CN106957283B - 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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- CN106957283B CN106957283B CN201710131614.7A CN201710131614A CN106957283B CN 106957283 B CN106957283 B CN 106957283B CN 201710131614 A CN201710131614 A CN 201710131614A CN 106957283 B CN106957283 B CN 106957283B
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- chloride
- propylene oxide
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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 reacts chlorine with water to generate hypochlorous acid and hydrogen chloride, and first removes hydrogen chloride with calcium carbonate before propylene chlorohydrin action process, avoids chlorine and is in contact with propylene gas and generates dichloropropane and chloropropyl alcohol and contact generation dichloropropane with hydrogen chloride；Same propylene and chlorine inventory, the present invention are remarkably improved the yield of propylene oxide.Saponification distillation process of the present invention only steams propylene oxide, and no stripping dichloropropane operation can significantly reduce energy consumption；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 or commodity calcium carbonate is made that hypochlorous acid reaction generates, and the neutralized ratio of sodium chloride-containing obtains industrial sodium chloride for Electrolytic Alkali or evaporation and concentration, membrane separation concentration.
Description
Technical field:
The present invention relates to a kind of chemical products production technologies, more particularly to a kind of life of Organic chemical products propylene oxide
Production. art.
Background technique:
Propylene oxide is a kind of important Organic chemical products, is to be only second to polypropylene and acrylonitrile in Propylene Series product
The third-largest derivative and chlor-alkali industry balance chlorine a kind of product.
Industrialized Synthesis of Propylene Oxide mainly has chlorohydrination, conjugated oxidation and hydrogen peroxide straight both at home and abroad at present
Meet oxidizing process (HPPO).Wherein hydrogen peroxide direct oxidation method cost of material is low, and propylene oxide and water are only generated in production process, does not have
There are other joint product, process flow is simple, and product yield is high, and it is substantially pollution-free, it is a kind of environmental-friendly process for cleanly preparing.
But joint construction hydrogen peroxide plant is needed using the technique propylene oxide；Conjugated oxidation is also known as Halcon method, including iso-butane conjugated oxidation
With ethylbenzene conjugated oxidation, cooxidation is carried out with propylene by iso-butane or ethylbenzene respectively and is reacted, the tert-butyl alcohol or styrene, coproduction are generated
Propylene oxide.Conjugated oxidation process flow is long, and raw material variety is more, requires height to purified propylene, technological operation is in higher pressure
Lower progress, high equipment cost, construction investment are big.Meanwhile only a yield is less in conjugated oxidation production for propylene oxide
Joint product, only propylene oxide match the advantage that Shi Caineng shows the technique with the other joint product market demand, furthermore oxygen altogether
The COD of sewage value that change method generates is also higher, needs biggish processing cost.
Propylene oxide by chlorohydrination production history is long, and main processes are alcoholizing propenyl chloride, chloropropyl alcohol saponification and produce
Product purification.The characteristics of method is mature production technology, and construction investment is few, and to the of less demanding of raw material propylene, product cost is lower,
With stronger market cost competitiveness.The shortcomings that chlorohydrination is that water resources consumption is big, generates a large amount of waste water and waste residue, every production
1 ton of propylene oxide generates the saponification waste-water of 40 ~ 50 tons of chlorides and 2 tons or more of waste residue.Saponification waste-water temperature height, pH value
High, chloride content height, COD value are high and suspension content is high, it is difficult to handle；In addition, propylene oxide by chlorohydrination production process material
Severe corrosion to equipment, equipment material require 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 lower, its saponification waste-water
It is difficult to handle, it has also become restrict the bottleneck of method production.China's production of propylene oxide is in dilemma at present, turns off environmental protection not
Qualified propylene oxide by chlorohydrination manufacturer not can guarantee the chlorine balance of chlor-alkali industry then in the short time；Guarantee that saponification is useless
Water environmental protection processing is qualified, then mass customization increases, and profit margin reduces, and Business survival is difficult.
Technological improvement upgrading is carried out to using chlorine and propylene as traditional propylene oxide by chlorohydrination production technology of raw material, is formed
A kind of novel technique of alcoholizing propenyl chloride propylene oxide, while so that production of propylene oxide is met environmental requirement, and has
Good profit margin is an urgent demand of current China's propylene oxide industry.
Summary of the invention:
The purpose of the present invention is to provide a kind of new alcoholizing propenyl chloride Synthesis of Propylene Oxide, and the technique is with same
Propylene and chlorine consumption can produce the relatively high purpose product propylene oxide in more market price, reduce or do not generate market
Price relatively low by-product dichloropropane and dichlorodiisopropyl ether, the invention can also make neutralized ratio be easy to environmental protection treatment or money
Sourceization utilizes.
The purpose of the present invention is what is be achieved through the following technical solutions:
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, the production technology include:
A. raw material chlorine and water enter reaction generation hypochlorous acid and hydrogen chloride in hypochlorous acid reaction member (1)；Hypochlorous acid out
The hypochlorous acid and hydrochloride aqueous solution and calcium carbonate of reaction member (1) enter dehydrochlorination reaction unit (2), the carbon in the unit
Sour calcium and hcl reaction generate calcium chloride and water and carbon dioxide；By carbon dioxide and the solid slag discharge system brought by calcium carbonate
System；Hypochlorous acid reaction member (1) and dehydrochlorination reaction unit (2) or union operation, chlorine gas and water, calcium carbonate enter secondary together
Chloric acid reaction member (1)；
B. go out the liquid phase material and propylene or propylene and inert gas of the removing hydrogen chloride of dehydrochlorination reaction unit (2)
Into propylene chlorohydrin action process unit (3), is reacted in the unit inner propene with hypochlorous acid and generate chloropropyl alcohol；By unreacted propylene
And inert gas discharge chlorohydrin action unit (3)；
C. go out the liquid phase material containing chloropropyl alcohol and saponification agent sodium hydroxide or hydrogen of propylene chlorohydrin action process unit (3)
Calcium oxide enters saponification rectification cell (4), and chloropropyl alcohol and sodium hydroxide or calcium hydroxide reaction generate ring in the unit
Ethylene Oxide, water and sodium chloride or calcium chloride make the propylene oxide generated flash distillation, distillation or rectifying leave saponification rectification cell
(4)；Purification is not refining to obtain product propylene oxide；
D. the liquid phase material for going out saponification rectification cell (4) enters saponification liquor sedimentation separation unit (5) and carries out sedimentation point
From light phase is neutralized ratio, and heavy phase is the solid slag that dichloropropane, dichlorodiisopropyl ether and saponification agent are brought into；
E. the neutralized ratio transmitting system for going out saponification liquor sedimentation separation unit (5) carries out environmental protection treatment.
A kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, to the soap of saponification liquor sedimentation separation unit (5) out
Change addition sodium carbonate in raffinate to be reacted with calcium chloride, so that the calcium chloride in neutralized ratio is switched to sodium chloride and generate carbonic acid
Calcium；Neutralized ratio removing calcium chloride reacts Calcium Carbonate Cyclic generated 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, the out saponification of saponification liquor sedimentation separation unit (5)
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, propylene chlorohydrin action process unit (3) are contained out
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.
The advantages and effects of the present invention are:
1. being provided with hypochlorous acid reaction member, chlorine can be fully converted into hypochlorous acid, in the alcoholizing propenyl chloride of subsequent progress
In reaction process, no chlorine contacts with the direct gas phase of propylene and generates dichloropropane；
2. being provided with dehydrochlorination reaction unit, reacted with calcium carbonate with the hydrogen chloride that hypochlorination's process generates,
During the propylene chlorohydrin action process of subsequent progress, no chloropropyl alcohol contacts with hydrogen chloride and generates dichloropropane；
3. generating by-product dichloropropane, under chlorine and the identical situation of propylene inventory, chloropropyl alcohol due to avoiding
Concentration is high, and then can get more purpose product propylene oxide after saponification；
4. chloropropyl alcohol saponification rectification cell only steams propylene oxide, dichloropropane and dichloro are steamed without stripping
Diisopropyl ether is separated if having dichloropropane and dichlorodiisopropyl ether in neutralized ratio using the method for sedimentation, can be bright
The aobvious operation temperature for reducing saponification rectification cell, significantly reduces energy consumption；
5. in and calcium carbonate used in hydrogen chloride generates calcium chloride, and the calcium chloride after saponification in raffinate is anti-with sodium carbonate again
Sodium chloride and calcium carbonate should be generated, removing hydrogen chloride is circularly used for after precipitation of calcium carbonate, or commodity are made in winnofil
Calcium carbonate；
6. the neutralized ratio for going out removing calcium chloride reaction member is single sodium-chloride water solution, concentration can be evaporated
Obtain industrial sodium chloride or in chlor-alkali industry for fused salt electrolysis；Saponification waste-water is easily handled and resourcebility utilizes.
Detailed description of the invention:
Fig. 1 is the alcoholizing propenyl chloride propylene oxide for first removing hydrogen chloride, then carrying out alcoholizing propenyl chloride and chloropropyl alcohol saponification
Technological process of production schematic diagram；
Fig. 2 is that the alcoholizing propenyl chloride propylene oxide of sodium carbonate is added into neutralized ratio using sodium hydroxide as saponification agent
Technological process of production schematic 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), dechlorination
Change hydrogen reaction member (2), propylene chlorohydrin action process unit (3), saponification rectification cell (4) and saponification liquor sedimentation separation unit
(5)；Saponification agent used is calcium hydroxide slurry, operating process are as follows: raw material chlorine and water enter in hypochlorous acid reaction member (1)
Reaction generates hypochlorous acid and hydrogen chloride；The hypochlorous acid of hypochlorous acid reaction member (1) and hydrochloride aqueous solution and calcium carbonate enter out
Dehydrochlorination reaction unit (2), calcium carbonate and hcl reaction generate calcium chloride and water and carbon dioxide in the unit；By two
Carbonoxide and the solid slag discharge system brought by calcium carbonate；The liquid phase object of the removing hydrogen chloride of dehydrochlorination reaction unit (2) out
Material enters propylene chlorohydrin action process unit (3) with propylene or propylene and inert gas, reacts in the unit inner propene with hypochlorous acid
Generate chloropropyl alcohol；By unreacted propylene and inert gas discharge chlorohydrin action unit (3)；Propylene chlorohydrin action process unit out
(3) the liquid phase material containing chloropropyl alcohol and calcium hydroxide enter saponification rectification cell (4), in the unit chloropropyl alcohol with
Saponification agent calcium hydroxide reaction generates propylene oxide, water and calcium chloride, and the propylene oxide rectifying generated is made to leave saponification essence
Evaporate unit (4)；Re-refine to obtain product propylene oxide；The liquid phase material of saponification rectification cell (4) enters saponification liquor sedimentation out
Separative unit (5) carries out sedimentation separation, and light phase is neutralized ratio, and heavy phase is dichloropropane, dichlorodiisopropyl ether and saponification agent band
The solid slag entered；The neutralized ratio transmitting system of saponification liquor sedimentation separation unit (5) carries out environmental protection treatment out.The technique of embodiment 1
General flow chart is shown in Fig. 1.
Embodiment 2
Embodiment 2 is substantially the same manner as Example 1, the difference is that saponification agent used is sodium hydroxide solution.
Embodiment 3
Embodiment 3 is substantially the same manner as Example 1, the difference is that adding soap after saponification liquor sedimentation separation unit (5)
Change raffinate dechlorination calcium unit (6), sodium carbonate, out saponification liquor sedimentation separation are added into neutralized ratio dechlorination calcium unit (6)
Generation sodium chloride is reacted in neutralized ratio dechlorination calcium unit (6) with sodium carbonate for the neutralized ratio of unit (5) and calcium carbonate is heavy
It forms sediment, Calcium Carbonate Cyclic enters dehydrochlorination reaction unit (2)；The liquid phase of neutralized ratio dechlorination calcium unit (6) is sodium chloride out
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, the difference is that time chlorine is added in raw material chlorine together with water and calcium carbonate
Sour reaction member (1).
Embodiment 5
Embodiment 5 is substantially the same manner as Example 1, the difference is that propylene chlorohydrin action process unit (3) contains chlorine out
Propyl alcohol liquid phase material carries out saponification using traditional saponification technology and propylene oxide is made.
Embodiment 6
Embodiment 6 is substantially the same manner as Example 3, the difference is that further in neutralized ratio dechlorination calcium unit (6)
After add sodium chloride solution be concentrated by evaporation operation.
Embodiment 7
Embodiment 7 is substantially the same manner as Example 3, the difference is that the chlorination of neutralized ratio dechlorination calcium unit (6) out
Sodium solution removes Electrolytic Alkali.
Claims (4)
1. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide, which is characterized in that the production technology includes:
A. raw material chlorine and water enter reaction generation hypochlorous acid and hydrogen chloride in hypochlorous acid reaction member (1)；Hypochlorous acid reacts out
The hypochlorous acid and hydrochloride aqueous solution and calcium carbonate of unit (1) enter dehydrochlorination reaction unit (2), the calcium carbonate in the unit
Calcium chloride and water and carbon dioxide are generated with hcl reaction；By carbon dioxide and the solid slag discharge system brought by calcium carbonate；
Hypochlorous acid reaction member (1) and dehydrochlorination reaction unit (2) or union operation, chlorine gas and water, calcium carbonate enter hypochlorous acid together
Reaction member (1)；
B. the liquid phase material and propylene or propylene and inert gas for the removing hydrogen chloride for going out dehydrochlorination reaction unit (2) enter
Propylene chlorohydrin action process unit (3) reacts with hypochlorous acid in the unit inner propene and generates chloropropyl alcohol；By unreacted propylene and lazy
Property gas discharge chlorohydrin action unit (3)；
C. go out the liquid phase material containing chloropropyl alcohol and saponification agent sodium hydroxide or hydroxide of propylene chlorohydrin action process unit (3)
Calcium enters saponification rectification cell (4), and chloropropyl alcohol and sodium hydroxide or calcium hydroxide reaction generate epoxy third in the unit
Alkane, water and sodium chloride or calcium chloride make the propylene oxide generated flash distillation, distillation or rectifying leave saponification rectification cell (4)；
Purification is not refining to obtain product propylene oxide；
D. the liquid phase material for going out saponification rectification cell (4) enters saponification liquor sedimentation separation unit (5) and carries 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；
E. the neutralized ratio transmitting system for going out saponification liquor sedimentation separation unit (5) carries out environmental protection treatment.
2. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide according to claim 1, which is characterized in that
Sodium carbonate is added in the neutralized ratio of saponification liquor sedimentation separation unit (5) out to be reacted with calcium chloride, makes in neutralized ratio
Calcium chloride switchs to sodium chloride and generates calcium carbonate；Neutralized ratio removing calcium chloride reacts Calcium Carbonate Cyclic generated and enters dechlorination
Change hydrogen reaction member (2), or obtains commodity calcium carbonate after further treatment.
3. according to claim 1 or a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide as claimed in claim 2,
It is characterized in that, the sodium chloride solution after the neutralized ratio removing calcium chloride of saponification liquor sedimentation separation unit (5) is for being electrolysed system out
Industrial sodium chloride is made in alkali, or evaporation and concentration, membrane separation concentration.
4. a kind of mono-acid method alcoholizing propenyl chloride Synthesis of Propylene Oxide according to claim 1, which is characterized 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 propylene oxide is made.
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| CN108440453A (en) * | 2018-03-28 | 2018-08-24 | 吴剑华 | A kind of double alkali chlorohydrination epoxides production methods |
| 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 |
| 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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