CN111482166A - Nano carbon-based material and preparation method thereof and etherification method of propylene oxide - Google Patents
Nano carbon-based material and preparation method thereof and etherification method of propylene oxide Download PDFInfo
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- CN111482166A CN111482166A CN201910081692.XA CN201910081692A CN111482166A CN 111482166 A CN111482166 A CN 111482166A CN 201910081692 A CN201910081692 A CN 201910081692A CN 111482166 A CN111482166 A CN 111482166A
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- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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Abstract
The disclosure relates to a nano carbon-based material and a preparation method thereof, and an etherification method of propylene oxide. The etherification method of the propylene oxide comprises the following steps: the propylene oxide and the etherifying agent are contacted to react in the presence of a catalyst, wherein the catalyst contains a nanocarbon-based material. According to the method, a special nano carbon-based material is used as a catalyst to catalyze the etherification reaction of the propylene oxide, the etherification of the propylene oxide can be realized under a mild condition, the raw material conversion rate is high, and the selectivity of a target product is optimized.
Description
Technical Field
The disclosure relates to a nano carbon-based material and a preparation method thereof, and an etherification method of propylene oxide.
Background
Carbon-based materials include carbon nanotubes, activated carbon, graphite, graphene, fullerenes, carbon nanofibers, nanodiamonds, and the like. Scientific research on nanocarbon catalysis began in the last 90 s of the century. Researches show that the surface chemical properties of the nano-carbon material (mainly carbon nano-tubes and graphene) can be flexibly regulated, and saturated and unsaturated functional groups containing heteroatoms such as oxygen, nitrogen and the like can be modified on the surface of the nano-carbon material, so that the nano-carbon material has certain acid-base properties and redox capability, and can be directly used as a catalyst material. Research and development of new catalytic materials related to fullerene (carbon nano tube) and broadening of the application of the new catalytic materials in the fields of petrochemical industry, fine chemical industry and the like have profound theoretical significance and huge potential application prospects.
Propylene glycol ether has important application in the chemical field, such as propylene glycol monomethyl ether, also called propylene glycol methyl ether, and has an ether group and a hydroxyl group in the molecular structure, so that the propylene glycol ether has very excellent solubility, has the characteristics of proper volatilization rate, reaction activity and the like, and has wide application. The existing production of propylene glycol ether is basically obtained by combining propylene as a raw material with alcohols. However, most of the propylene glycol ether production in the world currently adopts a chlorohydrin method and an oxidation method, wherein the chlorohydrin method is seriously corroded and polluted, and the oxidation method has large investment and co-produces a large amount of byproducts, so that the production of the propylene glycol ether is restricted from raw materials.
Disclosure of Invention
An object of the present disclosure is to provide a nanocarbon-based material having excellent catalytic performance for etherification of propylene oxide, and a method for preparing the same.
It is another object of the present disclosure to provide a process for the etherification of propylene oxide which results in higher propylene oxide conversion and propylene glycol ether selectivity.
To achieve the above object, a first aspect of the present disclosure: the preparation method of the nano carbon-based material comprises the following steps:
a. mixing carbohydrate with silica gel particles with the particle size of less than 20 meshes, and reacting in a closed reactor at 300-1500 ℃ for 1-24 hours to obtain a reacted material; wherein the number of carbon atoms of the carbohydrate is 10 or more;
b. and c, mixing the reacted material obtained in the step a with a mineralizer, treating for 1-48 h at 20-80 ℃, and collecting a solid product.
Optionally, the weight ratio of the carbohydrate, the silica gel particles and the mineralizer is 100: (1-500): (2-1000), preferably 100: (2-250): (5-500), wherein the silica gel particles are made of SiO2And (6) counting.
Optionally, the weight average molecular weight of the carbohydrate is 200-2000000, and preferably, the carbohydrate is sucrose, starch, lignin, cellulose, hemicellulose, complex polysaccharide or sugar derivative.
Optionally, the particle size of the silica gel particles is 20-10000 meshes, and preferably 30-8000 meshes.
Optionally, the mineralizer is hydrofluoric acid or sodium hydroxide, and the concentration of the mineralizer is more than 5 wt%, preferably 10-40 wt%.
Optionally, in step a, the initial oxygen content in the closed reactor is less than 20 vol%, preferably less than 10 vol%, more preferably less than 1 vol%.
In a second aspect of the present disclosure: there is provided a nanocarbon-based material prepared by the method according to the first aspect of the present disclosure.
A third aspect of the disclosure: provided is a method for etherifying propylene oxide, the method comprising: and (b) contacting propylene oxide and an etherifying agent to react in the presence of a catalyst, wherein the catalyst contains the nanocarbon-based material according to the second aspect of the present disclosure.
Optionally, the reaction is carried out in a slurry bed reactor, and the amount of the catalyst is 10-1000 mg, preferably 20-200 mg, based on 100m L of the propylene oxide.
Optionally, the reaction is carried out in a fixed bed reactor, and the weight hourly space velocity of the propylene oxide is 0.01-500 h-1Preferably 0.05 to 2 hours-1。
Optionally, the etherifying agent is methanol, ethanol, ethylene glycol or glycerol, or a combination of two or three thereof; and/or the presence of a gas in the gas,
the dosage of the etherifying agent is 10-500 m L, preferably 20-200 m L based on 100m L of the propylene oxide.
Optionally, the reaction conditions are: the temperature is 50-200 ℃, and preferably 60-180 ℃; the pressure is 0-20 MPa, preferably 0-1 MPa; the time is 1-72 h, preferably 2-24 h.
According to the technical scheme, the etherification reaction of the propylene oxide is catalyzed by adopting the special nano carbon-based material as the catalyst, the etherification of the propylene oxide can be realized under mild conditions, the raw material conversion rate is high, and the selectivity of a target product is optimized.
Additional features and advantages of the disclosure will be set forth in the detailed description which follows.
Detailed Description
The following describes in detail specific embodiments of the present disclosure. It should be understood that the detailed description and specific examples, while indicating the present disclosure, are given by way of illustration and explanation only, not limitation.
The first aspect of the disclosure: the preparation method of the nano carbon-based material comprises the following steps:
a. mixing carbohydrate with silica gel particles with the particle size of less than 20 meshes, and reacting in a closed reactor at 300-1500 ℃ for 1-24 hours to obtain a reacted material; wherein the number of carbon atoms of the carbohydrate is 10 or more;
b. and c, mixing the reacted material obtained in the step a with a mineralizer, treating for 1-48 h at 20-80 ℃, and collecting a solid product.
According to the present disclosure, the weight ratio of the carbohydrate, silica gel particles, and mineralizer is 100: (1-500): (2-1000), preferably 100: (2-250): (5-500), wherein the silica gel particles are made of SiO2And (6) counting.
According to the disclosure, in step a, the number of carbon atoms of the carbohydrate may further be 10 to 60000, and the weight average molecular weight thereof may be 200 to 2000000, and specific types may be, for example, sucrose, starch, lignin, cellulose, hemicellulose, a complex polysaccharide (such as lentinan, flammulina velutipes polysaccharide, hericium erinaceus polysaccharide, tremella polysaccharide, and ganoderma lucidum polysaccharide), or a sugar derivative (such as fructose-1, 6-diphosphate, chitin), and the like. The particle size of the silica gel particles can be further 20-10000 meshes, and is preferably 30-8000 meshes. The initial oxygen content in the closed reactor may be less than 20 vol%, preferably less than 10 vol%, more preferably less than 1 vol%, wherein the initial oxygen content refers to the oxygen content in the closed reactor at the start of the reaction.
According to the present disclosure, in step b, the mineralizer may be hydrofluoric acid or sodium hydroxide. The mineralizer may be in the form of an aqueous mineralizer solution having a certain concentration, and for example, may be an aqueous mineralizer solution having a concentration of greater than 5 wt%, preferably 10 to 40 wt%.
The method of collecting the solid product according to the present disclosure may be performed using conventional methods, such as filtration, centrifugation, and the like. The process may further comprise a step of drying after collecting the solid product, and the drying conditions may be conventional in the art, for example, the drying conditions may include: the temperature is 100-200 ℃, and the time is 1-24 h.
In a second aspect of the present disclosure: there is provided a nanocarbon-based material prepared by the method according to the first aspect of the present disclosure. The nano carbon-based material disclosed by the invention has excellent catalytic performance, and is particularly suitable for catalyzing etherification reaction of propylene oxide.
A third aspect of the disclosure: provided is a method for etherifying propylene oxide, the method comprising: and (b) contacting propylene oxide and an etherifying agent to react in the presence of a catalyst, wherein the catalyst contains the nanocarbon-based material according to the second aspect of the present disclosure.
The process of the present disclosure can be carried out in various conventional catalytic reactors, for example, can be carried out in a batch tank reactor or a three-neck flask, or in suitable other reactors such as fixed beds, moving beds, suspended beds, and the like.
In an alternative embodiment of the present disclosure, the reaction is carried out in a slurry bed reactor, and the catalyst may be used in an amount of 10 to 1000mg, preferably 20 to 200mg, based on 100m L of the propylene oxide.
In another alternative embodiment of the present disclosure, the reaction may be carried out in a fixed bed reactor. In this embodiment, the weight hourly space velocity of the propylene oxide may be 0.01 to 500 hours-1Preferably 0.05 to 2 hours-1。
According to the disclosure, the etherifying agent may be methanol, ethanol, ethylene glycol or glycerol, or a combination of two or three of them, and the amount of the etherifying agent may be 10 to 500m L, preferably 20 to 200m L, based on 100m L of the propylene oxide.
According to the present disclosure, the conditions of the reaction may be: the temperature is 50-200 ℃, and preferably 60-180 ℃; the pressure is 0-20 MPa, preferably 0-1 MPa; the time is 1-72 h, preferably 2-24 h. In order to make the reaction more sufficient, it is preferable that the reaction is carried out under stirring.
The method takes the nano carbon-based material as the catalyst to catalyze the etherification reaction of the propylene oxide, can realize the etherification of the propylene oxide under mild conditions, and has higher propylene oxide conversion rate and propylene glycol ether selectivity.
The present disclosure is described in detail below with reference to examples, but the scope of the present disclosure is not limited thereby.
Preparation examples 1 to 7 are for explaining the nanocarbon-based material and the preparation method thereof according to the present disclosure.
Preparation of example 1
10g of sucrose (weight average molecular weight of 342) and 10g of a mixture having a particle size of 500 mesh were mixedSilica gel particle (SiO)298 percent by weight) and then reacting for 24 hours in a closed reaction kettle (with the initial oxygen content of 0.5 volume percent) at 500 ℃ to obtain a reacted material; and mixing the reacted material with 15g of 10 wt% hydrofluoric acid solution, treating at 50 ℃ for 12h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the carbon-based nano-material C1.
Preparation of example 2
10g of starch (weight-average molecular weight of about 11000) and 15g of silica gel granules (SiO) having a particle size of 5000 mesh were mixed298 percent by weight) and then reacting for 18 hours in a closed reaction kettle (the initial oxygen content is 0.8 volume percent) at the temperature of 600 ℃ to obtain a reacted material; and mixing the reacted material with 25g of 12 wt% sodium hydroxide solution, treating at 40 ℃ for 16h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the nano carbon-based material C2.
Preparation of example 3
10g of sucrose (weight average molecular weight 342) and 30g of silica gel particles (SiO) having a particle size of 500 mesh298 percent by weight) and then reacting for 24 hours in a closed reaction kettle (with the initial oxygen content of 0.5 volume percent) at 500 ℃ to obtain a reacted material; and mixing the reacted material with 60g of hydrofluoric acid with the concentration of 8 wt%, treating at 50 ℃ for 12h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the carbon-based nano-material C3.
Preparation of example 4
10g of starch (weight-average molecular weight of about 7500) and 10g of silica gel granules (SiO) having a particle size of 25 mesh298 percent by weight) and then reacting for 24 hours in a closed reaction kettle (with the initial oxygen content of 0.5 volume percent) at 500 ℃ to obtain a reacted material; and mixing the reacted material with 15g of hydrofluoric acid with the concentration of 10 wt%, treating at 50 ℃ for 12h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the carbon-based nano-material C4.
Preparation of example 5
10g of sucrose (weight average molecular weight 342) and 10g of silica gel particles (SiO) having a particle size of 10000 mesh2In an amount of98 percent by weight) and then reacting for 24 hours in a closed reaction kettle (with the initial oxygen content of 0.5 volume percent) at 500 ℃ to obtain a reacted material; and mixing the reacted material with 15g of hydrofluoric acid with the concentration of 10 wt%, treating at 50 ℃ for 12h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the carbon-based nano-material C5.
Preparation of example 6
10g of sucrose (weight average molecular weight 342) and 10g of silica gel particles (SiO) having a particle size of 500 mesh298 percent by weight) and then reacting for 24 hours in a closed reaction kettle (the initial oxygen content is 5 percent by volume) at 500 ℃ to obtain a reacted material; and mixing the reacted material with 15g of 10 wt% hydrofluoric acid solution, treating at 50 ℃ for 12h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the carbon-based nano-material C6.
Preparation of example 7
10g of cellulose (weight average molecular weight of about 1600000) and 10g of silica gel particles (SiO) having a particle size of 500 mesh were mixed298 percent by weight) and then reacting for 24 hours in a closed reaction kettle (the initial oxygen content is 15 percent by volume) at 500 ℃ to obtain a reacted material; and mixing the reacted material with 15g of 10 wt% hydrofluoric acid solution, treating at 50 ℃ for 12h, filtering, washing, collecting a solid product, and drying at 120 ℃ for 2h to obtain the carbon-based nano-material C7.
Preparation of comparative example 1
The nanocarbon-based material was prepared according to the method of preparation example 1, except that the silica gel particles having a particle size of 10 meshes were used, and the nanocarbon-based material D1 was prepared.
Preparation of comparative example 2
The nanocarbon-based material was prepared according to the method of preparation example 1, except that sucrose in example 1 was replaced with the same amount of glucose, to prepare nanocarbon-based material D2.
Examples 1-12 are provided to illustrate methods of catalyzing the etherification of propylene oxide using nanocarbon-based materials of the present disclosure.
In the following examples and comparative examples, the oxidation products were analyzed by gas chromatography (GC: Agilent, 7890A) and gas chromatography-mass spectrometer (GC-MS: Thermo Fisher Trace ISQ). Conditions of gas chromatography: nitrogen carrier gas, temperature programmed at 140K: 60 ℃, 1 minute, 15 ℃/minute, 180 ℃, 15 minutes; split ratio, 10: 1; the injection port temperature is 300 ℃; detector temperature, 300 ℃. On the basis, the conversion rate of raw materials and the selectivity of target products are calculated by respectively adopting the following formulas:
propylene oxide conversion (% propylene oxide conversion) (molar amount of propylene oxide added before reaction-molar amount of propylene oxide remaining after reaction)/molar amount of propylene oxide added before reaction × 100%;
propylene glycol ether selectivity (% by mole of propylene glycol ether formed after the reaction)/the mole of propylene oxide added before the reaction × 100%.
Example 1
40mg of nanocarbon-based material C1 as a catalyst, 200m L methanol and 100m L propylene oxide were charged into a slurry bed reactor, sealed, stirred at 60 ℃ under 1.0MPa for 8 hours, and after separating the catalyst by centrifugation and filtration, the product was analyzed by gas chromatography, and the results are shown in Table 1.
Examples 2 to 7
Propylene oxide was catalytically etherified according to the method of example 1, except that the same amount of nanocarbon based materials C2-C7 were used instead of C1, respectively. The results of the analysis of the products are shown in Table 1.
Example 8
100mg of nanocarbon-based material C1 as a catalyst, 100m L ethylene glycol and 100m L propylene oxide were charged into a slurry bed reactor, sealed, stirred and reacted at 70 ℃ under 0.8MPa for 6 hours, and then the catalyst was separated by centrifugation and filtration, and the product was analyzed by gas chromatography, and the results are shown in Table 1.
Example 9
10mg of nanocarbon-based material C1 as a catalyst, 10m of L methanol and 100m of L propylene oxide were charged into a slurry bed reactor, sealed, stirred and reacted at 60 ℃ under 1.0MPa for 8 hours, and then the catalyst was separated by centrifugation and filtration, and the product was analyzed by gas chromatography, and the results are shown in Table 1.
Example 10
600mg of nanocarbon-based material C1 as a catalyst, 500m L methanol and 100m L propylene oxide were charged into a slurry bed reactor, sealed, stirred at 60 ℃ under 1.0MPa for 8 hours, and after separating the catalyst by centrifugation and filtration, the product was analyzed by gas chromatography, and the results are shown in Table 1.
Example 11
40mg of nanocarbon-based material C1 as a catalyst, 200m L methanol and 100m L propylene oxide were charged into a slurry bed reactor, sealed, stirred and reacted at 50 ℃ under 2.0MPa for 30 hours, and then the catalyst was separated by centrifugation and filtration, and the product was analyzed by gas chromatography, and the results are shown in Table 1.
Example 12
The nano carbon-based material C1 is used as a catalyst and filled in a fixed bed reactor, methanol and propylene oxide are fed into the reactor, and the weight hourly space velocity of the propylene oxide is 2h-1The results of the analysis of the oxidation products by gas chromatography after 8 hours at 60 ℃ and 1.0MPa with methanol in an amount of 200m L based on 100m L propylene oxide are shown in Table 1.
Comparative example 1
Propylene oxide was catalytically etherified according to the method of example 1, except that the nanocarbon-based material D1 was used as a catalyst. The results of the analysis of the products are shown in Table 1.
Comparative example 2
Propylene oxide was catalytically etherified according to the method of example 1, except that the nanocarbon-based material D2 was used as a catalyst. The results of the analysis of the products are shown in Table 1.
Comparative example 3
Propylene oxide was catalytically etherified according to the method of example 1, except that the nanocarbon-based material C1 was not used as a catalyst. The results of the analysis of the products are shown in Table 1.
TABLE 1
| Examples | Percent conversion of propylene oxide% | Propylene glycol ether selectivity% |
| Example 1 | 95 | 94 |
| Example 2 | 93 | 92 |
| Example 3 | 90 | 91 |
| Example 4 | 88 | 87 |
| Example 5 | 85 | 84 |
| Example 6 | 84 | 83 |
| Example 7 | 82 | 81 |
| Example 8 | 92 | 93 |
| Example 9 | 86 | 85 |
| Example 10 | 82 | 81 |
| Example 11 | 80 | 80 |
| Example 12 | 92 | 93 |
| Comparative example 1 | 40 | 76 |
| Comparative example 2 | 36 | 78 |
| Comparative example 3 | 22 | 73 |
As can be seen from table 1, the nano carbon-based material of the present disclosure is used as a catalyst to catalyze the etherification reaction of propylene oxide, which is beneficial to improving the conversion rate of propylene oxide and the selectivity of propylene glycol ether.
The preferred embodiments of the present disclosure have been described in detail above, however, the present disclosure is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present disclosure within the technical idea of the present disclosure, and these simple modifications all fall within the protection scope of the present disclosure.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various combinations that are possible in the present disclosure are not described again.
In addition, any combination of various embodiments of the present disclosure may be made, and the same should be considered as the disclosure of the present disclosure, as long as it does not depart from the spirit of the present disclosure.
Claims (10)
1. A preparation method of a nano carbon-based material is characterized by comprising the following steps:
a. mixing carbohydrate with silica gel particles with the particle size of less than 20 meshes, and reacting in a closed reactor at 300-1500 ℃ for 1-24 hours to obtain a reacted material; wherein the number of carbon atoms of the carbohydrate is 10 or more;
b. and c, mixing the reacted material obtained in the step a with a mineralizer, treating for 1-48 h at 20-80 ℃, and collecting a solid product.
2. The method of claim 1, wherein the weight ratio of carbohydrate, silica gel particles, and mineralizer is 100: (1-500): (2-1000), preferably 100: (2-250): (5-500), wherein the silica gel particles are made of SiO2And (6) counting.
3. The method according to claim 1 or 2, wherein the weight average molecular weight of the carbohydrate is 200 to 2000000, preferably the carbohydrate is sucrose, starch, lignin, cellulose, hemicellulose, complex polysaccharides or sugar derivatives; and/or the presence of a gas in the gas,
the particle size of the silica gel particles is 20-10000 meshes, preferably 30-8000 meshes; and/or the presence of a gas in the gas,
the mineralizer is hydrofluoric acid or sodium hydroxide, and the concentration of the mineralizer is more than 5 wt%, preferably 10-40 wt%.
4. A process according to claim 1 or 2, wherein in step a the initial oxygen content in the closed reactor is less than 20 vol%, preferably less than 10 vol%, more preferably less than 1 vol%.
5. The nanocarbon-based material prepared by the method according to any one of claims 1 to 4.
6. A method for etherifying propylene oxide, the method comprising: reacting propylene oxide with an etherifying agent in contact in the presence of a catalyst, wherein the catalyst comprises the nanocarbon-based material according to claim 5.
7. The process according to claim 6, wherein the reaction is carried out in a slurry bed reactor, and the catalyst is used in an amount of 10 to 1000mg, preferably 20 to 200mg, based on 100m L of the propylene oxide.
8. The method of claim 6, wherein the reaction is carried out in a fixed bed reactor, and the weight hourly space velocity of the propylene oxide is 0.01-500 h-1Preferably 0.05 to 2 hours-1。
9. The method according to any one of claims 6 to 8, wherein the etherifying agent is methanol, ethanol, ethylene glycol or glycerol, or a combination of two or three thereof; and/or the presence of a gas in the gas,
the dosage of the etherifying agent is 10-500 m L, preferably 20-200 m L based on 100m L of the propylene oxide.
10. A process according to any one of claims 6 to 8, wherein the reaction conditions are: the temperature is 50-200 ℃, and preferably 60-180 ℃; the pressure is 0-20 MPa, preferably 0-1 MPa; the time is 1-72 h, preferably 2-24 h.
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| CN108479707A (en) * | 2018-05-25 | 2018-09-04 | 黄智慧 | A kind of preparation method of material for air purification |
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| CN114436917A (en) * | 2020-10-30 | 2022-05-06 | 中国石油化工股份有限公司 | Thioether oxidation method |
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