CN104109137B - Oxide purification process - Google Patents
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- CN104109137B CN104109137B CN201310129861.5A CN201310129861A CN104109137B CN 104109137 B CN104109137 B CN 104109137B CN 201310129861 A CN201310129861 A CN 201310129861A CN 104109137 B CN104109137 B CN 104109137B
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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Abstract
The present invention relates to a kind of oxide purification process, mainly solve prior art is entrained with expoxy propane and extractant in extractive distillation column overhead stream, cause the problem that expoxy propane yield is low, extractant loss is big. The present invention comprises the steps of a) crude propene oxide solution by employing and enters extraction distillation column, and tower top obtains logistics 2, obtains logistics 3 at the bottom of tower; Logistics 3 enters solvent recovery tower, and tower top obtains product propylene, is extracted agent logistics 5 at the bottom of tower; Logistics 5 is divided into logistics 6 and logistics 7 two strands; C) enter phase separator after logistics 2 condensation, after oil-water separation, obtain oil reservoir 8 and water layer 9; D) oil reservoir 8 and logistics 6 are back to extractive distillation column overhead; E) logistics 7 enters water scrubber bottom, and water layer 9 enters water scrubber top, obtains waste water streams at the bottom of tower, and tower top obtains logistics 11; Logistics 11 enters the technical scheme of phase separator and solves this problem preferably, can be used in the commercial production of oxide purification.
Description
Technical field
The present invention relates to a kind of oxide purification process, in more detail, the invention mainly relates to containing oxide purification process as impurity of water, acetaldehyde, methanol and methyl formate.
Background technology
Expoxy propane is important organic compound raw material, is the third-largest propylene analog derivative being only second to polypropylene and acrylonitrile. Hydrogen phosphide cumene (CHP), hydrogen peroxide ethylbenzene (EBHP) are in the presence of an epoxidation catalyst, it is obtained by reacting in propylene oxide process with propylene, target product, except expoxy propane, also generates the oxygenatedchemicalss such as water, methanol, acetaldehyde, methyl formate. In order to obtain meeting the high-purity expoxy propane that polymerization requires, it is necessary to the magazins' layout contained in expoxy propane is removed. Owing to methyl formate and expoxy propane relative volatility are close to 1, acetaldehyde is close with expoxy propane boiling temperature, expoxy propane and water, and methanol is respectively formed the features such as azeotropic mixture, and the method for conventional distillation has been difficult to the purification of expoxy propane.
As the purification process of expoxy propane, all report to some extent in the patents of invention such as US5133839, US5262017, US5354430/1, US7285187, US8093412, US20120077996. For the purification of expoxy propane, it is currently mainly used C7~C20The method that straight chain and side chain hydro carbons, glycols, acetone, water carry out extractive distillation as extractant. Such as, US4971661 discloses one and uses acetone as extractant, and expoxy propane is refined. Disclosed in US3607669, the alkane of octane etc is effective to removing water. Disclosed in US5133839, the hydrocarbon such as octane are effective to removing in expoxy propane the impurity such as contained methanol, propionic aldehyde, acetone. Disclosed in US5354430/1, glycol is effective to removing the oxygenatedchemicalss such as water impurity, propionic aldehyde, acetone. US20120077996 adopts the mode that glycol and the double; two extractant multi-stage counter current extraction of normal octane and normal octane extracting rectifying combine to carry out expoxy propane purification, utilizes extraction process to reduce separation process energy consumption.
Due in extracting rectifying process, acetaldehyde, water, methanol, methyl formate impurity remove system from extractive distillation column overhead, a certain amount of expoxy propane and extractant can be carried secretly, if this fraction of stream can cause the loss of expoxy propane and extractant as waste water directly outer row.
Summary of the invention
The technical problem to be solved is to be entrained with expoxy propane and extractant in prior art in extractive distillation column overhead stream, causes the problem that expoxy propane yield is low, extractant loss is big, it is provided that a kind of new oxide purification process. The method has the advantages that expoxy propane yield is high, extractant loss is low.
For solving above-mentioned technical problem, the technical solution used in the present invention is as follows: a kind of oxide purification process, comprises the steps of
A) the crude propene oxide solution 1 containing water, acetaldehyde, methanol and methyl formate impurity enters extraction distillation column, and after extractive distillation, tower top obtains logistics 2, obtains logistics 3 at the bottom of tower;
B) logistics 3 enters solvent recovery tower, and after separation, tower top obtains product propylene 4, is extracted agent logistics 5 at the bottom of tower; Logistics 5 is divided into logistics 6 and logistics 7 two strands;
C) enter phase separator after logistics 2 condensation, after oil-water separation, obtain oil reservoir 8 and water layer 9;
D) oil reservoir 8 and logistics 6 are back to extractive distillation column overhead;
E) logistics 7 enters water scrubber bottom, and water layer 9 enters water scrubber top, after separation, obtains the waste water streams 10 of moisture, acetaldehyde, methanol and methyl formate at the bottom of tower, and tower top obtains logistics 11; Logistics 11 enters phase separator.
In technique scheme, it is preferable that in described crude propene oxide solution, the concentration expressed in percentage by weight of expoxy propane is 97.0 ~ 99.9%.
Preferably, the theoretical cam curve of described extraction distillation column is 55 ~ 80 pieces, and operation pressure is 160 ~ 250kPa, and bottom temperature is less than 130 DEG C, and solvent ratio is 3 ~ 7.
Preferably, the theoretical cam curve of described water scrubber is 20 ~ 40 pieces, and operation pressure is 160 ~ 220kPa, and solvent ratio is 3 ~ 6.
Preferably, described extractant is selected from C7~C10Straight-chain hydrocarbons, C7~C10At least one in branched-chain hydrocarbons, glycol or acetone.
It is highly preferred that described extractant is selected from C7~C8Straight-chain hydrocarbons.
Most preferably, described extractant at least one in normal octane or normal heptane.
Preferably, described phase separator has multilayer insulating panel structure.
Preferably, logistics 6 is (400 ~ 500) with the weight ratio of logistics 7: 1.
Preferably, logistics 2 first contacts with deionized water or water vapour logistics 12 before condensing, and the weight ratio of logistics 2 and logistics 12 is (40 ~ 60): 1.
In the inventive method, described pressure refers both to absolute pressure.
The method of oxide purification of the present invention, the mode adopting extracting rectifying and liquid-liquid extraction to combine, effectively remove water, methanol, acetaldehyde, methyl formate impurity, reclaim the expoxy propane in waste water and extractant, obtain polymer grade product propylene. When being embodied as, described method may comprise steps of:
(1) extractant adds to extraction distillation column tower reactor or solvent recovery tower tower reactor.
(2) crude propene oxide solution enters extraction distillation column with solvent recovery tower reactor liquid heat exchange to 60 ~ 80 DEG C, top gaseous phase sprays into deionized water or water vapour, in tower top phase separator, oil-water separation operation is carried out after condensation, multilayer insulating panel is had in phase separator, with the extractant of recovery, the oil reservoir separated is mixed the backflow as extraction distillation column, and the water layer of separation enters water scrubber.
(3) extractive distillation tower reactor liquid mainly contains expoxy propane and extractant, enter solvent recovery tower, tower top separates and obtains product propylene, tower reactor reclaims and is extracted agent, it is cooled to 40 ~ 50 DEG C through subcooler after extractant and extraction distillation column charging heat exchange, coolant is divided into two strands, and one mixes with extractive distillation column overhead phase separator oil reservoir as backflow, and another stock enters water scrubber.
(4) water layer of phase separator is from the charging of water scrubber top, the extractant reclaimed is from bottom charging, the expoxy propane in aqueous phase and extractant are reclaimed in liquid-liquid extraction, water scrubber tower top oil reservoir mainly contains expoxy propane and extractant, it is recycled into extractive distillation column overhead phase separator, water scrubber tower reactor water layer mainly contains water, acetaldehyde, methanol, methyl formate, as wastewater treatment.
(5) solvent recovery column overhead obtains the purity polymer grade product propylene more than 99.99wt%.
Impurity in crude propene oxide solution described in the inventive method, mainly includes water, acetaldehyde, methanol, methyl formate, is specifically shown in table 1.
Table 1
In impurity in expoxy propane, water, acetaldehyde, methanol, methyl formate are to the relative volatility of expoxy propane close to 1, and conventional distillation is difficult to separate. Extractive distillation is commonly used to separate the relative volatility system close or equal to 1, and by introducing a kind of highly polar extractant, the component stronger due to itself and mixture Semi-polarity has higher affinity, thus can change its relative volatility.
Expoxy propane and water, acetaldehyde, methanol, methyl formate impurity relative volatility in equilibrium conditions during to use extractant normal heptane, normal octane compare. Condition is under 1atm, is separately added into the extractant normal heptane of weight ratio 3 ~ 5 times, normal octane is measured in the expoxy propane containing above-mentioned impurity, and water impurity, acetaldehyde, methanol, methyl formate and the change of expoxy propane relative volatility are as follows. Its result is as shown in table 2.
Table 2
It can be seen that by adding extractant normal heptane, normal octane, expoxy propane relative volatility is increased by water impurity, acetaldehyde, methanol, methyl formate, it is easy to separate. By adding deionized water or steam, make acetaldehyde and water be fully contacted, reach as far as possible to balance each other dividing in mutually, make acetaldehyde separate completely. But owing to expoxy propane and water section are miscible, dissolubility 40.5wt% in water when 20 DEG C; Water dissolubility 12.8wt% in expoxy propane, has PART EPOXY propane losses, carries a part of extractant simultaneously secretly in waste water. Adding normal heptane, normal octane in waste water, it is possible to reduce expoxy propane dissolubility in water, as shown in table 3, normal heptane, the expoxy propane that normal octane is dissolved in water is extracted to oil reservoir, recycles, and reduces wastewater treatment expense simultaneously. For 1000kg/h waste water, adding 200kg/h extractant, waste water composition and situation of change are as shown in table 3.
Table 3
As can be seen from Table 3, adding extractant normal heptane, after normal octane, in water layer, water content is almost constant, and expoxy propane loss amount reduces by 57%, extracts dosage loss amount and reduces by 96.5%.
The inventive method adopts the mode that extracting rectifying and liquid-liquid extraction combine, and effectively removes water, methanol, acetaldehyde, methyl formate impurity, increases water scrubber simultaneously and utilizes extractant of the same race to reclaim the expoxy propane in waste water and extractant. The method extraction efficiency is high, it is possible to obtaining the purity polymer grade product propylene more than 99.99wt%, the expoxy propane response rate reaches 99.2 ~ 99.8%, achieves good technique effect.
Accompanying drawing explanation
Fig. 1 is the process flow diagram of the inventive method.
In Fig. 1, T101 is extraction distillation column, T102 is solvent recovery tower, T103 is water scrubber, D-101 is phase separator, 1 is crude propene oxide solution, 2 is extraction distillation column T-101 top gaseous phase logistics, 3 is extraction distillation column T-101 tower reactor output streams, 4 is product propylene, 5 is solvent recovery tower T-102 tower reactor output streams, 6 is extraction distillation column T-101 tower extractant feed logistics, 7 is water scrubber T-103 extractant feed logistics, 8 is phase separator D-101 oil phase logistics, 9 is phase separator D-101 aqueous phase logistics, 10 is water scrubber T-103 tower reactor aqueous phase output streams, 11 is water scrubber T-103 tower top oil phase output streams, 12 is deionized water or water vapour logistics, 13 is extraction distillation column T-101 reflux stream.
In Fig. 1, containing water, acetaldehyde, methanol, methyl formate impurity crude propene oxide solution 1 enter extraction distillation column T-101 with solvent recovery tower reactor liquid 5 heat exchange to 60 ~ 80 DEG C, extraction distillation column adopts C7~C10Hydrocarbon as extractant, extraction distillation column solvent ratio (logistics 6 flow and crude propene oxide solution feed 1 flow ratio) is 4 ~ 6, top gaseous phase sprays into deionized water or water vapour 12, in tower top phase separator D-101, oil-water separation operation is carried out after condensation, multilayer insulating panel is had in phase separator, the oil reservoir 8 of separation is mixed the backflow 13 as extraction distillation column with the extractant 6 reclaimed, the water layer 9 separated enters water scrubber T-103, T101 tower theoretical cam curve 55 ~ 80, operation Stress control is at 160 ~ 250kPa, and the strict bottom temperature that controls is less than 130 DEG C. Extractive distillation tower reactor liquid 3 mainly contains expoxy propane and extractant, enter solvent recovery tower T-102, tower top separates and obtains product propylene 4, tower reactor reclaims and is extracted agent 5, T102 tower theoretical cam curve 20 ~ 40, operation Stress control is cooled to 40 ~ 50 DEG C through subcooler after 160 ~ 220kPa, extractant 5 and extraction distillation column charging 1 heat exchange, coolant is divided into two strands, and logistics 6 mixes with extractive distillation column overhead phase separator oil reservoir and enters water scrubber as reflux stream 7; The water layer 9 of phase separator is from the charging of water scrubber top, the extractant 7 reclaimed is from bottom charging, the expoxy propane in aqueous phase and extractant are reclaimed in liquid-liquid extraction, water scrubber tower top oil phase output streams 11 mainly contains expoxy propane and extractant, it is recycled into extraction distillation column phase separator D-101, water scrubber tower reactor aqueous phase output streams 10 mainly contains water, acetaldehyde, methanol, methyl formate and a small amount of expoxy propane and extractant, as wastewater treatment. Solvent recovery column overhead obtains the purity polymer grade product propylene 4 more than 99.99wt%, and as shown in table 4, the expoxy propane response rate is more than 99.6% for product propylene composition.
Table 4
| Composition | Content, wt |
| Expoxy propane | > 0.9999 |
| Water | 1~20 ppm |
| Aldehyde (in propionic aldehyde) | 1~20 ppm |
| Methanol | 1~20 ppm |
| Methyl formate | 2~20 ppm |
It should be noted that the extractant disclosed in the present invention can use one pack system, it is possible to use the mixture of these compounds. From the view point of industrial implementation, it is preferable that the normal heptane that is industrially readily available, normal octane.
The invention will be further elaborated by the examples below.
Detailed description of the invention
[embodiment 1]
Crude propene oxide solution (logistics 1) enters extraction distillation column T-101 with solvent recovery tower reactor liquid (logistics 5) heat exchange to 80 DEG C, extraction distillation column adopts normal octane as extractant, extraction distillation column solvent ratio (extractant stream 6 and crude propene oxide solution feed 1 flow ratio) is 4, top gaseous phase sprays into deionized water (logistics 12), in tower top phase separator D-101, oil-water separation operation is carried out after condensation, multilayer insulating panel is had in phase separator, the oil reservoir (logistics 8) separated is mixed the backflow (logistics 13) as extraction distillation column with the extractant (logistics 6) reclaimed, the water layer (logistics 9) separated enters water scrubber T-103, T101 tower theoretical cam curve 70, operation Stress control is at 200kPa, bottom temperature 100 DEG C, the composition of crude propene oxide solution is as shown in table 5.
Table 5
| Composition | Content, wt |
| Water | 0.008 |
| Acetaldehyde | 0.001 |
| Methanol | 0.001 |
| Methyl formate | 0.001 |
| Expoxy propane | 0.989 |
Extractive distillation tower reactor liquid (logistics 3) mainly contains expoxy propane and extractant, enter solvent recovery tower T-102, tower top separates and obtains product propylene (logistics 4), tower reactor reclaims and is extracted agent (logistics 5), T102 tower theoretical cam curve 30, operation Stress control is at 180kPa, it is cooled to 40 DEG C through subcooler after extractant (logistics 5) and extraction distillation column charging (logistics 1) heat exchange, coolant is divided into two parts, a part (logistics 6) mixes with extractive distillation column overhead phase separator oil reservoir as backflow, and a part (logistics 7) enters water scrubber;The weight ratio of logistics 6 and logistics 7 is 420:1.
The water layer (logistics 9) of phase separator is from the charging of water scrubber top, the extractant (logistics 7) reclaimed is from bottom charging, the expoxy propane in aqueous phase and extractant are reclaimed in liquid-liquid extraction, water scrubber tower top oil reservoir (logistics 11) mainly contains expoxy propane and extractant, it is recycled into extraction distillation column phase separator D-101, water scrubber tower reactor water layer (logistics 10) mainly contains water, acetaldehyde, methanol, methyl formate, forms as shown in table 6 as wastewater treatment, logistics 9 and logistics 10.
Table 6
As can be seen from Table 6, after liquid-liquid extraction, waste water oxypropylene content reduces by 86.5%, and extractant content reduces by 93.75%.
Solvent recovery column overhead obtains the purity polymer grade product propylene (logistics 4) more than 99.99wt%, and as shown in table 7, the expoxy propane response rate is 99.75% to product propylene composition.
Table 7
| Composition | Content, wt |
| Expoxy propane | > 0.9999 |
| Water | 2 ppm |
| Aldehyde (in propionic aldehyde) | 2 ppm |
| Methanol | 2 ppm |
| Methyl formate | 3 ppm |
[embodiment 2]
Crude propene oxide solution (logistics 1) enters extraction distillation column T-101 with solvent recovery tower reactor liquid (logistics 3) heat exchange to 70 DEG C, extraction distillation column adopts normal heptane as extractant, extraction distillation column solvent ratio (extractant stream 6 and crude propene oxide solution feed 1 flow ratio) is 5:1, top gaseous phase sprays into middle pressure steam (logistics 12), in tower top phase separator D-101, oil-water separation operation is carried out after condensation, multilayer insulating panel is had in phase separator, the oil reservoir (logistics 8) separated is mixed the backflow (logistics 13) as extraction distillation column with the extractant (logistics 6) reclaimed, the water layer (logistics 9) separated enters water scrubber T-103, T101 tower theoretical cam curve 75, operation Stress control is at 200kPa, bottom temperature 95 DEG C, the composition of crude propene oxide solution is as shown in table 8.
Table 8
| Composition | Content, wt |
| Water | 0.008 |
| Acetaldehyde | 0.001 |
| Methanol | 0.001 |
| Methyl formate | 0.001 |
| Expoxy propane | 0.989 |
Extractive distillation tower reactor liquid (logistics 3) mainly contains expoxy propane and extractant, enter solvent recovery tower T-102, tower top separates and obtains product propylene (logistics 4), tower reactor reclaims and is extracted agent (logistics 5), T102 tower theoretical cam curve 30, operation Stress control is at 180kPa, it is cooled to 40 DEG C through subcooler after extractant (logistics 5) and extraction distillation column charging (logistics 1) heat exchange, coolant is divided into two parts, a part (logistics 6) mixes with extractive distillation column overhead phase separator oil reservoir as backflow, and a part (logistics 7) enters water scrubber; The weight ratio of logistics 6 and logistics 7 is 495:1.
The water layer (logistics 9) of phase separator is from the charging of water scrubber top, the extractant (logistics 7) reclaimed is from bottom charging, the expoxy propane in aqueous phase and extractant are reclaimed in liquid-liquid extraction, water scrubber tower top oil reservoir (logistics 11) mainly contains expoxy propane and extractant, it is recycled into extraction distillation column phase separator D-101, water scrubber tower reactor water layer (logistics 10) mainly contains water, acetaldehyde, methanol, methyl formate, forms as shown in table 9 as wastewater treatment, logistics 9 and logistics 10.
Table 9
As can be seen from Table 9, after liquid-liquid extraction, waste water oxypropylene content reduces by 93.2%, and extractant content reduces by 96.6%.
Solvent recovery column overhead obtains the purity polymer grade product propylene (logistics 4) more than 99.99wt%, and as shown in table 10, the expoxy propane response rate is 99.70% to product propylene composition.
Table 10
| Composition | Content, wt |
| Expoxy propane | > 0.9999 |
| Water | 1 ppm |
| Aldehyde (in propionic aldehyde) | 1 ppm |
| Methanol | 1 ppm |
| Methyl formate | 2 ppm |
From the above it can be seen that the enforcement present invention can separate with economic and convenient method and obtain polymer grade expoxy propane qualified products.
Claims (6)
1. an oxide purification process, comprises the steps of
A) the crude propene oxide solution 1 containing water, acetaldehyde, methanol and methyl formate impurity enters extraction distillation column, and after extractive distillation, tower top obtains logistics 2, obtains logistics 3 at the bottom of tower;
B) logistics 3 enters solvent recovery tower, and after separation, tower top obtains product propylene 4, is extracted agent logistics 5 at the bottom of tower; Logistics 5 is divided into logistics 6 and logistics 7 two strands;
C) enter phase separator after logistics 2 condensation, after oil-water separation, obtain oil reservoir 8 and water layer 9;
D) oil reservoir 8 and logistics 6 are back to extractive distillation column overhead;
E) logistics 7 enters water scrubber bottom, and water layer 9 enters water scrubber top, after separation, obtains the waste water streams 10 of moisture, acetaldehyde, methanol and methyl formate at the bottom of tower, and tower top obtains logistics 11; Logistics 11 enters phase separator;
The theoretical cam curve of described water scrubber is 20��40 pieces, and operation pressure is 160��220kPa, and solvent ratio is 3��6;
Described extractant at least one in normal octane or normal heptane.
2. oxide purification process according to claim 1, it is characterised in that in described crude propene oxide solution, the concentration expressed in percentage by weight of expoxy propane is 97.0��99.9%.
3. oxide purification process according to claim 1, it is characterised in that the theoretical cam curve of described extraction distillation column is 55��80 pieces, and operation pressure is 160��250kPa, and bottom temperature is less than 130 DEG C, and solvent ratio is 3��7.
4. oxide purification process according to claim 1, it is characterised in that described phase separator has multilayer insulating panel structure.
5. oxide purification process according to claim 1, it is characterised in that the weight ratio of logistics 6 and logistics 7 is (400��500): 1.
6. oxide purification process according to claim 1, it is characterised in that logistics 2 first contacts with deionized water or water vapor stream 12 before condensing, and the weight ratio of logistics 2 and logistics 12 is (40��60): 1.
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| CN105524027A (en) * | 2014-10-27 | 2016-04-27 | 中国石油化工股份有限公司 | Epoxypropane composition |
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| CN105669599A (en) * | 2016-03-04 | 2016-06-15 | 无锡智归科技有限公司 | Epoxypropane refinement system and method |
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| CN109851577B (en) * | 2017-11-30 | 2021-05-28 | 中国石油化工股份有限公司 | Method for purifying butylene oxide |
| PT3719008T (en) | 2017-11-30 | 2023-03-23 | China Petroleum & Chem Corp | Alkylene oxide production method and production system |
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| CN109851581B (en) * | 2017-11-30 | 2021-06-18 | 中国石油化工股份有限公司 | Method for purifying butylene oxide |
| CN109851586B (en) * | 2017-11-30 | 2021-05-28 | 中国石油化工股份有限公司 | Process for purifying propylene oxide |
| CN109851589B (en) * | 2017-11-30 | 2021-05-28 | 中国石油化工股份有限公司 | Propylene oxide purification method and purification apparatus |
| CN109020926B (en) * | 2017-12-19 | 2021-09-28 | 华东理工大学 | Method for separating and purifying propylene oxide from propylene gas-phase epoxidation product |
| HUE062399T2 (en) * | 2018-10-11 | 2023-10-28 | Sumitomo Chemical Co | Propylene oxide purification system and method for producing propylene oxide |
| CN112851601B (en) * | 2019-11-27 | 2022-11-22 | 北京诺维新材科技有限公司 | Method for purifying alkylene oxide |
| CN113801076A (en) * | 2020-06-16 | 2021-12-17 | 江苏怡达化学股份有限公司 | Propylene oxide rectification process |
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