CN115231986A - Process for producing methane chloride by using hydrogen chloride gas as byproduct of chlorinated ethylene carbonate - Google Patents
Process for producing methane chloride by using hydrogen chloride gas as byproduct of chlorinated ethylene carbonate Download PDFInfo
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- CN115231986A CN115231986A CN202211065492.3A CN202211065492A CN115231986A CN 115231986 A CN115231986 A CN 115231986A CN 202211065492 A CN202211065492 A CN 202211065492A CN 115231986 A CN115231986 A CN 115231986A
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- China
- Prior art keywords
- gas
- chloride
- hydrogen chloride
- byproduct
- ethylene carbonate
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- 239000007789 gas Substances 0.000 title claims abstract description 73
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 38
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 title claims abstract description 34
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910000041 hydrogen chloride Inorganic materials 0.000 title claims abstract description 33
- 239000006227 byproduct Substances 0.000 title claims abstract description 26
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical class O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 34
- 239000000460 chlorine Substances 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- 238000005507 spraying Methods 0.000 claims abstract description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- OYOKPDLAMOMTEE-UHFFFAOYSA-N 4-chloro-1,3-dioxolan-2-one Chemical compound ClC1COC(=O)O1 OYOKPDLAMOMTEE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000001112 coagulating effect Effects 0.000 claims abstract description 5
- 150000003254 radicals Chemical group 0.000 claims abstract description 5
- 238000007347 radical substitution reaction Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 17
- 239000002699 waste material Substances 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 9
- 229960001701 chloroform Drugs 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000003345 natural gas Substances 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 238000013021 overheating Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000004062 sedimentation Methods 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012855 volatile organic compound Substances 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000011084 recovery Methods 0.000 abstract description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B7/00—Halogens; Halogen acids
- C01B7/01—Chlorine; Hydrogen chloride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/42—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a process for producing methane chloride by a byproduct hydrogen chloride gas of chlorinated ethylene carbonate, which comprises the following steps: s1, reacting straight-chain alkane with chlorine, generating chloroethylene carbonate and hydrogen chloride after free radical substitution, and respectively recovering liquid and gas after reaction, wherein the liquid is the chloroethylene carbonate, and the gas contains about 99% of hydrogen chloride, about 1% of chlorine and light organic matters; and S2, spraying saturated hydrochloric acid on the gas recovered after the reaction in the step S1 and coagulating light organic matters at low temperature to obtain refined gas. The method can produce the methane chloride by the byproduct hydrogen chloride gas in the production process of the chlorinated ethylene carbonate, realizes the high-efficiency utilization and recovery of tail gas, fully absorbs harmful gas and then discharges the harmful gas, is very environment-friendly, has very simple whole recovery process, convenient reaction conditions, very reasonable operation and convenient popularization and application.
Description
Technical Field
The invention relates to the technical field of chlorinated ethylene carbonate production, in particular to a process for producing methane chloride by using a byproduct hydrogen chloride gas of chlorinated ethylene carbonate.
Background
Methyl chloride, also known as methyl chloride, is an organic compound, has a chemical formula of CH3Cl, is colorless gas at normal temperature and pressure, is slightly soluble in water, is soluble in ethanol, chloroform, benzene, carbon tetrachloride, glacial acetic acid and the like, is mainly used as a raw material of organosilicon, and is also used as a solvent, a refrigerant, a spice and the like, and the preparation reaction equation of the methyl chloride is as follows: CH3OH + HCl → CH3Cl + H2O. As known, the preparation process of chlorinated ethylene carbonate generates hydrogen chloride, and if the hydrogen chloride is not recovered, resources are wasted and the environment is polluted, and the preparation reaction equation of the chlorinated ethylene carbonate is as follows: C3H4O3+ Cl2 → C3H3ClO3+ HCl, from which we assume whether it is possible to use hydrogen chloride generated during the production of vinyl chlorocarbonate to produce methyl chloride.
Disclosure of Invention
The invention aims to solve the defects in the prior art and provides a process for producing methane chloride by using a hydrogen chloride gas as a byproduct of chlorinated ethylene carbonate.
In order to achieve the purpose, the invention adopts the following technical scheme:
a process for producing methane chloride by using a byproduct hydrogen chloride gas of chlorinated ethylene carbonate comprises the following steps:
s1, reacting straight-chain alkane with chlorine, generating chloroethylene carbonate and hydrogen chloride after free radical substitution, and respectively recovering liquid and gas after reaction, wherein the liquid is the chloroethylene carbonate, and the gas contains about 99% of hydrogen chloride, about 1% of chlorine and light organic matters;
s2, spraying saturated hydrochloric acid and coagulating light organic matters at low temperature to the gas recovered after the reaction in the step S1 so as to obtain refined gas;
and S3, overheating the refined gas obtained in the step S2 and the gasified methanol gas, reacting in a synthesis kettle under the catalysis of a catalyst to generate methane chloride, spraying secondary water on the methane chloride gas to remove unreacted hydrogen chloride gas, byproduct waste liquid dichloromethane, trichloromethane and tetrachloromethane, separating the byproduct waste liquids dichloromethane, trichloromethane and tetrachloromethane through sedimentation and layering, burning natural gas, spraying liquid alkali to absorb and remove the byproduct waste liquid, spraying the methane chloride with secondary liquid alkali to remove unreacted chlorine and produce sodium hypochlorite solution, demisting by a demister, compressing by a methane chloride compressor, cooling and liquefying to generate a methane chloride product.
Preferably, the superheating temperature of the refined gas and the methanol in the step S3 is 120-140 ℃.
Preferably, the catalyst in step S3 is a zinc chloride solution.
Preferably, the tail gas generated by burning the natural gas in the step S3 is sprayed with secondary liquid alkali and absorbed by volatile organic compounds, so that the tail gas reaches the standard and is discharged at a high level.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, methane chloride can be produced by a byproduct hydrogen chloride gas in the production process of chlorinated ethylene carbonate, so that the tail gas is efficiently utilized and recovered, and harmful gases are fully absorbed and then discharged, therefore, the method is very environment-friendly, the whole recovery process is very simple, the reaction conditions are convenient to manufacture, the operation is very reasonable, and the method is convenient to popularize and apply.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments.
A process for producing methane chloride by using a byproduct hydrogen chloride gas of chlorinated ethylene carbonate comprises the following steps:
s1, reacting straight-chain alkane with chlorine, generating chloroethylene carbonate and hydrogen chloride after free radical substitution, and respectively recovering liquid and gas after reaction, wherein the liquid is the chloroethylene carbonate, and the gas contains about 99% of hydrogen chloride, about 1% of chlorine and light organic matters;
s2, spraying saturated hydrochloric acid and coagulating light organic matters at low temperature on the gas recovered after the reaction in the step S1 to obtain refined gas;
and S3, overheating the refined gas obtained in the step S2 and the gasified methanol gas, enabling the overheating temperature of the refined gas and the methanol to be 120-140 ℃, enabling the refined gas and the methanol to react in a synthesis kettle under the catalysis of a catalyst, enabling the catalyst to be a zinc chloride solution to generate methane chloride, enabling the methane chloride gas to be subjected to secondary water spraying to remove unreacted hydrogen chloride gas, byproduct waste liquid dichloromethane, trichloromethane and tetrachloromethane, enabling the byproduct waste liquid dichloromethane, trichloromethane and tetrachloromethane to be separated out in a sedimentation and layering mode, burning the gas by adopting natural gas, spraying liquid caustic soda to absorb and remove the byproduct waste liquid, enabling tail gas after burning of the natural gas to be sprayed by secondary liquid caustic soda and absorbed by volatile organic matters to reach the standard, discharging high sodium chlorate, spraying the methane chloride by secondary liquid caustic soda to remove unreacted chlorine and generate a secondary chlorine solution, then demisting a demister and compressing the secondary chlorine solution by a methane chloride compressor, and liquefying the gas after cooling to generate a methane chloride product.
The working principle is as follows: reacting straight-chain alkane with chlorine, and substituting with free radicals to generate chlorinated ethylene carbonate and hydrogen chloride, and respectively recovering reacted liquid and gas, wherein the liquid is the chlorinated ethylene carbonate, and the gas contains about 99% of hydrogen chloride, about 1% of chlorine and light organic matters; spraying saturated hydrochloric acid and coagulating light organic matters at low temperature to the gas recovered after the reaction in the step S1 so as to obtain refined gas; and (2) after the refined gas obtained in the step (S2) and the gasified methanol gas are overheated, the overheating temperature of the refined gas and the methanol is 120-140 ℃, the refined gas and the methanol react in a synthesis kettle under the catalysis of a catalyst, the catalyst is a zinc chloride solution to generate methane chloride, the methane chloride gas is subjected to secondary water spraying to remove unreacted hydrogen chloride gas, byproduct waste liquid dichloromethane, trichloromethane and tetrachloromethane, the byproduct waste liquid dichloromethane, trichloromethane and tetrachloromethane are separated out through sedimentation and layering, natural gas is adopted for burning, liquid alkali spraying is used for absorbing and removing the byproduct waste liquid, tail gas generated after the natural gas burning is sprayed by the secondary liquid alkali and absorbed by volatile organic matters to reach the standard and be discharged high, the methane chloride is sprayed by the secondary liquid alkali to remove unreacted chlorine and generate a sodium hypochlorite solution, and then demisted by a demister and compressed by a methane chloride compressor, and the gas is liquefied after cooling to generate a methane chloride product.
In conclusion, methane chloride can be produced by a byproduct hydrogen chloride gas in the production process of chlorinated ethylene carbonate, the efficient utilization and recovery of tail gas are realized, harmful gas is fully absorbed and then discharged, the process is very environment-friendly, the whole recovery process is very simple, the reaction conditions are convenient to manufacture, the operation is very reasonable, and the popularization and the application are convenient.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (4)
1. A process for producing methane chloride by a byproduct hydrogen chloride gas of chlorinated ethylene carbonate is characterized by comprising the following steps:
s1, reacting ethylene carbonate with chlorine, generating chloroethylene carbonate and hydrogen chloride after free radical substitution, and respectively recovering liquid and gas after reaction, wherein the liquid is the chloroethylene carbonate, and the gas contains about 99% of hydrogen chloride, about 1% of chlorine and light organic matters;
s2, spraying saturated hydrochloric acid and coagulating light organic matters at low temperature on the gas recovered after the reaction in the step S1 to obtain refined gas;
and S3, overheating the refined gas obtained in the step S2 and the gasified methanol gas, reacting in a synthesis kettle under the catalysis of a catalyst to generate methane chloride, spraying secondary water on the methane chloride gas to remove unreacted hydrogen chloride gas, byproduct waste liquid dichloromethane, trichloromethane and tetrachloromethane, separating the byproduct waste liquids dichloromethane, trichloromethane and tetrachloromethane through sedimentation and layering, burning natural gas, spraying liquid alkali to absorb and remove the byproduct waste liquid, spraying the methane chloride with secondary liquid alkali to remove unreacted chlorine and produce sodium hypochlorite solution, demisting by a demister, compressing by a methane chloride compressor, cooling and liquefying to generate a methane chloride product.
2. The process for producing methane chloride by the byproduct hydrogen chloride gas of chlorinated ethylene carbonate according to claim 1, wherein the superheating temperature of the refining gas and methanol in the step S3 is 120-140 ℃.
3. The process for producing methane chloride by the byproduct hydrogen chloride gas of chlorinated ethylene carbonate according to claim 1, wherein the catalyst in step S3 is zinc chloride solution.
4. The process for producing methane chloride by using the hydrogen chloride gas as the byproduct of chlorinated ethylene carbonate according to claim 1, wherein the tail gas obtained by burning the natural gas in the step S3 is sprayed with secondary liquid alkali and absorbed by volatile organic compounds, so that the tail gas reaches the standard and is discharged at a high level.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211065492.3A CN115231986A (en) | 2022-09-01 | 2022-09-01 | Process for producing methane chloride by using hydrogen chloride gas as byproduct of chlorinated ethylene carbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211065492.3A CN115231986A (en) | 2022-09-01 | 2022-09-01 | Process for producing methane chloride by using hydrogen chloride gas as byproduct of chlorinated ethylene carbonate |
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| Publication Number | Publication Date |
|---|---|
| CN115231986A true CN115231986A (en) | 2022-10-25 |
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|---|---|---|---|
| CN202211065492.3A Pending CN115231986A (en) | 2022-09-01 | 2022-09-01 | Process for producing methane chloride by using hydrogen chloride gas as byproduct of chlorinated ethylene carbonate |
Country Status (1)
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718623A (en) * | 2012-07-13 | 2012-10-10 | 自贡鸿鹤化工股份有限公司 | Method of producing methane chloride by using byproduct hydrogen chloride of tetrachloroethylene device |
| CN109942536A (en) * | 2019-04-16 | 2019-06-28 | 张家港瀚康化工有限公司 | A kind of reactive distillation prepares high-purity chloro for the method for ethylene carbonate |
| CN114437016A (en) * | 2022-02-28 | 2022-05-06 | 济源市恒顺新材料有限公司 | Production and manufacturing method of chlorinated ethylene carbonate |
-
2022
- 2022-09-01 CN CN202211065492.3A patent/CN115231986A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718623A (en) * | 2012-07-13 | 2012-10-10 | 自贡鸿鹤化工股份有限公司 | Method of producing methane chloride by using byproduct hydrogen chloride of tetrachloroethylene device |
| CN109942536A (en) * | 2019-04-16 | 2019-06-28 | 张家港瀚康化工有限公司 | A kind of reactive distillation prepares high-purity chloro for the method for ethylene carbonate |
| CN114437016A (en) * | 2022-02-28 | 2022-05-06 | 济源市恒顺新材料有限公司 | Production and manufacturing method of chlorinated ethylene carbonate |
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