Oxahydrofluoroether compound, and synthesis method therefor and use thereof

Abstract

The present application belongs to the technical field of the synthesis of fluorine-containing fine chemicals, and in particular relates to an oxahydrofluoroether compound, and a synthesis method therefor and the use thereof. The oxahydrofluoroether compound has a structure represented by formula (1): Formula (1) wherein Rf is F or CF3; R is methyl or ethyl; and n is an integer of 1-3. In the oxahydrofluoroether compound disclosed in the present application, the incorporation of oxygen atoms into a fluorocarbon chain structure makes the fluorine-containing segments of the hydrofluoroether more diverse, causing the structure not to be limited to perfluorocarbon chain structures anymore. In the oxahydrofluoroether compound, the oxygen atoms perform the function of reducing surface tension, and the greater the number of the oxygen atoms, the lower the surface tension. Compared with other hydrofluoroether solvents, the oxahydrofluoroether compound exhibits stronger permeability and better cleaning effect. Due to both the incorporation of oxygen atoms into the fluorocarbon chain structure and the presence of branched chains in the fluorocarbon chain, the oxahydrofluoroether compound is readily degradable, thereby offering improved environmental friendliness.

Description

An oxahydrofluoroether compound, its synthesis method and application Technical Field

[0001] This application belongs to the field of fluorine-containing fine chemical synthesis technology, and in particular relates to an oxahydrofluoroether compound, its synthesis method and application. Background Technology

[0002] With the rapid development of information technologies such as artificial intelligence, cloud computing, big data, and blockchain, the requirements for the processing performance and integration of data center servers and communication equipment are becoming increasingly higher, leading to a continuous increase in power density. In recent years, the demand for environmentally friendly electronic cleaning agents and fluorinated electronic coolants in this field has shown a high growth trend.

[0003] Hydrofluoroethers (HFLEs) are a class of ether compounds containing fluorine, carbon, hydrogen, and oxygen. Belonging to partially fluorinated ethers, they are a new generation of ozone-depleting substances, possessing a series of excellent properties such as low viscosity, low freezing point, low surface tension, and good electrochemical stability. Unlike chlorofluorocarbons (CFCs), HFLEs do not contain halogens other than fluorine and therefore have virtually no impact on the Earth's ozone layer; thus, their ozone depletion potential is zero. Furthermore, HFLEs degrade more readily in the Earth's atmosphere, resulting in a lower global warming potential (GWP), making them ideal substitutes for CFCs. HFLEs offer unparalleled advantages over other ozone-depleting substance substitutes in fields such as electronics, precision instrument cleaning agents, lubricant thinners, polymerization solvents, leak detection fluids, heat transfer media, electronic coolants, and medical anesthetics.

[0004] Therefore, developing novel, green, and environmentally friendly hydrofluoroether compounds has become an urgent problem to be solved. Summary of the Invention

[0005] To address the shortcomings of existing technologies, this application provides an oxahydrofluoroether compound, its synthesis method, and its applications.

[0006] The oxafluoroether compounds disclosed in this application contain only the halogen element fluorine and do not contain ozone-depleting substances. They are environmentally friendly compounds.

[0007] In a first aspect, this application provides an oxahydrofluoroether compound, which adopts the following technical solution:

[0008] An oxafluoroether compound, the structure of which is shown in formula (1):

[0009] Among them, R f F or CF3; R is methyl or ethyl; n is an integer from 1 to 3.

[0010] Preferably, the oxafluoroether compound is any one of the following:

[0011] CF3OCF(CF3)CF2OCH3;

[0012] CF3OCF(CF3)CF2OCF(CF3)CF2OCH3;

[0013] CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH3;

[0014] CF3OCF(CF3)CF2OCH2CH3;

[0015] CF3OCF(CF3)CF2OCF(CF3)CF2OCH2CH3;

[0016] CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3;

[0017] CF3CF2OCF(CF3)CF2OCH3;

[0018] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH3;

[0019] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH3;

[0020] CF3CF2OCF(CF3)CF2OCH2CH3;

[0021] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3;

[0022] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3.

[0023] More preferably, the oxafluoroether compound is any one of the following:

[0024] CF3OCF(CF3)CF2OCH3;

[0025] CF3OCF(CF3)CF2OCF(CF3)CF2OCH3;

[0026] CF3CF2OCF(CF3)CF2OCH3;

[0027] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH3;

[0028] CF3OCF(CF3)CF2OCH2CH3;

[0029] CF3OCF(CF3)CF2OCF(CF3)CF2OCH2CH3;

[0030] CF3CF2OCF(CF3)CF2OCH2CH3;

[0031] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3.

[0032] More preferably, the oxafluoroether compound is selected from the following substances:

[0033] CF3OCF(CF3)CF2OCH3 or CF3CF2OCF(CF3)CF2OCH2CH3.

[0034] Secondly, this application provides a method for synthesizing oxahydrofluoroether compounds, employing the following technical solution:

[0035] A method for synthesizing an oxafluoroether compound, the method comprising the following steps: reacting an acyl fluoride compound, an alkylating agent, and an alkali metal fluoride in a polar aprotic solvent to obtain the oxafluoroether compound.

[0036] Preferably, the structure of the acyl fluoride compound is shown in formula (2):

[0037] Among them, R f It is F or CF3; m is an integer from 1 to 3.

[0038] Preferably, the acyl fluoride compound is one or more of the following:

[0039] CF3OCF(CF3)COF;

[0040] CF3OCF(CF3)CF2OCF(CF3)COF;

[0041] CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF;

[0042] CF3CF2OCF(CF3)COF;

[0043] CF3CF2OCF(CF3)CF2OCF(CF3)COF;

[0044] CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF.

[0045] More preferably, the acyl fluoride compound is selected from the following substances:

[0046] CF3OCF(CF3)COF or CF3CF2OCF(CF3)COF.

[0047] Preferably, the alkylating agent is at least one of dialkyl sulfate, dialkyl carbonate, and halogenated hydrocarbon.

[0048] More preferably, the alkylating agent is a dialkyl sulfate.

[0049] More preferably, the dialkyl sulfate is dimethyl sulfate or diethyl sulfate.

[0050] Preferably, the alkali metal fluoride is at least one of potassium fluoride, sodium fluoride, cesium fluoride, and rubidium fluoride.

[0051] Preferably, the polar aprotic solvent is at least one selected from ethylene glycol dimethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol dimethyl ether, acetonitrile, N,N-dimethylformamide, N,N-diethylformamide, N-methylpyrrolidone, and dimethyl sulfoxide.

[0052] Preferably, the molar ratio of the acyl fluoride compound to the alkylating agent is 1:(1-1.5);

[0053] More preferably, the molar ratio of the acyl fluoride compound to the alkylating agent is 1:(1-1.2).

[0054] Preferably, the molar ratio of the alkali metal fluoride to the acyl fluoride compound is 1:(2-10);

[0055] More preferably, the molar ratio of the alkali metal fluoride to the acyl fluoride compound is 1:(4-8).

[0056] Preferably, the mass ratio of the acyl fluoride compound to the polar aprotic solvent is 1:(0.8-2).

[0057] More preferably, the mass ratio of the acyl fluoride compound to the polar aprotic solvent is 1:(0.8-1.8).

[0058] Preferably, the method for synthesizing the oxafluoroether compound includes the following steps:

[0059] (1) Under nitrogen protection, alkali metal fluorides are mixed with polar aprotic solvents;

[0060] (2) After cooling, under nitrogen protection, add acyl fluoride compounds and mix.

[0061] (3) Add the alkylating agent dropwise to the mixture obtained in step (2). After the addition is complete, heat the mixture to carry out the reaction.

[0062] (4) After cooling, add alkaline solution to mix, let stand, and distill to obtain oxahydrofluoroether compound with a purity ≥99.5%.

[0063] Preferably, the temperature after cooling in step (2) is 0-20℃.

[0064] Preferably, in step (2), the reaction pressure is adjusted to 0.01-1.0 MPa before cooling.

[0065] Preferably, the temperature after heating in step (3) is 30-120℃, and the reaction time is 2-24h.

[0066] Preferably, the temperature after cooling in step (4) is 20-30℃.

[0067] Preferably, the alkaline solution in step (4) is at least one of sodium hydroxide solution, potassium hydroxide solution, sodium carbonate solution, or potassium carbonate solution; the mass concentration of the alkaline solution is 5-50%.

[0068] More preferably, the alkaline solution is a sodium hydroxide solution with a mass concentration of 10-20%.

[0069] In one specific feasible implementation, the method for synthesizing the oxafluoroether compound includes the following specific steps:

[0070] S-1: Under nitrogen protection, anhydrous alkali metal fluorides are added to a stainless steel high-pressure reactor;

[0071] S-2: After evacuating and purging the reactor, continue to add the dried polar aprotic solvent; adjust the reaction pressure of the reactor to 0.01-1.0 MPa, stir to mix the materials evenly, and cool the reactor at the same time;

[0072] S-3: After the temperature of the reactor drops to 0-20℃, under nitrogen protection, add the acyl fluoride compound to the mixture obtained in S-2 and mix.

[0073] S-4: Then, alkylating agent is added dropwise to the mixture obtained in S-3 over 0.5 hours using a dropping funnel;

[0074] S-5: Then raise the temperature to 30-120℃ and continue the reaction for 2-24 hours before stopping the reaction;

[0075] S-6: When the temperature of the kettle drops to 20-30℃, transfer the mixture obtained in S-5 to a flask, add alkaline solution and continue stirring for a period of time, then let it stand and separate the liquids;

[0076] S-7: The lower fluorine phase is removed and distilled to obtain an oxahydrofluoroether compound with a purity ≥99.5%.

[0077] Thirdly, this application provides an application of an oxahydrofluoroether compound in the preparation of electronic cleaning agents, electronic fluorinated liquids, or solvents, employing the following technical solution:

[0078] The use of an oxafluoroether compound as described in the first aspect or an oxafluoroether compound prepared by the method described in the second aspect in the preparation of electronic cleaning agents, electronic fluorinated liquids or solvents.

[0079] The series of oxafluoroether compounds provided in this application can be applied in various fields: as electronic cleaning agents in semiconductor, liquid crystal, and hard disk manufacturing; as electronic fluorinated liquids for cooling and temperature control in various stages of semiconductor manufacturing (such as manufacturing cooling machines, cooling and temperature control of upper and lower electrodes in dry etching, exposure machines for chip pattern preparation, high and low temperature cooling control of chip testing systems, chip sorting equipment, etc.), cooling and heat dissipation of heat-generating components in military radar systems and wind turbines; and as solvents for electronic coatings and screen coating thinners.

[0080] In summary, this application includes at least one of the following beneficial technical effects:

[0081] 1. The oxafluoroether compounds disclosed in this application have more diverse fluorinated segments due to the insertion of oxygen atoms in the fluorocarbon chain structure, and the structure is no longer limited to the perfluorocarbon chain structure.

[0082] 2. The oxafluoroether compound disclosed in this application has oxygen atoms that reduce surface tension, and the more oxygen atoms present, the lower the surface tension; compared with other fluoroether solvents, it has stronger permeability and better cleaning effect.

[0083] 3. The oxafluoroether compounds disclosed in this application have the advantages of having oxygen atoms embedded in the fluorocarbon chain structure and having branches in the fluorocarbon chain, making them easy to degrade and improving their environmental friendliness. Attached Figure Description

[0084] Figure 1 shows the GC-MS spectrum of CF3CF2OCF(CF3)CF2OCH3 prepared in Example 2. Detailed Implementation

[0085] Experimental methods in the following embodiments of this application that do not specify specific conditions are generally performed under conventional conditions or as recommended by the manufacturer; experimental materials and reagents mentioned below are commercially available unless otherwise specified.

[0086] Unless otherwise defined, all technical and scientific terms used in this application have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used in this application's specification is for the purpose of describing particular embodiments only and is not intended to limit the scope of this application.

[0087] The terms “comprising” and “having”, and any variations thereof, are intended to cover non-exclusive inclusion. For example, a process, method, apparatus, product, or device that includes a series of steps is not limited to the steps or modules listed, but may optionally include steps not listed, or may optionally include other steps inherent to such process, method, product, or device.

[0088] The technical solution of this application will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this application, and not all embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this application.

[0089] Raw material source:

[0090] 1. Preparation of acyl fluoride compounds CF3OCF(CF3)COF, CF3OCF(CF3)CF2OCF(CF3)COF and CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF:

[0091] First, tetramethylethylenediamine (20.4 g) as catalyst and triethylene glycol dimethyl ether (498.5 g) as a non-protic polar solvent were sequentially introduced into a clean, dry, sealed 2L stainless steel high-pressure reactor. Then, the reactor was cooled while stirring at 200 rpm. When the reactor temperature dropped to -15°C, 50 g of carbonyl fluoride was introduced into the reactor, and stirring continued for 10 min after the addition. Next, hexafluoropropylene oxide (132.4 g) was introduced into the reactor at a rate of 0.1 g / min, and stirring continued for 1 h to terminate the reaction. The reaction solution was transferred to a separatory funnel and allowed to stand to separate into layers; the upper layer was the organic phase, and the lower layer was the fluorine phase. The samples were subjected to chromatographic analysis. The fluorine phase was a mixture containing CF3OCF(CF3)COF, CF3OCF(CF3)CF2OCF(CF3)COF, and CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF, with contents of 57.3%, 36.8%, and 3.91%, respectively.

[0092] The fluorine phase was subjected to distillation to obtain CF3OCF(CF3)COF (89.3g), CF3OCF(CF3)CF2OCF(CF3)COF (57.4g), and CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF (6.0g), with a purity ≥99%.

[0093] 2. Preparation of acyl fluoride compounds CF3CF2OCF(CF3)COF, CF3CF2OCF(CF3)CF2OCF(CF3)COF and CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF:

[0094] First, tetramethylethylenediamine (20.4 g) and triethylene glycol dimethyl ether (498.5 g), an aprotic polar solvent, were sequentially introduced into a clean, dry, sealed 2L stainless steel high-pressure reactor. Then, the reactor was cooled while stirring at 200 rpm. When the reactor temperature dropped to -15°C, trifluoroacetyl fluoride (125.8 g) was introduced into the reactor, and stirring continued for 10 min after the addition. Next, hexafluoropropylene oxide (132.4 g) was introduced into the reactor at a rate of 0.2 g / min, and stirring continued for 1 h to terminate the reaction. The reaction solution was transferred to a separatory funnel and allowed to stand to separate into layers; the upper layer was the organic phase, and the lower layer was the fluorine phase. The samples were subjected to chromatographic analysis, and the fluorine phase was a mixture containing CF3CF2OCF(CF3)COF, CF3CF2OCF(CF3)CF2OCF(CF3)COF and CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF, with contents of 30.2%, 52.6% and 15.1%, respectively.

[0095] The fluorine phase was subjected to distillation to obtain CF3CF2OCF(CF3)COF (66.3g), CF3CF2OCF(CF3)CF2OCF(CF3)COF (115.4g), and CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF (33.1g), with a purity ≥99%.

[0096] Example 1:

[0097] Preparation of CF3OCF(CF3)CF2OCH3:

[0098] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, potassium fluoride (25.00 g, 0.43 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried diethylene glycol dimethyl ether (800 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 0°C. Under nitrogen protection, CF3OCF(CF3)COF (500 g, 2.16 mol) was added to the mixture. Then, dimethyl sulfate (325.42 g, 2.58 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 60°C, and the mixture was stirred for another 8 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 10% sodium hydroxide aqueous solution (340 g) is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3OCF(CF3)CF2OCH3.

[0099] Example 2:

[0100] Preparation of CF3CF2OCF(CF3)CF2OCH3:

[0101] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, potassium fluoride (29.05 g, 0.50 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried tetraethylene glycol dimethyl ether (900 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 10°C. Under nitrogen protection, CF3CF2OCF(CF3)COF (557.84 g, 2.12 mol) was added to the mixture. Then, dimethyl sulfate (315.33 g, 2.5 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 90°C, and the mixture was stirred for another 8 h to terminate the reaction. After the reactor temperature dropped to room temperature (25°C), the reaction solution was transferred to a flask, and 320 g of 10% sodium hydroxide aqueous solution was added and stirred for 10 minutes. The stirring was then stopped and the mixture was allowed to stand for 0.5 h. The lower fluorine phase was released and distilled to obtain the target product CF3CF2OCF(CF3)CF2OCH3. The product structure was confirmed by GC-MS, as shown in Figure 1.

[0102] Example 3:

[0103] Preparation of CF3OCF(CF3)CF2OCF(CF3)CF2OCH3:

[0104] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, cesium fluoride (65.32 g, 0.43 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried diethylene glycol dimethyl ether (800 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 20°C. Under nitrogen protection, CF3OCF(CF3)CF2OCF(CF3)COF (655.7 g, 2.15 mol) was added to the mixture. Then, dimethyl sulfate (325.42 g, 2.58 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 90°C, and the mixture was stirred for another 8 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 10% sodium hydroxide aqueous solution (350 g) is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3OCF(CF3)CF2OCF(CF3)CF2OCH3.

[0105] Example 4:

[0106] Preparation of CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH3:

[0107] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, cesium fluoride (65.32 g, 0.43 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried diethylene glycol dimethyl ether (800 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 20°C. Under nitrogen protection, CF3CF2OCF(CF3)CF2OCF(CF3)COF (963.2 g, 2.15 mol) was added to the mixture. Then, dimethyl sulfate (325.42 g, 2.58 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 90°C, and the mixture was stirred for another 8 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 10% sodium hydroxide aqueous solution (350 g) is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH3.

[0108] Example 5:

[0109] Preparation of CF3OCF(CF3)CF2OCH2CH3:

[0110] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, potassium fluoride (25 g, 0.43 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried N,N-dimethylformamide (900 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 0°C. Under nitrogen protection, CF3OCF(CF3)COF (500 g, 2.16 mol) was added to the mixture. Then, diethyl sulfate (397.81 g, 2.58 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 60°C, and the mixture was stirred for another 8 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 15% sodium hydroxide aqueous solution (230 g) is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3OCF(CF3)CF2OCH2CH3.

[0111] Example 6:

[0112] Preparation of CF3OCF(CF3)CF2OCF(CF3)CF2OCH2CH3:

[0113] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, potassium fluoride (17.43 g, 0.3 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried N,N-dimethylformamide (1000 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 0°C. Under nitrogen protection, CF3OCF(CF3)CF2OCF(CF3)COF (796 g, 2 mol) was added to the mixture. Then, diethyl sulfate (320.72 g, 2.08 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 90°C, and the mixture was stirred for another 10 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 10% sodium hydroxide aqueous solution (70 g) is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3OCF(CF3)CF2OCF(CF3)CF2OCH2CH3.

[0114] Example 7:

[0115] Preparation of CF3CF2OCF(CF3)CF2OCH2CH3:

[0116] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, potassium fluoride (25 g, 0.43 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried N,N-dimethylformamide (900 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 0°C. Under nitrogen protection, CF3CF2OCF(CF3)COF (564 g, 2 mol) was added to the mixture. Then, diethyl sulfate (331.51 g, 2.15 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 80°C, and the mixture was stirred for 6 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 120 g of 10% sodium hydroxide aqueous solution is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3CF2OCF(CF3)CF2OCH2CH3.

[0117] Example 8:

[0118] Preparation of CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3:

[0119] In a 2L jacketed stainless steel high-pressure reactor equipped with a stirrer, pressure gauge, and feeding funnel, cesium fluoride (65.32 g, 0.43 mol) was added under nitrogen protection, followed by sealing the reactor. The reactor was then evacuated three times. Under nitrogen protection, dried diethylene glycol dimethyl ether (800 g) was added, and the reactor pressure was reduced to 0.01 MPa. While stirring at 300 rpm, the mixture was cooled to 20°C. Under nitrogen protection, CF3CF2OCF(CF3)CF2OCF(CF3)COF (896 g, 2 mol) was added to the mixture. Then, diethyl sulfate (333.03 g, 2.16 mol) was added dropwise over 0.5 h. The reactor temperature was raised to 90°C, and the mixture was stirred for 10 h to terminate the reaction. After the reactor temperature drops to room temperature (25°C), the reaction solution is transferred to a flask, 15% sodium hydroxide aqueous solution (90 g) is added and stirred for 10 minutes. The stirring is then turned off and the mixture is allowed to stand for 0.5 h. The lower fluorine phase is released and distilled to obtain the target product CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3.

[0120] The reaction results of Examples 1-8 are shown in Table 1.

[0121] Table 1. Reaction results of Examples 1-8

[0122] As shown in Table 1, the corresponding oxafluoroether compounds can be synthesized by reacting acyl fluoride compounds with dialkyl sulfate, and the yield of the target product is >80% and the purity is >99.5%, which shows that it has the potential for large-scale production.

[0123] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0124] The embodiments described above are merely illustrative of several implementation methods of this application, and while the descriptions are specific and detailed, they should not be construed as limiting the scope of this patent application. It should be noted that those skilled in the art can make various improvements and optimizations without departing from the concept of this application, and these improvements all fall within the scope of protection of this application. Therefore, the scope of protection of this patent application should be determined by the appended claims.

Claims

An oxafluoroether compound, characterized in that, The structure of the oxafluoroether compound is shown in formula (1): Among them, R f F or CF3; R is methyl or ethyl; n is an integer from 1 to 3. An oxahydrofluoroether compound according to claim 1, characterized in that, The oxafluoroether compound is any one of the following: CF3OCF(CF3)CF2OCH3; CF3OCF(CF3)CF2OCF(CF3)CF2OCH3; CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH3; CF3OCF(CF3)CF2OCH2CH3; CF3OCF(CF3)CF2OCF(CF3)CF2OCH2CH3; CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3; CF3CF2OCF(CF3)CF2OCH3; CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH3; CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH3; CF3CF2OCF(CF3)CF2OCH2CH3; CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3; CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)CF2OCH2CH3. A method for synthesizing an oxafluoroether compound, characterized in that, The synthesis method involves the following steps: reacting an acyl fluoride compound, an alkylating agent, and an alkali metal fluoride in a polar aprotic solvent to obtain an oxahydrofluoride compound. The method for synthesizing an oxafluoroether compound according to claim 3 is characterized in that, The structure of the acyl fluoride compound is shown in formula (2): Among them, R f It is F or CF3; m is an integer from 1 to 3. The method for synthesizing an oxafluoroether compound according to claim 4 is characterized in that, The acyl fluoride compound is one or more of the following: CF3OCF(CF3)COF; CF3OCF(CF3)CF2OCF(CF3)COF; CF3OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF; CF3CF2OCF(CF3)COF; CF3CF2OCF(CF3)CF2OCF(CF3)COF; CF3CF2OCF(CF3)CF2OCF(CF3)CF2OCF(CF3)COF. The method for synthesizing an oxafluoroether compound according to claim 3 is characterized in that: The alkylating agent is at least one of dialkyl sulfate, dialkyl carbonate, and haloalkanes. The alkali metal fluoride is at least one of potassium fluoride, sodium fluoride, cesium fluoride, and rubidium fluoride; The polar aprotic solvent is at least one of ethylene glycol dimethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol dibutyl ether, tetraethylene glycol monomethyl ether, tetraethylene glycol dimethyl ether, acetonitrile, N,N-dimethylformamide, N,N-diethylformamide, N-methylpyrrolidone, and dimethyl sulfoxide. The method for synthesizing an oxafluoroether compound according to claim 3 is characterized in that, The molar ratio of the acyl fluoride compound to the alkylating agent is 1:(1-1.5); The molar ratio of the alkali metal fluoride to the acyl fluoride compound is 1:(2-10); The mass ratio of the acyl fluoride compound to the polar aprotic solvent is 1:(0.8-2). The method for synthesizing oxafluoroether compounds according to claim 3 is characterized in that, The synthesis method includes the following steps: (1) Under nitrogen protection, alkali metal fluorides are mixed with polar aprotic solvents; (2) After cooling, under nitrogen protection, add acyl fluoride compounds and mix. (3) Add the alkylating agent dropwise to the mixture obtained in step (2). After the addition is complete, heat the mixture to carry out the reaction. (4) After cooling, add alkaline solution to mix, let stand, and distill to obtain oxahydrofluoroether compound with a purity ≥99.5%. The method for synthesizing an oxafluoroether compound according to claim 8 is characterized in that: The temperature after cooling in step (2) is 0-20℃; In step (2), the reaction pressure is adjusted to 0.01-1.0 MPa before cooling down; The temperature after heating in step (3) is 30-120℃, and the reaction time is 2-24h; The temperature after cooling in step (4) is 20-30℃; In step (4), the alkaline solution is at least one of sodium hydroxide solution, potassium hydroxide solution, sodium carbonate solution, or potassium carbonate solution; the mass concentration of the alkaline solution is 5-50%. The use of an oxafluoroether compound as described in claim 1 or 2, or an oxafluoroether compound prepared by the method described in any one of claims 3-9, in the preparation of electronic cleaning agents, electronic fluorinated liquids, or solvents.

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