of the obtained tetramethylpiperidinol hydrogenation liquid is 97.4%, and the finished product is obtained by cooling and crystallization, wherein the molar yield of the tetramethylpiperidinol is 95.3%.
It should be noted that the above-mentioned contents only illustrate the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and it will be apparent to those skilled in the art that several modifications and embellishments can be made without departing from the principle of the present invention, and these modifications and embellishments fall within the protection scope of the claims of the present invention.
Claims (10)
1. A continuous synthesis method of tetramethyl piperidinol is characterized by comprising the following steps:
1) preparing triacetonamine solution with a certain concentration by using an alcohol solvent as a raw material;
2) continuously feeding triacetonamine solution and hydrogen into a fixed bed reactor loaded with a catalyst at a proper temperature, and carrying out hydrogenation reduction under hydrogen pressure to prepare tetramethyl piperidinol hydrogenation liquid;
3) and carrying out desolventizing, cooling and crystallizing on the obtained tetramethyl piperidinol hydrogenation liquid to obtain the finished product tetramethyl piperidinol.
2. The continuous synthesis method of tetramethylpiperidinol according to claim 1, wherein the mass ratio of triacetonamine to the alcoholic solvent in step (1) is 1: 1-1: 5.
3. the continuous synthesis method of tetramethylpiperidinol according to claim 1, wherein the alcoholic solvent in step (1) is one or more of methanol, ethanol, propanol, isopropanol, butanol, 2-butanol, tert-butanol, pentanol, hexanol.
4. The continuous synthesis method of tetramethylpiperidinol as claimed in claim 1, wherein the continuous feeding temperature of triacetonamine solution and hydrogen in step (2) is 120-150 ℃.
5. The continuous synthesis method of tetramethylpiperidinol, according to claim 1, characterized in that the hydrogen pressure in step (2) is 1.0-5.0 Mpa.
6. The continuous synthesis method of tetramethylpiperidinol, according to claim 1, characterized in that, in the step (2), the catalyst comprises a carrier, an active metal component and an auxiliary metal.
7. The continuous synthesis method of tetramethylpiperidinol, according to claim 6, characterized in that, based on the weight of the final catalyst, the mass fraction of the active metal component is 15-25%, the sum of the mass fractions of the auxiliary metals is 1-10% or no auxiliary metal is added, and the rest is the carrier.
8. The continuous synthesis method of tetramethylpiperidinol, according to claim 6, characterized in that the carrier is 30-40 mesh silica.
9. The continuous synthesis method of tetramethylpiperidinol, according to claim 6, characterized in that the carrier is silica, the active metal component is nickel, and the auxiliary metal is one or both of iron and zinc.
10. The continuous synthesis method of tetramethylpiperidinol, according to claim 7, characterized in that the preparation method of the catalyst comprises the following steps: preparing metal salt containing active metal component and metal salt containing adjuvant metal into aqueous solution respectively according to the composition ratio of active metal component and adjuvant metal in the catalyst, weighing silicon oxide, mixing, soaking at room temperature, evaporating, drying at 120 deg.C, placing in tubular furnace, reducing at 450 deg.C, and making gas-liquid separationThe body flow rate is 200 mL/min; the metal salt of the active metal component is Ni (NO)3)2·6H2O、Fe(NO3)3·9H2O or Zn (NO)3)2·6H2O; the concentration of the metal salt aqueous solution containing the promoter metal is Ni (NO)3)2·6H2The concentration of O solution is 0.01mol/L, Fe (NO)3)3·9H2O or Zn (NO)3)2·6H2The concentration of the O solution is 0.03 mol/L.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010650A (en) * | 2022-06-15 | 2022-09-06 | 宿迁联盛科技股份有限公司 | Low-carbon-green synthesis process method for preparing tetramethyl piperidinol by continuous flow hydrogenation of triacetonamine |
| CN115382569A (en) * | 2022-08-03 | 2022-11-25 | 宿迁联盛科技股份有限公司 | Novel-efficient catalyst for preparing tetramethyl piperidinol by catalytic hydrogenation of triacetonamine and preparation method thereof |
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| DE2656764A1 (en) * | 1975-12-19 | 1977-07-07 | Ciba Geigy Ag | Hydroxypiperidene prepn. - by catalytic hydrogenation of an aq. oxopiperidene soln. esp. as stabilisers for polyolefins |
| CS235486B1 (en) * | 1982-12-27 | 1985-05-15 | Jiri Volf | Method of 2,2,6,6-tetramethyl-4-piperidinol preparation by means of continuous hydrogenation of 2,2,6,6-tetramethyl-4-piperidon |
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| TWI738491B (en) * | 2020-09-03 | 2021-09-01 | 台灣中油股份有限公司 | Preparation method of tetramethylpiperidinol |
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2022
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| DE2656764A1 (en) * | 1975-12-19 | 1977-07-07 | Ciba Geigy Ag | Hydroxypiperidene prepn. - by catalytic hydrogenation of an aq. oxopiperidene soln. esp. as stabilisers for polyolefins |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115010650A (en) * | 2022-06-15 | 2022-09-06 | 宿迁联盛科技股份有限公司 | Low-carbon-green synthesis process method for preparing tetramethyl piperidinol by continuous flow hydrogenation of triacetonamine |
| CN115382569A (en) * | 2022-08-03 | 2022-11-25 | 宿迁联盛科技股份有限公司 | Novel-efficient catalyst for preparing tetramethyl piperidinol by catalytic hydrogenation of triacetonamine and preparation method thereof |
| CN115382569B (en) * | 2022-08-03 | 2023-09-01 | 宿迁联盛科技股份有限公司 | Novel-efficient catalyst for preparing tetramethyl piperidinol by catalytic hydrogenation of triacetonamine and preparation method thereof |
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