CN108570369B - Cleaning compositions containing oxahydrofluoroether compounds and methods for cleaning - Google Patents

Abstract

The invention provides a cleaning composition containing an oxahydrofluoroether compound and a method for cleaning the same. The present invention relates to cleaning compositions comprising an oxahydrofluoroether compound, the cleaning compositions comprising an oxahydrofluoroether compound and (or) at least one lower alkyl alcohol, halogenated hydrocarbon, hydrofluorocarbon, fluoroolefin, and combinations thereof. The cleaning composition is an environment-friendly composition with almost zero ODP value, low GWP value and non-inflammability. The cleaning composition can effectively remove oil stains on the surface of equipment or parts, and residues such as a welding removing agent and the like.

Description

Cleaning compositions containing oxahydrofluoroether compounds and methods for cleaning

Technical Field

The invention relates to the technical field of cleaning, in particular to a cleaning composition containing oxa-hydrofluoroether and a cleaning application method. The cleaning composition is used for removing grease attached to articles such as integrated circuit electronic parts, precision machinery parts, glass substrates and the like, and flux of printed boards.

Background

Among many cleaning agents, fluorine-based cleaning agents account for a large proportion. However, conventional fluorine-based cleaning agents such as fluorodichloroethane HCFC-141b and dichloropentafluoropropane AK-225 are excessive ozone-depleting substances. With the increasing awareness of environmental protection, fluorine-based cleaning agents which are less or not destroyed to the ozone layer are developed and used for replacing cleaning agents which excessively consume the ozone layer, and the fluorine-based cleaning agents become important concerns of enterprises and academia.

Unlike chlorofluorocarbons, oxygen-hydrofluoroether compounds containing fluorine as the only halogen do not affect the earth's ozone layer. Such oxahydrofluoroether compounds exhibit an "ozone depletion potential" ODP of zero.

The oxahydrofluoroether compound is a polyhalogen oxyperfluoropolyether compound, has a chain segment structure of-CF 2-O-, and is easily degraded into carbon dioxide and fluoride salt in the earth atmosphere. Compared with perfluoroalkyl chain segments, the oxahydrofluoroether compound with a structure of-CF 2-O-has extremely low GWP value.

Disclosure of Invention

The invention provides a cleaning agent composition containing oxygen heterohydrofluoroether compound, trans-1, 2-chloroethylene (t-DCE) and lower alkyl alcohol (the number of carbon atoms is 1-3), which is characterized in that the cleaning agent composition is prepared by mixing the following raw materials in percentage by weight: 20-85 wt% of oxahydrofluoroether compound, 10-70 wt% of trans-1, 2-chloroethylene (t-DCE), and 0.1-10 wt% of lower alkyl alcohol (carbon atom number is 1-3).

The lower alkyl alcohol can be one or a mixture of methanol, ethanol, propanol or isopropanol.

The invention provides a cleaning agent composition containing oxygen heterohydrofluoroether compound, trans-1, 2-chloroethylene (t-DCE) and lower alkyl alcohol (the number of carbon atoms is 1-3), which is characterized in that the cleaning agent composition is prepared by mixing the following raw materials in percentage by weight: 20-85 wt% of oxahydrofluoroether compound, 10-70 wt% of trans-1, 2-chloroethylene (t-DCE) and 0.1-10 wt% of methanol.

The invention provides a cleaning agent composition containing oxygen heterohydrofluoroether compound, trans-1, 2-chloroethylene (t-DCE) and lower alkyl alcohol (the number of carbon atoms is 1-3), which is characterized in that the cleaning agent composition is prepared by mixing the following raw materials in percentage by weight: 20-85 wt% of oxahydrofluoroether compound, 10-70 wt% of trans-1, 2-chloroethylene (t-DCE) and 0.1-10 wt% of ethanol.

The invention provides a cleaning agent composition containing oxygen heterohydrofluoroether compound, trans-1, 2-chloroethylene (t-DCE) and lower alkyl alcohol (the number of carbon atoms is 1-3), which is characterized in that the cleaning agent composition is prepared by mixing the following raw materials in percentage by weight: 20-85 wt% of oxahydrofluoroether compound, 10-70 wt% of trans-1, 2-chloroethylene (t-DCE) and 0.1-10 wt% of isopropanol.

As a preferred technical scheme, the oxahydrofluoroether compound is represented by the general formula CF₃O(CF₂O)_mCF₂CF₂R is OR1, (OCF (CF)₃)CF₂)_nOR2 OR OCF₂CF₂OR3, R1, R2 and R3 are C1-C3 straight chain OR branched chain alkyl;

the oxahydrofluoroether compound is specifically CF₃O(CF₂O)_mCF₂CF₂OR1(Ⅰ)、CF₃O(CF₂O)_mCF₂CF₂(OCF(CF₃)CF₂)_nOR2(Ⅱ)、CF₃O(CF₂O)_mCF₂CF₂OCF₂CF₂OR₃(III), m is an integer of 0 to 6, and n is an integer of 0 to 6.

The oxahydrofluoroether compound is selected from the following:

CF₃OCF₂CF₂OR；CF₃OCF₂OCF₂CF₂OR；CF₃OCF₂OCF₂OCF₂CF₂OR；CF₃OCF₂OCF₂OCF₂OCF₂CF₂OR；CF₃OCF₂OCF₂OCF₂OCF₂OCF₂CF₂OR；

CF₃OCF₂CF₂OCF(CF₃)CF₂OR；CF₃OCF₂OCF₂CF₂OCF(CF₃)CF₂OR；CF₃O(CF₂O)₂CF₂CF₂OCF(CF₃)CF₂OR；CF₃O(CF₂O)₃CF₂CF₂OCF(CF₃)CF₂OR；CF₃OCF₂CF₂(OCF(CF₃)CF₂)₂OR；CF₃OCF₂OCF₂CF₂(OCF(CF₃)CF₂)₂OR；CF₃OCF₂CF₂(OCF(CF₃)CF₂)₃OR；CF₃OCF₂OCF₂CF₂(OCF(CF₃)CF₂)₃OR；

CF₃OCF₂CF₂OCF₂CF₂OR；CF₃OCF₂OCF₂CF₂OCF₂CF₂OR；CF₃OCF₂OCF₂OCF₂CF₂OCF₂CF₂OR；CF₃OCF₂OCF₂OCF₂OCF₂CF₂OCF₂CF₂OR；

preferably, the number of oxygen atoms/the number of fluorine atoms in the oxahydrofluoroether compound is not less than 1: 3. The invention provides a preparation method of the oxahydrofluoroether compound in the cleaning composition.

The oxahydrofluoroether compound is prepared by the following method: reacting fluorine-containing acyl fluoride compound with alkylating agent and fluoride salt to synthesize oxahydrofluoroether compound; the fluorine-containing acyl fluoride compound is selected from CF₃O(CF₂O)_mCF₂COF or CF₃O(CF₂O)_mCF₂CF₂(OCF(CF₃)CF₂)_nOCF(CF₃) COF; wherein m is an integer of 0 to 6; n is an integer of 0 to 6; the alkylating reagent is selected from one of dimethyl sulfate, diethyl sulfate, dipropyl sulfate and diisopropyl sulfate.

The oxahydrofluoroether compound is prepared by the following method: the oxo-hydrofluoroether compounds are synthesized using a reaction of a fluorinated or perfluorinated vinyl ether selected from the group consisting of CF and an alkylating agent₃O(CF₂O)mCF₂CF₂OCF＝CF₂The compound of (1), wherein m is an integer of 0 to 6; the alkylating agent is selected from the group consisting of methyl hypofluorites.

In some embodiments of the invention, the oxahydrofluoroether compound CF₃OCF₂OCF₂CF₂OCH₃The preparation method comprises the following steps:

taking 1.5-3moL CF₃OCF₂OCF₂COF, 1.5-3moL of anhydrous diethylene glycol dimethyl ether, 1.5-3moL of potassium fluoride, 0.0036-0.0108moL of phase transfer catalyst and 1.5-3moL of dimethyl sulfate are added into a 1-5L autoclave, stirred at the rotating speed of 200-53 r/min and heated to 48-53 ℃, and then the temperature is kept for 22-26 hours at 48-53 ℃ for reaction, 100-400g of potassium hydroxide aqueous solution with the mass fraction of 40-60% is added, the temperature is heated to 55-60 ℃, and the temperature is kept for 40-60 minutes at 55-60 ℃, then a separating funnel is used for separating, and the lower layer liquid is rectified to obtain a crude product. Distilling the crude product to obtain the target product CF₃OCF₂OCF₂CF₂OCH₃. Wherein the phase transfer catalyst is selected from one or a mixture of more of tetrabutylammonium chloride, tetrabutylammonium fluoride, trioctylmethylammonium chloride and tetradecyldimethylbenzylammonium chloride. Preferably, the phase transfer catalyst is a mixture of tetrabutylammonium fluoride and tetrabutylammonium chloride in a mass ratio of 1: 2.

Notably, CF₃OCF₂OCF₂COFs can be obtained both with reference to the preparation processes disclosed in the prior art, for example in US3721696, and also using techniques which have been developed per se.

In some embodiments of the invention, the oxahydrofluoroether compound CF is prepared₃OCF₂OCF₂CF₂OCF₂CF₂OCH₃The preparation process comprises the following steps:

adding 0.4-0.6 mol of potassium fluoride and 0.3-0.5 mol of tetraethylene glycol dimethyl ether into a 1.5-3L autoclave, and then adding 1.5-3mol of CF₃OCF₂OCF₂COF, reducing the temperature in the autoclave to-2-1 ℃ through a dry ice cold trap, and then, reducing the temperature to 0.3-0 ℃.Introducing 1.5-3mol of hexafluoropropylene oxide at a flow rate of 6g/min, continuously stirring at a rotating speed of 100-300 revolutions per minute for 20-50 minutes after the introduction is finished, carrying out addition reaction, and rectifying the crude product to obtain CF₃OCF₂OCF₂CF₂OCF(CF₃)COF；

Adding 0.5 to 1.5mol of CF₃OCF₂OCF₂CF₂OCF(CF₃) COF was dropped into a three-necked flask equipped with a reflux condenser containing 1 to 1.5mol of anhydrous sodium carbonate and 1.5 to 2mol of diethanol dimethyl ether, and the reaction internal temperature was maintained at 45 to 55 ℃ for 2.5 to 3.5 hours. Then heating to 138-142 ℃ at the speed of 1-5 ℃/min, preserving the heat at 140 ℃ for 30min for decarboxylation, and further rectifying the generated product to obtain the fluorine-containing vinyl ether CF₃OCF₂OCF₂CF₂OCF＝CF₂；

Adding 0.5 to 1mol of CF₃OCF₂OCF₂CF₂OCF＝CF₂0.4 to 0.8mol of tetraethylene glycol dimethyl ether is added into an autoclave, and then 0.7 to 0.9mol of methyl hypofluorite CH is introduced at a rate of 0.5 to 1.5g/min₃OF, heating to 58-62 ℃, and keeping the temperature at 58-62 ℃ for 3.5-4.5 hours for reaction. Separating the obtained product by a separating funnel to obtain a target product, and rectifying the target product to obtain a product CF₃OCF₂OCF₂CF₂OCF₂CF₂OCH₃。

The invention also provides a method for cleaning a cleaning composition containing the oxahydrofluoroether compound.

A method for cleaning, comprising:

a) contacting a surface comprising residues with a cleaning composition comprising an oxahydrofluoroether compound of claim 1 or2, and

b) removing the residue from the surface.

The residue comprises metalworking oil, sweat grease, rosin flux.

The present invention relates to cleaning compositions comprising an oxahydrofluoroether compound, the cleaning compositions comprising an oxahydrofluoroether compound and (or) at least one lower alkyl alcohol, halogenated hydrocarbon, hydrofluorocarbon, fluoroolefin, and combinations thereof. The cleaning composition is an environment-friendly composition with almost zero ODP value, low GWP value and non-inflammability. The cleaning composition can effectively remove oil stains on the surface of equipment or parts, and residues such as a welding removing agent and the like.

Detailed Description

In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below.

FIG. 1 is the CF product of example 1₃OCF₂OCF₂CF₂OCH₃GC-MS spectrum of (1).

The instruments and conditions used for the analysis were as follows:

an Agilent7980/5977E gas chromatography-mass spectrometer is adopted,

a chromatographic column: HP-5ms Quartz capillary chromatography column (30m 250 μm 0.25 μm, Agilent)

Column temperature: maintaining at 40 deg.C for 1min, then programming at 30 deg.C/min to 130 deg.C, then raising at 5 deg.C/min to 250 deg.C, then raising at 10 deg.C/min to 300 deg.C, and maintaining for 8 min;

carrier gas: helium, purity: 99.999%, flow rate of the split outlet: 1.2 ml/min;

sample inlet temperature: 280 deg.C

Ion source temperature: 230 deg.C

Quadrupole temperature: 150 ℃ C

Column carrier gas (flow rate): he (1.0ml/min, > 99.999%)

Sample introduction amount: 1.0 μ L

And (3) sample introduction mode: no shunt sampling;

a mass spectrum detector: EI source, 70eV.

Selective ion monitoring:

MS(EI)[m/e(species)]:

263(CF₃OCF₂OCF₂CFOCH₃ ⁺)，

197(CF₂OCF₂CF₂OCH₃ ⁺)，

135(CF₃OCF₂ ⁺)，

131(CF₂CF₂OCH₃ ⁺)，

119(C₂F₅ ⁺)，

97(C₂F₃O⁺)，

69(CF₃ ⁺)。

the raw materials in the examples are introduced:

isopropanol, CAS number: 67-63-0.

Absolute ethanol, CAS No.: 64-17-5.

Trans 1, 2-vinyl chloride (t-DCE), CAS number: 156-60-5.

Example 1

Oxahydrofluoroether compound CF₃OCF₂OCF₂CF₂OCH₃Preparation of

CF₃OCF₂OCF₂COFs were prepared according to the method shown in US patent US3721696A, example 1.

Preparation of CF₃OCF₂OCF₂The chromatographic conditions in the COF process were as follows:

chromatograph: agilent 7890;

a chromatographic column: coating 1% of SP-1000 with the length of 7.3m and the inner diameter of 3 mm-4 mm on a Carbopak B with the length of 0.15 mm-0.25 mm;

column temperature: maintaining at 60 deg.C for 2min, heating to 180 deg.C at 35 deg.C/min, and maintaining for 3 min;

vaporization temperature: 230 ℃;

a detector: 230 ℃;

carrier gas pressure: 60 kPa;

air pressure: 50 kPa;

hydrogen pressure: 60 kPa;

the split ratio is as follows: 1: 16.5;

sample introduction amount: 1 uL;

tail blowing: 40 mL/min;

purging the spacer: 5.4 mL/min.

Table 1: gas chromatography product composition analysis results table

Distilling and separating the product to obtain the fluorine-containing ether alkyl acyl fluoride CF₃OCF₂OCF₂And (3) COF. Taking CF₃OCF₂OCF₂COF (496g, 2mol), anhydrous diglyme (300mL, 2.1mol), potassium fluoride (139.2g, 2.4mol), phase transfer catalyst tetrabutyl ammonium chloride (2g, 0.0072mol) and dimethyl sulfate (252g, 2mol) are uniformly mixed in a 2L autoclave, stirred and heated to 52 ℃ at 300 revolutions per minute, and the temperature is kept at 52 ℃ for 24 hours; then adding 50% by mass of potassium hydroxide aqueous solution (200g), and uniformly mixing; heating the obtained mixture to 55 ℃, preserving the heat for 45 minutes at 55 ℃, then separating liquid by using a separating funnel, and collecting the lower layer liquid; rectifying the lower layer liquid to obtain the CF containing the target product₃OCF₂OCF₂CF₂OCH₃The crude product of (1). Distilling the crude product to obtain the target product CF with the purity of 99.5 percent and the yield of 96.4 percent₃OCF₂OCF₂CF₂OCH₃(b.p. ═ 76 ℃). The structure of the product was confirmed by 19F-NMR and GCMS.

Example 2

Oxahydrofluoroether compound CF₃OCF₂OCF₂CF₂OCH₃Preparation of

Fluorine-containing acyl fluoride CF₃OCF₂COF was prepared according to example 1.

Distilling and separating the product to obtain the fluorine-containing ether alkyl acyl fluoride CF₃OCF₂And (3) COF. Taking CF₃OCF₂COF (364g, 2mol), anhydrous diglyme (300mL, 2.1mol), potassium fluoride (139.2g, 2.4mol), phase transfer catalyst tetrabutylammonium chloride (2g, 0.0072mol) and dimethyl sulfate (252g, 2mol) were mixed well in a 2L autoclave, stirred at 300 rev/minHeating to 52 ℃, and keeping the temperature at 52 ℃ for 24 hours; then adding 50% by mass of potassium hydroxide aqueous solution (200g), and uniformly mixing; heating the obtained mixture to 50 ℃, preserving the heat at 50 ℃ for 30 minutes, then separating liquid by using a separating funnel, and collecting the lower layer liquid; rectifying the lower layer liquid to obtain the CF containing the target product₃OCF₂CF₂OCH₃The crude product of (1). Distilling the crude product to obtain the target product CF with the purity of 99.5 percent and the yield of 96.4 percent₃OCF₂CF₂OCH₃(b.p. ═ 48 ℃). The structure of the product was confirmed by 19F-NMR and GCMS.

Example 3

Hydrofluoroether CF₃OCF₂OCF₂CF₂OCF₂CF₂OCH₃Preparation of

CF₃OCF₂OCF₂COF was prepared according to example 1.

Into a 2L autoclave were charged potassium fluoride (30g, 0.516mol) and tetraglyme (100g, 0.45mol), mixed, followed by addition of fluoroether-containing alkylacyl fluoride CF₃OCF₂OCF₂COF (332g, 2 mol); reducing the temperature of the reaction system to 0 ℃ through a dry ice cold trap; then hexafluoropropylene oxide HFPO (415g, 2.5mol) was fed in at a rate of 0.5 g/min; after the feeding is finished, continuously stirring at 200 revolutions per minute for 30 minutes to carry out addition reaction; the addition reaction product is rectified to obtain CF₃OCF₂OCF₂CF₂OCF(CF₃) And (3) COF. After gas chromatography (conditions of chromatography as in example 1), the product CF₃OCF₂OCF₂CF₂OCF(CF₃) The content of COF was 78%.

CF is prepared by₃OCF₂OCF₂CF₂OCF(CF₃) COF (414g, 1.0mol) was dropped into a three-necked flask with a reflux condenser containing anhydrous sodium carbonate (127.2g, 1.2mol) and diethanol dimethyl ether (400g, 1.8mol), and the temperature of the reaction system was maintained at 50 ℃ and maintained at 50 ℃ for 3 hours; heating to 140 deg.C at a heating rate of 3 deg.C/min, maintaining at 140 deg.C for 30min, performing decarboxylation, collecting decarboxylationA product; rectifying the decarboxylation reaction product to obtain the fluorine-containing vinyl ether CF₃OCF₂OCF₂CF₂OCF＝CF₂(320g, 0.92mol) in a yield of 92%.

Reacting fluorine-containing vinyl ether CF₃OCF₂OCF₂CF₂OCF＝CF₂(278g, 0.8mol), tetraethylene glycol dimethyl ether (150g, 0.675mol) was charged into the autoclave, followed by feeding methyl hypofluorite CH at a rate of 1g/min₃OF (42g, 0.84mol), after the feeding is finished, keeping the temperature at 60 ℃ for reacting for 4 hours, and collecting a crude product; separating and rectifying the crude product by a separating funnel to obtain the target product CF₃OCF₂OCF₂CF₂OCF₂CF₂OCH₃(b.p. ═ 126 ℃ C.) (300g, 0.785mol) with a yield of 98%.

Test example 1

The abbreviations in the following tables indicate the following meanings:

t-DCE trans-dichloroethylene

MeOH methanol

EtOH ethanol

IPA, isopropyl alcohol

The cleaning agent compositions shown in Table 1 were measured for flash points at 25 ℃ and 40 ℃ and at the boiling point of the compositions by the method described in ASTM D92-90 using a Cleveland open flash point tester, and the results are shown in Table 1.

TABLE 1

Test example 2

The cleaning agent compositions shown in Table 1 were measured for flash points at 25 ℃ and 40 ℃ and at the boiling point of the compositions by the method described in ASTM D92-90 using a Cleveland open flash point tester, and the results are shown in Table 2.

TABLE 2

Application example 1

Cleaning of liquid crystal display screen

On the production line of the liquid crystal display screen, a cleaning agent is needed to remove residues of the beautifying glue and the sweat grease.

The liquid crystal display was cleaned at room temperature using the cleaning agent composition formed by the composition described in table 3 of the present invention, and the removal of the masking tape was evaluated visually for the display after cleaning. The results are shown in Table 3. In Table 3, O indicates excellent removal, Δ indicates slight residue, and X indicates residue or corrosive effect on the liquid crystal display panel.

TABLE 3

Example (b)	CF3OCF2CF2OCH3	t-DCE	MeOH	Conditions of glue removal
					1	85	14.5	0.5	O
2	83	16	1	O
					3	80	19.5	0.5	O
4	75	24.5	1	Δ
					5	70	29.5	0.5	×

Application example 2

Gear oil stain removal

The cleaning tests of the motor transmission gear oil were carried out using the solvent composition formed with the composition described in Table 4. That is, the gear is immersed in the engine oil to adhere the engine oil. After the test piece was taken out from the engine oil, it was dipped in the solvent composition kept at 40 ℃ and washed with ultrasonic waves for 5 minutes. The test piece after washing was visually evaluated for the removal of the engine oil. The results are shown in Table 4. In Table 4, O indicates excellent removal, Δ indicates slight residue, and X indicates residue.

TABLE 4

Example (b)	CF3OCF2OCF2CF2OCH3	t-DCE	MeOH	Residual situation
					1	85	14.5	0.3	×
2	80	19.5	0.5	×
					3	70	29.2	0.8	Δ
4	60	39.1	0.9	O
					5	50	49	1	O
6	40	58	2	O
					7	30	68	2	O
8	30	67	3	O
					9	26.5	70	3.5	O

The foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.

Claims (6)

1. Cleaning composition containing oxahydrofluoroether compoundThe cleaning composition is characterized by being prepared by mixing the following raw materials in percentage by weight: 80-85 wt% of oxahydrofluoroether compound, 14.5-19.5 wt% of trans-1, 2-chloroethylene (t-DCE), 0.5-1 wt% of lower alkyl alcohol with 1-3 carbon atoms; the oxahydrofluoroether compound is CF₃OCF₂CF₂OCH₃。

2. A cleaning composition containing an oxahydrofluoroether compound, wherein the cleaning composition is formed by mixing the following raw materials in parts by weight: 30-50 wt% of oxahydrofluoroether compound, 49-68 wt% of trans-1, 2-chloroethylene (t-DCE), 1-2 wt% of lower alkyl alcohol with 1-3 carbon atoms; the oxahydrofluoroether compound is CF₃OCF₂OCF₂CF₂OCH₃。

3. A cleaning composition containing an oxahydrofluoroether compound of claim 2, wherein said oxahydrofluoroether compound is CF₃OCF₂OCF₂CF₂OCH₃(ii) a The CF₃OCF₂OCF₂CF₂OCH₃The preparation method comprises the following steps:

taking 1.5-3moL CF₃OCF₂OCF₂COF, 1.5-3moL of anhydrous diethylene glycol dimethyl ether, 1.5-3moL of potassium fluoride, 0.0036-0.0108moL of phase transfer catalyst and 1.5-3moL of dimethyl sulfate are added into a 1-5L autoclave, stirred at the rotating speed of 200-53 r/min and heated to 48-53 ℃, and then the mixture is subjected to heat preservation at 48-53 ℃ for 22-26 hours for reaction, 100-400g of potassium hydroxide aqueous solution with the mass fraction of 40-60% is added, the mixture is heated to 55-60 ℃, and the mixture is subjected to heat preservation at 55-60 ℃ for 40-60 minutes, then a separating funnel is used for separating, and the lower layer liquid is rectified to obtain a crude product; distilling the crude product to obtain the target product CF₃OCF₂OCF₂CF₂OCH₃；

The phase transfer catalyst is selected from one or a mixture of tetrabutylammonium chloride, tetrabutylammonium fluoride, trioctylmethylammonium chloride and tetradecyldimethylbenzylammonium chloride.

4. A cleaning composition containing an oxahydrofluoroether compound according to claim 3, wherein the phase transfer catalyst is a mixture of tetrabutylammonium fluoride and tetrabutylammonium chloride in a mass ratio of 1: 2.

5. A method for cleaning, comprising:

a) contacting a surface comprising residues with a cleaning composition comprising an oxahydrofluoroether compound of claim 1 or2, and

b) removing the residue from the surface.

6. The method for cleaning of claim 5, wherein the residue comprises metalworking oil, sweat, rosin flux.

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