CN112299948A - Preparation method of 1, 1, 1-trifluoro-2-chloroethane - Google Patents
Preparation method of 1, 1, 1-trifluoro-2-chloroethane Download PDFInfo
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- CN112299948A CN112299948A CN202011385144.5A CN202011385144A CN112299948A CN 112299948 A CN112299948 A CN 112299948A CN 202011385144 A CN202011385144 A CN 202011385144A CN 112299948 A CN112299948 A CN 112299948A
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- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 claims abstract description 15
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- 239000002841 Lewis acid Substances 0.000 claims abstract description 10
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 10
- 239000000758 substrate Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 10
- 230000004913 activation Effects 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 6
- 229910003074 TiCl4 Inorganic materials 0.000 claims description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 5
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 4
- 229910004770 HSO3F Inorganic materials 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical group O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-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
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- DBUQEYQQFXCLAW-UHFFFAOYSA-N [Sb].ClF Chemical compound [Sb].ClF DBUQEYQQFXCLAW-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A preparation method of 1, 1, 1-trifluoro-2-chloroethane comprises the steps of taking hydrogen fluoride and 1, 1-difluoro-2, 1-dichloroethane as reaction substrates, and taking liquid-phase Lewis acid as a catalyst to react to obtain the 1, 1, 1-trifluoro-2-chloroethane. The invention provides a new route for synthesizing R133 a; 1, 1-difluoro-1, 2-dichloroethane is used as a by-product of 1, 1-difluoro-1-chloroethane, so that the industrial chain is prolonged, the by-product treatment cost is reduced, and the environmental pollution is reduced; the conversion rate of the 1, 1-difluoro-1, 2-dichloroethane reaches more than 99 percent, the selectivity of R133a reaches more than 95 percent, and the production cost of R133a is obviously reduced.
Description
Technical Field
The application relates to a preparation method of 1, 1, 1-trifluoro-2-chloroethane.
Background
1, 1, 1-trifluoro-2-chloroethane (abbreviation HCFC133a, R133a) is a raw material for preparing refrigerant 1, 1, 1, 2-tetrachloroethane, can also be used for preparing 2, 2, 2-trifluoroethanol and HCFC123, and can also introduce trifluoroethyl into the compound through related reactions, so that the raw material for providing trifluoroethyl is cheap.
Many methods for producing HCFC133a have been described in the literature, and among many of the published synthetic routes, only two synthetic routes using trichloroethylene or tetrachloroethylene as a starting material are industrially valuable. Can be divided into two main categories, the first category is Cr2O3/AlF3Synthesizing HCFC133a by trifluoroethylene or tetrachloroethylene gas phase fluorination reaction as a catalyst; the second method is to synthesize HCFC133a by taking trichloroethylene and anhydrous hydrogen fluoride as raw materials and carrying out liquid phase catalytic fluorination, wherein the first method belongs to a gas-solid reaction, the reaction temperature and the reaction pressure are higher, the corresponding engineering equipment investment is larger, and the production cost is increased. The second type of liquid phase fluorination process for the preparation of HCFC133a generally uses an antimony chlorofluoride catalyst. In the methods of the above two patents, the fluorination efficiency of the catalyst decreases as the reaction proceeds, and the low catalytic efficiency means that the consumption of the catalyst increases and the production cost increases.
The trichloroethylene is wide in application range and large in market demand, so that the raw material is very pretty and high in price. The high price of trichloroethylene directly leads to the high selling price of R133a of the environment-friendly refrigerant, the reduction of the production cost of R133a is a technical problem which is eagerly solved by technicians, and the key point is to find a new method for synthesizing 1, 1, 1-trifluoro-2-chloroethane.
Disclosure of Invention
In order to solve the problems, the application provides a preparation method of 1, 1, 1-trifluoro-2-chloroethane, hydrogen fluoride and 1, 1-difluoro-2, 1-dichloroethane are used as reaction substrates, and liquid phase Lewis acid is used as a catalyst to react to obtain the 1, 1, 1-trifluoro-2-chloroethane.
Preferably, the reaction temperature is 30-160 ℃, preferably 50-120 ℃, and the reaction pressure is 0.1-2.0MPa, preferably 0.3-0.7MPa gauge pressure.
Preferably, the liquid phase Lewis acid is SbCl5、SnCl4、TiCl4、HSO3Cl、HSO3F, one or a mixture of several of the F in any proportion.
Preferably, the mass of the liquid phase Lewis acid is 5 to 30%, preferably 10 to 20% of the mass of the added reaction substrate.
Preferably, the mass ratio of the hydrogen fluoride to the 1, 1-difluoro-2, 1-dichloroethane is 1: 1-10, preferably 1: 4-6.
Preferably, the liquid phase lewis acid is activated before being used for catalytic reaction.
Preferably, the activation treatment is performed as follows: mixing Lewis acid and hydrogen fluoride, wherein the activation temperature is 70-90 ℃, and the activation time is 4-8 h.
Preferably, the antimony pentachloride put into the reactor is added with anhydrous hydrogen fluoride into the reactor by a diaphragm metering pump for several times, and the temperature is raised to the set temperature and kept for the set time to ensure that the activation of the catalyst is finished. Then slowly cooling, continuously feeding 1, 1-difluoro-1, 2-dichloroethane and anhydrous hydrogen fluoride for reaction, and washing, alkali washing and rectifying the reaction product to obtain the final product.
Preferably, the temperature rise time during catalyst activation is controlled to 2 hours, and the temperature is kept constant for 6 hours when the temperature rises to about 80 ℃.
Preferably, during the reaction, the liquid level of the reactor is not higher than 60%, the reaction temperature is 45-55 ℃, and the reaction pressure is 0.6-0.8 MPa.
This application can bring following beneficial effect:
1. the invention provides a new route for synthesizing R133 a;
1, 1-difluoro-1, 2-dichloroethane is used as a by-product of 1, 1-difluoro-1-chloroethane, so that the industrial chain is prolonged, the by-product treatment cost is reduced, and the environmental pollution is reduced;
the conversion rate of the 3.1, 1-difluoro-1, 2-dichloroethane reaches more than 99 percent, the selectivity of R133a reaches more than 95 percent, and the production cost of R133a is obviously reduced.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this application, illustrate embodiment(s) of the application and together with the description serve to explain the application and not to limit the application. In the drawings:
fig. 1 is a schematic flow chart of the present application.
Detailed Description
In order to clearly explain the technical features of the present invention, the present application will be explained in detail by the following embodiments in combination with the accompanying drawings.
As shown in the drawings, the following detailed description is given by way of example in order to more clearly explain the overall concept of the present application.
In addition, in the description of the present application, it is to be understood that the terms "center", "upper", "lower", "front", "rear", "left", "right", "vertical", "horizontal", "top", "bottom", "inner", "outer", "axial", "radial", "circumferential", and the like, indicate orientations and positional relationships based on those shown in the drawings, are only for convenience of description and simplicity of description, and do not indicate or imply that the referenced devices or elements must have a particular orientation, be constructed and operated in a particular orientation, and thus, are not to be construed as limiting the present application.
The embodiments in the present specification are described in a progressive manner, and the same and similar parts among the embodiments are referred to each other, and each embodiment focuses on the differences from the other embodiments.
Furthermore, the terms "first", "second" and "first" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more of that feature. In the description of the present application, "a plurality" means two or more unless specifically limited otherwise.
In this application, unless expressly stated or limited otherwise, the terms "mounted," "connected," "secured," and the like are to be construed broadly and can include, for example, fixed connections, removable connections, or integral parts; the connection can be mechanical connection, electrical connection or communication; either directly or indirectly through intervening media, either internally or in any other relationship. The specific meaning of the above terms in the present application can be understood by those of ordinary skill in the art as appropriate.
In this application, unless expressly stated or limited otherwise, the first feature "on" or "under" the second feature may be directly contacting the first and second features or indirectly contacting the first and second features through intervening media. In the description herein, reference to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the application. In this specification, the schematic representations of the terms used above are not necessarily intended to refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
Fig. 1 is a specific flow diagram of the present application, as shown in the following example:
specific example 1:
1.0Kg of antimony pentachloride catalyst is put into a 10.0L reactor, 6.0Kg of anhydrous hydrogen fluoride is added into the reactor 5 times by a diaphragm metering pump, the temperature rise time is controlled to be 2 hours, and when the temperature rises to about 80 ℃, the temperature is kept for 6 hours, so that the catalyst is ensured to be activated completely. Then slowly cooling to 40 ℃. Then, according to the mass ratio of 1, 1-difluoro-1, 2-dichloroethane: anhydrous hydrogen fluoride ═ 6: 1, 0.7Kg/h, controlling the liquid level of the reactor to be not higher than 60%, the reaction temperature to be about 50 ℃ and the reaction pressure to be 0.6-0.8 Mpa. The reaction product is subjected to water washing, alkali washing, rectification and other systems to obtain about 99.5% of R133 a.
Specific example 2:
the continuous feeding ratio of 1, 1-difluoro-1, 2-dichloroethane to anhydrous hydrogen fluoride was changed on the basis of example 1 to 5: 1, 0.7Kg/h, and the reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 3:
the continuous feeding ratio of 1, 1-difluoro-1, 2-dichloroethane to anhydrous hydrogen fluoride was changed on the basis of example 1 to 4: 1, 0.7Kg/h, and the reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 4:
the reaction temperature was changed to 55 ℃ on the basis of example 1, and the reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 5:
the reaction temperature was changed to 60 ℃ on the basis of example 1, and the reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 6:
the catalyst was changed to SnCl4 based on example 1, and the reaction conditions were the same as in example 1, and the results are shown in Table 1.
Specific example 7:
the catalyst was changed to TiCl4 on the basis of example 1, the remaining reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 8:
the catalyst was changed to HSO3Cl on the basis of example 1, and the reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 9:
the catalyst was changed to HSO3F on the basis of example 1, and the reaction conditions were the same as in example 1, and the reaction results are shown in Table 1.
Specific example 10:
the catalyst was changed to TiCl4 and HSO3Cl (mass ratio 1: 1) on the basis of example 1, and the reaction results were shown in Table 1, except that the reaction conditions were the same as in example 1.
Specific example 11:
the catalyst was changed to TiCl4 and HSO3Cl (mass ratio 2: 1) on the basis of example 1, and the reaction results were shown in Table 1, except that the reaction conditions were the same as in example 1.
TABLE 1
Therefore, the conversion rate of the 1, 1-difluoro-1, 2-dichloroethane reaches more than 99%, the selectivity of R133a reaches more than 95%, and the production cost of R133a is obviously reduced.
The embodiments in the present specification are described in a progressive manner, and the same and similar parts among the embodiments are referred to each other, and each embodiment focuses on the differences from the other embodiments. In particular, for the system embodiment, since it is substantially similar to the method embodiment, the description is simple, and for the relevant points, reference may be made to the partial description of the method embodiment.
The above are merely examples of the present application and are not intended to limit the present application. Various modifications and changes may occur to those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the scope of the claims of the present application.
Claims (10)
1. A preparation method of 1, 1, 1-trifluoro-2-chloroethane is characterized in that: hydrogen fluoride and 1, 1-difluoro-1, 2-dichloroethane are used as reaction substrates, and liquid phase Lewis acid is used as a catalyst to react to obtain the 1, 1, 1-trifluoro-2-chloroethane.
2. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: the reaction temperature is 30-160 ℃, preferably 50-120 ℃, and the reaction pressure is gauge pressure of 0.1-2.0MPa, preferably 0.3-0.7 MPa.
3. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: the liquid phase Lewis acid isSbCl5、SnCl4、TiCl4、HSO3Cl、HSO3F, one or a mixture of several of the F in any proportion.
4. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: the mass of the liquid phase Lewis acid is 5-30%, preferably 10-20% of the mass of the added reaction substrate.
5. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: the mass ratio of the hydrogen fluoride to the 1, 1-difluoro-2, 1-dichloroethane is 1: 1-10, preferably 1: 4-6.
6. The process according to claim 5 for the preparation of 1, 1, 1-trifluoro-2-chloroethane, wherein: the liquid phase Lewis acid is activated and then used for catalytic reaction.
7. The process according to claim 6 for the preparation of 1, 1, 1-trifluoro-2-chloroethane, wherein: the activation treatment was carried out as follows: the activation temperature is 70-90 ℃, and the activation time is 4-8 h.
8. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: adding anhydrous hydrogen fluoride into antimony pentachloride put into a reactor for several times through a diaphragm metering pump, heating to a set temperature, and keeping for a set time to ensure that the catalyst is activated completely; then slowly cooling, continuously feeding 1, 1-difluoro-1, 2-dichloroethane and anhydrous hydrogen fluoride for reaction, and washing, alkali washing and rectifying the reaction product to obtain the final product.
9. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: the temperature rise time is controlled to be 2 hours when the catalyst is activated, the temperature is raised to about 80 ℃, and the temperature is kept for 6 hours.
10. The process for preparing 1, 1, 1-trifluoro-2-chloroethane according to claim 1, wherein: during the reaction, the liquid level of the reactor is not higher than 60%, the reaction temperature is 45-55 ℃, and the reaction pressure is 0.6-0.8 MPa.
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| CN102120715A (en) * | 2010-12-29 | 2011-07-13 | 江苏康泰氟化工有限公司 | Preparation method of 1,1,1-trifluoro-2-chloroethane |
| CN103508841A (en) * | 2012-06-15 | 2014-01-15 | 中化蓝天集团有限公司 | Method for preparing 1,1-difluoro-1,2-dichloroethane |
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