CN106957283A - A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide - Google Patents
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide Download PDFInfo
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- CN106957283A CN106957283A CN201710131614.7A CN201710131614A CN106957283A CN 106957283 A CN106957283 A CN 106957283A CN 201710131614 A CN201710131614 A CN 201710131614A CN 106957283 A CN106957283 A CN 106957283A
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- chloride
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- propylene
- saponification
- calcium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
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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
Abstract
The present invention gives a kind of new alcoholizing propenyl chloride Synthesis of Propylene Oxide.The present invention first makes chlorine and water react generation hypochlorous acid and hydrogen chloride, and first remove hydrogen chloride with calcium carbonate before propylene chlorohydrin action process, it is to avoid chlorine and propylene gas are in contact generation dichloropropane and chloropropyl alcohol contacts with hydrogen chloride and generates dichloropropane；Same propylene and chlorine inventory, the present invention are remarkably improved the yield of expoxy propane.Saponification distillation process of the present invention only steams expoxy propane, and no stripping dichloropropane operation can significantly reduce energy ezpenditure；Calcium chloride sodium carbonate conversion in neutralized ratio turns to sodium chloride and calcium carbonate, Calcium Carbonate Cyclic is used to remove the hydrogen chloride of hypochlorous acid reaction generation or commodity calcium carbonate is made, and the neutralized ratio of sodium chloride-containing is used for Electrolytic Alkali or evaporation and concentration, membrane separation concentration obtain industrial sodium chloride.
Description
Technical field：
The present invention relates to a kind of chemical products production technology, more particularly to a kind of production work of Organic chemical products expoxy propane
Skill.
Background technology：
Expoxy propane is a kind of important Organic chemical products, be only second in Propylene Series product polypropylene and propylene it is fine
Three big derivatives, are also a kind of product that chlor-alkali industry balances chlorine.
Industrialized Synthesis of Propylene Oxide mainly has chlorohydrination, conjugated oxidation and hydrogen peroxide straight both at home and abroad at present
Connect oxidizing process（HPPO）.Wherein hydrogen peroxide direct oxidation method cost of material is low, and expoxy propane and water are only generated in production process, does not have
There are other joint product, technological process is simple, and product yield is high, substantially pollution-free, is a kind of environment-friendly process for cleanly preparing.
But joint construction hydrogen peroxide plant is needed using the technique expoxy propane；Conjugated oxidation is also known as Halcon method, including iso-butane conjugated oxidation
With ethylbenzene conjugated oxidation, cooxidation reaction, the generation tert-butyl alcohol or styrene, coproduction are carried out with propylene by iso-butane or ethylbenzene respectively
Expoxy propane.Conjugated oxidation technological process is long, and raw material variety is more, requires high to purified propylene, technological operation is in higher pressure
Lower to carry out, high equipment cost, construction investment is big.Meanwhile, simply a yield is less in conjugated oxidation production for expoxy propane
Joint product, only expoxy propane can just show the advantage of the technique when being matched with the other joint product market demand, in addition oxygen altogether
The COD of sewage value that change method is produced is also higher, needs larger processing cost.
Propylene oxide by chlorohydrination production history is long, and its main processes is alcoholizing propenyl chloride, chloropropyl alcohol saponification and production
Product are refined.The characteristics of method is mature production technology, and construction investment is few, to the less demanding of raw material propylene, and product cost is relatively low,
With stronger market cost competitiveness.The shortcoming of chlorohydrination is that water resources consumption is big, produces a large amount of waste water and waste residue, often produces
1 ton of expoxy propane produces the saponification waste-water and more than 2 tons of waste residue of 40 ~ 50 tons of chlorides.Saponification waste-water temperature is high, pH value
High, chloride content is high, COD value is high and suspension content is high, it is difficult to handle；In addition, propylene oxide by chlorohydrination production process material
Serious to equipment corrosion, equipment material requires high；Another deficiency of propylene oxide by chlorohydrination is byproduct dichloropropane and dichloro
Diisopropyl ether price is low.
China's Synthesis of Propylene Oxide is still based on chlorohydrination.Although the method product cost is relatively low, its saponification waste-water
It is difficult to handle, it has also become restrict the bottleneck of method production.Current China production of propylene oxide is in dilemma, turns off environmental protection not
Qualified propylene oxide by chlorohydrination manufacturer, then can not ensure the chlorine balance of chlor-alkali industry in the short time；Ensure that saponification is given up
Water environmental protection processing is qualified, then mass customization is raised, and profit margin reduces, and Business survival is difficult.
To carrying out technological improvement upgrading by traditional propylene oxide by chlorohydrination production technology of raw material of chlorine and propylene, formed
A kind of novel technique of alcoholizing propenyl chloride expoxy propane, while the production of propylene oxide is met environmental requirement, has again
Good profit margin, is an urgent demand of current China's expoxy propane industry.
The content of the invention：
It is an object of the invention to provide a kind of new alcoholizing propenyl chloride Synthesis of Propylene Oxide, the technique is with same propylene
More market price high purpose product expoxy propane relatively can be produced by being consumed with chlorine, reduced or do not produced the market price
Relatively low accessory substance dichloropropane and dichlorodiisopropyl ether, the invention can also make neutralized ratio be easy to environmental protection treatment or recycling
Utilize.
The purpose of the present invention is achieved through the following technical solutions：
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, described production technology includes：
A. raw material chlorine and water enter hypochlorous acid reaction member（1）Interior reaction generation hypochlorous acid and hydrogen chloride；
B. hypochlorous acid reaction member is gone out（1）Hypochlorous acid and hydrochloride aqueous solution and calcium carbonate enter dehydrochlorination reaction unit
（2）, calcium carbonate generates calcium chloride and water and carbon dioxide with hcl reaction in the unit；By carbon dioxide and by calcium carbonate
The solid slag discharge system brought into；
C. dehydrochlorination reaction unit is gone out（2）Removing hydrogen chloride liquid phase material and propylene or propylene and inert gas enter
Propylene chlorohydrin action process unit（3）, in the unit inner propene and hypochlorous acid reaction generation chloropropyl alcohol；By unreacted propylene and lazy
Property gas discharge chlorohydrin action unit（3）；
D. propylene chlorohydrin action process unit is gone out（3）The liquid phase material containing chloropropyl alcohol and saponification agent NaOH or hydroxide
Calcium enters saponification rectification cell（4）, chloropropyl alcohol and NaOH or calcium hydroxide reaction generation epoxy third in the unit
Alkane, water and sodium chloride or calcium chloride, make the expoxy propane of generation flash, distill or saponification rectification cell are left in rectifying（4）；
Refine or be not refining to obtain product expoxy propane；
E. saponification rectification cell is gone out（4）Liquid phase material enter saponification liquor sedimentation separation unit（5）Carry out sedimentation separation,
Light phase is neutralized ratio, and heavy phase is the solid slag that dichloropropane, dichlorodiisopropyl ether and saponification agent are brought into；
F. saponification liquor sedimentation separation unit is gone out（5）Neutralized ratio transmitting system carry out environmental protection treatment.
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, hypochlorous acid reaction member（1）It is anti-with dehydrochlorination
Answer unit（2）Or union operation, chlorine gas and water, calcium carbonate enter hypochlorous acid reaction member together（1）.
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, or to going out saponification liquor sedimentation separation unit（5）'s
Sodium carbonate is added in neutralized ratio to be reacted with calcium chloride, the calcium chloride in neutralized ratio is switched to sodium chloride and is generated carbonic acid
Calcium；Neutralized ratio removing calcium chloride reacts generated Calcium Carbonate Cyclic and enters dehydrochlorination reaction unit（2）, or through further
Processing obtains commodity calcium carbonate.
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, goes out saponification liquor sedimentation separation unit（5）Saponification
Sodium chloride solution after raffinate removing calcium chloride is used for Electrolytic Alkali, or industrial chlorination is made in evaporation and concentration, membrane separation concentration
Sodium.
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, goes out propylene chlorohydrin action process unit（3）Contain
The liquid phase material of chloropropyl alcohol carries out the obtained ring of saponification by the method for saponification in existing propylene oxide by chlorohydrination technology
Ethylene Oxide.
Advantages of the present invention is with effect：
1. being provided with hypochlorous acid reaction member, chlorine can be fully converted into hypochlorous acid, in the propylene chlorohydrin action process subsequently carried out
During, no chlorine contacts with the direct gas phase of propylene and generates dichloropropane；
2. being provided with dehydrochlorination reaction unit, the hydrogen chloride generated with calcium carbonate with hypochlorination's process is reacted, rear
During the continuous propylene chlorohydrin action process carried out, no chloropropyl alcohol contacts with hydrogen chloride and generates dichloropropane；
3. due to avoiding generation accessory substance dichloropropane, in the case of chlorine and propylene inventory identical, chloropropyl alcohol concentration
Height, and then more purpose product expoxy propane can be obtained after saponification；
4. chloropropyl alcohol saponification rectification cell only steams expoxy propane, steam dichloropropane without stripping and dichloro two is different
Propyl ether, if having dichloropropane and dichlorodiisopropyl ether in neutralized ratio, is separated using the method for sedimentation, can substantially be dropped
The operation temperature of low saponification rectification cell, significantly reduces energy ezpenditure；
5. in and hydrogen chloride used by calcium carbonate generation calcium chloride, calcium chloride after saponification in raffinate reacts with sodium carbonate again gives birth to
Into sodium chloride and calcium carbonate, it is circularly used for removing hydrogen chloride after precipitation of calcium carbonate, or winnofil is made into commodity carbonic acid
Calcium；
6. the neutralized ratio for going out to remove calcium chloride reaction member is single sodium-chloride water solution, concentration can be evaporated and obtained
Industrial sodium chloride is used for fused salt electrolysis in chlor-alkali industry；Saponification waste-water is easily handled and resourcebility is utilized.
Brief description of the drawings：
Fig. 1 is first to remove hydrogen chloride, then carries out the alcoholizing propenyl chloride production of propylene oxide of alcoholizing propenyl chloride and chloropropyl alcohol saponification
Process flow diagram；
Fig. 2 is the alcoholizing propenyl chloride production of propylene oxide for adding sodium carbonate into neutralized ratio using NaOH as saponification agent
Process flow diagram.
Specific embodiment：
Embodiment 1
The mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide of embodiment 1 includes hypochlorous acid reaction member（1）, dehydrochlorination
Reaction member（2）, propylene chlorohydrin action process unit（3）, saponification rectification cell（4）With saponification liquor sedimentation separation unit（5）；
Saponification agent used is calcium hydroxide slurry, and operating process is：Raw material chlorine and water enter hypochlorous acid reaction member（1）Interior reaction
Generate hypochlorous acid and hydrogen chloride；Go out hypochlorous acid reaction member（1）Hypochlorous acid and hydrochloride aqueous solution and calcium carbonate enter dechlorination
Change hydrogen reaction member（2）, calcium carbonate generates calcium chloride and water and carbon dioxide with hcl reaction in the unit；By titanium dioxide
Carbon and the solid slag discharge system brought into by calcium carbonate；Go out dehydrochlorination reaction unit（2）Removing hydrogen chloride liquid phase material with
Propylene or propylene and inert gas enter propylene chlorohydrin action process unit（3）, react and generate in the unit inner propene and hypochlorous acid
Chloropropyl alcohol；By unreacted propylene and inert gas discharge chlorohydrin action unit（3）；Go out propylene chlorohydrin action process unit（3）
The liquid phase material containing chloropropyl alcohol and calcium hydroxide enter saponification rectification cell（4）, chloropropyl alcohol and soap in the unit
Agent calcium hydroxide reaction generation expoxy propane, water and calcium chloride, make the expoxy propane rectifying of generation leave saponification rectifying
Unit（4）；Re-refine to obtain product expoxy propane；Go out saponification rectification cell（4）Liquid phase material enter saponification liquor sedimentation point
From unit（5）Sedimentation separation is carried out, light phase is neutralized ratio, and heavy phase is brought into for dichloropropane, dichlorodiisopropyl ether and saponification agent
Solid slag；Go out saponification liquor sedimentation separation unit（5）Neutralized ratio transmitting system carry out environmental protection treatment.The technique stream of embodiment 1
Journey sketch is shown in Fig. 1.
Embodiment 2
Embodiment 2 is substantially the same manner as Example 1, and difference is that saponification agent used is sodium hydroxide solution.
Embodiment 3
Embodiment 3 is substantially the same manner as Example 1, and difference is in saponification liquor sedimentation separation unit（5）After to set up saponification residual
Liquid dechlorination calcium unit（6）, to neutralized ratio dechlorination calcium unit（6）Interior addition sodium carbonate, goes out saponification liquor sedimentation separation unit
（5）Neutralized ratio and sodium carbonate in neutralized ratio dechlorination calcium unit（6）Interior reaction generation sodium chloride and precipitation of calcium carbonate, carbon
Sour calcium is recycled into dehydrochlorination reaction unit（2）；Go out neutralized ratio dechlorination calcium unit（6）Liquid phase be sodium chloride solution.
The process flow diagram of embodiment 3 is shown in Fig. 2.
Embodiment 4
Embodiment 4 is substantially the same manner as Example 1, and it is anti-that difference is that raw material chlorine adds hypochlorous acid together with water and calcium carbonate
Answer unit（1）.
Embodiment 5
Embodiment 5 is substantially the same manner as Example 1, and difference is propylene chlorohydrin action process unit（3）Contain chloropropyl alcohol
Liquid phase material carries out saponification using traditional saponification technology and expoxy propane is made.
Embodiment 6
Embodiment 6 is substantially the same manner as Example 3, and difference is further in neutralized ratio dechlorination calcium unit（6）After increase
If sodium chloride solution is concentrated by evaporation operation.
Embodiment 7
Embodiment 7 is substantially the same manner as Example 3, and difference is neutralized ratio dechlorination calcium unit（6）Sodium chloride it is molten
Liquid removes Electrolytic Alkali.
Claims (5)
1. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, it is characterised in that described production technology includes：
A. raw material chlorine and water enter hypochlorous acid reaction member（1）Interior reaction generation hypochlorous acid and hydrogen chloride；
B. hypochlorous acid reaction member is gone out（1）Hypochlorous acid and hydrochloride aqueous solution and calcium carbonate enter dehydrochlorination reaction unit
（2）, calcium carbonate generates calcium chloride and water and carbon dioxide with hcl reaction in the unit；By carbon dioxide and by calcium carbonate
The solid slag discharge system brought into；
C. dehydrochlorination reaction unit is gone out（2）Removing hydrogen chloride liquid phase material and propylene or propylene and inert gas enter
Propylene chlorohydrin action process unit（3）, in the unit inner propene and hypochlorous acid reaction generation chloropropyl alcohol；By unreacted propylene and lazy
Property gas discharge chlorohydrin action unit（3）；
D. propylene chlorohydrin action process unit is gone out（3）The liquid phase material containing chloropropyl alcohol and saponification agent NaOH or hydroxide
Calcium enters saponification rectification cell（4）, chloropropyl alcohol and NaOH or calcium hydroxide reaction generation epoxy third in the unit
Alkane, water and sodium chloride or calcium chloride, make the expoxy propane of generation flash, distill or saponification rectification cell are left in rectifying（4）；
Refine or be not refining to obtain product expoxy propane；
E. saponification rectification cell is gone out（4）Liquid phase material enter saponification liquor sedimentation separation unit（5）Carry out sedimentation separation,
Light phase is neutralized ratio, and heavy phase is the solid slag that dichloropropane, dichlorodiisopropyl ether and saponification agent are brought into；
F. saponification liquor sedimentation separation unit is gone out（5）Neutralized ratio transmitting system carry out environmental protection treatment.
2. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide according to claim 1, it is characterised in that secondary
Chloric acid reaction member（1）With dehydrochlorination reaction unit（2）Or union operation, it is anti-that chlorine gas and water, calcium carbonate enter hypochlorous acid together
Answer unit（1）.
3. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide according to claim 1, it is characterised in that to
Go out saponification liquor sedimentation separation unit（5）Neutralized ratio in add sodium carbonate reacted with calcium chloride, make in neutralized ratio
Calcium chloride switchs to sodium chloride and generates calcium carbonate；Neutralized ratio removing calcium chloride reacts generated Calcium Carbonate Cyclic and enters dechlorination
Change hydrogen reaction member（2）, or commodity calcium carbonate is obtained after further treatment.
4. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide according to claim 1 and claim 3, its
It is characterised by, goes out saponification liquor sedimentation separation unit（5）Neutralized ratio removing calcium chloride after sodium chloride solution be used for be electrolysed make
Industrial sodium chloride is made in alkali, or evaporation and concentration, membrane separation concentration.
5. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide according to claim 1, it is characterised in that go out
Propylene chlorohydrin action process unit（3）Containing chloropropyl alcohol liquid phase material or by the soap in existing propylene oxide by chlorohydrination technology
Change method carries out saponification and expoxy propane is made.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108341399A (en) * | 2018-04-09 | 2018-07-31 | 吴剑华 | A kind of production of chlorohydrination epoxides hypochlorous acid preparation facilities and its application method |
| CN108440453A (en) * | 2018-03-28 | 2018-08-24 | 吴剑华 | A kind of double alkali chlorohydrination epoxides production methods |
| CN108658898A (en) * | 2018-06-05 | 2018-10-16 | 吴剑华 | A kind of improved chlorohydrination epoxy chloropropane production method |
| CN108773834A (en) * | 2018-07-24 | 2018-11-09 | 航锦科技股份有限公司 | A kind of synthetic method of high concentration hypochlorous acid for propylene oxide |
| CN110734422A (en) * | 2019-10-30 | 2020-01-31 | 吴剑华 | Production method of propylene carbonate or ethylene carbonate |
| CN112250644A (en) * | 2020-10-14 | 2021-01-22 | 吴剑华 | Hypochlorous acid preparation device for preparing epoxide by using chlorohydrin method and using method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108440453A (en) * | 2018-03-28 | 2018-08-24 | 吴剑华 | A kind of double alkali chlorohydrination epoxides production methods |
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| WO2021083022A1 (en) * | 2019-10-30 | 2021-05-06 | 吴剑华 | Method for producing propylene carbonate or ethylene carbonate |
| CN112250644A (en) * | 2020-10-14 | 2021-01-22 | 吴剑华 | Hypochlorous acid preparation device for preparing epoxide by using chlorohydrin method and using method |
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