CN106496163B - A kind of process for separation and purification of propylene oxide - Google Patents
A kind of process for separation and purification of propylene oxide Download PDFInfo
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- CN106496163B CN106496163B CN201610919722.6A CN201610919722A CN106496163B CN 106496163 B CN106496163 B CN 106496163B CN 201610919722 A CN201610919722 A CN 201610919722A CN 106496163 B CN106496163 B CN 106496163B
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- rectifying column
- propylene oxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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Abstract
The present invention provides a kind of process for separation and purification of propylene oxide, include the following steps: Step 1: by acid solution and unsubstituted NH2The mixture of based compound composition reacts in pipeline or reactor with crude propene oxide；Step 2: by aqueous slkali and unsubstituted NH2Material mixing after reacting in the mixture and step 1 of based compound composition, pH are controlled between 10~15, are reacted in pipeline or reactor；Step 3: the crude propene oxide after reacting in step 2 is introduced rectifying column, and extractant is introduced in the top of crude propene oxide；Step 4: will include acid solution and unsubstituted NH2Rectifying column is added above the extractant feed points or its in the mixture of based compound；Step 5: producing the propylene oxide of purifying from rectifying column.The present invention can effectively remove the low boiling impurity of propylene oxide carrying, effectively improve the purity of product propylene.
Description
Technical field
The invention belongs to the technical field of purification of propylene oxide, more particularly, to a kind of separating-purifying side of propylene oxide
Method.
Background technique
Propylene oxide is important Organic Chemicals, is that the third-largest propylene at present in addition to polypropylene and acrylonitrile spreads out
Biology.Its maximum purposes is synthesizing polyether glycol, and then manufactures polyurethane, in the distribution of the purposes in the U.S. and West Europe, this side
The purposes in face accounts for 60% and 70% or more respectively.Propylene oxide can also be used to manufacture nonionic surfactant and propenyl, third
Glycol, alcohol ether, propene carbonate, poly- Propanolamine, propionic aldehyde, synthetic glycerine, organic acid, synthetic resin, foamed plastics, plasticizer,
Emulsifier, wetting agent, detergent, fungicide, fumigant etc..Fine chemicals derived from propylene oxide is almost applied to all works
In industry department and daily life.
The production technology of propylene oxide mainly has chlorohydrination, conjugated oxidation (PO/SM method, PO/TAB method), cumene oxidation
Method (CHP method) and direct oxidation method.Wherein the major defect of chlorohydrination is that have corrosion to equipment, generates in production process and largely contains
There are waste water, the waste residue of organic chloride, environmental protection pressure is very big.Conjugated oxidation compares chlorohydrination, reduces environmental protection pressure, but its
Long flow path, investment is high, joint product yield is high, and economic benefit is restricted clearly by joint product.Direct oxidation method is special
Under the catalytic action of molecular sieve catalyst, propylene and hydrogen peroxide single step reaction are obtained into the process of propylene oxide.This technique is anti-
Mild condition is answered, product yield is high, and without other joint product, the three wastes are few, and it is substantially pollution-free, belong to environmental-friendly clean manufacturing
Technique, which represent the developing direction of Synthesis of Propylene Oxide.
In the production technology of hydrogen peroxide Direct Epoxidation propylene, due to the presence of impurity in raw material and depositing for circulation solvent
, in reaction product can containing impurity such as a small amount of but miscellaneous aldehyde, ether, alcohol, ketone, in these impurity especially methyl formate,
Formaldehyde, acetaldehyde, acetone, propionic aldehyde etc., boiling point and propylene oxide are not much different, and are difficult to be separated using common separate mode.
However the presence of these impurity is very big to downstream polyethers Influence of production, therefore the separating-purifying process for refining of propylene oxide is direct
Oxidizing process technique success, if the key with the market competitiveness.
In the prior art for that can not be carried out for several impurity contained effective in the method for the purification of crude propene oxide
Removal, or removal need for quite a long time.
Summary of the invention
In view of this, the present invention is directed to propose a kind of process for separation and purification of propylene oxide, by the first in crude propene oxide
The relative volatilities such as alcohol, formaldehyde, methyl formate and propylene oxide very close to impurity effectively remove, obtain the epoxy third of high-purity
Alkane product, while process is simple.
In order to achieve the above objectives, the technical scheme of the present invention is realized as follows:
A kind of process for separation and purification of propylene oxide, includes the following steps:
Step 1: acid solution and unsubstituted NH2The mixture of based compound composition in pipeline or is reacted with crude propene oxide
1~60min, preferably 1~10min are reacted in device, reaction temperature is 20~60 DEG C, preferably 35~45 DEG C；
Step 2: by aqueous slkali and unsubstituted NH2Substance after being reacted in the mixture and step 1 of based compound composition
Mixing, the control of mixed pH value of solution is between 10~15, preferably between 11~14, react 1 in pipeline or reactor~
60min, preferably 2~15min, reaction temperature are 20~60 DEG C, preferably 35~45 DEG C；
Step 3: by the crude propene oxide after being reacted in step 2 rectifying column from top downwards total number of theoretical plate 1/2~
Rectifying column, and drawing at the 1/5~1/2 of the downward total number of theoretical plate in top in the top of crude propene oxide are introduced at 4/5
Enter extractant；
Step 4: will include acid solution and unsubstituted NH2The mixture of based compound, in the extractant feed points or
Rectifying column is added in its top；
Step 5: producing the propylene oxide of purifying from rectifying column, extraction position is on mixture feed points in step 4
Side, tower top or the lateral extraction position for meeting extraction condition；
The step 4 can be omitted；
The unsubstituted NH2The methyl formate that contains in the total additional amount and crude propene oxide of based compound and aldehydes rub
You are the unsubstituted NH than being 0.5~5, preferably 0.8~2, in the step 22In the total amount and crude propene oxide of based compound
The molar ratio of the ester impurities contained is 0.8~2；
The acid solution is 0.01%~2%, preferably 0.05%~1% in the mass fraction being added in mixture.
A kind of process for separation and purification of propylene oxide, includes the following steps:
Step 1: by aqueous slkali and unsubstituted NH2The mixture of based compound composition is mixed with crude propene oxide, is mixed
PH value of solution after conjunction controls between 10~15, and preferably between 11~14,1~60min is reacted in pipeline or reactor, excellent
It is selected as 2~15min, reaction temperature is 20~60 DEG C, preferably 35~45 DEG C；
Step 2: by the crude propene oxide after being reacted in above-mentioned steps one rectifying column from top downwards total number of theoretical plate 1/
Rectifying column is introduced at 2~4/5, and in the top of crude propene oxide at the 1/5~1/2 of the downward total number of theoretical plate in top
Introduce extractant；
Step 3: will include acid solution and unsubstituted NH2After the mixture of based compound, in the extractant feed points
Or rectifying column is added in its top；
Step 4: producing the propylene oxide of purifying from rectifying column, extraction position is on mixture feed points in step 4
Side, tower top or the lateral extraction position for meeting extraction condition；
The unsubstituted NH2Mole of the methyl formate and aldehyde that contain in the total additional amount and crude propene oxide of based compound
Than being 0.5~5, preferably 0.8~2；Unsubstituted NH in the step 12Contain in the total amount and crude propene oxide of based compound
The molar ratio of some ester impurities is 0.8~2；
The acid solution is 0.01%~2%, preferably 0.05%~1% in the mass fraction being added in mixture.
Further, the unsubstituted NH2Based compound includes one of hydrazine, hydrazine hydrate, methyl hydrazine, hydrazonium salt or ethyl hydrazine
Or it is a variety of.
Further, the aqueous slkali includes sodium hydroxide solution, potassium hydroxide solution, carbon acid solution sodium solution, carbonic acid
One of hydrogen sodium solution or calcium hydroxide emulsion are a variety of.
Further, the acid solution includes one of organic acid or inorganic acid or a variety of, and the organic acid includes first
Acid, acetic acid or propionic acid, the inorganic acid include hydrochloric acid, sulfuric acid or phosphoric acid.
Further, the extractant includes any one in water, propylene glycol, ethylene glycol or propylene glycol monomethyl ether.
Further, the rectifying column be plate distillation column or packed tower, the 0.1~3barG of tower top pressure, preferably
0.15~1barG；Total number of theoretical plate of the rectifying column is 30~90 pieces, and reflux ratio is 0.5~3, preferably 1~2.1.
Further, the crude propene oxide is rectifying column from the 2/3~5/7 of the downward total number of theoretical plate in top,
The extractant feed points are from the 1/4~4/9 of the downward total number of theoretical plate in top.
Compared with the existing technology, the process for separation and purification of propylene oxide of the present invention has the advantage that
The process for separation and purification of propylene oxide of the present invention, the low boiling point that can effectively remove propylene oxide carrying are miscellaneous
Matter effectively improves the purity of product propylene, while this method has mild condition, and the reaction time is short, propylene oxide yield
Height, the advantages such as operating cost is low.
Specific embodiment
Unless otherwise stated, term used herein all has the meaning that those skilled in the art routinely understand, in order to
It is easy to understand the present invention, some terms used herein have been subjected to following definitions.
All number marks, such as pH, temperature, time, concentration, including range, are all approximations.It is to be understood that although
Term " about " is all added before always not describing all number marks explicitly.While it will also be understood that, although always not clear
Narration, reagent described herein is only example, and equivalent is known in the art.
Below with reference to embodiment, the present invention will be described in detail.
It is to containing propylene oxide 90%, methanol 9%, acetaldehyde 300ppm, methyl formate in comparative example and embodiment
300ppm, propionic aldehyde 100ppm, remaining lock out operation carried out for the crude propene oxide of water.
Total number of theoretical plate of rectifying column is 65 pieces.
X% in comparative example 1~2 and Examples 1 to 5, is mass fraction.
Comparative example 1
Be 1000kg/h crude propene oxide by flow with flow it is that the solution that 5kg/h contains 20% hydrazine hydrate mixes, uses
After pH is adjusted to 13 by sodium hydroxide solution, by pipe reaction 5min, rectifying column then is added at the 42nd piece of theoretical plate
In.The aqueous solution containing 1% hydrazine hydrate that flow is 120kg/h is added at the 22nd piece of theoretical plate of rectifying column to be extracted,
Rectifying column operating pressure is 0.1barG, reflux ratio 2.
It is 898.2kg/h propylene oxide 99.92%, acetaldehyde 63ppm, propionic aldehyde 10ppm, formic acid in overhead extraction flow
Methyl esters is 36ppm, and methanol is the product propylene of 14ppm.
Comparative example 2
By flow be 1000kg/h crude propene oxide and flow is that 5kg/h contains 20% hydrazine hydrate, the solution of 0.5% acetic acid
Mixing, is added in rectifying column from the 42nd piece of theoretical plate after pipe reaction 8min, adds at the 22nd piece of theoretical plate of rectifying column
Inbound traffics be 120kg/h containing 1% hydrazine hydrate, the aqueous solution of 0.1% acetic acid extracted, rectifying column operating pressure
0.1barG, reflux ratio 2.
In overhead extraction 897.8kg/h propylene oxide 99.93%, acetaldehyde 23ppm, propionic aldehyde 5ppm, methyl formate 116ppm,
The product propylene of methanol 17ppm.
Embodiment 1
By flow be 1000kg/h crude propene oxide and flow is that 5kg/h contains 20% hydrazine hydrate and 0.5% acetic acid
The solution of solution mixes, by pipe reaction 2min, 35 DEG C of reaction temperature.Then pH is adjusted to 13 using sodium hydroxide solution
Afterwards, 5min is reacted in the duct, 35 DEG C of reaction temperature.It is added in rectifying column from the 42nd piece of theoretical plate, rectifying column operation pressure
Power 0.1barG, reflux ratio 2 are added flow at the 22nd piece of theoretical plate of rectifying column as 120kg/h and contain 1% hydrazine hydrate,
0.1% acetic acid, remaining carries out extracting rectifying for the mixture of water.
In overhead extraction 898.6kg/h propylene oxide 99.95%, acetaldehyde 21ppm, propionic aldehyde 5ppm, formic acid solution methyl esters
36ppm, the product propylene of methanol 15ppm.
Embodiment 2
By flow be 1000kg/h crude propene oxide and flow is that 5kg/h contains 20% hydrazine hydrate and the mixture of hydrazine,
And 0.5% sulfuric acid solution mixing, by pipe reaction 2min, 40 DEG C of reaction temperature.Then use sodium carbonate liquor will
After pH is adjusted to 13.5,5min is reacted in the duct, 40 DEG C of reaction temperature.It is added in rectifying column from the 42nd piece of theoretical plate,
Rectifying column operating pressure 0.1barG, reflux ratio 2, it is containing for 120kg/h that flow is added at the 22nd piece of theoretical plate of rectifying column
The mixed liquor of the mixture and 0.1% sulfuric acid and acetic acid of 1% hydrazine hydrate and hydrazine, remaining carries out extraction essence for the mixture of water
It evaporates.
In overhead extraction 898.6kg/h propylene oxide 99.96%, acetaldehyde 20ppm, propionic aldehyde 4ppm, methyl formate 33ppm,
The product propylene of methanol 14ppm.
Embodiment 3
By flow be 1000kg/h crude propene oxide and flow is the methyl hydrazine that 5kg/h contains 20%, uses potassium hydroxide
After pH is adjusted to 13 by solution, 5min is reacted in the duct, 35 DEG C of reaction temperature.Rectifying column is added to from the 42nd piece of theoretical plate
In, rectifying column operating pressure 0.1barG, reflux ratio 2, it is containing for 120kg/h that flow is added at the 22nd piece of theoretical plate of rectifying column
There is 1% methyl hydrazine, 0.1% formic acid, remaining carries out extracting rectifying for the mixture of water.
In overhead extraction 898.6kg/h propylene oxide 99.94%, acetaldehyde 22ppm, propionic aldehyde 5ppm, methyl formate 39ppm,
The product propylene of methanol 16ppm.
Embodiment 4
By flow be 1000kg/h crude propene oxide and flow is the methyl hydrazine that 5kg/h contains 20%, contains 0.5% first
The solution mixing of acid, by pipe reaction 4min, 35 DEG C of reaction temperature.Then using potassium hydroxide solution and 20% water beetle
Base hydrazine is mixed, and after pH is adjusted to 13, reacts 5min in the duct, and 35 DEG C of reaction temperature.By the substance after reaction from
It is added in rectifying column at 42 pieces of theoretical plates, rectifying column operating pressure 0.1barG, reflux ratio 2, in the 22nd piece of theoretical plate of rectifying column
1% methyl hydrazine that contains that flow is 180kg/h is added in place, and 0.1% phosphoric acid, remaining carries out extraction essence for the mixture of ethylene glycol
It evaporates.
In overhead extraction 898.6kg/h propylene oxide 99.96%, acetaldehyde 25ppm, propionic aldehyde 6ppm, methyl formate 33ppm,
The product propylene of methanol 13ppm.
Embodiment 5
By flow be 1000kg/h crude propene oxide and flow is that 5kg/h contains 20% hydrazine and the mixture of hydrazine hydrate,
The solution of 0.5% acetic acid mixes, by pipe reaction 2min, 35 DEG C of reaction temperature.Then potassium hydroxide and bicarbonate are used
After pH is adjusted to 13 by the mixed solution of sodium, 5min is reacted in the duct, 35 DEG C of reaction temperature.By the substance after reaction from the 42nd
It is added in rectifying column at block theoretical plate, rectifying column operating pressure 0.1barG, reflux ratio 2, at the 22nd piece of theoretical plate of rectifying column
The water that flow is 120kg/h is added and carries out extracting rectifying.
In overhead extraction 898.6kg/h propylene oxide 99.93%, acetaldehyde 27ppm, propionic aldehyde 5ppm, methyl formate 37ppm,
The product propylene of methanol 12ppm.
Examples 1 to 5 by being added suitable acid solution in the reaction, and with unsubstituted NH2Based compound, aqueous slkali
The cooperation of equal substances, so that the content of the impurity such as acetaldehyde, propionic aldehyde and methyl formate has obtained further removal, propylene oxide is received
Rate is higher, while process is simpler, and the reaction time is short.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of process for separation and purification of propylene oxide, characterized by the following steps:
Step 1: acid solution and unsubstituted NH2The mixture and crude propene oxide of based compound composition are anti-in pipeline or reactor
1~60min is answered, reaction temperature is 20~60 DEG C；
Step 2: by aqueous slkali and unsubstituted NH2Material mixing after being reacted in the mixture and step 1 of based compound composition,
Mixed pH value of solution control reacts 1~60min between 10~15 in pipeline or reactor, and reaction temperature is 20~60
℃；
Step 3: by the crude propene oxide after being reacted in step 2 in rectifying column at the 1/2~4/5 of the downward total number of theoretical plate in top
Rectifying column is introduced, and introduces extraction at the 1/5~1/2 of the downward total number of theoretical plate in top in the top of crude propene oxide
Solvent；
Step 4: will include acid solution and unsubstituted NH2The mixture of based compound, in the extractant feed points or thereon
Rectifying column is added in side；
Step 5: producing the propylene oxide of purifying from rectifying column, tower top is in extraction position or meets laterally adopting for extraction condition
Out position；
The step 4 can be omitted；
The unsubstituted NH2The molar ratio of the methyl formate and aldehydes that contain in the total additional amount and crude propene oxide of based compound
It is 0.5~5, the unsubstituted NH in the step 22The ester impurities contained in the total amount and crude propene oxide of based compound
Molar ratio is 0.8~2；
The acid solution is 0.01%~2% in the mass fraction being added in mixture.
2. a kind of process for separation and purification of propylene oxide, characterized by the following steps:
Step 1: by aqueous slkali and unsubstituted NH2The mixture of based compound composition is mixed with crude propene oxide, after mixing
PH value of solution control between 10~15, in pipeline or reactor react 1~60min, reaction temperature be 20~60 DEG C；
Step 2: by the crude propene oxide after being reacted in above-mentioned steps one rectifying column from top downwards total number of theoretical plate 1/2~
Rectifying column, and drawing at the 1/5~1/2 of the downward total number of theoretical plate in top in the top of crude propene oxide are introduced at 4/5
Enter extractant；
Step 3: will include acid solution and unsubstituted NH2The mixture of based compound, in the extractant feed points or thereon
Rectifying column is added in side；
Step 4: producing the propylene oxide of purifying from rectifying column, tower top is in extraction position or meets laterally adopting for extraction condition
Out position；
The unsubstituted NH2The molar ratio of the methyl formate and aldehyde that contain in the total additional amount and crude propene oxide of based compound is
0.5~5；Unsubstituted NH in the step 12The ester impurities contained in the total amount and crude propene oxide of based compound rub
You are than being 0.8~2；
The acid solution is 0.01%~2% in the mass fraction being added in mixture.
3. the process for separation and purification of propylene oxide according to claim 1, it is characterised in that: in pipeline in the step 1
Or in reactor the reaction time be 1~10min, the reaction time is 2~15min in pipeline or reactor in the step 2,
Reaction temperature in the pipeline or reactor is 35~45 DEG C.
4. the process for separation and purification of propylene oxide according to claim 2, it is characterised in that: in pipeline in the step 1
Or in reactor the reaction time be 2~15min, the reaction temperature in the pipeline or reactor is 35~45 DEG C.
5. the process for separation and purification of propylene oxide according to claim 1 or 2, it is characterised in that: the unsubstituted NH2Base
Compound includes one of hydrazine, hydrazine hydrate, methyl hydrazine, hydrazonium salt or ethyl hydrazine or a variety of.
6. the process for separation and purification of propylene oxide according to claim 1 or 2, it is characterised in that: the aqueous slkali includes
One of sodium hydroxide solution, potassium hydroxide solution, sodium carbonate liquor, sodium bicarbonate solution or calcium hydroxide emulsion are more
Kind.
7. the process for separation and purification of propylene oxide according to claim 1 or 2, it is characterised in that: the acid solution includes
One of organic acid or inorganic acid are a variety of, and the organic acid includes formic acid, acetic acid or propionic acid, and the inorganic acid includes salt
Acid, sulfuric acid or phosphoric acid.
8. the process for separation and purification of propylene oxide according to claim 1 or 2, it is characterised in that: the extractant packet
Include any one in water, propylene glycol, ethylene glycol or propylene glycol monomethyl ether.
9. the process for separation and purification of propylene oxide according to claim 1 or 2, it is characterised in that: the rectifying column is plate
Formula rectifying column or packed tower, the 0.1~3barG of tower top pressure；Total number of theoretical plate of the rectifying column is 30~90 pieces, reflux
Than being 0.5~3.
10. the process for separation and purification of propylene oxide according to claim 1 or 2, it is characterised in that: the crude propene oxide
Feeding point is rectifying column from the 2/3~5/7 of the downward total number of theoretical plate in top, and the extractant feed points are from the downward premier in top
At the 1/4~4/9 of plate number.
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| CN1714087A (en) * | 2002-11-26 | 2005-12-28 | 德古萨股份公司 | Process for the purification of crude propene oxide |
| CN103864723A (en) * | 2014-03-18 | 2014-06-18 | 中国石油集团东北炼化工程有限公司吉林设计院 | Technology for purifying epoxypropane |
| CN105906584A (en) * | 2016-03-01 | 2016-08-31 | 江苏怡达化学股份有限公司 | Method for removing aldehydes in epoxypropane reaction mixture |
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2016
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4369096A (en) * | 1978-03-11 | 1983-01-18 | Bayer Aktiengesellschaft | Process for the purification of epoxides |
| CN1714087A (en) * | 2002-11-26 | 2005-12-28 | 德古萨股份公司 | Process for the purification of crude propene oxide |
| CN103864723A (en) * | 2014-03-18 | 2014-06-18 | 中国石油集团东北炼化工程有限公司吉林设计院 | Technology for purifying epoxypropane |
| CN105906584A (en) * | 2016-03-01 | 2016-08-31 | 江苏怡达化学股份有限公司 | Method for removing aldehydes in epoxypropane reaction mixture |
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