Method for preparing diiodosilane
A novel synthesis method for diiodosilane using stable compounds in controlled conditions addresses safety and cost issues, enabling high-purity production with reduced risks and improved efficiency.
Patent Information
- Application Number
- TW114112826
- Authority / Receiving Office
- TW · TW
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2024-07-16
- Filing Date
- 2025-04-02
- Publication Date
- 2026-07-11
- Estimated Expiration
- 2045-04-01
AI Technical Summary
Existing methods for synthesizing diiodosilane face challenges such as the use of flammable and toxic raw materials, high production costs, explosion risks, and the formation of carcinogenic byproducts, leading to reduced yield and safety concerns.
A method involving the reaction of a compound represented by specific chemical formulas with iodine in a mixed solvent at controlled temperatures, followed by filtration and distillation to produce high-purity diiodosilane, using stable and easy-to-handle materials.
Ensures process safety, reduces energy consumption, and facilitates the production of high-purity diiodosilane with improved yield and ease of handling, making it suitable for commercial applications.
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Abstract
Description
Technical Field
[0001] This invention relates to a method for preparing diiodosilane. Prior Technology
[0002] Diiodosilane (SiH2I2) is a compound that plays an important role in semiconductor manufacturing and new material development. With the continuous development of the semiconductor industry, the demand for this compound is also increasing.
[0003] To synthesize diiodosilane, traditional techniques primarily employ a method that replaces the Si-Cl bonds in dichlorosilane (SiH2Cl2) with Si-I bonds using expensive lithium iodide or similar materials. However, dichlorosilane, as a raw material, is a flammable gas at room temperature and reacts with moisture to produce hydrogen chloride gas (a toxic substance), thus requiring special care during storage.
[0004] On the other hand, a synthetic method for preparing diiodosilane by reacting phenylsilane with iodine has been proposed. However, phenylsilane, as a raw material, has the following problems: its high price reduces production efficiency; it can explode upon contact with moisture; and it is difficult to store due to its high water absorption. In addition, the reaction is highly exothermic, which may cause an explosion risk. Therefore, the process is not only dangerous but also leads to reduced yield and the formation of benzene (a carcinogen) as a reaction byproduct.
[0005] Technical documents
[0006] Patent documents
[0007] Patent Document 1: US2016-0264426A1 Summary of the Invention
[0008] [The problem the invention aims to solve]
[0009] An embodiment of the present invention provides a preparation method that can obtain high-purity diiodosilane while ensuring process safety and productivity.
[0010] [Methods used to solve problems]
[0011] One aspect of the present invention is a method for preparing diiodosilane, which may include the following steps: preparing diiodosilane (SiH2I2) by reacting a compound represented by the following chemical formula 1 with iodine (I2). [Chemical Formula 1] (in, R represents hydrogen or -NR1R2; R1 and R2 are each independently hydrogen or C1-C10 alkyl; A is either -NR3R4 or -OR5; R3 to R5 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl, or -SiR11R12R13; R3 and R4 can be linked via C3-C7 alkylene or C2-C7 heteroalkylene to form a heterocycle; The heterocycles and the alkyl groups of R3 to R5 can be substituted with -SiR14R15R16 or -OSiR17R18R19; R11 through R19 are each independently hydrogen or C1-C10 alkyl.
[0012] The compound represented by the chemical formula 1 may be represented by the following chemical formula 2 or chemical formula 3. [Chemical Formula 2] [Chemical Formula 3] (in, A, R1, and R2 are defined in the same way as in chemical formula 1 above; R21 and R22 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl, or -SiR11R12R13; R11 through R13 are each independently hydrogen or C1-C10 alkyl.
[0013] R1, R2, R21 and R22 can each be hydrogen or C1-C4 alkyl.
[0014] R5 can be a C1-C10 alkyl or -L1-OSiR17R18R19; L1 can be a C1-C10 alkyl; R17 to R19 can each be hydrogen or a C1-C10 alkyl.
[0015] The compound represented by chemical formula 2 may be represented by chemical formula 4 or chemical formula 5. [Chemical Formula 4] [Chemical Formula 5] (in, R31 and R32 are each independently hydrogen, C1-C7 alkyl, C6-C12 aryl, or -SiR11R12R13; or R31 and R32 can be linked via C3-C7 alkyl groups or *-L2-X1-L3-* to form heterocycles; L2 and L3 are each independently C1-C3 alkyl groups; X1 is a single bond, -O-, or -NR35; R35 is either hydrogen or -SiR14R15R16; R33 is a C1-C4 alkyl group; R34 is a C1-C4 alkyl group or -OSiR17R18R19; R11 through R19 are each independently hydrogen or C1-C7 alkyl.
[0016] The compounds represented by chemical formula 1 may be selected from the following structures: .
[0017] The method for preparing diiodosilane according to an exemplary embodiment may further include the step of reacting hydrogen iodide (HI).
[0018] The reaction can be carried out in a mixed solvent containing ester organic solvents and halogenated hydrocarbon organic solvents.
[0019] The reaction can be carried out at temperatures ranging from 10°C to 40°C.
[0020] The method for preparing diiodosilane according to an exemplary embodiment may further include the following steps: after the reaction, the iodate is filtered and purified by distillation.
[0021] [Invention Effects]
[0022] The preparation method of an exemplary embodiment is conducive to commercialization because it uses a starting material that is liquid and stable at room temperature, making it easy to store and process the starting material.
[0023] The preparation method according to one exemplary embodiment can generate little heat during the reaction, thus ensuring excellent process safety and saving energy used for cooling. Furthermore, the iodate, a reaction byproduct, can be safely and conveniently removed by filtration, and high-purity diiodosilane can be obtained through a simple process. Implementation
[0024] Unless otherwise defined in this specification, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used in this specification is for the purpose of effectively describing particular embodiments only and is not intended to be limiting of the invention.
[0025] Unless otherwise specified in the context, the singular form used in this specification may also be intended to include the plural form.
[0026] Unless otherwise stated to the contrary, when a component is described as "including", "having", "containing" or "having", it does not mean that other components are excluded, but rather that other components may be included, and does not exclude elements, materials or processes not listed herein.
[0027] The numerical ranges used in this specification include the lower limit, the upper limit, and all values within these ranges; increments logically derived from the forms and magnitudes within the defined ranges; all double-limited values; and all possible combinations of the upper and lower limits within numerical ranges defined in different forms. Unless otherwise specifically defined in this specification, values outside the defined numerical ranges that may occur due to experimental errors or rounding are also included within the defined numerical ranges.
[0028] The term "alkyl" in this specification refers to an organic radical induced from an aliphatic hydrocarbon by removing a hydrogen atom, which may be in straight-chain or branched form. Examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tributyl, pentyl, hexyl, ethylhexyl, etc.
[0029] The term "alkylene" in this specification refers to a divalent organic radical induced from an aliphatic hydrocarbon by removing two hydrogen atoms, which may be in straight-chain or branched form. Examples include, but are not limited to, methylene, ethylene, propylene, isopropylene, butene, isobutylene, tert-butene, pentene, hexene, octene, nonene, etc.
[0030] The term "heteroalkyl" in this specification refers to an alkyl group containing one or more heteroatoms selected from B, N, O, S, P (=O), Si, and P, and the term alkyl group is the same as defined above.
[0031] The term "aryl" in this specification refers to an organic radical induced from an aromatic hydrocarbon by the removal of a hydrogen atom, comprising monocyclic or fused rings, each ring suitably comprising 4 to 7 ring atoms, preferably 5 or 6 ring atoms, and may even include multiple aryl groups linked by single bonds. Examples include, but are not limited to, phenyl, naphthyl, biphenyl, and fluorenyl.
[0032] Unless otherwise defined in this specification, “about” may be considered as a value within 30%, 25%, 20%, 15%, 10% or 5% of the specified value.
[0033] The present invention will now be described in detail. However, these are merely illustrative examples, and the present invention is not limited to the specific embodiments described herein.
[0034] An exemplary embodiment of the present invention provides a preparation method that can obtain high-purity diiodosilane while ensuring process safety and productivity.
[0035] Specifically, a method for preparing diiodosilane according to an exemplary embodiment may include the following steps: preparing diiodosilane (SiH2I2) by reacting a compound represented by the following chemical formula 1 with iodine (I2). [Chemical Formula 1] (in, R represents hydrogen or -NR1R2; R1 and R2 are each independently hydrogen or C1-C10 alkyl; A is either -NR3R4 or -OR5; R3 to R5 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl, or -SiR11R12R13; R3 and R4 can be linked via C3-C7 alkylene or C2-C7 heteroalkylene to form a heterocycle; The heterocycles and the alkyl groups of R3 to R5 can be substituted with -SiR14R15R16 or -OSiR17R18R19; R11 through R19 are each independently hydrogen or C1-C10 alkyl.
[0036] As an example, R1 and R2 may each be hydrogen or C1-C7 alkyl, specifically hydrogen or C1-C4 alkyl.
[0037] As an example, R3 and R4 can each be hydrogen, C1-C7 alkyl, C6-C12 aryl, or -SiR11R12R13 independently.
[0038] As an example, R3 and R4 can each be hydrogen, C1-C4 alkyl, C6-C12 aryl, or -SiR11R12R13 independently.
[0039] As an example, R11 to R13 may each be independently hydrogen or C1-C7 alkyl, may be hydrogen or C1-C4 alkyl, and may specifically be hydrogen or methyl.
[0040] As an example, R3 and R4 can be linked via C3-C7 alkyl groups or *-L2-X1-L3-* to form heterocycles; L2 and L3 can each be independently C1-C3 alkyl groups; X1 can be a single bond, -O- or -NR35; R35 can be hydrogen or -SiR14R15R16; R14 to R16 can each be independently hydrogen or C1-C7 alkyl groups.
[0041] As an example, R14 to R16 may each be independently hydrogen or C1-C4 alkyl, specifically hydrogen or methyl.
[0042] The compound represented by the chemical formula 1 may be represented by the following chemical formula 2 or chemical formula 3. [Chemical Formula 2] [Chemical Formula 3] (in, A, R1, and R2 are defined as described in Chemical Formula 1; R21 and R22 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl, or -SiR11R12R13; R11 through R13 are each independently hydrogen or C1-C10 alkyl.
[0043] As an example, R21 and R22 can each be independently hydrogen, C1-C7 alkyl, C6-C12 aryl or -SiR11R12R13; specifically, R21 and R22 can each be independently hydrogen, C1-C4 alkyl, C6-C12 aryl or -SiR11R12R13.
[0044] As an example, R1, R2, R21 and R22 may each be hydrogen or C1-C4 alkyl.
[0045] As an example, R1 and R21 may be the same as each other and may be hydrogen or C1-C4 alkyl.
[0046] As an example, R2 and R22 may be the same as each other and may be hydrogen or C1-C4 alkyl.
[0047] As an example, R5 can be a C1-C10 alkyl or -L1-OSiR17R18R19; L1 can be a C1-C10 alkyl; R17 to R19 can each be hydrogen or a C1-C10 alkyl.
[0048] As an example, R5 can be a branched C3-C10 alkyl or -L1-OSiR17R18R19; L1 can be a branched C3-C10 alkyl; R17 to R19 can each be hydrogen or C1-C10 alkyl independently.
[0049] As an example, R5 can be a branched C3-C7 alkyl or -L1-OSiR17R18R19; L1 can be a branched C3-C7 alkyl; R17 to R19 can each be hydrogen or C1-C7 alkyl independently.
[0050] As an example, R17 to R19 may each be independently hydrogen or C1-C4 alkyl, specifically hydrogen or methyl.
[0051] The compound represented by chemical formula 2 may be represented by chemical formula 4 or chemical formula 5. [Chemical Formula 4] [Chemical Formula 5] (in, R31 and R32 are each independently hydrogen, C1-C7 alkyl, C6-C12 aryl, or -SiR11R12R13; or R31 and R32 can be linked via C3-C7 alkyl groups or *-L2-X1-L3-* to form heterocycles; L2 and L3 are each independently C1-C3 alkyl groups; X1 is a single bond, -O-, or -NR35; R35 is either hydrogen or -SiR14R15R16; R33 is a C1-C4 alkyl group; R34 is a C1-C4 alkyl group or -OSiR17R18R19; R11 through R19 are each independently hydrogen or C1-C7 alkyl.
[0052] As an example, R31 and R32 can each be hydrogen, C1-C4 alkyl, C6-C12 aryl, or -SiR11R12R13 independently.
[0053] Specifically, the compound represented by the chemical formula 1 may be selected from, but is not limited to, the following structures.
[0054] According to the preparation method of an exemplary embodiment, the reaction can be carried out in an organic solvent, and the organic solvent is not particularly limited as long as it can readily dissolve the starting material. As an example, it may include: alcohol solvents such as methanol, ethanol, n-propanol, isopropanol, n-butanol and isobutanol; ester solvents such as ethyl acetate, butyl acetate and 3-methoxy-3-methylbutylacetic acid; ether solvents such as dimethyl ether and dibutyl ether; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone and acetophenone; and halogenated hydrocarbon solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, trichloroethylene and perfluoropropane.
[0055] Specifically, the reaction can be carried out in a mixed solvent containing ester organic solvents and halogenated hydrocarbon organic solvents, and the molar ratio of the ester organic solvent to the halogenated hydrocarbon organic solvent in the mixed solvent can be 1:10 to 100, or 1:20 to 100, or 1:20 to 70, or 1:30 to 70, or 1:40 to 70.
[0056] The reaction can be carried out at a temperature of 10°C to 40°C or 20°C to 40°C for 10 to 40 hours, or 10 to 30 hours, or 20 to 30 hours.
[0057] The method for preparing diiodosilane according to an exemplary embodiment may further include the following steps: after the reaction, the iodate is filtered and purified by distillation.
[0058] Specifically, a method for preparing diiodosilane according to an exemplary embodiment may include the following steps: adding iodine to a haloalkanes organic solvent; adding a compound represented by the chemical formula 1 and an ester organic solvent and reacting; and after the reaction, filtering and purifying the generated iodate by distillation.
[0059] The preparation method according to an exemplary embodiment may further include the step of reacting hydrogen iodide (HI), in which case it may include the following steps: adding iodine to a haloalkanes organic solvent; adding the compound represented by the chemical formula 1 and an ester organic solvent and reacting; further stirring after bubbling the hydrogen iodide; and filtering and purifying the iodate generated by the reaction by distillation.
[0060] The exemplary embodiments described above will be explained in more detail below. However, the following embodiments are for illustrative purposes only and are not limited to the scope of the patent application.
[0061] Synthesis of diiodosilane
[0062] [Example 1]
[0063] Under an anhydrous and inert atmosphere, 1028 g (4.05 mol) of diiodine (I₂) and 464 mL (5.79 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture of 253 g (1.93 mol) of diisopropylaminosilane and 9.5 mL (0.1 mol) of ethyl acetate was slowly added under internal temperature conditions between 5 °C and 25 °C, and the mixture was stirred at room temperature for 24 hours. After the reaction was complete, diisopropylammonium iodide was removed by filtration of the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 38 °C to 40 °C and 8 to 9 torr to prepare 176 g of diiodosilane (yield 32.13%, NMR purity 98.72%).
[0064] 1H NMR (C6D6): 3.50 ppm (s, 2H)
[0065] 29Si NMR(C6D6):-98.8ppm(s, 1Si)
[0066] [Example 2]
[0067] Under an anhydrous and inert atmosphere, 34.8 g (0.14 mol) of diiodine and 23.4 g (0.20 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture of 10 g (0.07 mol) of disilylphenylamine and 0.29 g (0.003 mol) of ethyl acetate was slowly added under internal temperature conditions between 5°C and 30°C, and the mixture was stirred at room temperature for 24 hours. After the reaction was complete, aniline hydroiodide was removed by filtration of the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 38°C to 40°C and 8 to 9 torr to prepare 11.9 g of diiodosilane (yield 32%, NMR purity 98.13%).
[0068] 1H NMR (C6D6): 3.57 ppm (s, 2H)
[0069] 29Si NMR (C6D6): -100.1ppm (s, 1Si).
[0070] [Example 3]
[0071] Under an anhydrous and inert atmosphere, 40.3 g (0.16 mol) of diiodine and 27.1 g (0.23 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture containing 10 g (0.08 mol) of 1,3-disilylimidazolidine and 0.33 g (0.004 mol) of ethyl acetate was slowly added at an internal temperature between 5°C and 30°C. The mixture was then stirred at room temperature for 24 hours. After the reaction was complete, imidazolidine dihydroiodide was removed by filtration of the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 38°C to 40°C and 8 to 9 torr to prepare 5.4 g of diiodosilane (25% yield).
[0072] 1H NMR (C6D6): 3.57 ppm (s, 2H)
[0073] 29Si NMR (C6D6): -98.8ppm (s, 1Si).
[0074] [Example 4]
[0075] Under an anhydrous and inert atmosphere, 30.6 g (0.12 mol) of diiodine and 20.5 g (0.17 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture of 10 g (0.06 mol) of bis(diethylamino)silane and 0.25 g (0.003 mol) of ethyl acetate was slowly added at an internal temperature between 5°C and 25°C, and the mixture was stirred at room temperature for 24 hours. After the reaction was complete, diethylamine hydroiodide was removed by filtration of the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 30°C to 35°C and 3 to 5 torr to prepare 4.6 g of diiodosilane (yield 28%).
[0076] 1H NMR (C6D6): 3.57 ppm (s, 2H)
[0077] 29Si NMR (C6D6): -98.8ppm (s, 1Si).
[0078] [Example 5]
[0079] Under an anhydrous and inert atmosphere, 30.6 g (0.12 mol) of diiodine and 20.5 g (0.17 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture of 10 g (0.06 mol) of bis(diethylamino)silane and 0.25 g (0.003 mol) of ethyl acetate was slowly added while maintaining an internal temperature between 15°C and 30°C. The mixture was then stirred at room temperature for 24 hours. After cooling to 0°C, 7.3 g (0.06 mol) of hydrogen iodide (HI) was bubbled in, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, diethylamine hydroiodide was removed by filtering the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 30°C to 35°C and 3 to 5 torr to prepare 4.6 g of diiodosilane (yield 28.8%).
[0080] 1H NMR (C6D6): 3.50 ppm (s, 2H)
[0081] 29Si NMR(C6D6):-98.8ppm(s, 1Si)
[0082] [Example 6]
[0083] Under an anhydrous and inert atmosphere, 30.6 g (0.12 mol) of diiodine and 20.5 g (0.17 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture of 10 g (0.06 mol) of bis(tertbutylamino)silane and 0.25 g (0.003 mol) of ethyl acetate was slowly added at an internal temperature between 5°C and 25°C. The mixture was then stirred at room temperature for 24 hours. After the reaction was complete, the tertbutylamino hydroiodide was removed by filtration of the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 30°C to 35°C and 3 to 5 torr to prepare 3.7 g of diiodosilane (yield 23%).
[0084] 1H NMR (C6D6): 3.57 ppm (s, 2H)
[0085] 29Si NMR(C6D6):-98.8ppm(s, 1Si)
[0086] [Example 7]
[0087] Under an anhydrous and inert atmosphere, 30.6 g (0.12 mol) of diiodine and 20.5 g (0.17 mol) of chloroform were added to a flame-dried 100 mL flask. A mixture of 10 g (0.06 mol) of bis(tertbutylamino)silane and 0.25 g (0.003 mol) of ethyl acetate was slowly added while maintaining an internal temperature between 15°C and 30°C. The mixture was then stirred at room temperature for 12 hours. After cooling to 0°C, 7.3 g (0.06 mol) of hydrogen iodide (HI) was bubbled in, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the tertbutylamino hydroiodide was removed by filtration of the reaction mixture, and the solvent was removed from the resulting filtrate under reduced pressure. The mixture was purified by distillation at 30°C to 35°C and 3 to 5 torr to prepare 3.7 g of diiodosilane (yield 23%).
[0088] 1H NMR (C6D6): 3.50 ppm (s, 2H)
[0089] 29Si NMR(C6D6):-98.8ppm(s,1Si)
[0090] As described above, the present invention is illustrated by specific details and limited embodiments and comparative examples, but these are provided only to help to understand the present invention more fully. The present invention is not limited to the above embodiments, and those skilled in the art can make various modifications and variations based on these descriptions.
[0091] Therefore, the spirit of the present invention should not be limited to the described embodiments, and is not limited to the scope of the patent application described below. All equivalents that are equivalent to or have equivalent modifications to the scope of the patent application are within the scope and spirit of the present invention.
Claims
1. A method for preparing diiodosilane, the method comprising the steps of: preparing diiodosilane by reacting a compound represented by the following chemical formula 1 with iodine, [Chemical Formula 1] wherein, R is hydrogen or -NR1R2; R1 and R2 are each independently hydrogen or C1-C10 alkyl; A is -NR3R4; R3 to R4 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl or -SiR11R12R13; said R3 and R4 can be linked via C3-C7 alkylene or C2-C7 heteroalkylene to form a heterocycle; said heterocycle and the alkylene of R3 to R4 can be substituted by -SiR14R15R16; R11 to R16 are each independently hydrogen or C1-C10 alkyl.
2. The method for preparing diiodosilane as described in claim 1, wherein, The compound represented by the stated chemical formula 1 is represented by the following chemical formula 2 or chemical formula 3: [Chemical Formula 2] [Chemical Formula 3] wherein A, R1 and R2 are the same as defined in claim 1; R21 and R22 are each independently hydrogen, C1-C10 alkyl, C6-C12 aryl or -SiR11R12R13; R11 to R13 are each independently hydrogen or C1-C10 alkyl.
3. The method for preparing diiodosilane as described in claim 2, wherein, R1, R2, R21 and R22 are each independently hydrogen or C1-C4 alkyl.
4. The method for preparing diiodosilane as described in claim 2, wherein, The compound represented by the aforementioned chemical formula 2 is represented by the following chemical formula 4, [Chemical Formula 4] wherein R31 and R32 are each independently hydrogen, C1-C7 alkyl, C6-C12 aryl or -SiR11R12R13; or R31 and R32 can be linked via C3-C7 alkyl or *-L2-X1-L3-* to form a heterocycle; L2 and L3 are each independently C1-C3 alkyl; X1 is a single bond, -O- or -NR35; R35 is hydrogen or -SiR14R15R16; R11 to R16 are each independently hydrogen or C1-C7 alkyl.
5. The method for preparing diiodosilane as described in claim 1, wherein, The compounds represented by the chemical formula 1 are selected from the following structures:
6. The method for preparing diiodosilane as described in claim 1, wherein, The preparation method also includes a step of reacting hydrogen iodide.
7. The method for preparing diiodosilane as described in claim 1, wherein, The reaction is carried out in a mixed solvent containing ester organic solvents and halogenated hydrocarbon organic solvents.
8. The method for preparing diiodosilane as described in claim 1, wherein, The reaction was carried out at temperatures ranging from 10°C to 40°C.
9. The method for preparing diiodosilane as described in claim 1, wherein, The preparation method further includes the following steps: After the reaction, the iodate is filtered and purified by distillation.