CN114249630A - Preparation method and application of chlorohydrin - Google Patents
Preparation method and application of chlorohydrin Download PDFInfo
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- CN114249630A CN114249630A CN202011018025.6A CN202011018025A CN114249630A CN 114249630 A CN114249630 A CN 114249630A CN 202011018025 A CN202011018025 A CN 202011018025A CN 114249630 A CN114249630 A CN 114249630A
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- chlorohydrin
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- concentration
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- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000243 solution Substances 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 238000007127 saponification reaction Methods 0.000 claims abstract description 12
- 239000002699 waste material Substances 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001336 alkenes Chemical class 0.000 claims abstract description 8
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000001110 calcium chloride Substances 0.000 claims description 7
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000012267 brine Substances 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- -1 ethylene, propylene, chloropropene Chemical class 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 238000002203 pretreatment Methods 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 6
- 239000002351 wastewater Substances 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- RZWHKKIXMPLQEM-UHFFFAOYSA-N 1-chloropropan-1-ol Chemical compound CCC(O)Cl RZWHKKIXMPLQEM-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- DLNUGFUWSWBWQZ-UHFFFAOYSA-N 1,1-dichloro-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)C(Cl)Cl DLNUGFUWSWBWQZ-UHFFFAOYSA-N 0.000 description 4
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000003945 chlorohydrins Chemical class 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C07C29/66—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens by addition of hypohalogenous acids, which may be formed in situ, to carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention provides a preparation method and application of chlorohydrin. The method comprises the following steps: reacting chlorine and olefin in a high-concentration salt water solution to obtain a chlorohydrin solution; the salt content of the high-concentration saline solution is more than or equal to 10 wt%. The invention realizes the chlorohydrination reaction in the high-concentration chloride ion aqueous solution. The chlorohydrin solution and alkali are subjected to saponification reaction to prepare epoxy alkane, and saponification waste liquid is remained after the epoxy alkane is separated; most of the saponified waste liquid is used as high-concentration salt water solution for chlorohydrination reaction, and the rest saponified waste liquid is concentrated and crystallized to obtain solid salt product, so that the discharge of salt-containing waste water is reduced and even eliminated, and the green production of preparing epoxy alkane by chlorohydrination is realized.
Description
Technical Field
The invention belongs to the field of chlorohydrins preparation, and particularly relates to a preparation method and application of chlorohydrins.
Background
The chlorohydrin process is one of industrially important processes for producing epoxides, such as the reaction of chlorine gas and propylene in water to produce an aqueous chloropropanol solution, which is directly contacted with lime milk to produce propylene oxide by saponification. At present, over 50 percent of propylene oxide products are industrially prepared and produced by a chlorohydrin method. The main reaction and the side reaction of chlorine and propylene in water to prepare the chloropropanol aqueous solution are as follows, and the main byproducts include dichloropropane, dichlorodiisopropyl ether, chloropropone and the like.
Main reaction:
Cl2+H2O→HClO+HCl (1)
side reaction:
the chlorohydrin method for preparing the epoxide has the advantages of mature process, high reaction yield, less side reaction and low equipment requirement. However, the existing process for preparing epoxide by chlorohydrin method has the defect of large amount of waste water, for example, when one ton of propylene oxide is produced by chlorohydrin method, the waste water containing 2-3 wt% of calcium chloride or sodium chloride is by-produced about 50t, and the waste water with low salt content and large amount needs to be discharged after biochemical treatment to reach the standard, so that the environmental protection pressure is large, and the industrial application of chlorohydrin method is limited.
Disclosure of Invention
The invention provides a preparation method of chlorohydrin, which comprises the following steps: reacting chlorine and olefin in a high-concentration salt water solution to obtain a chlorohydrin solution;
the salt content of the high-concentration saline solution is more than or equal to 10 wt%.
According to an embodiment of the invention, the salt content of the high strength brine solution is 10-50 wt%, more preferably 20-35 wt%, exemplary 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt% or any combination of any two of the above.
According to an embodiment of the present invention, the salt in the high-concentration brine solution is at least one of a chloride of a group I element and a chloride of a group II element. For example, the salt is at least one of sodium chloride, potassium chloride, magnesium chloride, and calcium chloride; more preferably, the salt is sodium chloride and/or calcium chloride.
According to an embodiment of the invention, the olefin is ethylene, propylene, chloropropene or butene.
According to an embodiment of the invention, the temperature of the reaction is 10-120 deg.C, such as 20-100 deg.C, such as 30-80 deg.C, more preferably 40-60 deg.C, and exemplary 30 deg.C, 40 deg.C, 50 deg.C, 60 deg.C, 70 deg.C, 80 deg.C.
According to an embodiment of the invention, the pressure of the reaction is 0.1-0.5MPa, such as 0.2-0.4MPa, exemplary 0.1MPa, 0.2MPa, 0.3MPa, 0.4MPa, 0.5 MPa.
According to an embodiment of the invention, the molar ratio of the feed of chlorine to olefin is 1 (1.01-1.3), for example 1 (1.05-1.175), and as another example 1 (1.1-1.15).
According to an embodiment of the invention, the chlorohydrin solution has a concentration of chlorohydrin of 1.0 to 10.0 wt.%, preferably 2.0 to 5.0 wt.%, illustratively 2.0 wt.%, 2.45 wt.%, 3.0 wt.%, 3.3 wt.%, 4.0 wt.%, 4.5 wt.%, 5.0 wt.%.
According to an embodiment of the present invention, the aqueous solution of the salt with high concentration may be selected from a saponification waste liquid obtained by preparing an alkylene oxide from the chlorohydrin solution and an alkaline substance through a saponification reaction, separating the alkylene oxide, and then performing a pretreatment, which is prepared by a method known in the art (for example, dissolving the salt in water to form an aqueous solution of the salt with high concentration), or a saponification waste liquid obtained by preparing an alkylene oxide.
Preferably, the pre-treatment comprises at least one of filtration, neutralization and cooling.
Preferably, the alkaline substance is selected from at least one of alkaline substances containing group I elements and/or group II elements, such as hydroxides and/or basic salts thereof, for example, at least one of sodium hydroxide, calcium hydroxide, and sodium carbonate.
According to an embodiment of the present invention, the preparation process of the chlorohydrin may be performed in a chlorohydrination reaction apparatus known in the art.
The invention also provides a preparation method of the chlorohydrins and/or application of chlorohydrin solution prepared by the method in preparation of alkylene oxide.
The invention has the beneficial effects that:
chlorine and olefin are reacted in an aqueous solution of a salt having a concentration of 10 wt% or more to prepare a chlorohydrin solution, and chlorohydrination in a high-concentration aqueous solution of chloride ions is achieved. The chlorohydrin solution and alkali are subjected to saponification reaction to prepare epoxy alkane, and saponification waste liquid is remained after the epoxy alkane is separated; most of the saponified waste liquid is used as high-concentration salt water solution for chlorohydrination reaction, and the rest saponified waste liquid is concentrated and crystallized to obtain solid salt product, so that the discharge of salt-containing waste water is reduced and even eliminated, and the green production of preparing epoxy alkane by chlorohydrination is realized.
Detailed Description
The technical solution of the present invention will be further described in detail with reference to specific embodiments. It is to be understood that the following examples are only illustrative and explanatory of the present invention and should not be construed as limiting the scope of the present invention. All the technologies realized based on the above-mentioned contents of the present invention are covered in the protection scope of the present invention.
Unless otherwise indicated, the raw materials and reagents used in the following examples are all commercially available products or can be prepared by known methods.
The analysis conditions for the products in the following examples are as follows:
an analytical instrument: agilent GC 7820; a chromatographic column: 30 m.times.530 μm.times.0.25 μm DB-FFAP; a detector: FID; sample inlet temperature: 225 ℃, detector temperature: and (3) temperature programming at 240 ℃: maintaining at 40 deg.C for 5min, 30 deg.C/min to 230 deg.C for 5min, H2：0.1Mpa，AIR：0.1Mpa，N2: 0.075Mpa, tail-blown: 0.1 MPa.
Example 1
The reaction device is a 1000ml four-neck round bottom glass flask, and is provided with mechanical stirring, the stirring speed is 100rpm, two bottom inserting tubes are respectively arranged in two bottle mouths, one bottom inserting tube is used for introducing chlorine, and the other bottom inserting tube is used for introducing propylene. 20 wt% of calcium chloride solution is respectively added into the two flasks, the total volume of the calcium chloride solution is 800ml, the reaction temperature is controlled by a hot water bath at 50 ℃, and the reaction flasks are wrapped by black plastic cloth to be protected from light.
Chlorine gas was introduced subsurface at a rate of 52ml/min (2.3mmol/min), and propylene was introduced subsurface at a rate of 62ml/min (2.7 mmol/h).
The gas phase is removed from the gas phase space of the reaction bottle and is absorbed by alkali liquor and ethyl acetate.
And analyzing the contents of chloropropanol and impurities in the reaction material, and analyzing the contents of propylene and impurities in the gas phase removed from the reaction bottle.
The comprehensive analysis was carried out after 200min of aeration reaction, and the results were as follows:
3.02 wt% of chloropropanol, 0.14 wt% of dichloropropane, 0.08 wt% of dichlorodiisopropyl ether and 0.010 wt% of chloropropone.
Examples 2 to 5
The reaction apparatus, the amount of charge, and the control conditions were the same as in example 1 except for the concentration of calcium chloride in the calcium chloride solution. After the reaction was carried out under aeration for 200min, the contents of chloropropanol and major impurities in the reaction solution were determined, and the results are shown in Table 1.
TABLE 1
Example 6
The reaction apparatus, the amount of feed and the control conditions were the same as in example 1, except that the added brine solution was a sodium chloride solution containing 21 wt% of sodium chloride. After the reaction solution is aerated for 200min, the contents of chloropropanol and main impurities in the reaction solution are measured, and the results are as follows:
3.12 percent of chloropropanol, 0.130 percent of dichloropropane, 0.085 percent of dichlorodiisopropyl ether and 0.015 percent of chloropropone.
Example 7
The reaction apparatus, the amount of feed and the control conditions were the same as in example 1, except that the reaction solution before the introduction of chlorine gas and propylene was a saponified waste solution. The saponified waste liquid was obtained by subjecting the 3.02 wt% chloropropanol aqueous solution obtained in example 1 and lime milk (calcium hydroxide emulsion) to saponification, separating propylene oxide from the saponified liquid, and was filtered to remove solid residues therefrom, and was analyzed to contain 18.5 wt% calcium chloride, 0.02 wt% calcium hydroxide, and 0.02 wt% propylene glycol (propylene oxide hydrolysate).
After the reaction is carried out for 200min by introducing gas, the contents of chloropropanol and main impurities in the reaction liquid are measured, and the results are as follows:
2.98 wt% of chloropropanol, 0.19 wt% of dichloropropane, 0.095 wt% of dichlorodiisopropyl ether, 0.013 wt% of chloropropone and no propylene glycol.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for preparing chlorohydrin, comprising the steps of: reacting chlorine and olefin in a high-concentration salt water solution to obtain a chlorohydrin solution;
the salt content of the high-concentration saline solution is more than or equal to 10 wt%.
2. The method of preparing chlorohydrin according to claim 1, wherein the salt content of the aqueous solution of the highly concentrated salt is 10 to 50 wt.%, preferably 20 to 35 wt.%.
3. The method of producing chlorohydrin according to claim 1 or 2, wherein the salt in the high-concentration brine solution is at least one of a chloride of a group I element and a chloride of a group II element.
4. The method of preparing chlorohydrin according to claim 3, wherein the salt is one of sodium chloride, potassium chloride, magnesium chloride, and calcium chloride; preferably, the salt is sodium chloride or calcium chloride.
5. The method of producing chlorohydrin according to any one of claims 1 to 4, wherein the olefin is ethylene, propylene, chloropropene or butene.
6. A process for the preparation of a chlorohydrin as claimed in any one of claims 1 to 5 wherein the reaction temperature is in the range of from 10 ℃ to 120 ℃, such as from 20 ℃ to 100 ℃, and such as from 30 ℃ to 80 ℃.
Preferably, the pressure of the reaction is from 0.1 to 0.5MPa, for example from 0.2 to 0.4 MPa.
Preferably, the molar feed ratio of chlorine to olefin is 1 (1.01-1.3), for example 1 (1.05-1.175).
7. The method of preparing chlorohydrin according to any one of claims 1 to 6 wherein the chlorohydrin solution has a concentration of 1.0 to 10.0 wt.%, preferably 2.0 to 5.0 wt.%, based on the weight of chlorohydrin.
8. The method of producing chlorohydrin according to any one of claims 1 to 7, wherein the aqueous solution of a salt having a high concentration is selected from a saponification waste liquid obtained by preparing an alkylene oxide from the chlorohydrin solution and an alkaline substance through a saponification reaction, and the saponification waste liquid is a liquid obtained by separating the alkylene oxide and then pretreating the mixture.
Preferably, the pre-treatment comprises at least one of filtration, neutralization and cooling.
9. Process for the preparation of a chlorohydrin according to claim 8 wherein the alkaline substance is at least one selected from alkaline substances containing group I elements and/or group II elements, such as hydroxides and/or basic salts thereof, preferably at least one of sodium hydroxide, calcium hydroxide, sodium carbonate.
10. Use of a chlorohydrin solution obtained by a process for the preparation of a chlorohydrin according to any one of claims 1 to 9 or a process for the preparation of a chlorohydrin according to any one of claims 1 to 9 for the preparation of an alkylene oxide.
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| CN202011018025.6A CN114249630A (en) | 2020-09-24 | 2020-09-24 | Preparation method and application of chlorohydrin |
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| CN202011018025.6A CN114249630A (en) | 2020-09-24 | 2020-09-24 | Preparation method and application of chlorohydrin |
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| CN202011018025.6A Pending CN114249630A (en) | 2020-09-24 | 2020-09-24 | Preparation method and application of chlorohydrin |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1051550A (en) * | 1989-11-06 | 1991-05-22 | 中国石油化工总公司上海石油化工研究所 | The improvement of olefin chlorine alcoholization process |
| CN1134140A (en) * | 1993-11-23 | 1996-10-23 | 陶氏化学公司 | Process for producing alkylene oxide |
| CN101074216A (en) * | 2007-04-23 | 2007-11-21 | 锦化化工集团氯碱股份有限公司 | Close-circulating chlorohydrination reactor and reactive method during production of epoxy-propane |
| CN102992967A (en) * | 2012-11-20 | 2013-03-27 | 于加全 | Method for improving concentration of chlorohydrination reaction chlorophydrin by circular reaction |
| CN111732559A (en) * | 2020-06-17 | 2020-10-02 | 吴剑华 | Chlorohydrin method epoxide production method of cyclic calcium carbonate dehydrochlorination |
-
2020
- 2020-09-24 CN CN202011018025.6A patent/CN114249630A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1051550A (en) * | 1989-11-06 | 1991-05-22 | 中国石油化工总公司上海石油化工研究所 | The improvement of olefin chlorine alcoholization process |
| CN1134140A (en) * | 1993-11-23 | 1996-10-23 | 陶氏化学公司 | Process for producing alkylene oxide |
| CN101074216A (en) * | 2007-04-23 | 2007-11-21 | 锦化化工集团氯碱股份有限公司 | Close-circulating chlorohydrination reactor and reactive method during production of epoxy-propane |
| CN102992967A (en) * | 2012-11-20 | 2013-03-27 | 于加全 | Method for improving concentration of chlorohydrination reaction chlorophydrin by circular reaction |
| CN111732559A (en) * | 2020-06-17 | 2020-10-02 | 吴剑华 | Chlorohydrin method epoxide production method of cyclic calcium carbonate dehydrochlorination |
Non-Patent Citations (1)
| Title |
|---|
| 张旭之等: "丙烯衍生物工学", vol. 1, 31 May 1995, 化学工业出版社, pages: 279 - 292 * |
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