CN110922299A - Continuous preparation method of high-content 2-chloroethanol - Google Patents
Continuous preparation method of high-content 2-chloroethanol Download PDFInfo
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- CN110922299A CN110922299A CN201911078623.XA CN201911078623A CN110922299A CN 110922299 A CN110922299 A CN 110922299A CN 201911078623 A CN201911078623 A CN 201911078623A CN 110922299 A CN110922299 A CN 110922299A
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- chloroethanol
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- ethylene glycol
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- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 51
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000001361 adipic acid Substances 0.000 claims abstract description 8
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 6
- 239000011259 mixed solution Substances 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 229960002446 octanoic acid Drugs 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 238000010025 steaming Methods 0.000 claims description 3
- 229940005605 valeric acid Drugs 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 13
- 238000010992 reflux Methods 0.000 abstract description 12
- 239000007788 liquid Substances 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 6
- 238000003860 storage Methods 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000000975 dye Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000575 pesticide Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 208000005156 Dehydration Diseases 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- -1 carboxylic acid compound Chemical class 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Images
Classifications
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- 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
- C07C29/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a continuous preparation method of high-content 2-chloroethanol, which comprises the specific steps of taking quantitative ethylene glycol, 36% hydrochloric acid, water and catalyst adipic acid as base materials, reacting at 110-120 ℃ until reflux occurs, and continuously dripping mixed solution of the ethylene glycol, the 36% hydrochloric acid and the water; meanwhile, the generated 2-chloroethanol and water are azeotropically evaporated at the temperature, and by controlling the reflux ratio to be 2:3, one part of condensate liquid reflows to the packed tower, and the other part enters a receiving tank to obtain about 42 percent of crude 2-chloroethanol. And finally, dehydrating the crude product with benzene and water, removing benzene, and performing reduced pressure rectification to obtain the 2-chloroethanol with the content of more than 99%. The method has high reaction efficiency and low raw material cost, and the obtained 2-chloroethanol is suitable for production of intermediates in the industries of medicines, dyes and pesticides. And the method adopts relatively safe ethylene glycol to replace ethylene oxide as a raw material, and has small transportation, storage and use dangers.
Description
Technical Field
The invention belongs to the field of organic chemical industry, and particularly relates to a continuous preparation method of high-content 2-chloroethanol.
Background
2-chloroethanol is an important organic solvent and an organic synthetic raw material, is not only an important raw material for synthesizing polysulfide rubber, but also is widely used in the industries of medicines, dyes and pesticides. There are two main processes for the industrial preparation of 2-chloroethanol, namely the chloric acid process and the ethylene oxide process. The chlorine acid method is that ethylene and chlorine gas are simultaneously introduced into water, the chlorine gas reacts with the water to generate hypochlorous acid, and the hypochlorous acid and the ethylene are added to produce 2-chloroethanol. The 2-chloroethanol aqueous solution obtained by the method has low content, and can obtain 90-95% of 2-chloroethanol only by long-time azeotropic dehydration and vacuum rectification, and a byproduct dichloroethane is inevitably included in the product. In addition, there is a great danger in the transportation, storage and use of chlorine and ethylene.
At present, ethylene oxide and hydrogen chloride (or hydrochloric acid) are generally adopted as raw materials at home and abroad to produce high-concentration 2-chloroethanol, the process comprises the steps of carrying out liquid-phase synthesis on the ethylene oxide and the hydrogen chloride under certain conditions, dehydrating and rectifying to obtain the high-concentration 2-chloroethanol, although the purity of the product can reach more than 98%, the heat release in the whole reaction process is obvious, discontinuous production is realized, and the raw material ethylene oxide is a toxic, flammable and explosive liquefied gas, so that the long-distance transportation, storage and use are not easy.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to overcome the defects in the prior art and provide a continuous preparation method of 2-chloroethanol with the total yield (calculated by HCl) of more than 90 percent.
The technical scheme is as follows: in order to solve the above technical problems, the present invention provides a continuous preparation method of high content 2-chloroethanol, which comprises,
(A) under the condition of a catalyst adipic acid, controlling the temperature at 110-;
(B) putting the crude product into a rectifying still, adding benzene as a water-carrying agent, and keeping the top temperature at 67-72 ℃ to remove enough water;
(C) heating and keeping the kettle temperature at 110 ℃ and 130 ℃, and removing sufficient water-carrying agent benzene;
(D) cooling the rectifying still to 60 +/-5 deg.c, opening and maintaining the vacuum degree of-0.095 to-0.1 MPa, and steaming out high content 2-chloroethanol at 65-130 deg.c.
The mass ratio of each substance in the base material in the step (A) is ethylene glycol: 36% hydrochloric acid: h2Catalyst = (8.45-8.50): (5.10-5.15): (1.30-1.31): 1.
the mass ratio of each substance in the base material in the step (A) is ethylene glycol: 36% hydrochloric acid: h2O catalyst = 8.5: 5.1: 1.3: 1.
The mass ratio of each substance in the mixed solution continuously dripped in the step (A) is ethylene glycol: 36% hydrochloric acid: h2O=2.2 :3.6 : 1。
The catalyst is one of oxalic acid, propionic acid, butyric acid, succinic acid, valeric acid, caproic acid, adipic acid and caprylic acid.
In the step (B), the input amount of the water-carrying agent benzene is 30 percent of the weight of the crude product.
Under the action of a catalyst, ethylene glycol reacts with hydrochloric acid to generate 2-chloroethanol, and the reaction equation is as follows:
the catalyst for the reaction may be a carboxylic acid compound such as oxalic acid, propionic acid, butyric acid, succinic acid, valeric acid, caproic acid, adipic acid, caprylic acid, or the like.
As the reaction proceeds, 2-chloroethanol produced in the system increases, and a side reaction with unreacted hydrochloric acid occurs to produce 1, 2-dichloroethane. In order to reduce side reaction, 2-chloroethanol and water are azeotropically removed by a technology of distillation while reaction.
The 2-chloroethanol and water are subjected to azeotropic distillation, the azeotropic temperature is 97.8 ℃, the water mass in the azeotropic distillation composition accounts for 57.7 percent, and the generated 2-chloroethanol can be completely brought out by azeotropic distillation only by considering that enough water is required in the system, so that corresponding water is added into the bottom material and the mixed solution. Meanwhile, the system temperature is determined to be 110-120 ℃, and the azeotropic temperature of the 2-chloroethanol and the water is fully satisfied.
The azeotrope vapor rises to the top of the column and is condensed by a condenser to realize partial reflux. The reflux liquid flows into the packed tower, is uniformly distributed together with the packing in the packed tower, and falls into a reaction system after fully absorbing the hydrogen chloride in the azeotropic steam, so that the utilization rate of the hydrochloric acid is improved.
The acid-resistant packing with large flux, small resistance and high efficiency, such as ceramic Raschig ring, pall ring, rectangular saddle ring, stepped ring, ceramic corrugated packing, etc. is selected to form a gas-liquid contact area in the packing tower, so that the reflux liquid can be fully contacted with the ascending steam.
In the reaction distillation process, the dropping speed of the mixed liquid is controlled to keep balance with the receiving speed of the crude product in the receiving tank, and continuous preparation is realized.
The adding amount of the water-carrying agent benzene is 30% of the weight of the added crude product, after the dehydration stage is finished, sufficient benzene is continuously removed by heating, and the removed benzene can be continuously recycled as the water-carrying agent in the next dehydration stage.
In the process of vacuum rectification, front distillate is distilled out at the kettle temperature of 65-80 ℃, and can be used in a rectification kettle in the next rectification stage after being independently collected. The 2-chloroethanol with the purity of more than 99 percent is obtained by steaming at the kettle temperature of between 80 and 130 ℃.
Has the advantages that: compared with the prior art, the invention has the following remarkable advantages:
according to the invention, 2-chloroethanol and water are subjected to azeotropic removal in time by a technology of reaction and distillation, azeotrope steam rises to the top of the tower, after being condensed by a condenser, a part of condensate liquid flows back to a packed tower, reflux liquid flows into the packed tower and is uniformly distributed together with a filler in the packed tower, hydrogen chloride in the azeotropic steam is fully absorbed and then falls into a reaction system, the utilization rate of hydrochloric acid is improved, the other part of the condensate liquid enters a receiving tank to obtain a 2-chloroethanol crude product with the concentration of about 42%, and finally the 2-chloroethanol with the concentration of more than 99% is obtained after the crude product is subjected to benzene-carrying water dehydration, debenzolization and reduced pressure rectification. The method has high reaction efficiency and low raw material cost, and the obtained 2-chloroethanol is suitable for production of intermediates in the industries of medicines, dyes and pesticides. And the method adopts relatively safe ethylene glycol to replace ethylene oxide as a raw material, and has small transportation, storage and use dangers.
Drawings
FIG. 1 is a flow chart of step (A) in the present invention.
Detailed Description
Example 1
330g of ethylene glycol, 200g of hydrochloric acid (36%), 51g of water and 39g of adipic acid are put into a reaction kettle, stirred and heated until the temperature in the kettle reaches 110 ℃, reflux appears, and the mixed solution is dropwise added into the kettle at the speed of 150g/h (the weight ratio of the ethylene glycol to the 36% hydrochloric acid to the water is 2.2: 3.6: 1). When the condenser at the top of the tower just generates condensate, the control of the reflux ratio is immediately opened, the reflux ratio is kept at 2:3 and the temperature in the kettle is kept at 113 +/-3 ℃, so that the crude product of the 2-chloroethanol is obtained, the content is 42 percent, the acid value (calculated by HCl) is 0.07 percent, and the yield of the 2-chloroethanol (calculated by HCl) in the reaction stage is 99.3 percent.
And putting 800g of the crude product and 240g of water-carrying agent benzene into a rectifying still, heating and keeping the top temperature at 67-72 ℃, distilling at normal pressure, and removing lower-layer water by layers. Heating is continued, and benzene in the system is removed at the kettle temperature of 110 ℃ and 130 ℃.
Cooling the liquid in the reactor after benzene removal to about 60 ℃, maintaining the vacuum degree to about-0.095 Mpa for vacuum rectification, obtaining 2-chloroethanol with the content of 98.5% (GC analysis) at the temperature of 65-130 ℃, and the yield of the dehydration and purification stages reaches 95%.
Example 2
500 ethylene glycol, 303g hydrochloric acid (36%), 77g water and 59g adipic acid are put into a reaction kettle, stirred and heated until the temperature in the kettle reaches 110 ℃ and reflux appears, and the mixed solution is dripped into the kettle at the speed of 180g/h (the weight ratio of ethylene glycol, 36% hydrochloric acid and water is 2.2: 3.6: 1). When the condenser at the top of the tower just generates condensate, the control of the reflux ratio is immediately opened, the reflux ratio is kept at 2:3 and the temperature in the kettle is kept at 115 +/-3 ℃, so that the crude product of the 2-chloroethanol is obtained, the content is 41.8 percent, the acid value (calculated by HCl) is 0.07 percent, and the yield of the 2-chloroethanol (calculated by HCl) in the reaction stage is 99 percent.
Putting 800g of the crude product and 240g of water-carrying agent benzene into a rectifying still, and dehydrating at the top temperature of 67-72 ℃. Benzene is removed at the temperature of 110 ℃ and 130 ℃.
Cooling the liquid in the reactor after benzene removal to about 60 ℃, and carrying out vacuum rectification under the vacuum degree of-0.095 Mpa. Firstly distilling out 2-chloroethanol front cut fraction at the temperature of 65-80 ℃ and then distilling out 99.4% (GC analysis) of 2-chloroethanol at the temperature of 80-130 ℃, wherein the yield of dehydration and purification stages reaches 93%.
The present invention provides a thought and a method, and a method and a way for implementing the technical scheme are many, the above is only a preferred embodiment of the present invention, it should be noted that, for a person skilled in the art, a plurality of improvements and modifications can be made without departing from the principle of the present invention, and the improvements and modifications should be regarded as the protection scope of the present invention, and each component not explicitly described in the embodiment can be implemented by the prior art.
Claims (6)
1. A continuous preparation method of high-content 2-chloroethanol is characterized by comprising the following steps: which comprises the steps of (a) preparing a mixture of,
(A) under the condition of a catalyst adipic acid, controlling the temperature at 110-;
(B) putting the crude product into a rectifying still, adding benzene as a water-carrying agent, and keeping the top temperature at 67-72 ℃ to remove enough water;
(C) heating and keeping the kettle temperature at 110 ℃ and 130 ℃, and removing sufficient water-carrying agent benzene;
(D) cooling the rectifying still to 60 +/-5 deg.c, opening and maintaining the vacuum degree of-0.095 to-0.1 MPa, and steaming out high content 2-chloroethanol at 65-130 deg.c.
2. The continuous process for the preparation of high contents of 2-chloroethanol as claimed in claim 1, characterized in that: the mass ratio of each substance in the base material in the step (A) is ethylene glycol: 36% hydrochloric acid: h2Catalyst = (8.45-8.50): (5.10-5.15): (1.30-1.31): 1.
3. the continuous process for the preparation of high contents of 2-chloroethanol as claimed in claim 1, characterized in that: the mass ratio of each substance in the base material in the step (A) is ethylene glycol: 36% hydrochloric acid: h2O catalyst = 8.5: 5.1: 1.3: 1.
4. The continuous process for the preparation of high contents of 2-chloroethanol as claimed in claim 1, characterized in that: the mass ratio of each substance in the mixed solution continuously dripped in the step (A) is ethylene glycol: 36% hydrochloric acid: h2O=2.2 : 3.6 : 1。
5. The continuous process for the preparation of high contents of 2-chloroethanol as claimed in claim 1, characterized in that: the catalyst is one of oxalic acid, propionic acid, butyric acid, succinic acid, valeric acid, caproic acid, adipic acid and caprylic acid.
6. The continuous process for the preparation of high contents of 2-chloroethanol as claimed in claim 1, characterized in that: in the step (B), the input amount of the water-carrying agent benzene is 30 percent of the weight of the crude product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115108885A (en) * | 2022-06-29 | 2022-09-27 | 河北工业大学 | Production process for co-production of chlorohydrin and dichloroethane |
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2019
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115108885A (en) * | 2022-06-29 | 2022-09-27 | 河北工业大学 | Production process for co-production of chlorohydrin and dichloroethane |
| CN115108885B (en) * | 2022-06-29 | 2023-06-13 | 河北工业大学 | Production process for co-production of chloroethanol and dichloroethane |
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