WO2015008695A1 - トリフルオロエチレンの保存方法およびトリフルオロエチレンの保存容器 - Google Patents
トリフルオロエチレンの保存方法およびトリフルオロエチレンの保存容器 Download PDFInfo
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- WO2015008695A1 WO2015008695A1 PCT/JP2014/068477 JP2014068477W WO2015008695A1 WO 2015008695 A1 WO2015008695 A1 WO 2015008695A1 JP 2014068477 W JP2014068477 W JP 2014068477W WO 2015008695 A1 WO2015008695 A1 WO 2015008695A1
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- Prior art keywords
- trifluoroethylene
- volume
- ppm
- oxygen
- storage container
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Classifications
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17C—VESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
- F17C5/00—Methods or apparatus for filling containers with liquefied, solidified, or compressed gases under pressures
- F17C5/02—Methods or apparatus for filling containers with liquefied, solidified, or compressed gases under pressures for filling with liquefied gases
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17C—VESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
- F17C1/00—Pressure vessels, e.g. gas cylinder, gas tank, replaceable cartridge
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17C—VESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
- F17C5/00—Methods or apparatus for filling containers with liquefied, solidified, or compressed gases under pressures
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17C—VESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
- F17C2221/00—Handled fluid, in particular type of fluid
- F17C2221/03—Mixtures
- F17C2221/038—Refrigerants
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F17—STORING OR DISTRIBUTING GASES OR LIQUIDS
- F17C—VESSELS FOR CONTAINING OR STORING COMPRESSED, LIQUEFIED OR SOLIDIFIED GASES; FIXED-CAPACITY GAS-HOLDERS; FILLING VESSELS WITH, OR DISCHARGING FROM VESSELS, COMPRESSED, LIQUEFIED, OR SOLIDIFIED GASES
- F17C2270/00—Applications
- F17C2270/01—Applications for fluid transport or storage
Definitions
- the present invention relates to a method for storing trifluoroethylene and a storage container, and more particularly to a method for stably storing trifluoroethylene for storage and transportation, and a container in which trifluoroethylene is stably stored.
- Such trifluoroethylene is stored and transported by being pressure-filled in a sealed container at a temperature below room temperature, or by being liquefied and filled under cooling.
- the trifluoroethylene thus filled in the sealed container is in a gas-liquid state having a gas phase and a liquid phase.
- the gas-liquid trifluoroethylene can be stably held without causing a reaction such as polymerization in order to maintain the quality as a refrigerant and prevent the adhesion of impurities (solid) in the container. It has been demanded.
- a fluoroolefin causes a polymerization reaction by using oxygen as a radical source.
- oxygen as a radical source.
- tetrafluoroethylene is polymerized in the presence of a trace amount of oxygen of 1 to several tens ppm, and in some cases, the polymerization reaction proceeds explosively.
- Patent Document 1 describes that tetrafluoroethylene undergoes polymerization at an oxygen concentration of 1.4 ppm to produce polytetrafluoroethylene. For this reason, when storing the fluoroolefin, it is important to handle it while excluding oxygen to the limit.
- Patent Document 2 discloses a method of adding a stabilizer such as alkylcatechols or alkoxyphenols in order to maintain a stable state of hydrofluoropropene (a state in which no acid is formed) even in the presence of air.
- Patent Document 3 discloses a stabilization method in which an aliphatic alcohol having 1 to 4 carbon atoms is added as a stabilizer to hydrofluoropropene.
- both of the methods of Patent Document 2 and Patent Document 3 are methods for stabilizing the entire cooling system by stabilizing the refrigerant composition on the premise of the presence of refrigerating machine oil, for storage and transportation. Since the conditions are different from the stabilization of the refrigerant in the container, it is difficult to apply this method to the preservation of the refrigerant in the container.
- the method of adding a stabilizer requires the removal of the stabilizer before use as a refrigerant, which not only has a large process load, but also the physical purification method such as distillation completely removes the stabilizer. In some cases, it cannot be removed, which is not preferable for quality control.
- JP 2008-308480 A International Publication No. 2010/098451 International Publication No. 2010/098447
- the present invention has been made in response to the above problems, and in trifluoroethylene filled in a container for storage and transportation, a method for stably storing the trifluoroethylene without causing a reaction such as polymerization. And a container in which trifluoroethylene is stably stored.
- the method for storing trifluoroethylene according to the present invention is a method for storing trifluoroethylene in a sealed container, wherein the trifluoroethylene is stored in a state where a gas phase and a liquid phase coexist in the sealed container,
- the oxygen concentration in the gas phase at a temperature of 25 ° C. is maintained at 1000 ppm by volume or less.
- the oxygen concentration is preferably 1 to 1000 ppm by volume, more preferably 3 to 1000 ppm by volume, and further preferably 3 to 300 ppm by volume. Preferably, 3 to 50 ppm by volume is most preferable.
- the storage container for trifluoroethylene of the present invention is a sealed storage container filled with trifluoroethylene in a state where the gas phase and the liquid phase coexist, and the oxygen storage gas at a temperature of 25 ° C. is stored in the gas phase.
- the concentration is 1000 ppm by volume or less.
- the oxygen concentration is preferably 1 to 1000 ppm by volume, more preferably 3 to 1000 ppm by volume, and further preferably 3 to 300 ppm by volume. Preferably, 3 to 50 ppm by volume is most preferable.
- the method for storing trifluoroethylene and the container for storing trifluoroethylene according to the present invention the polymerization reaction of trifluoroethylene and the like are suppressed, so that the trifluoroethylene can be maintained with high purity and high quality.
- the trifluoroethylene storage method and the trifluoroethylene storage container of the present invention storage can be performed at low cost.
- the oxygen concentration in the gas phase of trifluoroethylene refers to the oxygen concentration when the gas temperature is 25 ° C.
- the polymerization of trifluoroethylene proceeds when the oxygen concentration in the gas phase is 0 to 1 ppm by volume. I found it not. Based on this finding, even if the oxygen concentration in the gas phase was 1 ppm by volume or higher, it was possible to estimate the oxygen concentration at which the polymerization did not proceed to the extent that substantial inconvenience occurred. Since the presence of oxygen is allowed up to a certain oxygen concentration, it is not necessary to eliminate the oxygen concentration to the limit close to 0 ppm by volume. Thereby, the manufacturing cost of trifluoroethylene for storage can be suppressed.
- the upper limit of the allowable oxygen concentration range is 1000 ppm by volume or less, preferably 300 ppm by volume or less, and more preferably 50 ppm by volume or less.
- trifluoroethylene is stored in a sealed container in a state where the gas phase and the liquid phase coexist under pressure, and the concentration of oxygen in the gas phase at a temperature of 25 ° C. is 1000 ppm by volume or less. It is characterized by holding. Since trifluoroethylene is maintained in a gas-liquid coexistence state in the sealed container, trifluoroethylene exhibits a saturated vapor pressure in the gas phase.
- the oxygen concentration can also be referred to as a content ratio indicating how much oxygen is contained in the gas phase of trifluoroethylene.
- the volume of the gas phase in the storage container increases, but even in the gas phase with the increased volume, the oxygen concentration is maintained at 1000 ppm by volume or less.
- the oxygen concentration in the gas phase is usually in equilibrium with the oxygen concentration in the liquid phase trifluoroethylene, so that the oxygen in the gas phase is not present unless oxygen enters the storage container when a part of the trifluoroethylene is taken out. It is believed that the concentration does not substantially increase.
- the trifluoroethylene storage container of the present invention is a sealed storage container filled with trifluoroethylene in a state where the gas phase and the liquid phase coexist, and the oxygen concentration of the gas phase at a temperature of 25 ° C. , 1000 ppm by volume or less.
- a storage container for trifluoroethylene does not require a special structure or constituent material as long as it is a sealed container capable of enclosing trifluoroethylene in a gas-liquid coexistence state under internal pressure, and has a wide range of forms and functions.
- a storage tank which is a fixed storage container
- a pressure container such as a filling cylinder used for transportation, a secondary filling cylinder (service can), and the like can be given.
- a constituent material of the storage container for example, carbon steel, manganese steel, chrome molybdenum steel and other low alloy steels, stainless steel, aluminum alloys, and the like can be used.
- the oxygen concentration in the gas phase is 1000 ppm by volume or less. If the oxygen concentration in the gas phase is 1000 ppm by volume or less, reactions such as polymerization of liquid phase and gas phase trifluoroethylene can be sufficiently prevented.
- a more preferable oxygen concentration in the gas phase is 1 to 1000 ppm by volume, preferably 3 to 1000 ppm by volume, more preferably 3 to 300 ppm by volume, and most preferably 3 to 50 ppm by volume. It is.
- Oxygen concentration in the gas phase is achieved by pressurizing trifluoroethylene to generate a liquid, and then injecting this liquid into a sealed container in which the oxygen concentration is reduced to 1000 ppm by volume or less by previously degassing the air under vacuum. can do.
- a liquid of trifluoroethylene is injected into the container, the space in the container is quickly saturated with vapor from the liquid.
- the oxygen concentration in the gas phase filled with the saturated vapor of trifluoroethylene is 1000 ppm by volume or less.
- non-condensable gas such as nitrogen is excluded together with oxygen, but the total content of non-condensable gas is 1.5% by volume at a temperature of 25.0 ° C. It is preferable that the amount does not exceed (15000 volume ppm).
- trifluoroethylene can be stored at low cost.
- the storage method of the present invention is evaluated by, for example, sealing a gas-liquid trifluoroethylene together with a predetermined amount of oxygen in a sealed container, heating the whole to a predetermined temperature and holding it at a constant temperature for a predetermined time, This is done by identifying and analyzing the reaction product in the liquid phase of ethylene.
- This evaluation corresponds to an accelerated test with a heat load.
- the heating temperature can be set in the range of ⁇ 70 to 300 ° C., which is the set temperature range of the thermostatic bath.
- the heat treatment time can be arbitrarily set.
- the identification and analysis of the reaction product can be carried out, for example, by the method described in the examples described later.
- Examples 1 to 7 and 11 are examples, and examples 8 to 10 and 12 are comparative examples.
- Examples 1 to 10 Insert an intubation tube made of Pyrex (registered trademark) that weighed in advance into a pressure resistant container made of SUS316 (maximum operating temperature 300 ° C., maximum operating pressure 20 MPa) with an internal volume of 200 cc, and after sealing the pressure container, was evacuated. The intubation tube was inserted in order to confirm whether or not a polymer was formed in the pressure test vessel.
- Pyrex registered trademark
- SUS316 maximum operating temperature 300 ° C., maximum operating pressure 20 MPa
- Examples 11 to 12 Insert an intubation tube made of Pyrex (registered trademark) that weighed in advance into a pressure resistant container made of SUS316 (maximum operating temperature 300 ° C., maximum operating pressure 20 MPa) with an internal volume of 200 cc, and after sealing the pressure container, was evacuated. The intubation tube was inserted in order to confirm whether or not a polymer was formed in the pressure test vessel.
- Pyrex registered trademark
- SUS316 maximum operating temperature 300 ° C., maximum operating pressure 20 MPa
- Example 12 where the solid material was observed with the naked eye, the solid material in the inner intubation was collected, each spectrum was dissolved in deuterated acetone 1 H-NMR, 13 C- NMR and 19 F-NMR was measured.
- the solid substance was identified by the peak assignment of the measured NMR spectrum, it was a trifluoroethylene homopolymer. This is presumed to be generated by polymerization of trifluoroethylene.
- Examples 1 to 7 and 11 no trifluoroethylene homopolymer, which is a solid product that causes a practical problem in the liquid phase, was observed.
- the solid product was Is not observed, indicating that the polymerization reaction of trifluoroethylene has not occurred.
- Examples 8-10 and 12 show the formation of a homopolymer of trifluoroethylene. This shows that the method of the present invention is effective as a stable storage method that does not cause a polymerization reaction over a long period of time.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
しかしながら、酸素を極限まで排除するためには、製造工程において酸素を極限まで除去する工程を新たに設ける等の措置が必要となるため、それに伴うコストが増加してしまう。また、酸素を極限まで除去する工程等を行うことで収率が低くなる場合もあり、製造コストが増加してしまう。
トリフルオロエチレンが、酸素存在下で自己重合反応に対してどの程度安定であるかについては、不明な点が多い。冷媒としての品質を保持し、安価で、安全かつ安定的に貯蔵および輸送を行うために、トリフルオロエチレンに重合反応を生じさせることなく保存する方法が求められている。
なお、以下、トリフルオロエチレンの気相における酸素濃度は、気体温度が25℃の場合の酸素濃度をいう。
気相におけるより好ましい酸素濃度は、1~1000体積ppmであり、さらに3~1000体積ppmであることが好ましく、さらに3~300体積ppmであることが好ましく、さらに最も好ましくは3~50体積ppmである。
なお、密閉容器を真空脱気する際には、酸素とともに窒素等の非凝縮性気体も除外されるが、非凝縮性気体の含有量の合計は、温度25.0℃で1.5体積%(15000体積ppm)を超えない量となるようにすることが好ましい。
内容積200ccのSUS316製耐圧容器(最高使用温度300℃、最高使用圧力20MPa)内に、予め重量を計測したパイレックス(登録商標)製の内挿管を挿入し、耐圧容器を密閉した後、容器内の真空排気を行った。なお、内挿管は耐圧試験容器内での重合物の生成の有無を確認するために挿入した。
次いで、このように所定濃度の酸素とともにトリフルオロエチレンが封入された耐圧容器を、熱風循環型恒温槽内に設置し、60℃の恒温状態で20日間放置した。
内容積200ccのSUS316製耐圧容器(最高使用温度300℃、最高使用圧力20MPa)内に、予め重量を計測したパイレックス(登録商標)製の内挿管を挿入し、耐圧容器を密閉した後、容器内の真空排気を行った。なお、内挿管は耐圧試験容器内での重合物の生成の有無を確認するために挿入した。
次いで、このように所定濃度の酸素とともにトリフルオロエチレンが封入された耐圧容器を、熱風循環型恒温槽内に設置し、80℃の恒温状態で5日間放置した。
なお、2013年7月16日に出願された日本特許出願2013-147575号の明細書、特許請求の範囲および要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
Claims (12)
- トリフルオロエチレンを密閉された保存容器内で保存する方法であって、前記保存容器内でトリフルオロエチレンを気相と液相とが共存する状態で保存し、前記気相の、温度25℃における酸素の濃度を1000体積ppm以下に保持することを特徴とするトリフルオロエチレンの保存方法。
- 前記酸素の濃度を、1~1000体積ppmに保持する、請求項1に記載のトリフルオロエチレンの保存方法。
- 前記酸素の濃度を、3~1000体積ppmに保持する、請求項1に記載のトリフルオロエチレンの保存方法。
- 前記酸素の濃度を、3~300体積ppmに保持する、請求項1に記載のトリフルオロエチレンの保存方法。
- 前記酸素の濃度を、3~50体積ppmに保持する、請求項1に記載のトリフルオロエチレンの保存方法。
- 前記気相の、酸素以外の非凝縮性気体の温度25℃における濃度が1.5体積%以下である、請求項1~5のいずれか一項に記載のトリフルオロエチレンの保存方法。
- 未充填の保存容器内を脱気して保存容器内の酸素を除去した後、液状のトリフルオロエチレンを充填して密閉し、密閉された保存容器内でトリフルオロエチレンを保存する、請求項1~6のいずれか一項に記載のトリフルオロエチレンの保存方法。
- 気相と液相とが共存する状態でトリフルオロエチレンが充填されている、密閉された保存容器であり、前記気相の、温度25℃における酸素の濃度が1000体積ppm以下であることを特徴とするトリフルオロエチレンの保存容器。
- 前記酸素の濃度が、1~1000体積ppmである、請求項8に記載のトリフルオロエチレンの保存容器。
- 前記酸素の濃度が、3~1000体積ppmである、請求項8に記載のトリフルオロエチレンの保存容器。
- 前記酸素の濃度が、3~300体積ppmである、請求項8に記載のトリフルオロエチレンの保存容器。
- 前記酸素の濃度が、3~50体積ppmである、請求項8に記載のトリフルオロエチレンの保存容器。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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JP2015527275A JP6421752B2 (ja) | 2013-07-16 | 2014-07-10 | トリフルオロエチレンの保存方法およびトリフルオロエチレンの保存容器 |
CN201480037894.XA CN105358511A (zh) | 2013-07-16 | 2014-07-10 | 三氟乙烯的保存方法及三氟乙烯的保存容器 |
EP14826313.0A EP3023404B1 (en) | 2013-07-16 | 2014-07-10 | Trifluoroethylene storage method and trifluoroethylene storage vessel |
US14/995,566 US9638371B2 (en) | 2013-07-16 | 2016-01-14 | Storage method for trifluoroethylene, and storage container for trifluoroethylene |
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JP2013-147575 | 2013-07-16 | ||
JP2013147575 | 2013-07-16 |
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US14/995,566 Continuation US9638371B2 (en) | 2013-07-16 | 2016-01-14 | Storage method for trifluoroethylene, and storage container for trifluoroethylene |
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EP (1) | EP3023404B1 (ja) |
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JP2017204520A (ja) * | 2016-05-10 | 2017-11-16 | Jsr株式会社 | 半導体洗浄用組成物の保管方法および洗浄方法 |
JP2018529705A (ja) * | 2015-09-30 | 2018-10-11 | アルケマ フランス | トリフルオロエチレンの安定な組成物 |
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JP6421752B2 (ja) | 2018-11-14 |
EP3023404B1 (en) | 2020-04-22 |
EP3023404A1 (en) | 2016-05-25 |
CN110041163A (zh) | 2019-07-23 |
EP3023404A4 (en) | 2017-02-22 |
JPWO2015008695A1 (ja) | 2017-03-02 |
CN105358511A (zh) | 2016-02-24 |
US20160123534A1 (en) | 2016-05-05 |
US9638371B2 (en) | 2017-05-02 |
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