CN112979429B - Tandem method and equipment for preparing glycol ether compound - Google Patents
Tandem method and equipment for preparing glycol ether compound Download PDFInfo
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- CN112979429B CN112979429B CN201911282438.2A CN201911282438A CN112979429B CN 112979429 B CN112979429 B CN 112979429B CN 201911282438 A CN201911282438 A CN 201911282438A CN 112979429 B CN112979429 B CN 112979429B
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- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
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Abstract
The application discloses a method and equipment for preparing glycol ether compounds in series. The tandem type method for preparing the glycol ether compound comprises the following steps: s100, contacting a material containing a polyhydroxy compound and an alcohol compound with a hydrogenation catalyst in a hydrogen atmosphere, and reacting I to obtain an intermediate containing a dihydric alcohol compound; s200, contacting the intermediate containing the glycol compounds with an etherification catalyst to react II to obtain glycol ether compounds; wherein the glycol ether compound is a monoether compound. The method provides a series catalytic reaction process according to the characteristics of the sugar alcohol hydrogenation and etherification, directly prepares an ether compound by the sugar alcohol hydrogenation and etherification, and has important significance.
Description
Technical Field
The application relates to a method and equipment for preparing glycol ether compounds in series, belonging to the technical field of chemical synthesis.
Background
The polyhydroxy compound contains a large amount of hydroxyl, and low-carbon dihydric alcohol can be prepared with high atom economy by hydrogenation. The low-carbon dihydric alcohol can be used for preparing important ether compounds by catalytic etherification with the low-carbon alcohol. At present, few reports are reported on the technology for preparing glycol ether directly through hydrogenation and etherification reactions. The reaction involves various reactions, different types of reactions have different requirements on catalysts and reaction conditions, different catalysts have different catalytic functions, and the catalysts are also inactivated under certain reaction conditions, so that the respective special catalytic performance is difficult to exert. Therefore, the preparation by one-stage method has great difficulty.
Disclosure of Invention
According to one aspect of the application, a tandem type method for preparing glycol ether compounds is provided, and a tandem catalytic reaction process is provided according to the characteristics of hydrogenation and etherification of sugar alcohol, so that the method has important significance for directly preparing ether compounds by hydrogenation and etherification of sugar alcohol.
A tandem process for the preparation of glycol ether based compounds, the process comprising at least the steps of:
s100, contacting a material containing a polyhydroxy compound and an alcohol compound with a hydrogenation catalyst in a hydrogen atmosphere, and reacting I to obtain an intermediate containing a dihydric alcohol compound;
s200, contacting the intermediate containing the glycol compounds with an etherification catalyst to react II to obtain glycol ether compounds;
wherein the glycol ether compound is a monoether compound.
Preferably, the glycol ether compounds in the application are low-carbon glycol ether compounds, and the number of carbon atoms is 2-6.
In the present application, the hydrogenation catalyst is any suitable catalyst in the prior art, and the hydrogenation catalyst is not strictly limited. The following are preferred hydrogenation catalysts in combination:
alternatively, the hydrogenation catalyst herein comprises any of Ni-Ce/C, Ni-La/C.
In the present application, the preparation method of the hydrogenation catalyst is any suitable method in the prior art, and comprises the following steps: impregnation, coprecipitation, deposition, etc. The preparation of the hydrogenation catalyst is not strictly limited in this application.
In the present application, the etherification catalyst is any suitable catalyst in the prior art, and the etherification catalyst is not strictly limited.
Alternatively, the etherification catalyst herein comprises any one of HZSM-5, Hbeta, HY, ion exchange resin.
Optionally, in step S100, the polyhydroxy compound comprises at least one of glucose, sorbitol, xylitol, glycerol;
optionally, the alcohol compound comprises at least one of ethanol and propanol.
Optionally, the molar ratio of the polyhydroxy compound to the alcohol compound is 5: 1-1: 20.
preferably, the molar ratio of the polyhydroxy compound to the alcohol compound is 1:1-1: 10.
Optionally, in step S100, the diol compound includes at least one of ethylene glycol, propylene glycol, butylene glycol, and pentylene glycol.
Alternatively, in step S100, the conditions of reaction i are:
the reaction temperature is 20-500 ℃;
the reaction pressure is 2-10 MPa;
the volume space velocity of the polyhydroxy compound is 0.1-1h-1；
The volume space velocity of the alcohol compound is 0.1-1h-1；
The volume space velocity of the hydrogen is 400--1。
Specifically, in step S100, the upper limit of the reaction temperature is independently selected from any one of 200 ℃, 220 ℃ and 500 ℃; the lower limit of the reaction temperature is independently selected from any one of 20 ℃, 200 ℃ and 220 ℃.
In step S100, the upper limit of the reaction pressure is independently any one value selected from the group consisting of 5MPa, 6MPa, and 10 MPa; the lower limit of the reaction pressure is independently selected from any one of 2MPa, 5MPa and 6 MPa.
Alternatively, in step S200, the conditions of reaction ii:
the reaction temperature is 20-500 ℃;
the reaction pressure is 0.1-1 MPa.
Specifically, in step S200, the upper limit of the reaction temperature is independently selected from 300 ℃, 400 ℃, 500 ℃; the lower limit of the reaction temperature is independently selected from the group consisting of 20 deg.C, 300 deg.C, and 400 deg.C.
In step S200, the upper limit of the reaction pressure is independently selected from 0.3MPa, 0.5MPa, 1 MPa; the lower limit of the reaction pressure is independently selected from 0.1MPa, 0.3MPa, 0.5 MPa.
Optionally, after the step S200, a step S300 is further included;
s300, contacting the obtained monoether compound with an etherification catalyst to react III to obtain the glycol ether compound;
wherein the glycol ether compound is a diether compound.
Alternatively, in step S300, the conditions of reaction iii:
the reaction temperature is 20-300 ℃;
the reaction pressure is 0.1-1 MPa.
Specifically, in step S300, the upper limit of the reaction temperature is independently selected from 150 ℃, 200 ℃, 300 ℃; the lower limit of the reaction temperature is independently selected from the group consisting of 20 deg.C, 150 deg.C, and 200 deg.C.
Alternatively, the reaction temperature in step S300 is lower than the reaction temperature in step S200.
Optionally, step S200 and step S300 are both performed in an inert atmosphere;
the inert atmosphere includes any one of nitrogen and inert gas.
According to another aspect of the application, the tandem type equipment for preparing the glycol ether compound is also provided, and comprises a first-stage reactor and a second-stage reactor;
the first-stage reactor is connected with the second-stage reactor through a pipeline;
the first stage reactor is used for contacting a material containing polyhydroxy compounds and alcohol compounds with a hydrogenation catalyst in a hydrogen atmosphere to react I to obtain an intermediate containing glycol compounds;
the second section of reactor is used for contacting the intermediate containing the dihydric alcohol compound with an etherification catalyst to react II to obtain the dihydric alcohol ether compound, and the dihydric alcohol ether compound is a monoether compound.
Optionally, the apparatus further comprises a third stage reactor;
the third-stage reactor is connected with the second-stage reactor through a pipeline;
the third-stage reactor is used for contacting the obtained monoether compound with an etherification catalyst to react III to obtain the glycol ether compound; the glycol ether compound is a diether compound.
The invention aims to provide a tandem catalytic reaction process for hydrogenation and etherification. The catalyst with different functions and operation conditions used by each section of reactor are characterized in that the first section of reactor utilizes the function of catalytic hydrogenation to realize the cracking of polyhydroxy compounds and other raw materials into lower dihydric alcohols such as ethylene glycol, propylene glycol and the like, the second section of reactor utilizes the high-temperature etherification of the generated lower dihydric alcohol solution to generate monoether compounds, and then the third section of reaction is utilized to carry out low-temperature etherification to prepare diether compounds.
In order to achieve the purpose, the invention provides the following technical scheme:
the sugar alcohol and the low-carbon alcohol raw materials can pass through three catalytic reactors connected in series, and the low-carbon glycol ether is generated under the action of a hydrogenation catalyst and an etherification catalyst.
The specific process method comprises the following steps:
the first stage reactor R1 is filled with a catalyst with hydrogenation function; the reactor is provided with a heating function, and the temperature range is from room temperature to 500 ℃. The raw material liquids F1 and F2 and hydrogen G1 enter the reactor after being preheated, a gas-liquid separation tank S1 is connected below the reactor, after the reaction liquid and the hydrogen undergo gas-liquid separation, the hydrogen G1 returns to the reactor R1 to continue to circulate and participate in the reaction, and the reaction liquid P1 is pumped into a second-stage reactor R2.
The second stage reactor R2 of the invention provides high temperature catalytic etherification reaction, and the reactor is filled with solid etherification catalyst and provided with a heating furnace, and the temperature range is room temperature to 500 ℃. The reaction liquid P1 and nitrogen G2 of the first stage reactor enter the reactor, after the reaction of the catalytic bed layer, the reaction liquid P2 enters a gas-liquid separation tank S2 of the second stage reactor, and the cooled reaction liquid P2 and nitrogen G2 enter a third stage reactor R3.
The third stage reactor R3 of the invention provides low temperature catalytic etherification reaction, the etherification reaction catalyst is put into the reactor, and the reactor is provided with a heating furnace, and the temperature range is from room temperature to 300 ℃. The reaction liquid P2 from the second stage reactor and nitrogen G2 were fed into the third stage reactor R3, and after the catalytic reaction, the reaction liquid P3 was fed into the third gas-liquid separation tank S3, and after cooling, the reaction liquid P3 was collected and analyzed.
In the present application, the term "glycol ether compound" refers to an ether compound prepared from a glycol.
The beneficial effects that this application can produce include:
1) the tandem type method for preparing the glycol ether compounds provides a new process for converting and utilizing renewable resources aiming at preparing the glycol ether compounds by converting the renewable biomass resources.
2) The tandem type method for preparing the glycol ether compound has the advantages that a novel tandem catalytic reaction process is provided for the reaction of preparing the glycol ether by the polyhydroxy compound, and a novel process route for preparing important compounds by coupling hydrogenation and etherification is realized.
Drawings
FIG. 1 is a process flow diagram of one embodiment of the present application.
R1-R3 are respectively a first stage reactor, a second stage reactor and a third stage reactor;
g1 and G2 are hydrogen and nitrogen respectively,
f1 and F2 are sorbitol solution and ethanol, respectively;
S1-S3 are respectively a first separating tank, a second separating tank and a third separating tank;
P1-P3 are the first reaction solution, the second reaction solution and the third reaction solution, respectively.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
The raw materials in the examples of the present application were all purchased commercially, unless otherwise specified.
In the application, the hydrogenation catalyst is Ni-Ce/C, and the specific preparation method is to adopt an isometric impregnation method. Weighing a certain amount of nickel nitrate and cerium nitrate according to the loading capacity, dissolving in water, adding an activated carbon catalyst, uniformly stirring, standing for 24 hours, drying for 12 hours, grinding, screening and storing. Reduction was carried out at 450 ℃ for 3h before use.
In this application, the etherification catalyst was HZSM-5 purchased from southern Kao university catalyst works, and Amberlyst-15 purchased from southern university synthetic chemical Co., Ltd.
Example 1
The first stage reactor R1 was charged with 10ml of hydrogenation catalyst (Ni-Ce/C, loading of Ni and Ce in the catalyst was 10 wt% to 1 wt%), and the second stage reactor R2 was charged with 10ml of etherification catalyst (specifically HZSM-5, silicon to aluminum atomic ratio 50). The first stage reactor was heated to 200 ℃ and 100ml/min of hydrogen G1 (volume space velocity of 600 h) was introduced-1) The system pressure was adjusted to 5 MPa. 20ml of nitrogen was introduced into the second stage, the pressure was adjusted to 0.5MPa, and the second stage reactor R2 was heated to 200 ℃. The raw material solution of sorbitol F1 and the ethanol solution F2 (the molar ratio is 1:2) are pumped in, and different flow rates are set (the volume space velocity of the sorbitol F1 is 0.5h-1The volume space velocity of the ethanol solution is 0.5h-1) And the reaction liquid enters a reactor R1, the reaction liquid enters a gas-liquid separation tank S1, hydrogen G1 returns to the reactor R1 to continuously circulate and participate in the reaction, reaction liquid P1 is pumped into an R2 reactor, the reaction liquid P2 enters a second reactor gas-liquid separation tank S2 after catalytic reaction of a catalytic bed, and the cooled reaction liquid P2 is collected. The product is mainly monoethyl ether.
Example 2
The first stage reactor R1 was charged with 10ml of hydrogenation catalyst (Ni-Ce/C, loading of Ni and Ce in the catalyst was 10 wt% versus 1 wt%), and the second stage reactor R2 was charged with 10ml of etherification catalyst (Hbeta catalyst, silicon to aluminum atomic ratio 40). The first stage reactor was heated to 220 ℃ and 150ml/min of hydrogen G1 (volume space velocity of 900 h) was introduced-1) The system pressure was adjusted to 6 MPa. 10ml of nitrogen was introduced into the second stage, the pressure was adjusted to 0.3MPa, and the second stage reactor R2 was heated to 150 ℃. The raw material solution of xylitol F1 and ethanol F2 (molar ratio of 1:6) were pumped in at different flow rates (volume space velocity of xylitol F1 was 0.2 h)-1The volume space velocity of the ethanol solution is 0.6h-1) Then the reaction liquid enters the reactor R1, the reaction liquid enters a gas-liquid separation tank S1, and the hydrogen G1 returns to the reactor R1 to continuously circulate and participate in the reactionThe reaction liquid P1 is pumped into the R2 reactor, after catalytic reaction of the catalyst bed, the reaction liquid P2 enters a gas-liquid separation tank S2 of a second reactor, and the cooled reaction liquid P2 is collected. The product is mainly monoethyl ether.
Example 3
The first stage reactor R1 was charged with 10ml of hydrogenation catalyst (Ni-La/C catalyst, Ni and La loading in catalyst of 10 wt% to 2 wt%), and the second and third stage reactors R2 and R3 were charged with 10ml of etherification catalyst (HZSM-5 silicon aluminum atomic ratio 50 and Amberlyst 15). The first stage reactor was heated to 220 ℃ and 100ml/min hydrogen G1 was introduced (volume space velocity 600 h)-1) The system pressure was adjusted to 5 MPa. 10ml of nitrogen was introduced into the second stage reactor, the pressure was adjusted to 0.3MPa, and the second stage reactor R2 was heated to 200 ℃. 10ml of nitrogen was introduced into the third stage reactor, the pressure was adjusted to 0.3MPa, and the third stage reactor R3 was heated to 120 ℃. Pumping raw material solution of glycerol solution F1 and ethanol solution F2 (the molar ratio of the two is 1:4, and the volume space velocity of the glycerol solution is 0.2h-1The volume space velocity of the ethanol solution is 0.4h-1) And the reaction liquid enters the reactor R1, the reaction liquid enters a gas-liquid separation tank S1, the hydrogen G1 returns to the reactor R1 to continuously circulate and participate in the reaction, the reaction liquid P12 is pumped into the R2 reactor, and after the catalytic reaction of the catalytic bed layer, the reaction liquid P2 enters a gas-liquid separation tank S2 of a second reactor. And pumping the reaction liquid P2 into a third reactor, reacting, feeding into a third separation tank, and collecting the cooled reaction liquid P3. The product is mainly diethyl ether.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (9)
1. A tandem process for the preparation of glycol ether compounds, characterized in that the process comprises at least the following steps:
s100, contacting a material containing a polyhydroxy compound and an alcohol compound with a hydrogenation catalyst in a hydrogen atmosphere, and reacting I to obtain an intermediate containing a dihydric alcohol compound;
s200, contacting the intermediate containing the glycol compounds with an etherification catalyst to react II to obtain glycol ether compounds;
wherein the glycol ether compound is a monoether compound;
the molar ratio of the polyhydroxy compound to the alcohol compound is 5: 1-1: 20;
the volume space velocity of the polyhydroxy compound is 0.1-1h-1；
The volume airspeed of the alcohol compound is 0.1-1h-1；
The method adopts equipment comprising a first-stage reactor and a second-stage reactor;
the first-stage reactor is connected with the second-stage reactor through a pipeline;
the first stage reactor is used for contacting a material containing polyhydroxy compounds and alcohol compounds with a hydrogenation catalyst in a hydrogen atmosphere to react I to obtain an intermediate containing glycol compounds;
the second section of reactor is used for contacting the intermediate containing the glycol compounds with an etherification catalyst to react II to obtain the glycol ether compounds, and the glycol ether compounds are monoether compounds;
in step S100, the polyhydroxy compound includes at least one of glucose, sorbitol, xylitol, and glycerol;
the alcohol compound comprises at least one of ethanol and propanol.
2. The tandem method for preparing glycol ethers according to claim 1, wherein in step S100, the glycol compounds comprise at least one of ethylene glycol, propylene glycol, butylene glycol, and pentylene glycol.
3. The tandem process for preparing glycol ethers according to claim 1, wherein in step S100, the conditions of reaction i are:
the reaction temperature is 20-500 ℃;
the reaction pressure is 2-10 MPa;
the volume space velocity of the hydrogen is 400-1000h-1。
4. The tandem process for preparing glycol ethers according to claim 1, wherein in step S200, the conditions of reaction ii:
the reaction temperature is 20-500 ℃;
the reaction pressure is 0.1-1 MPa.
5. The tandem glycol ether compound production method according to claim 1, further comprising, after the step S200, a step S300;
s300, contacting the obtained monoether compound with an etherification catalyst to react III to obtain the glycol ether compound;
wherein the glycol ether compound is a diether compound.
6. The tandem process for producing glycol ethers of claim 5, wherein in step S300, the conditions of reaction III:
the reaction temperature is 20-300 ℃;
the reaction pressure is 0.1-1 MPa.
7. The tandem process for producing glycol ether based compounds according to claim 5, wherein the reaction temperature in step S300 is lower than the reaction temperature in step S200.
8. The tandem process for preparing glycol ethers of claim 5, wherein step S200 and step S300 are both carried out in an inert atmosphere;
the inert atmosphere includes any one of nitrogen and inert gas.
9. The in-line process for the preparation of glycol ethers of claim 1, wherein the apparatus further comprises a third stage reactor;
the third-stage reactor is connected with the second-stage reactor through a pipeline;
the third-stage reactor is used for contacting the obtained monoether compound with an etherification catalyst to react III to obtain the glycol ether compound; the glycol ether compound is a diether compound.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101613253A (en) * | 2008-06-25 | 2009-12-30 | 中国科学院大连化学物理研究所 | The catalytic cracking method of a kind of sugar and sugar alcohol |
| CN105585455A (en) * | 2014-11-17 | 2016-05-18 | 中国科学院大连化学物理研究所 | Method of preparing ethylene glycol monomethyl ether through continuous etherification method |
| CN105777504A (en) * | 2014-12-22 | 2016-07-20 | 中国科学院大连化学物理研究所 | Preparation method for double-terminated glycol ether |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101613253A (en) * | 2008-06-25 | 2009-12-30 | 中国科学院大连化学物理研究所 | The catalytic cracking method of a kind of sugar and sugar alcohol |
| CN105585455A (en) * | 2014-11-17 | 2016-05-18 | 中国科学院大连化学物理研究所 | Method of preparing ethylene glycol monomethyl ether through continuous etherification method |
| CN105777504A (en) * | 2014-12-22 | 2016-07-20 | 中国科学院大连化学物理研究所 | Preparation method for double-terminated glycol ether |
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