CN117229118A - Method for separating cyclohexanone and cyclohexanol in cyclohexane - Google Patents
Method for separating cyclohexanone and cyclohexanol in cyclohexane Download PDFInfo
- Publication number
- CN117229118A CN117229118A CN202210640660.0A CN202210640660A CN117229118A CN 117229118 A CN117229118 A CN 117229118A CN 202210640660 A CN202210640660 A CN 202210640660A CN 117229118 A CN117229118 A CN 117229118A
- Authority
- CN
- China
- Prior art keywords
- cyclohexane
- cyclohexanone
- cyclohexanol
- extractant
- phase
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 188
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 117
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000000605 extraction Methods 0.000 claims abstract description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- 238000007254 oxidation reaction Methods 0.000 claims description 30
- 230000003647 oxidation Effects 0.000 claims description 29
- 239000003513 alkali Substances 0.000 claims description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 17
- 230000001590 oxidative effect Effects 0.000 claims description 13
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000011268 mixed slurry Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 238000000926 separation method Methods 0.000 abstract description 25
- 238000004821 distillation Methods 0.000 abstract description 10
- 238000000638 solvent extraction Methods 0.000 abstract description 4
- 239000012071 phase Substances 0.000 description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- 239000002699 waste material Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- OHLUUHNLEMFGTQ-AZXPZELESA-N n-methylacetamide Chemical class C[15NH]C(C)=O OHLUUHNLEMFGTQ-AZXPZELESA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 150000007960 acetonitrile Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present application provides a process for separating cyclohexanone and cyclohexanol in cyclohexane, said process comprising: and (3) adding an extractant into the cyclohexane phase containing cyclohexanone and cyclohexanol for extraction, and separating to obtain the extractant phase containing cyclohexanone and cyclohexanol and cyclohexane. The application adopts a solvent extraction separation mode to replace cyclohexane distillation separation, and has the advantage of obviously reducing steam consumption.
Description
Technical Field
The application relates to the technical field of cyclohexanone industrial production, in particular to a method for separating cyclohexanone and cyclohexanol in cyclohexane.
Background
Cyclohexanone is an important chemical production raw material and is mainly used for producing caprolactam. At present, the domestic cyclohexanone industrial production technology route is mainly divided into two types, namely a cyclohexene hydration technology route and a cyclohexane oxidation technology route. The cyclohexene hydration process for producing cyclohexanone has the disadvantage of requiring the use of a large amount of noble metal catalyst.
The technological route of cyclohexane oxidation method is that cyclohexane is oxidized in air in oxidation kettle to obtain oxidizing solution, the main components of oxidizing solution are cyclohexane about 96%, cyclohexanone and cyclohexanol about 3%, by-product acid about 0.3%, by-product lipid about 0.3% and by-product peroxide about 0.3%. To remove these by-products entrained in the oxidizing liquid, the oxidizing liquid is fed into a decomposing tank. In the decomposing kettle, a certain proportion of sodium hydroxide aqueous solution is added into the oxidizing solution, and the sodium hydroxide aqueous solution is used for neutralizing acids and decomposing lipid and peroxide. Sodium hydroxide is added into the decomposing kettle for decomposition reaction, and then the mixture is sent into a waste alkali separating device for standing and layering. The upper layer is cyclohexane phase, and the lower layer is alkali water phase. Wherein the cyclohexane of the upper layer contains cyclohexanone and cyclohexanol. And (5) carrying out incineration treatment on the lower alkaline water phase. The small amount of cyclohexanone and cyclohexanol contained in cyclohexane was then subjected to multistage distillation separation (see FIG. 1). The main problem of the route is high energy consumption, and about 7 tons of steam are required to be consumed for producing one ton of cyclohexanone. The section with the largest steam consumption is a distillation separation process of cyclohexane, cyclohexanone and cyclohexanol, and the separation process accounts for about 30% of the steam consumption in the whole production process.
Therefore, the separation of cyclohexane from cyclohexanone and cyclohexanol by another low energy separation is critical to reduce steam consumption.
In view of this, the present application has been made.
Disclosure of Invention
In the separation process of cyclohexane, cyclohexanone and cyclohexanol, the solvent extraction separation mode is adopted to replace the distillation separation of cyclohexane, so that the method has the advantage of obviously reducing steam consumption. Meanwhile, the selection of the extractant is explored, and the extraction effect is ensured.
It is an object of the present application to provide a process for separating cyclohexanone and cyclohexanol in cyclohexane.
It is a second object of the present application to provide a process for preparing cyclohexanone by oxidizing cyclohexane.
In order to achieve the above object of the present application, the following technical solutions are specifically adopted:
the first aspect of the present application provides a process for separating cyclohexanone and cyclohexanol in cyclohexane, comprising the steps of:
adding an extractant into a cyclohexane phase containing cyclohexanone and cyclohexanol for extraction, and separating to obtain an extractant phase containing cyclohexanone and cyclohexanol and cyclohexane;
the cyclohexane phase containing cyclohexanone and cyclohexanol is obtained by adding alkali into an oxidation solution after cyclohexane oxidation for separation;
wherein the solubility of the extractant in cyclohexane at room temperature is less than 5%, and the total solubility of cyclohexanone and cyclohexanol in the extractant is more than five times of the total solubility of cyclohexanone and cyclohexanol in cyclohexane.
Cyclohexane phase
Cyclohexane is subjected to oxidation and alkali adding processes and waste alkali is separated to obtain a cyclohexane phase containing cyclohexanone and cyclohexanol.
The oxidation process and the alkali addition process of cyclohexane can be carried out according to the conventional process in the art, for example, cyclohexane is oxidized by air to obtain an oxidation solution (containing cyclohexane, about 3% of ketol, acid, lipid and other byproducts); the oxidation solution is added with strong alkali and then layered to obtain an aqueous phase and a cyclohexane phase (the sum of the mass concentration of cyclohexanone and cyclohexanol is about 3%).
Extraction separation
The cyclohexanone and cyclohexanol in the cyclohexane phase containing cyclohexanone and cyclohexanol are extracted and separated using an extractant.
The extractant is selected from organic solvents that all meet the following conditions:
1. is not compatible (miscible) with cyclohexane.
Only immiscible solvents are used for solvent extraction, and representative solvents include methanol, acetonitrile, dimethyl sulfoxide, N-methylacetamide, and the like. By immiscible is meant herein that the extractant has a solubility in cyclohexane of less than 5% at room temperature, i.e. the cyclohexane has a saturated organic solvent content of less than 5%.
The extractant should have as little solubility in cyclohexane as possible. Since the extractant extracts cyclohexanone and cyclohexanol in cyclohexane, after the cyclohexane and the extractant are subjected to two-phase standing separation, the extractant dissolved in the cyclohexane phase is as low as possible, so long as the extractant content in the cyclohexane is as low as possible, and the extractant loss is less. Through experimental comparison, the saturated methanol content in cyclohexane at room temperature is 14.37%, the saturated acetonitrile content in cyclohexane is 3.21%, the saturated dimethyl sulfoxide content in cyclohexane is 1.43%, and the saturated N-methylacetamide content in cyclohexane is 0.41%.
2. The total solubility of cyclohexanone and cyclohexanol in the extractant (solubility of cyclohexanone in the extractant + solubility of cyclohexanol in the extractant) is more than five times the total solubility of cyclohexanone and cyclohexanol in cyclohexane (solubility of cyclohexanone in cyclohexane + solubility of cyclohexanol in cyclohexane).
After the extracting agent extracts the cyclohexanone and cyclohexanol in the cyclohexane, the content of the cyclohexanone and cyclohexanol in the extracting agent phase is as high as possible compared with the content of the cyclohexanone and cyclohexanol in the cyclohexane phase, so that good extraction effect can be ensured. After the extraction is completed according to the fixed conditions, the contents of cyclohexanone and cyclohexanol dissolved in different extracting agents/the contents of cyclohexanone and cyclohexanol in cyclohexane have the following relationship: methanol 2:1, acetonitrile 5:1, dimethyl sulfoxide 11:1, N-methylacetamide 21:1.
In addition, in order to facilitate the separation of the extractant from cyclohexanone and cyclohexanol in the later stage, the separation is generally performed by distillation, and in order to reduce the distillation energy consumption, a low boiling point solvent is selected as much as possible.
In some embodiments, the extractant is one or more selected from acetonitrile, dimethyl sulfoxide, N-methylacetamide, N-dimethylacetamide, preferably the extractant is acetonitrile.
The manner of extraction is not particularly limited and may be carried out using liquid-liquid extraction apparatus and forms known in the art.
In some embodiments, the mass ratio of extractant to cyclohexane phase is 1:5 to 1:50, preferably 1:30.
The extraction ratio is less than 1:5, the consumption of the extractant is excessive, the effect of concentrating cyclohexanone and cyclohexanol into the extractant cannot be achieved, the extraction ratio is more than 1:50, the consumption of the extractant is less, the cyclohexanone and cyclohexanol in the cyclohexane phase cannot be completely extracted into the extractant, and the recovery rate of the cyclohexanone and cyclohexanol in the extracted and recovered cyclohexane can be reduced.
In some embodiments, the extraction temperature is 25 ℃ to 150 ℃, preferably 90 ℃.
In some embodiments, the extraction time is from 1 minute to 100 minutes, preferably 10 minutes.
In some embodiments, the number of extractions is 1-5, preferably 3.
In some embodiments, the process further comprises distilling the extractant phase comprising cyclohexanone and cyclohexanol to separate the extractant from the cyclohexanone and cyclohexanol.
After the extractant is separated from the cyclohexanone and the cyclohexanol, the extractant is continuously returned for use, and the cyclohexanone and the cyclohexanol enter the next working procedure.
In order to solve the problem of separating cyclohexanone and cyclohexanol from cyclohexane in the cyclohexanone oxidation process. The application selects the extractant which is not compatible with cyclohexane to extract low-content cyclohexanone and cyclohexanol in cyclohexane, the solubility of the cyclohexanone and the cyclohexanol in the extractant is more than five times of that in the cyclohexane, the dosage of the extractant is less than the total amount of the cyclohexane, the extractant and the cyclohexane are not extracted in equal proportion, and the extractant plays a role in concentrating the cyclohexanone and the cyclohexanol in a large proportion in the extraction process. After multiple extractions, the cyclohexanone and the cyclohexanol are all concentrated into an extractant, the cyclohexanone and the cyclohexanol hardly exist in the cyclohexane, the extractant containing the cyclohexanone and the cyclohexanol with higher concentration is insoluble with the cyclohexane, and the extractant phase and the cyclohexane phase can be separated by standing and separation. After the extraction is finished, the cyclohexanone and cyclohexanol remained in the cyclohexane can meet the technological index requirement. The content of cyclohexanone and cyclohexanol in the cyclohexane phase is lower than that after separation by original distillation, and the cyclohexanone and cyclohexanol can be completely extracted and concentrated into extractant. In addition, the boiling point of the extractant is lower, the extractant is easier to separate from cyclohexanone and cyclohexanol, and the overall steam consumption can be effectively reduced.
The second aspect of the application provides a process for preparing cyclohexanone by oxidizing cyclohexane, comprising the following steps:
oxidizing cyclohexane to obtain an oxidation solution;
adding alkali solution into the oxidation solution, mixing and stirring to obtain mixed slurry;
standing and phase-separating the mixed slurry to obtain a water phase and a cyclohexane phase containing cyclohexanone and cyclohexanol;
the cyclohexane phase comprising cyclohexanone and cyclohexanol is treated as described above.
The process for preparing cyclohexanone by oxidizing cyclohexane can be implemented according to the system shown in fig. 2, but is not limited to the system shown in fig. 2:
the system comprises an oxidation kettle, a decomposition kettle, a waste alkali separation device and an extraction tank which are connected in sequence;
the oxidation kettle comprises an air inlet, a feed inlet, a discharge port and a tail gas discharge port, the decomposition kettle comprises a feed inlet and a discharge port, the waste alkali separation device comprises a feed inlet, a waste alkali separation port and a discharge port, and the extraction tank comprises a feed inlet, a bottom discharge port and an upper discharge port;
the discharge port of the oxidation kettle is communicated with the feed port of the decomposition kettle, the discharge port of the decomposition kettle is communicated with the feed port of the waste alkali separation device, and the discharge port of the waste alkali separation device is communicated with the feed port of the extraction tank;
cyclohexane enters from a feed port of an oxidation kettle, air enters from an air inlet of the oxidation kettle, oxidation is carried out in the oxidation kettle to obtain an oxidation liquid, the oxidation liquid is discharged from a discharge port of the oxidation kettle to enter a feed port of a decomposition kettle, alkali liquor is added in the decomposition kettle and stirred to obtain mixed slurry, the mixed slurry is discharged from the discharge port of the decomposition kettle to enter a feed port of a waste alkali separating device, phase separation is carried out in the waste alkali separating device to obtain a cyclohexane phase and waste alkali, the waste alkali is discharged from the waste alkali separating port, the cyclohexane phase is discharged from the discharge port of the waste alkali separating device to enter the feed port of an extraction tank for extraction separation to obtain an extractant phase containing cyclohexanone and cyclohexanol and a cyclohexane phase, the extractant phase containing cyclohexanone and cyclohexanol is discharged from the discharge port, and the cyclohexane phase is discharged from the other discharge port;
the system may further comprise a solvent recovery column; the solvent recovery tower comprises a feed inlet, a bottom discharge outlet and an upper discharge outlet; the discharge port of the extraction tank is communicated with the feed port of the solvent recovery tower;
the extracting agent phase containing cyclohexanone and cyclohexanol is discharged from a discharge port of the extraction tank and enters a feed port of the solvent recovery tower for distillation to obtain extracting agent and cyclohexanone and cyclohexanol, the cyclohexanone and the cyclohexanol are discharged from the discharge port, and the extracting agent is discharged from the other discharge port;
the other discharge port of the extraction tank can be further communicated with the feed port of the oxidation kettle, and the cyclohexane phase can be returned to the oxidation kettle again. The cyclohexane phase obtained can be returned to the cyclohexane oxidation process to participate in the oxidation reaction again, but is not limited thereto.
The beneficial effects are that:
the application selects the extractant which is not compatible with cyclohexane but has better solubility with cyclohexanone and cyclohexanol, and the boiling point of the extractant is low. The whole extraction process is a process of concentrating cyclohexanone and cyclohexanol in a large proportion. Separating the extracting agent from the cyclohexanone and the cyclohexanol by distillation. The whole process can play a role in multistage distillation and separation in the original technological process, and the steam consumption in the whole process can be greatly reduced.
The present application has been described in detail hereinabove, but the above embodiments are merely exemplary in nature and are not intended to limit the present application. Furthermore, there is no intention to be bound by any theory presented in the preceding prior art or summary or the following examples.
Unless explicitly stated otherwise, numerical ranges throughout this application include any subrange therein and any numerical value incremented by the smallest subunit in which a given value is present. Unless explicitly stated otherwise, numerical values throughout this application represent approximate measures or limits to include minor deviations from the given value and ranges of embodiments having about the stated value and having the exact value noted. Except in the operating examples provided last, all numerical values of parameters (e.g., amounts or conditions) in this document (including the appended claims) should be construed in all cases as modified by the term "about" whether or not "about" actually appears before the numerical value. "about" means that the recited value allows for slight imprecision (with some approximation to the exact value; approximately or reasonably close to the value; approximated). "about" as used herein at least means variations that can be produced by ordinary methods of measuring and using these parameters if the imprecision provided by "about" is not otherwise understood in the art with this ordinary meaning. For example, "about" may include a change of less than or equal to 10%, less than or equal to 5%, less than or equal to 4%, less than or equal to 3%, less than or equal to 2%, less than or equal to 1%, or less than or equal to 0.5%.
Drawings
Fig. 1 shows a schematic diagram of a system for producing cyclohexanone by oxidizing cyclohexane according to the prior art.
Figure 2 shows a schematic diagram of the system for producing cyclohexanone by oxidizing cyclohexane according to the present application.
Detailed Description
The application is further illustrated by the following examples, which are provided for illustrative purposes only and are not to be construed as limiting the scope of the application as claimed.
Unless otherwise indicated, all materials, reagents, methods and the like used in the examples are those conventionally used in the art.
The cyclohexane phase sample of the example was a cyclohexane phase sample discharged from a discharge port of a waste alkali separation apparatus in a factory using the production apparatus of FIG. 1, and the cyclohexane content of the sample was measured to be 96.5%, and the sum of the cyclohexanone and cyclohexanol contents was about 3%.
Example 1
The extractant acetonitrile was added to the cyclohexane phase sample. The extractant amount was acetonitrile, sample=1:30 (mass ratio). Extraction was carried out at 90℃for 10 minutes. After the extraction is completed, standing and separating are carried out. The upper layer is cyclohexane phase, and the lower layer is acetonitrile phase. And extracting the sample for three times, replacing fresh extractant each time, and finally combining the obtained three extraction phases. The cyclohexane and acetonitrile phases were subjected to gas chromatography.
The chromatographic conditions were as follows:
chromatographic column: HP-INNOWAX 30 m.times.0.32 mm.times.0.25. Mu.m;
sample inlet temperature: 250 ℃, detector temperature: 300 ℃;
column incubator: constant temperature 150 ℃;
the content of cyclohexanone and cyclohexanol in both phases was tested.
The experimental results are as follows:
the acetonitrile content in the cyclohexane phase was 3.20%.
Example 2
The extractant dimethyl sulfoxide was added to the cyclohexane phase sample. The extractant dosage was dimethyl sulfoxide, sample=1:30 (mass ratio). Extraction was carried out at 90℃for 10 minutes. After the extraction is completed, standing and separating are carried out. The upper layer is cyclohexane phase, and the lower layer is dimethyl sulfoxide phase. And extracting the sample for three times, replacing fresh extractant each time, and finally combining the obtained three extraction phases. The cyclohexane phase and the dimethyl sulfoxide phase were subjected to gas chromatography to test the content of cyclohexanone and cyclohexanol in both phases (test method was the same as in example 1).
The experimental results are as follows:
the dimethyl sulfoxide content in the cyclohexane phase was 1.43%.
Example 3
The extractant N-methylacetamide was added to the cyclohexane phase sample. The extractant amount was N-methylacetamide: sample=1:30 (mass ratio). Extraction was carried out at 90℃for 10 minutes. After the extraction is completed, standing and separating are carried out. The upper layer is cyclohexane phase, and the lower layer is N-methylacetamide. And extracting the sample for three times, replacing fresh extractant each time, and finally combining the obtained three extraction phases. The cyclohexane phase and N-methylacetamide were subjected to gas chromatography to test the content of cyclohexanone and cyclohexanol in both phases (test method was the same as in example 1).
The experimental results are as follows:
the N-methylacetamide content in the cyclohexane phase was 0.41%.
Comparative example 1
The extractant methanol was added to the cyclohexane phase sample. The extractant dosage is methanol: sample=1:5 (mass ratio). Extraction was carried out at 90℃for 10 minutes. After the extraction is completed, standing and separating are carried out. The upper layer is cyclohexane phase, and the lower layer is methanol. And extracting the sample for three times, replacing fresh extractant each time, and finally combining the obtained three extraction phases. The cyclohexane phase and methanol were subjected to gas chromatography to test the content of cyclohexanone and cyclohexanol in the two phases (test method was the same as in example 1).
The experimental results are as follows:
methanol in cyclohexane phase was 14.37%.
Since the content of dissolved methanol in the cyclohexane phase is too high and reaches 14.37%, the recovery rate of the methanol for the cyclohexanone and cyclohexanol in the cyclohexane phase is reduced, and even after the extraction is finished, the high cyclohexanone and cyclohexanol still remain in the cyclohexane phase, the recovery rate of the extraction is low, and the effect of completely recovering the cyclohexanone and cyclohexanol in the cyclohexane phase cannot be achieved.
The above embodiments are only for illustrating the technical solution of the present application, and are not limited thereto. Although the application has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: modifications may be made to the technical solutions described in the foregoing embodiments, or equivalents may be substituted for some or all of the technical features thereof, without departing from the spirit and scope of the present application as defined in the claims; and such modifications or substitutions are intended to be within the scope of the present application as defined by the claims.
Claims (10)
1. A process for separating cyclohexanone and cyclohexanol in cyclohexane, comprising the steps of:
adding an extractant into a cyclohexane phase containing cyclohexanone and cyclohexanol for extraction, and separating to obtain an extractant phase containing cyclohexanone and cyclohexanol and cyclohexane;
wherein the solubility of the extractant in cyclohexane at room temperature is less than 5%, and the total solubility of cyclohexanone and cyclohexanol in the extractant is more than five times of the total solubility of cyclohexanone and cyclohexanol in cyclohexane.
2. The method according to claim 1, wherein the extractant is one or more selected from acetonitrile, dimethyl sulfoxide, N-methylacetamide, N-dimethylacetamide, and preferably the extractant is acetonitrile.
3. The method according to claim 1, characterized in that the mass ratio of extractant to cyclohexane phase is 1:5-1:50, preferably 1:30.
4. The process according to claim 1, characterized in that the extraction temperature is 25 ℃ to 150 ℃, preferably 90 ℃.
5. The method according to claim 1, characterized in that the extraction time is 1 minute to 100 minutes, preferably 10 minutes.
6. The method according to claim 1, characterized in that the number of extractions is 1-5, preferably 3.
7. The method according to claim 1, wherein the method further comprises: the extractant phase comprising cyclohexanone and cyclohexanol is distilled to separate the extractant from the cyclohexanone and cyclohexanol.
8. The process according to claim 1, characterized in that the cyclohexane phase comprising cyclohexanone and cyclohexanol is obtained by: adding alkali solution into the oxidized solution after cyclohexane oxidation, mixing and stirring, and separating phases to obtain a water phase and a cyclohexane phase containing cyclohexanone and cyclohexanol.
9. A method for preparing cyclohexanone by oxidizing cyclohexane, which is characterized by comprising the following steps:
oxidizing cyclohexane to obtain an oxidation solution;
adding alkali solution into the oxidation solution, mixing and stirring to obtain mixed slurry;
standing and phase-separating the mixed slurry to obtain a water phase and a cyclohexane phase containing cyclohexanone and cyclohexanol;
a cyclohexane phase comprising cyclohexanone and cyclohexanol is treated by a method according to any of claims 1 to 8 to obtain an extractant phase comprising cyclohexanone and cyclohexanol and cyclohexane.
10. The method according to claim 9, wherein the method further comprises: the cyclohexane obtained was used for cyclohexane oxidation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210640660.0A CN117229118A (en) | 2022-06-07 | 2022-06-07 | Method for separating cyclohexanone and cyclohexanol in cyclohexane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210640660.0A CN117229118A (en) | 2022-06-07 | 2022-06-07 | Method for separating cyclohexanone and cyclohexanol in cyclohexane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117229118A true CN117229118A (en) | 2023-12-15 |
Family
ID=89084909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210640660.0A Pending CN117229118A (en) | 2022-06-07 | 2022-06-07 | Method for separating cyclohexanone and cyclohexanol in cyclohexane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117229118A (en) |
-
2022
- 2022-06-07 CN CN202210640660.0A patent/CN117229118A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106831471B (en) | A method of removing a small amount of acid or glacial acetic acid and refining DMF | |
| CN105271413B (en) | A kind of method for extracting tungsten from phosphotungstic acid/phosphotungstate solution | |
| CN106588599A (en) | Purification method of PODE (polyoxymethylene dimethyl ether) | |
| CN107033107A (en) | A kind of method for preparing epoxychloropropane | |
| CN100486953C (en) | Method for retrieving organic acid, ester from cyclic ethane oxidation liquid | |
| JP2011520851A (en) | Re-evaluation of waste aqueous streams in the process of producing propylene oxide and styrene together | |
| CN106588590A (en) | Refinement method for polyoxymethylene dimethyl ether | |
| CN107311878B (en) | Device for recycling glycine waste liquid and method for recycling glycine waste liquid | |
| CN106117011B (en) | A kind of refining methd of discrimination method production crude sodium formate byproduct from neopentyl glycol production | |
| CN111533097A (en) | Yellow phosphorus oxidation dearsenification method | |
| CN117229118A (en) | Method for separating cyclohexanone and cyclohexanol in cyclohexane | |
| CN112194299A (en) | Resource treatment method of waste liquid | |
| CN106397183A (en) | Method for separating levulinic acid, formic acid and furfural from acid catalysis hydrolyzates of biomass | |
| CN101555238A (en) | Method for tetrahydrofuran recycling | |
| CN103757246A (en) | Method for producing high-purity gold | |
| CN213113165U (en) | Continuous production device for preparing and producing mixed dibutyl dibasic acid from nylon acid | |
| CN108220615A (en) | A kind of purifying technique of gold | |
| CN209778702U (en) | Device for separating n-butyl alcohol and n-butyl ether by extraction and rectification processes | |
| JPH08133995A (en) | Production of propylene oxide and styrene monomer | |
| RU2307824C2 (en) | Method of extraction of phenol and biphenols | |
| CN112574059A (en) | Separation of N, N-dimethylacetamide-acetic acid mixed system | |
| CN101613311A (en) | From neutralized rearrangement mixture, reclaim the system and method for hexanolactam | |
| CN106045829B (en) | A kind of epoxy carboxylic acids' ester prepares the green synthesis process of 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal | |
| CN106587058B (en) | A kind of KOH activation method prepares the recycling of the KOH in super-activated carbon technique and absorbent charcoal fine purification method | |
| CN105315128B (en) | Method for preparing KA oil through cyclohexane oxidation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |