CN111039801A - Utilization method of cyclohexane oxidation by-product light oil - Google Patents
Utilization method of cyclohexane oxidation by-product light oil Download PDFInfo
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- CN111039801A CN111039801A CN201811190604.1A CN201811190604A CN111039801A CN 111039801 A CN111039801 A CN 111039801A CN 201811190604 A CN201811190604 A CN 201811190604A CN 111039801 A CN111039801 A CN 111039801A
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- light oil
- ammonia
- aminocyclohexanol
- product
- reaction
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- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000006227 byproduct Substances 0.000 title claims abstract description 16
- 230000003647 oxidation Effects 0.000 title claims abstract description 12
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 95
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 28
- PQMCFTMVQORYJC-UHFFFAOYSA-N 2-aminocyclohexan-1-ol Chemical compound NC1CCCCC1O PQMCFTMVQORYJC-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 238000009835 boiling Methods 0.000 claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 12
- 238000001816 cooling Methods 0.000 claims abstract description 11
- 238000011084 recovery Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 230000006835 compression Effects 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 abstract description 26
- 230000008901 benefit Effects 0.000 abstract description 5
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 20
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- -1 light oil Chemical compound 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a utilization method of light oil as a byproduct of oxidation of epoxy cyclohexane, which comprises the following steps: (1) taking light oil which is a byproduct of cyclohexane oxidation as a raw material, and reacting the light oil with liquid ammonia or ammonia gas, wherein the mass ratio of the light oil to the ammonia is 100:4-136, the reaction temperature is 90-150 ℃, and the reaction time is 0.5-2 h; (2) cooling the reaction product to 60-80 ℃, and recovering excessive ammonia; (3) separating low-boiling point components from the product after ammonia recovery to obtain a crude product of 2-aminocyclohexanol; (4) and (3) rectifying and separating the crude product of the 2-aminocyclohexanol under the protection of nitrogen to obtain the 2-aminocyclohexanol. The invention provides a method for preparing 2-aminocyclohexanol, which can realize high value-added utilization of light oil under a mild condition and has high economic benefit.
Description
Technical Field
The invention relates to a method for utilizing a byproduct of oxidation of epoxy cyclohexane, namely light oil, in particular to a method for preparing 2-aminocyclohexanol by refining and utilizing the byproduct of oxidation of epoxy cyclohexane.
Background
Cyclohexanone is the main raw material for preparing bulk chemical caprolactam, and the preparation of cyclohexanone by cyclohexane oxidation is one of the main methods for industrial production of cyclohexanone. When cyclohexane is used for preparing cyclohexanone, a byproduct distilled from the top of a light tower is a low-boiling-point byproduct of light oil, the composition of the byproduct is complex and is not easy to separate, the byproduct contains various components such as n-amyl alcohol, cyclohexane, n-butyl alcohol, cyclohexanone and the like, the boiling point range is usually 80-160 ℃, the boiling points of the n-amyl alcohol, the epoxycyclohexane and the like are close, and the light oil is difficult to separate directly by means of rectification and the like, so the light oil is usually used as fuel for processing, and the economic benefit is low. The content of the main components of the impurities in the light oil, namely the cyclohexene oxide and the n-amyl alcohol reaches 55-80wt%, wherein the cyclohexene oxide has high reaction activity and can react with ammonia, alcohol, acid and the like to prepare related products, so that the recycling and utilization of the cyclohexene oxide in the light oil are widely concerned.
At present, various patents disclose technologies for recovering cyclohexene oxide from light oil byproducts, such as chinese patents CN 1059675C, CN 1060169C, CN106316990A, CN104098438B, and CN103508982A, mainly use chemical reactions and other methods to increase the boiling point difference of components difficult to separate, so as to achieve the separation purpose and then react to generate cyclohexene oxide; also, patent describes a method for producing chemicals such as adipic acid from light oil as a raw material, such as CN 102464579B. Although these patents provide a method for utilizing light oil, with the change of domestic chemical production energy and the change of downstream requirements, both cyclohexene oxide and adipic acid have a surplus situation, so that the economical efficiency of light oil utilization is reduced.
The 2-aminocyclohexanol is a fine chemical product with wider application range and great development value, has active groups such as amino, hydroxyl and the like, can be used as a pesticide and a medical precursor, can also be used as a raw material for preparing an amine curing agent, and has stronger economic benefit. The invention provides a simple method for preparing 2-aminocyclohexanol by taking light oil as a raw material, can realize high value-added utilization of the light oil under a mild condition, and has high economic benefit.
Disclosure of Invention
The invention aims to: the method for utilizing the light oil with high added value is provided; (2) a method for preparing 2-aminocyclohexanol at low cost is provided.
The purpose of the invention is realized by the following technical scheme: a method for utilizing light oil as a byproduct of oxidation of epoxy cyclohexane comprises the following steps: (1) taking light oil which is a byproduct of cyclohexane oxidation as a raw material, and reacting the light oil with liquid ammonia or ammonia gas, wherein the mass ratio of the light oil to the ammonia is 100:4-136, the reaction temperature is 90-150 ℃, and the reaction time is 0.5-2 h; (2) cooling the reaction product to 60-80 ℃, and recovering excessive ammonia; (3) separating low-boiling point components from the product after ammonia recovery to obtain a crude product of 2-aminocyclohexanol; (4) and (3) rectifying and separating the crude product of the 2-aminocyclohexanol under the protection of nitrogen to obtain the 2-aminocyclohexanol.
The mass ratio of the light oil to the ammonia in the step (1) is preferably 100: 34-136.
The reaction temperature in step (1) is preferably 110-150 ℃.
The reaction time in the step (1) is preferably 0.5-1 h.
And (3) when the temperature of the excessive ammonia in the step (2) is 60-80 ℃, reducing the pressure to normal pressure, separating the excessive ammonia from the reaction system, cooling and compressing the excessive ammonia, and recycling the excessive ammonia.
The low boiling point component in step (3) is a component having a boiling point lower than that of 2-aminocyclohexanol.
The rectification separation in the step (4) is to separate the 2-aminocyclohexanol by utilizing a vacuum rectification method.
The invention discloses a method for utilizing light oil as a byproduct of oxidation of cyclohexene oxide, which has low cost of raw materials and is realized by the following reaction of the cyclohexene oxide in the presence of ammonia:
the invention has the remarkable characteristics that: the method has the advantages of relatively mild reaction conditions, simple operation, short reaction time, lower energy consumption and the like, is suitable for large-scale production, and can improve the competitiveness of industrial chains.
Detailed Description
In order to better understand the present invention, the following examples are further provided to illustrate the content of the present invention, but the content of the present invention is not limited to the following examples.
Example 1
Adding 100.0g of light oil (the content of cyclohexene oxide is 20 wt%) into a reaction kettle, introducing ammonia gas at room temperature to dissolve the ammonia gas in the light oil, weighing the amount of the introduced ammonia gas, stopping introducing the ammonia gas when the amount of the introduced ammonia gas reaches 4.0g, closing valves, heating to 90 ℃, reacting for 2 hours, cooling to 80 ℃, slowly opening a valve, reducing the pressure, recovering the excessive ammonia gas to the normal pressure, and analyzing the product by chromatography, wherein the conversion rate of the cyclohexene oxide is 95.2% and the selectivity is 75.1%.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 14.0g of 2-aminocyclohexanol distillate.
Example 2
Adding 100.0g of light oil (the content of cyclohexene oxide is 20 wt%) into a reaction kettle, introducing ammonia gas at room temperature to dissolve the ammonia gas in the light oil, weighing the amount of the introduced ammonia gas, stopping introducing the ammonia gas when the amount of the introduced ammonia gas reaches 15.0g, closing valves, heating to 90 ℃, reacting for 2 hours, cooling to 80 ℃, slowly opening a valve, reducing the pressure, recovering the excessive ammonia gas to the normal pressure, and analyzing the product by chromatography, wherein the conversion rate of the cyclohexene oxide is 97.3%, and the selectivity is 85.1%.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 15.3g of 2-aminocyclohexanol distillate.
Example 3
Adding 100.0g of light oil (the content of cyclohexene oxide is 20 wt%) into a reaction kettle, introducing ammonia gas at room temperature to dissolve the ammonia gas in the light oil, weighing the amount of the introduced ammonia gas, stopping introducing the ammonia gas when 34.0g of the ammonia gas is reached, closing valves, heating to 150 ℃, reacting for 0.5 hour, cooling to 80 ℃, slowly opening a valve, reducing the pressure, recovering the excessive ammonia gas to the normal pressure, and analyzing the product by chromatography, wherein the conversion rate of the cyclohexene oxide is 99.9% and the selectivity is 95.1%.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 19.5g of 2-aminocyclohexanol distillate.
Example 4
Adding 100.0g of light oil (the content of cyclohexene oxide is 20 wt%) into a reaction kettle, introducing liquid ammonia at room temperature to fully mix ammonia and the light oil, weighing the amount of the introduced liquid ammonia, stopping introducing ammonia when the amount of the introduced liquid ammonia reaches 68.0g, closing valves, heating to 110 ℃, reacting for 2 hours, cooling to 80 ℃, slowly opening a valve, reducing the pressure to normal pressure, recovering excessive ammonia, and analyzing a product by chromatography, wherein the conversion rate of the cyclohexene oxide is 100.0% and the selectivity is 98.1%.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 20.3g of 2-aminocyclohexanol distillate.
Example 5
Referring to example 4, the reaction time was changed to 1h, and the product was chromatographed with 98.0% conversion of epoxycyclohexane and 98.9% selectivity.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 19.5g of 2-aminocyclohexanol distillate.
Example 6
Adding 100.0g of light oil (the content of cyclohexene oxide is 40 wt%) into a reaction kettle, introducing ammonia gas at room temperature to dissolve the ammonia gas in the light oil, weighing the amount of the introduced ammonia gas, stopping introducing the ammonia gas when the amount of the introduced ammonia gas reaches 8.0g, closing valves, heating to 150 ℃, reacting for 0.5 hour, cooling to 60 ℃, slowly opening a valve, reducing the pressure to normal pressure, recovering excessive ammonia gas, and analyzing a product by chromatography, wherein the conversion rate of the cyclohexene oxide is 97.1% and the selectivity is 70.8%.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 24.2g of 2-aminocyclohexanol distillate.
Example 7
Adding 100.0g of light oil (the content of cyclohexene oxide is 40 wt%) into a reaction kettle, introducing ammonia gas at room temperature to fully mix the liquid ammonia with the light oil, weighing the amount of the introduced liquid ammonia, stopping introducing the liquid ammonia when 136.0g of the liquid ammonia is obtained, closing valves, heating to 110 ℃, reacting for 1 hour, cooling to 60 ℃, slowly opening a valve, reducing the pressure to normal pressure, recovering excessive ammonia gas, and analyzing the product by chromatography, wherein the conversion rate of the cyclohexene oxide is 99.2% and the selectivity is 96.1%.
And distilling the crude product after ammonia recovery to remove components with boiling points lower than 160 ℃, carrying out reduced pressure rectification on high-boiling-point substances at the bottom of the kettle, and collecting 38.4g of 2-aminocyclohexanol distillate.
Claims (7)
1. A utilization method of cyclohexane oxidation by-product light oil is characterized by comprising the following steps:
taking light oil which is a byproduct of cyclohexane oxidation as a raw material, and reacting the light oil with liquid ammonia or ammonia gas, wherein the mass ratio of the light oil to the ammonia is 100:4-136, the reaction temperature is 90-150 ℃, and the reaction time is 0.5-2 h;
cooling the reaction product to 60-80 ℃, and recovering excessive ammonia;
separating low-boiling point components from the product after ammonia recovery to obtain a crude product of 2-aminocyclohexanol;
and (3) rectifying and separating the crude product of the 2-aminocyclohexanol under the protection of nitrogen to obtain the 2-aminocyclohexanol.
2. The method of claim 1, wherein the mass ratio of light oil to ammonia is 100: 34-136.
3. The method of claim 1, wherein the reaction temperature is 110 ℃ to 150 ℃.
4. The method of claim 1, wherein the reaction time is from 0.5 to 1 hour.
5. The method of claim 1, wherein the excess ammonia in step (2) is separated from the reaction system after reducing the pressure to normal pressure at 60-80 ℃, and is recycled after cooling and compression.
6. The process according to claim 1, wherein the low boiling component in step (3) is a component having a boiling point lower than that of 2-aminocyclohexanol.
7. The method of claim 1, wherein the rectification separation in the step (4) is a method of separating 2-aminocyclohexanol by using vacuum rectification.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811190604.1A CN111039801A (en) | 2018-10-12 | 2018-10-12 | Utilization method of cyclohexane oxidation by-product light oil |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811190604.1A CN111039801A (en) | 2018-10-12 | 2018-10-12 | Utilization method of cyclohexane oxidation by-product light oil |
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| CN111039801A true CN111039801A (en) | 2020-04-21 |
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| CN201811190604.1A Pending CN111039801A (en) | 2018-10-12 | 2018-10-12 | Utilization method of cyclohexane oxidation by-product light oil |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112920397A (en) * | 2021-04-08 | 2021-06-08 | 红宝丽集团股份有限公司 | Polyether polyol and preparation method thereof |
| CN113072453A (en) * | 2021-04-08 | 2021-07-06 | 红宝丽集团股份有限公司 | Preparation method of 2-aminocycloalkanol |
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| CN112920397A (en) * | 2021-04-08 | 2021-06-08 | 红宝丽集团股份有限公司 | Polyether polyol and preparation method thereof |
| CN113072453A (en) * | 2021-04-08 | 2021-07-06 | 红宝丽集团股份有限公司 | Preparation method of 2-aminocycloalkanol |
| CN112920397B (en) * | 2021-04-08 | 2023-12-01 | 红宝丽集团股份有限公司 | Polyether polyol and preparation method thereof |
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