WO2021177260A1 - Methods for producing iodofluoroalkane and fluoroolefin - Google Patents

Abstract

Novel production methods are provided by which an iodofluoroalkane and a fluoroolefin can be efficiently produced in high yield. One of the methods is for producing an iodofluoroalkane represented by the general formula (2): R¹CF₂CH₂I (wherein R¹ represents a fluoroalkyl group having 1-10 carbon atoms), and includes a step in which a fluoroalkyl alcohol represented by the general formula (1): R¹CF₂CH₂OH (wherein R¹ represents a fluoroalkyl group having 1-10 carbon atoms) is reacted with iodine in a solvent in the presence of triphenylphosphine, the solvent including at least one compound selected from the group consisting of sulfur-atom-containing compounds and amides.

Description

Method for producing fluoroalkane iodide and fluoroolefin

The present disclosure relates to a method for producing fluoroalkane iodide and fluoroolefin.

The fluoroolefin 2,3,3,4,5,4-hexafluoro-1-butene (HFO-1336 mcyf) is promising as a next-generation refrigerant. HFO-1336 mcyf can be produced, for example, from 1,1,1,2,2,3,3-heptafluoro-4-iodobutane (IHFB), which is a fluoroalkane iodide.
As a method for producing IHFB, for example, first, 2,2,3,3,4,5,4-heptafluoro-1-butanol (7FB) is reacted with p-toluenesulfonyl chloride to produce 1,1-di. A method is known in which -H-perfluorobutyl p-toluenesulfonate is obtained, and then this and NaI are heated in diethylene glycol until the reaction vessel temperature reaches 220 ° C. to react (Non-Patent Document 1). ).
As another method for producing IHFB, for example, 7FB is first reacted with 1,1,1,3,3,3-hexamethyldisilazane (HMDS) to obtain C ₃ F ₇ CH ₂ OSiMe ₃ . Next, _{a method is known in which Ph 3} PICl is added thereto, reflux is carried out in hexane, the solvent is distilled off, and the obtained powder is thermally decomposed at 160 to 190 ° C. (Non-Patent Document 2).
As another method for producing fluoroalkane iodide, for example, HCF ₂ (CF ₂ ) ₃ CH ₂ OH or HCF ₂ (CF ₂ ) ₉ CH ₂ OH, triphenylphosphine, imidazole and iodine are used as diethyl ether. A method of reacting in a mixed solvent of acetonitrile is known (Non-Patent Document 3).

An object of the present disclosure is to provide a novel production method capable of efficiently producing fluoroalkane iodide and fluoroolefin in high yield.

Item 1. General formula (2): R ¹ CF ₂ CH ₂ I
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
It is a method for producing fluoroalkane iodide represented by.
General formula (1): R ¹ CF ₂ CH ₂ OH
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
Includes a step of reacting a fluorine-containing alkyl alcohol represented by (1) with iodine in the presence of triphenylphosphine in a solvent.
A production method, wherein the solvent contains at least one selected from the group consisting of compounds containing sulfur atoms and amides.
Item 2. Item 2. The iodide according to Item 1, wherein the solvent contains at least one selected from the group consisting of N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA) and N-methylpyrrolidone (NMP). Method for producing fluoroalkane.
Item 3. Item 3. The method for producing a fluoroalkane iodide according to Item 1 or 2, wherein R ^{1 is a perfluoroalkyl group having 1 to 2 carbon atoms.}
Item 4. Item 3. The method for producing a fluoroalkane iodide according to any one of Items 1 to 3, wherein 1.5 to 5 mol of iodine is reacted with 1 mol of the fluorine-containing alkyl alcohol.
Item 5. The method for producing a fluoroalkane iodide according to any one of Items 1 to 4, wherein the step of reacting with iodine is carried out at a temperature of 40 to 150 ° C.
Item 6. General formula (3): R ¹ CF = CH ₂
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
It is a method for producing a fluoroolefin represented by
A production method comprising a step of dehalogenating the fluoroalkane iodide obtained by the method for producing a fluoroalkane iodide according to any one of Items 1 to 5 in the presence of a catalyst.
Item 7. General formula (2): R ¹ CF ₂ CH ₂ I
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
Fluoroalkane iodide represented by and / or
General formula (3): R ¹ CF = CH ₂
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
Contains fluoroolefins represented by
Further, the general formula (4): R ¹ CF ₂ CH ₂ OC (= O) R ²
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms, and R ² represents an alkyl group having −H or 1 to 3 carbon atoms).
Compounds represented by and / or
General formula (5): R ¹ CF ₂ CH ₃
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
A composition comprising a compound represented by.
Item 8. Item 2. The composition according to Item 7, wherein the total content of the compound represented by the general formula (4) and the compound represented by the general formula (5) is 20% by mass or less of the total composition.

The present disclosure provides a novel production method capable of efficiently producing fluoroalkane iodide and fluoroolefin in high yield.

The disclosure includes the following embodiments:
The present disclosure describes the general formula (2): R ¹ CF ₂ CH ₂ I
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
It is a method for producing fluoroalkane iodide represented by.
General formula (1): R ¹ CF ₂ CH ₂ OH
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
Includes a step of reacting a fluorine-containing alkyl alcohol represented by (1) with iodine in the presence of triphenylphosphine in a solvent.
The present invention relates to a production method, wherein the solvent contains at least one selected from the group consisting of a compound containing a sulfur atom and an amide.

In the above general formula (1), R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms. The fluorine-containing alkyl group having 1 to 10 carbon atoms is not particularly limited as long as it is an alkyl group having 1 to 10 carbon atoms in which one or more -H is substituted with -F, and is a linear or branched chain. It may be in the shape or ring shape. Further, as the fluorine-containing alkyl group having 1 to 10 carbon atoms, a perfluoroalkyl group having 1 to 10 carbon atoms is preferably mentioned.
Examples of linear and branched perfluoroalkyl groups having 1 to 10 carbon atoms include -CF ₃ , -C ₂ F ₅ , -C ₃ F ₇ , -C ₄ F ₉ , and -C ₅ F _11. , -C ₆ F ₁₃ , -C ₇ F ₁₅ , -C ₈ F ₁₇ , -C ₉ F ₁₉ , -C ₁₀ F _21, etc. -C _n F _{2n + 1} (n = 1 to 10) and the like. Examples of the cyclic perfluoroalkyl group having 1 to 10 carbon atoms include -C ₃ F ₅ , -C ₄ F ₇ , -C ₅ F ₉ , -C ₆ F ₁₁ , -C ₇ F ₁₃ , and -C _{8. F 15, -C 9 F 17,} -C 10 -C such _{F 19 n F 2n-1 (} n = 1 ~ 10) , and the like.
Further, from the viewpoint that fluoroalkane iodide can be easily synthesized (with high reaction efficiency) and obtained in high yield, ^{the carbon number of R 1} is preferably 1 to 3, more preferably 1 to 2, and particularly preferably 2.
As described above, as the fluorine-containing alkyl group having 1 to 10 carbon atoms, a perfluoroalkyl group having 1 to 3 carbon atoms is preferable, a perfluoroalkyl group having 1 to 2 carbon atoms is more preferable, and a perfluoroalkyl group having 2 carbon atoms is more preferable. Alkyl groups are particularly preferred.
As the fluorine-containing alkyl alcohol represented by the general formula (1), 2,2,3,3,4,5,4-heptafluoro-1-butanol (7FB) is particularly preferable.

As the fluorine-containing alkyl group having 1 to 10 carbon atoms ^{of R 1} in the general formula (2), examples (preferably examples, etc.) of the fluorine-containing alkyl group having 1 to 10 carbon atoms ^{in R 1 in the above general formula (1).} (Including) and the same.
As the fluoroalkane iodide represented by the general formula (2), 1,1,1,2,2,3,3-heptafluoro-4-iodobutane (IHFB) is particularly preferable.

The solvent used in the iodination reaction step (step of reacting with iodine) contains at least one selected from the group consisting of compounds containing sulfur atoms and amides. Examples of the solvent include amides such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA) and N-methylpyrrolidone (NMP); sulfur atoms such as dimethyl sulfoxide (DMSO) and sulfolane ( Examples thereof include compounds containing S).
The solvent may be used alone or in combination of two or more.

The solvent preferably contains amide from the viewpoint of easy synthesis of fluoroalkane iodide (with high reaction efficiency) and high yield; N, N-dimethylformamide (DMF), N, N-dimethyl. More preferably, it comprises at least one selected from the group consisting of acetamide (DMA) and N-methylpyrrolidone (NMP); the group consisting of N, N-dimethylformamide (DMF) and N, N-dimethylacetamide (DMA). It is more preferable to include at least one selected from the above; it is particularly preferable to include N, N-dimethylacetamide (DMA).

In the above iodination reaction, first, a salt: [Ph ₃ PI] ⁺ I ⁻ is produced _{by the reaction of triphenylphosphine (PPh 3} ) and iodine (I _2). Subsequently, the ^{_{salt: [Ph 3 PI] + I}} - a fluorine-containing alkyl alcohol of the general formula (1) react, the ^{_{salt: [R 1 CF 2 CH 2}} O-PPh 3] + I - is produced, Finally, a fluoroalkane iodide is obtained by a nucleophilic substitution reaction (SN2 reaction) of iodide ions. Here, when the solvent is an amide, the solubility of each of the salts (active species) is further improved, so that the reaction between the fluoroalkyl alcohol and the salt (active species) and / or the iodide ion. It is considered that the reactivity of the nucleophilic substitution reaction (SN2 reaction) is further improved and fluoroalcohol iodide can be obtained in a higher yield.

Further, by increasing the amount of iodine and triphenylphosphine used, the amount of each of the above salts (active species) produced can be increased, and the yield of fluoroalkane iodide can be improved.
In the above iodination reaction, the amount of iodine used is not particularly limited, but from the viewpoint of ease of synthesis of the target product (reaction efficiency, etc.), yield, etc., 1. 5 to 5 mol is preferable, 2 to 4 mol is more preferable, and 2.5 to 3.0 mol is further preferable.
In the above iodination reaction, the amount of triphenylphosphine used is not particularly limited, but from the viewpoint of ease of synthesis of the target product (reaction efficiency, etc.), yield, etc., the amount of triphenylphosphine used is based on 1 mol of fluorine-containing alkyl alcohol. 1.5 to 5 mol is preferable, 2 to 4 mol is more preferable, and 2.5 to 3.0 mol is further preferable.

In the above iodination reaction, a base can be added to the reaction system. The base does not particularly affect the iodination reaction and can remove the by-product HI.
The base is not particularly limited, and for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkali metal alkoxides such as potassium tert-butoxide and sodium methoxydo; triethylamine, pyridine and imidazole. Such as amines; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate and the like can be mentioned. These bases can be used alone or in combination of two or more. Of these, amines are preferable, and aromatic amines such as imidazole are more preferable, from the viewpoint of removing by-products.
When the base is used, the amount used is not particularly limited, but from the viewpoint of removing by-products and the like, 1.0 to 5 mol is preferable with respect to 1 mol of the fluorine-containing alkyl alcohol, and 1.0 to 1.0 to 4 mol is more preferable, and 1.0 to 3.0 mol is even more preferable.

The reaction temperature of the iodination reaction is not particularly limited, but is preferably 40 to 150 ° C., more preferably 50 to 140 ° C. from the viewpoint of ease of synthesis (reaction efficiency, etc.) and yield of the target product. 80 to 120 ° C. is more preferable.
The reaction pressure of the iodination reaction is not particularly limited, and the reaction can be carried out at normal pressure (atmospheric pressure).

The reaction time of the iodination reaction is not particularly limited, but is preferably 0.1 to 240 hours, preferably 0.3 to 24 hours, from the viewpoint of ease of synthesis of the target product (reaction efficiency, etc.) and yield. Is more preferable, and 1 to 8 hours is even more preferable.

After the above iodination reaction, the obtained fluoroalkane iodide can also be purified.
The purification method is not particularly limited, but for example, by adding a solvent (for example, water or the like) to the solution after the reaction and separating the liquids, unreacted iodine is separated and recovered in the aqueous layer, and the organic layer is also used. Examples thereof include a method of obtaining fluoroalkane iodide by distilling.

The conventional method for producing fluoroalkane iodide requires high temperature conditions, goes through a multi-step reaction, and the reaction is difficult to proceed depending on the substrate. Therefore, the yield of the target product is not always high, and scale-up is not easy. It was a thing.
However, since the method for producing fluoroalkane iodide of the present disclosure is a one-step reaction under mild conditions, fluoroalkane iodide can be efficiently produced in a high yield and can be easily scaled up. ..

Further, the present disclosure describes the general formula (3): R ¹ CF = CH ₂
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
It is a method for producing a fluoroolefin represented by
The present invention relates to a production method including a step of dehalogenating the fluoroalkane iodide obtained by the above-mentioned production method of fluoroalkane iodide in the presence of a catalyst.

As the fluorine-containing alkyl group having 1 to 10 carbon atoms ^{of R 1} in the general formula (3), examples (preferably examples, etc.) of the fluorine-containing alkyl group having 1 to 10 carbon atoms ^{in R 1 in the above general formula (1).} (Including) and the same.
As the fluoroolefin represented by the general formula (3), 2,3,3,4,5,4-hexafluoro-1-butene (HFO-1336 mcyf) is particularly preferable.

In the method for producing a fluoroolefin, the process for producing a fluoroalkane iodide is as described above.
Further, the intermediate fluoroalkane iodide may be produced by the above-mentioned iodination reaction step, and then the fluoroalkane iodide may be purified and then used in the next dehalogenation step, without purifying the fluoroalkane iodide. It may be used in the next dehalogenation step.

In the dehalogenation step, the catalyst is not particularly limited, and for example, a transition metal is preferable.
Examples of transition metals include zinc, magnesium, copper, tin, mercury, zinc alloys and the like. Examples of the zinc alloy include Zn / Cu, Zn / Sn, Zn / Hg and the like. The transition metal may be used alone or in combination of two or more.
Since zinc powder can be covered with oxides or form a thin oxide film on the surface, it is preferable to remove oxides and the like to give an active surface when used as a catalyst. The oxide film removing agent is not particularly limited as long as it can remove the oxide film on the surface of the zinc particles and does not affect the subsequent reaction. Examples of the oxide film removing agent include dihalogenated hydrocarbons such as 1,2-diiodoethane, 1,2-dibromoethane, and 1,2-dichloroethane; chlorotrimethylsilane, dichlorodimethylsilane, trichloromethylsilane, tetrachlorosilane, and the like. Halogenated silane; examples thereof include water, hydrogen chloride, a diethyl ether solution of hydrogen chloride, boron trifluoride / diethyl ether complex, boron trifluoride / dibutyl ether complex, diethyl aluminum chloride and the like.
The particle size of the zinc particles is preferably 3 mm or less, more preferably 1 mm or less, still more preferably 200 μm or less from the viewpoint of dispersibility in a solvent; from the viewpoint of handleability of zinc particles and ease of separation from products. Therefore, 1 μm or more is preferable. The particle size of the zinc particles is a value measured by a laser diffraction method.

A solvent can be used in the dehalogenation step. The solvent is not particularly limited, but for example, ethers such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, tetrahydrofuran (THF); N, N-dimethylformamide (DMF), N, N- Amides such as dimethylacetamide (DMA) and N-methylpyrrolidone (NMP); compounds containing sulfur atoms such as dimethyl sulfoxide (DMSO) and sulfolane; water and the like.
The solvent may be used alone or in combination of two or more.
In the above solvent, ether and amide are preferable, and THF and DMA are more preferable, from the viewpoint of ease of synthesis of fluoroolefin (reaction efficiency and the like) and yield.

The reaction temperature of the dehalogenation reaction is not particularly limited, but is preferably 20 to 200 ° C., more preferably 30 to 180 ° C., from the viewpoint of ease of synthesis of the target product (reaction efficiency, etc.) and yield. , 50-160 ° C. is more preferable.
The reaction pressure of the dehalogenation reaction is not particularly limited, and the reaction can be carried out at normal pressure (atmospheric pressure).

The reaction time of the dehalogenation reaction is not particularly limited, but is preferably 10 minutes to 48 hours, preferably 30 minutes to 24 hours, from the viewpoint of ease of synthesis of the target product (reaction efficiency, etc.) and yield. More preferably, 1 to 10 hours is even more preferable.

After the above dehalogenation reaction, the obtained fluoroolefin can also be purified.
The purification method is not particularly limited, and examples thereof include a method of separating and recovering by distillation and rectification, which is usually performed; a method of purifying by filtration and liquid separation; a method of purifying by combining the above methods. It is also possible to recover the solvent during purification and use it again.

Since the method for producing the fluoroolefin is carried out following the method for producing the fluoroalkane iodide, which can efficiently obtain the intermediate fluoroalkane iodide in a high yield, the fluoroolefin can be produced efficiently in a high yield. Can be manufactured.

Further, the present disclosure describes the general formula (2): R ¹ CF ₂ CH ₂ I.
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
Fluoroalkane iodide represented by and / or
General formula (3): R ¹ CF = CH ₂
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
Contains fluoroolefins represented by
Further, the general formula (4): R ¹ CF ₂ CH ₂ OC (= O) R ²
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms, and R ² represents an alkyl group having −H or 1 to 3 carbon atoms).
Compounds represented by and / or
General formula (5): R ¹ CF ₂ CH ₃
(In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
The present invention relates to a composition containing a compound represented by.

Examples of the fluorine-containing alkyl group of the general formula (2) to carbon atoms of ^{R 1} in (5) 1-10, an exemplary fluorine-containing alkyl group having 1 to 10 carbon atoms for ^{R 1} in the above general formula (1) ( The same as (including preferred examples) can be mentioned.
^{Examples of the alkyl group having 1 to 3 carbon atoms of R 2} in the general formula (4) include a methyl group, an ethyl group and a propyl group, and a methyl group is preferable.

The compound represented by the general formula (4) is by-produced in, for example, an iodination reaction, and the compound represented by the general formula (5) is by-produced in, for example, a dehalogenation reaction.
The total content of the compound represented by the general formula (4) and the compound represented by the general formula (5) is 20% by mass of the entire composition from the viewpoint of containing a larger amount of fluoroalkane iodide and / or fluoroolefin. The following is preferable, and 15% by mass or less is more preferable.

The above composition can be preferably used, for example, as an intermediate component, a refrigerant, or the like.
For example, the content of the fluoroalkane iodide represented by the general formula (2) is high (for example, 80% by mass or more of the entire composition), and the content of the compound represented by the general formula (4) is low (for example, the composition). The composition (20% by mass or less of the whole product) can be preferably used as an intermediate component for producing a fluoroolefin represented by the general formula (3).
For example, the content of the fluoroolefin represented by the general formula (3) is high (for example, 80% by mass or more of the entire composition), and the content of the compound represented by the general formula (5) is low (for example, the entire composition). The composition (20% by mass or less) can be preferably used as a refrigerant or the like.

Although the embodiments have been described above, it will be understood that various modifications of the forms and details are possible without deviating from the purpose and scope of the claims.

The following will be described in more detail with examples. However, the present disclosure is not limited to the embodiments of these examples.

(Example 1)
2,2,3,3,4,5,4-heptafluoro-1-butanol (7FB) in an amount of 50.06 g (0.25 mol), iodine in 190.23 g (0.75 mol), triphenylphosphine in 196. 60 g (0.75 mol) and 17.21 g (0.25 mol) of imidazole were added to 212 ml of N, N-dimethylacetamide (DMA) and mixed. The mixed solution was stirred at 120 ° C. for 6 hours to react. The reaction product was distilled under reduced pressure (pressure 0.04 kPa, oil bath temperature 75 ° C.) to obtain 1,1,1,2,2,3,3-heptafluoro-4-iodobutane (IHFB). The yield was 98%. The by-product was acetic acid- (1H, 1H-heptafluorobutyl ester) (4%).

(Comparative Example 1)
1.53 g (0.77 x 10 ^-2 mol) of 7FB, 2.86 g (1.1 x 10 ^-2 mol) of iodine, 2.95 g (1.1 x 10 ^-2 mol) of triphenylphosphine, imidazole 1 .53g the (2.3 × ^{10 -2} mol) was added to a mixed solvent of acetonitrile diethyl ether and 6.5ml of 3.5 ml, were mixed. The mixed solution was stirred at 40 ° C. for 3 hours to react. However, the reaction did not proceed and IHFB could not be obtained.

(Comparative Example 2)
The 7FB 1.52g (0.76 × ^{10 -2} mol), iodine 7.61 g (0.03 mol), triphenylphosphine 7.87g (0.03 mol), triethylene glycol dimethyl ether 5.8ml Added and mixed. The mixed solution was stirred at 120 ° C. for 6 hours to react. However, the reaction did not proceed and IHFB could not be obtained.

(Comparative Example 3)
1.56 g (0.78 x 10 ^-2 mol) of 7 FB, 2.88 g (1.1 x 10 ^-2 mol) of iodine, 2.96 g (1.1 x 10 ^-2 mol) of triphenylphosphine, 5 It was added to .7 ml of tetrahydrofuran (THF) and mixed. The mixed solution was stirred at 80 ° C. for 3 hours to react. However, the reaction did not proceed and IHFB could not be obtained.

(Example 2)
10.02 g (0.03 mol) of IHFB and 4.85 g (0.07 mol) of zinc powder (particle size 150 μm or less) were added to 57 ml of N, N-dimethylacetamide (DMA) and mixed. The mixture is stirred at 120 ° C., 0.59 g (0.003 mol) of 1,2-dibromoethane is added, and the mixture is stirred for 4 hours to react, and 2,3,3,4,5,4- Hexafluoro-1-butene (HFO-1336 mcyf) was obtained. The yield was 88%. The by-product was 1,1,1,2,2,3,3-heptafluorobutane (HFC-347ccd) (11%).

(Example 3)
1.00 g (0.003 mol) of IHFB and 0.42 g (0.006 mol) of zinc were added to 0.99 ml of N, N-dimethylacetamide (DMA) and 0.99 ml of water and mixed. The mixed solution was stirred at 100 ° C. for 4 hours and reacted to obtain HFO-1336 mcyf. The yield was 97%. The by-product was HFC-347ccd (3%).

In Examples 1 to 3 above, using the production method of the present disclosure, fluoroalkane iodide and fluoroolefin could be efficiently produced in high yield. On the other hand, in Comparative Examples 1 to 3, the reaction did not proceed because the fluorinated alkyl alcohol as a raw material could not be sufficiently dissolved in the solvent, and the desired fluoroalkane iodide could not be obtained.

Claims (8)

1. General formula (2): R ¹ CF ₂ CH ₂ I
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
   It is a method for producing fluoroalkane iodide represented by.
   General formula (1): R ¹ CF ₂ CH ₂ OH
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
   Includes a step of reacting a fluorine-containing alkyl alcohol represented by (1) with iodine in the presence of triphenylphosphine in a solvent.
   A production method, wherein the solvent contains at least one selected from the group consisting of compounds containing sulfur atoms and amides.
2. The iodine according to claim 1, wherein the solvent contains at least one selected from the group consisting of N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA) and N-methylpyrrolidone (NMP). A method for producing fluoroalkane.
3. The method for producing a fluoroalkane iodide according to claim 1 or 2, wherein R ^{1 is a perfluoroalkyl group having 1 to 2 carbon atoms.}
4. The method for producing a fluoroalkane iodide according to any one of claims 1 to 3, wherein 1.5 to 5 mol of iodine is reacted with 1 mol of the fluorine-containing alkyl alcohol.
5. The method for producing fluoroalkane iodide according to any one of claims 1 to 4, wherein the step of reacting with iodine is carried out at a temperature of 40 to 150 ° C.
6. General formula (3): R ¹ CF = CH ₂
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
   It is a method for producing a fluoroolefin represented by
   A production method comprising a step of dehalogenating the fluoroalkane iodide obtained by the method for producing a fluoroalkane iodide according to any one of claims 1 to 5 in the presence of a catalyst.
7. General formula (2): R ¹ CF ₂ CH ₂ I
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
   Fluoroalkane iodide represented by and / or
   General formula (3): R ¹ CF = CH ₂
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
   Contains fluoroolefins represented by
   Further, the general formula (4): R ¹ CF ₂ CH ₂ OC (= O) R ²
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms, and R ² represents an alkyl group having −H or 1 to 3 carbon atoms).
   Compounds represented by and / or
   General formula (5): R ¹ CF ₂ CH ₃
   (In the formula, R ¹ represents a fluorine-containing alkyl group having 1 to 10 carbon atoms)
   A composition comprising a compound represented by.
8. The composition according to claim 7, wherein the total content of the compound represented by the general formula (4) and the compound represented by the general formula (5) is 20% by mass or less of the total composition.