CN113816825A - Method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste - Google Patents
Method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste Download PDFInfo
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- CN113816825A CN113816825A CN202111097452.2A CN202111097452A CN113816825A CN 113816825 A CN113816825 A CN 113816825A CN 202111097452 A CN202111097452 A CN 202111097452A CN 113816825 A CN113816825 A CN 113816825A
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- difluoro
- dichloroethane
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- VLIDBBNDBSNADN-UHFFFAOYSA-N 1,1-dichloro-2,2-difluoroethane Chemical compound FC(F)C(Cl)Cl VLIDBBNDBSNADN-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000002920 hazardous waste Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 14
- 239000012279 sodium borohydride Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 7
- UPVJEODAZWTJKZ-UHFFFAOYSA-N 1,2-dichloro-1,2-difluoroethene Chemical group FC(Cl)=C(F)Cl UPVJEODAZWTJKZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 2
- 239000012044 organic layer Substances 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000012074 organic phase Substances 0.000 description 8
- FQAMAOOEZDRHHB-UHFFFAOYSA-N 1,2,2-trichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)C(Cl)Cl FQAMAOOEZDRHHB-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000382 dechlorinating effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000011194 food seasoning agent Nutrition 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 description 1
- IDSKMUOSMAUASS-UHFFFAOYSA-N 1,2-dichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)Cl IDSKMUOSMAUASS-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- KURKJXZWCPWPFX-UHFFFAOYSA-N 2,2-difluoroacetyl chloride Chemical compound FC(F)C(Cl)=O KURKJXZWCPWPFX-UHFFFAOYSA-N 0.000 description 1
- PFJLHSIZFYNAHH-UHFFFAOYSA-N 2,2-difluoroethyl acetate Chemical compound CC(=O)OCC(F)F PFJLHSIZFYNAHH-UHFFFAOYSA-N 0.000 description 1
- HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical group FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- -1 HCFC-142 Chemical compound 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste, comprising the following steps of I, synthetic reaction; step two, distillation; and step three, rectifying. The method has the main advantages that hazardous wastes are comprehensively utilized, 1, 2-trichloro-2, 2-difluoroethane (R122) is contained in the hazardous wastes generated in the production of the 1, 1-difluoro-1-chloroethane (R142b), and the R142b hazardous wastes are mainly treated by incineration at present and pollute the environment. Wherein R122 contained in the product can be dechlorinated to generate 1, 1-difluoro-2, 2-dichloroethylene, and then hydrogenated to generate 1, 1-difluoro-2, 2-dichloroethane (R132 a).
Description
Technical Field
The invention belongs to the field of chemical reaction synthesis, and particularly relates to a method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste.
Background
1, 1-difluoro-2, 2-dichloroethane is also called R132a or HCFC-132a, is mainly used for preparing polymer monomers and used as an intermediate of freon, is used for preparing polymer monomers, and can prepare 1, 1-difluoro-2-chloroethylene monomers under the action of alcohol alkali from HCFC-132 a; 1,1, 1-trifluoro-2, 2-dichloroethane (R123) and 1,1, 1-trichloro-2, 2, 2-trifluoroethane (R113a) can be prepared by fluorination and chlorination from HCFC-132a as intermediates of freon, and R123 and R113a are important intermediates of the freon for pesticide and medicine. The production method of R132a is described in patent literature. WO2006/69108,2006 and A1 report that hfc-152a prepares R132a by introducing chlorine into a gas phase and chlorinating the chlorine under illumination, but the conversion rate is only about 60 percent, the selectivity is not high, and by-products such as HCFC-142b, HCFC-142, HCFC-132b and the like exist, so that the process is not suitable for industrial production.
Disclosure of Invention
The purpose of the invention is as follows: in order to solve the defects of the prior art, the invention provides a method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste, and the hazardous waste which can only be incinerated originally is changed into a product with considerable economic value.
The technical scheme is as follows: a method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste comprises the following steps:
step one, synthetic reaction: adding 1, 1-difluoro-2, 2-dichloroethylene and water into a reaction kettle, adding a proper amount of solvent, cooling to within 5 ℃, slowly dropwise adding a sodium borohydride solution, controlling the indoor temperature to be not more than 10 ℃, preserving heat for 2-3h after dropwise adding is finished, then dropwise adding dilute acid to adjust the pH value, stirring for 1 hour, layering, and collecting an organic layer.
Step two, distillation: distilling at normal pressure, and collecting 55-65 deg.C fraction;
step three, rectification: then rectifying to obtain the 1, 1-difluoro-2, 2-dichloroethane, wherein the total reaction yield is 90 percent.
Further, the molar ratio of the 1, 1-difluoro-2, 2-dichloroethylene to the sodium borohydride is 1: 1.
Further, the solvent used by the sodium borohydride solution is one or more of diethylene glycol dimethyl ether, DMF and THF, and diethylene glycol dimethyl ether is preferably used.
Further, the solvent amount is 1 to 3 times, preferably 2.5 times of the weight of the difluorodichloroethylene.
Further, the molar ratio of the 1, 1-difluoro-2, 2-dichloroethylene to the water is 1: 3-6, preferably 1: 4-5.
Further, the concentration of the sodium borohydride solution is 1M.
Further, the dropping temperature of the sodium borohydride solution is-10-30 ℃, and preferably 0-10 ℃.
Further, the temperature of the heat preservation reaction is 0-30 ℃, and preferably 10-20 ℃.
Further, the temperature of the dropwise addition of the dilute hydrochloric acid is 0-30 ℃, and preferably 10-20 ℃.
Further, the amount of the dropwise diluted acid is to adjust the pH value of the reaction solution to 3-4.
Further, collecting fractions at 55-65 ℃ during the distillation in the second step.
Further, the rectifying tower used in the step three is a packed tower, the theoretical plate number is 30-45, the reflux ratio is 3-6:1, and the tower top temperature is 58-60 ℃.
Further, the content of the 1, 1-difluoro-2, 2-dichloroethane obtained by the rectification in the step three is more than 98 percent, and the yield is more than 90 percent.
Has the advantages that: the method has the main advantages that hazardous wastes are comprehensively utilized, 1,1, 2-trichloro-2, 2-difluoroethane (R122) is contained in the hazardous wastes generated in the production of the 1, 1-difluoro-1-chloroethane (R142b), and the 1, 1-difluoro-1-chloroethane (R142b) hazardous wastes are mainly subjected to incineration treatment at present and pollute the environment. The process comprises rectifying and recovering 1,1, 2-trichloro-2, 2-difluoroethane (R122), dechlorinating to obtain 1, 1-difluoro-2, 2-dichloroethylene, and hydrogenating to obtain 1, 1-difluoro-2, 2-dichloroethane.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below so that those skilled in the art can better understand the advantages and features of the present invention, and thus the scope of the present invention will be more clearly defined. The embodiments described herein are only a few embodiments of the present invention, rather than all embodiments, and all other embodiments that can be derived by one of ordinary skill in the art without inventive faculty based on the embodiments described herein are intended to fall within the scope of the present invention.
Detailed description of the preferred embodiment 1
In a four-necked flask were placed 33.25 g (0.25 mol) of difluorodichloroethylene, 22.5 g (1.25 mol) of water and 100ml of diethylene glycol dimethyl ether. Stirring is started, the temperature is reduced to below 5 ℃, and 250 ml (0.25 mol) of 1.00M sodium borohydride is added dropwise within 5 hours. Stirring was continued for 1 hour after completion of the dropwise addition. 20ml of 3M nitric acid were added at 20 ℃. The organic phase was then collected in layers.
The collected organic phase is distilled at normal pressure, 38g of fractions at the temperature of 55-65 ℃ are collected, and then the collected fractions are rectified to obtain 32gR132a with the content of 99.91% and the yield of 95%. The rectification adopts a 70mm glass rectification column, and the filler is filled by a stainless steel wire mesh with a flow ratio of 4: 1.
Specific example 2
In a four-necked flask were placed 33.25 g (0.25 mol) of difluorodichloroethylene, 18 g (1 mol) of water and 100ml of THF. Stirring is started, the temperature is reduced to below 5 ℃, and 250 ml (0.25 mol) of 1.00M sodium borohydride is added dropwise within 5 hours. Stirring was continued for 1 hour after completion of the dropwise addition. 60ml of 1M hydrochloric acid are added at 20 ℃. The organic phase was then collected in layers.
The collected organic phase was first distilled at atmospheric pressure to collect 35.3g of fraction at 55-65 ℃ and then the collected fraction was rectified to yield 30.7gR132a with a content of 99.89% and a yield of 91%. The rectification adopts a 70mm glass rectification column, and the filler is filled by a stainless steel wire mesh with a flow ratio of 3: 1.
Specific example 3
In a four-necked flask were placed 33.25 g (0.25 mol) of difluorodichloroethylene, 22.5 g (1.25 mol) of water and 100ml of diethylene glycol dimethyl ether. Stirring is started, the temperature is reduced to below 5 ℃, and 200 ml (0.25 mol) of 1.00M sodium borohydride is added dropwise within 5 hours. Stirring was continued for 1 hour after completion of the dropwise addition. 60ml of dilute hydrochloric acid 1M are added at 20 ℃. The organic phase was then collected in layers.
The collected organic phase was distilled at atmospheric pressure to collect 32g of fraction at 55-65 deg.C, and then the collected fraction was rectified to yield 30.71gR132a with a content of 99.9% and a yield of 90.9%. The rectification adopts a 70mm glass rectification column, and the seasonings are filled by a stainless steel wire mesh with the flow ratio of 4: 1.
Specific example 4
In a four-necked flask were placed 33.25 g (0.25 mol) of difluorodichloroethylene, 20 g (1.11 mol) of water and 100ml of diethylene glycol dimethyl ether. Stirring is started, the temperature is reduced to below 10 ℃, and 200 ml (0.25 mol) of 1.00M sodium borohydride is added dropwise within 5 hours. Stirring was continued for 1 hour after completion of the dropwise addition. 20ml of 3M nitric acid were added at 30 ℃. The organic phase was then collected in layers.
The collected organic phase was first distilled at atmospheric pressure to collect 33.67g of fraction at 55-65 ℃ and then the collected fraction was rectified to yield 30.44gR132a with a content of 99.58% and a yield of 90.2%. The rectification adopts a 70mm glass rectification column, and the seasonings are filled by a stainless steel wire mesh with the flow ratio of 4: 1.
In the invention, the content of the 1, 1-difluoro-2, 2-dichloroethane obtained by rectification is more than 98 percent, and the yield is more than 90 percent.
In the invention, the 1, 1-difluoro-2, 2-dichloroethane can be oxidized to prepare difluoroacetyl chloride, difluoroacetic acid and difluoroethyl acetate.
The method has the main advantages that hazardous wastes are comprehensively utilized, 1,1, 2-trichloro-2, 2-difluoroethane (R122) is contained in the hazardous wastes generated in the production of the 1, 1-difluoro-1-chloroethane (R142b), and the 1, 1-difluoro-1-chloroethane (R142b) hazardous wastes are mainly subjected to incineration treatment at present and pollute the environment. The process comprises rectifying and recovering 1,1, 2-trichloro-2, 2-difluoroethane (R122), dechlorinating to obtain 1, 1-difluoro-2, 2-dichloroethylene, and hydrogenating to obtain 1, 1-difluoro-2, 2-dichloroethane.
Claims (13)
1. A method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste is characterized by comprising the following steps: the method comprises the following steps:
step one, synthetic reaction: adding 1, 1-difluoro-2, 2-dichloroethylene and water into a reaction kettle, adding a proper amount of solvent, cooling to within 5 ℃, slowly dropwise adding a sodium borohydride solution, controlling the indoor temperature to be not more than 10 ℃, preserving heat for 2-3 hours after dropwise adding, then dropwise adding dilute acid to adjust the pH value, stirring for 1 hour, layering, and collecting an organic layer;
step two, distillation: distilling at normal pressure, and collecting 55-65 deg.C fraction;
step three, rectification: then rectifying to obtain the 1, 1-difluoro-2, 2-dichloroethane, wherein the total reaction yield is 90 percent.
2. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the molar ratio of the 1, 1-difluoro-2, 2-dichloroethylene to the sodium borohydride is 1: 1.
3. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the solvent used by the sodium borohydride solution is one or more of diethylene glycol dimethyl ether, DMF and THF, and diethylene glycol dimethyl ether is preferably used.
4. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the solvent amount is 1 to 3 times, preferably 2.5 times of the weight of the difluorodichloroethylene.
5. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the mol ratio of the 1, 1-difluoro-2, 2-dichloroethylene to the water is 1: 3-6, preferably 1: 4-5.
6. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the concentration of the sodium borohydride solution is 1M.
7. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the dropping temperature of the sodium borohydride solution is-10-30 ℃, and preferably 0-10 ℃.
8. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the temperature of the heat preservation reaction is 0-30 ℃, and preferably 10-20 ℃.
9. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the temperature of the dropwise addition of the dilute hydrochloric acid is 0-30 ℃, and preferably 10-20 ℃.
10. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the amount of the dropwise diluted acid is to adjust the pH value of the reaction solution to 3-4.
11. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: and collecting fractions at 55-65 ℃ during the distillation in the second step.
12. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: the conditions for obtaining the 1, 1-difluoro-2, 2-dichloroethane by rectification in the step three are that the used rectifying tower is a packed tower, the number of theoretical plates is 30-45, the reflux ratio is 3-6:1, and the temperature at the top of the tower is 58-60 ℃.
13. The method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste according to claim 1, characterized in that: and step three, the content of the 1, 1-difluoro-2, 2-dichloroethane obtained by rectification is more than 98 percent, and the yield is more than 90 percent.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111097452.2A CN113816825A (en) | 2021-09-18 | 2021-09-18 | Method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste |
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| CN202111097452.2A CN113816825A (en) | 2021-09-18 | 2021-09-18 | Method for synthesizing 1, 1-difluoro-2, 2-dichloroethane by using R142b hazardous waste |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104692997A (en) * | 2015-02-11 | 2015-06-10 | 巨化集团技术中心 | Preparation method of 1,1-difluoro-2-chloroethane |
| CN105152852A (en) * | 2015-09-16 | 2015-12-16 | 湖南城市学院 | Preparation method of 1-bromo-1-chloro-2,2-difluoroethylene |
| CN105461509A (en) * | 2015-12-01 | 2016-04-06 | 仇颖超 | Liquid-phase production method for difluorotrichloroethane |
| CN109320394A (en) * | 2018-11-13 | 2019-02-12 | 山东华安新材料有限公司 | A kind of method of difluoro dichloroethanes synthesis difluoromono-chloroethane |
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2021
- 2021-09-18 CN CN202111097452.2A patent/CN113816825A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104692997A (en) * | 2015-02-11 | 2015-06-10 | 巨化集团技术中心 | Preparation method of 1,1-difluoro-2-chloroethane |
| CN105152852A (en) * | 2015-09-16 | 2015-12-16 | 湖南城市学院 | Preparation method of 1-bromo-1-chloro-2,2-difluoroethylene |
| CN105461509A (en) * | 2015-12-01 | 2016-04-06 | 仇颖超 | Liquid-phase production method for difluorotrichloroethane |
| CN109320394A (en) * | 2018-11-13 | 2019-02-12 | 山东华安新材料有限公司 | A kind of method of difluoro dichloroethanes synthesis difluoromono-chloroethane |
Non-Patent Citations (1)
| Title |
|---|
| 大连轻工业学院编写: "精细有机合成单元反应与合成设计", pages: 260 - 155 * |
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