JP5082843B2 - Method for recovering fluorine-containing alcohol - Google Patents
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Description
本発明は、含フッ素アルコールと水とを含有する混合液から、含フッ素アルコールを回収する技術に関する。 The present invention relates to a technique for recovering a fluorinated alcohol from a mixed liquid containing a fluorinated alcohol and water.
含フッ素アルコールは、ＣＤ−ＲやＤＶＤ−Ｒ等の情報記録媒体を製造する際、記録層となる色素の溶媒として利用されており、大容量記録メディアの製造には欠かせないものである。
上記記録媒体の製造工程においては、水を含んだ含フッ素アルコールの廃液が大量に発生する。この廃液から含フッ素アルコールを回収し、再利用できれば、環境負荷の低減および製造コストの削減が図られるため、低コストで含フッ素アルコールと水との混合液から水を除去する技術が望まれている。The fluorine-containing alcohol is used as a solvent for a dye serving as a recording layer when an information recording medium such as a CD-R or DVD-R is manufactured, and is indispensable for manufacturing a large-capacity recording medium.
In the manufacturing process of the recording medium, a large amount of waste liquid of fluorine-containing alcohol containing water is generated. If the fluorinated alcohol can be recovered from this waste liquid and reused, the environmental burden and manufacturing costs can be reduced. Therefore, a technique for removing water from a mixed liquid of fluorinated alcohol and water at low cost is desired. Yes.
しかし、含フッ素アルコールと水との混合液は共沸組成を有する場合があるため、蒸留で水を除去することは非常に困難である。例えば、含フッ素アルコールの一種である２，２，３，３−テトラフルオロプロパノール（以下、ＴＦＰＯという。）と水との混合液の共沸組成は、ＴＦＰＯ ７３質量％、水 ２７質量％である。 However, since a mixed solution of a fluorinated alcohol and water may have an azeotropic composition, it is very difficult to remove water by distillation. For example, the azeotropic composition of a mixture of 2,2,3,3-tetrafluoropropanol (hereinafter referred to as TFPO), which is a kind of fluorinated alcohol, and water is 73% by mass of TFPO and 27% by mass of water. .
特許文献１には、ＴＦＰＯと水との混合液からＴＦＰＯを回収するにあたり、パーベーパレーション法によって水を分離する方法が開示されているが、より簡便で効率的な方法が望まれていた。 Patent Document 1 discloses a method of separating water by a pervaporation method when recovering TFPO from a mixed solution of TFPO and water. However, a simpler and more efficient method has been desired.
本発明は、含フッ素アルコールと水とを含有する混合液から水を分離し、含フッ素アルコールを簡便に回収する方法の提供を目的とする。 An object of the present invention is to provide a method for separating water from a mixed solution containing a fluorinated alcohol and water and easily recovering the fluorinated alcohol.
本発明は、含フッ素アルコールおよび水を含有する混合液中の含フッ素アルコールを回収するにあたり、上記混合液に酸を添加し、２層分離させる工程を有することを特徴とする含フッ素アルコールの回収方法を提供する。
本発明においては、酸を添加することにより、含フッ素アルコールの水酸基の解離（水酸基からプロトンが脱離すること）平衡が非解離側に大きく移動し、水の溶解性が低下することから層分離が起こると考えられる。この現象は、フッ素原子が疎水性であること、フッ素原子の効果によって水酸基が解離しやすくなっていること、含フッ素アルコールが大きな比重を有する化合物であることにも関係していると考えられる。
含フッ素アルコールの比重は水よりも大きいため、主として含フッ素アルコールを含有する層が下に形成され、主として水を含有する層が上に形成される。The present invention includes a step of adding an acid to the above mixed solution and separating the two layers into a mixture when recovering the fluorinated alcohol in the mixed solution containing the fluorinated alcohol and water. Provide a method.
In the present invention, by adding an acid, the dissociation of the hydroxyl group of the fluorinated alcohol (the proton is desorbed from the hydroxyl group) moves greatly to the non-dissociation side, and the water solubility decreases, so that the layers are separated. Is thought to occur. This phenomenon is considered to be related to the fact that the fluorine atom is hydrophobic, the hydroxyl group is easily dissociated by the effect of the fluorine atom, and the fluorine-containing alcohol is a compound having a large specific gravity.
Since the specific gravity of the fluorinated alcohol is greater than that of water, a layer mainly containing the fluorinated alcohol is formed below, and a layer mainly containing water is formed on the top.
本発明では２層分離させる工程において、主として水を含有する上層と、主として含フッ素アルコールを含有する下層とに層分離させることができる。この層分離によれば、下層中の含フッ素アルコールの含有割合を８０質量％以上、特には９０質量％以上の高濃度にできる。よって、この下層をさらに蒸留等によって精製すれば、水と共沸することなく高純度の含フッ素アルコールが簡便に得られる。 In the present invention, in the step of separating the two layers, the layer can be separated into an upper layer mainly containing water and a lower layer mainly containing a fluorinated alcohol. According to this layer separation, the content ratio of the fluorinated alcohol in the lower layer can be set to a high concentration of 80% by mass or more, particularly 90% by mass or more. Therefore, if this lower layer is further purified by distillation or the like, a high-purity fluorinated alcohol can be easily obtained without azeotroping with water.
本発明における含フッ素アルコールとしては、パーフルオロ−ｔ−ブタノール等のパーフルオロアルキル基を有するアルコール類、２，２，３，３，３−ペンタフルオロプロパノール、１，１，１，３，３，３−ヘキサフルオロ−２−プロパノール、２，２，２−トリフルオロエタノール等のフルオロアルコール類、フルオロフェノール類、および下式１で表される化合物が挙げられる。
Ｈ−（ＣＲｆＦＣＦ２）ｎ−ＣＲ１Ｒ２−ＯＨ ・・・式１
ただし、Ｒｆはフッ素原子または炭素数１〜４のポリフルオロアルキル基、Ｒ１、Ｒ２はそれぞれ独立に水素原子または炭素数１〜３のアルキル基、ｎは１〜４の整数である。Examples of the fluorine-containing alcohol in the present invention include alcohols having a perfluoroalkyl group such as perfluoro-t-butanol, 2,2,3,3,3-pentafluoropropanol, 1,1,1,3,3, Examples thereof include fluoroalcohols such as 3-hexafluoro-2-propanol and 2,2,2-trifluoroethanol, fluorophenols, and compounds represented by the following formula 1.
H- (CR f FCF 2) n -CR 1 R 2 -OH ··· Formula 1
However, R f is a fluorine atom or a polyfluoroalkyl group having 1 to 4 carbon atoms, R 1, R 2 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, n represents an integer of 1 to 4.
式１で表される化合物としては、具体的には、Ｈ（ＣＦ２）２ＣＨ２ＯＨ （ＴＦＰＯ）、Ｈ（ＣＦ２）４ＣＨ２ＯＨ、ＨＣＦ２ＣＦ２ＣＨ（ＣＨ３）ＯＨ、ＨＣＦ２ＣＦ２Ｃ（ＣＨ３）２ＯＨ、ＨＣ（ＣＦ３）ＦＣＦ２ＣＨ２ＯＨ、ＨＣ（ＣＦ３）ＦＣＦ２ＣＨ（ＣＨ３）ＯＨ、ＨＣ（ＣＦ３）ＦＣＦ２Ｃ（ＣＨ３）２ＯＨが挙げられる。Specific examples of the compound represented by Formula 1 include H (CF 2 ) 2 CH 2 OH (TFPO), H (CF 2 ) 4 CH 2 OH, HCF 2 CF 2 CH (CH 3 ) OH, and HCF. 2 CF 2 C (CH 3 ) 2 OH, HC (CF 3 ) FCF 2 CH 2 OH, HC (CF 3 ) FCF 2 CH (CH 3 ) OH, HC (CF 3 ) FCF 2 C (CH 3 ) 2 OH Is mentioned.
本発明において処理される、含フッ素アルコールおよび水を含有する混合液中の水の含有割合は５０質量％以下であるのが好ましく、特には２５質量％以下であるのが好ましい。上記水の含有割合が大きすぎる場合は、酸をより多く添加することが必要となる他、２層分離後の蒸留工程において、より時間がかかる傾向があるため、あらかじめ単蒸留する等をして水をある程度除去しておくのが好ましい。 The content of water in the mixed solution containing the fluorinated alcohol and water treated in the present invention is preferably 50% by mass or less, and particularly preferably 25% by mass or less. If the water content is too large, it will be necessary to add more acid, and in the distillation step after separation of the two layers, it will take more time. It is preferable to remove some water.
本発明において使用する酸としては無機酸が好ましく、硫酸、硝酸、塩酸、フッ酸等の強酸がより好ましく、なかでも硫酸、硝酸、塩酸が好ましい。また、２層分離させる工程の後、得られた下層をさらに蒸留する蒸留工程を行う場合に、蒸留装置を腐食させにくいという観点から、特には硫酸を用いるのが好ましい。 The acid used in the present invention is preferably an inorganic acid, more preferably a strong acid such as sulfuric acid, nitric acid, hydrochloric acid, and hydrofluoric acid, and sulfuric acid, nitric acid, and hydrochloric acid are particularly preferable. Moreover, when performing the distillation process which further distills the obtained lower layer after the process of carrying out 2 layer separation, it is preferable to use a sulfuric acid especially from a viewpoint that it is hard to corrode a distillation apparatus.
本発明においては、酸を、含フッ素アルコールおよび水を含有する混合液中の水に対して、プロトン（Ｈ＋）がモル比換算で０．１０以上（酸は１００％解離したものとみなす。）となる量添加するのが好ましく、特には０．１５以上、さらには０．２０以上となる量の酸を添加するのが好ましい。上記モル比が０．１未満である場合は、下層における水の含有割合が大きくなるとともに、層分離しにくくなる。
なお、通常、酸を過剰に添加しても特にメリットはないので、酸の添加量は、２層分離が起こり、下層における含フッ素アルコールの含有割合が一定以上となる最低限の量とするのが好ましい。In the present invention, the acid is regarded as a proton (H + ) converted to a molar ratio of 0.10 or more (the acid is 100% dissociated) with respect to the water in the mixed liquid containing the fluorinated alcohol and water. It is preferable to add an amount of acid that is 0.15 or more, more preferably 0.20 or more. When the molar ratio is less than 0.1, the content of water in the lower layer is increased and the layers are difficult to separate.
Normally, there is no particular merit even if the acid is excessively added, so the amount of acid added is the minimum amount that causes separation of the two layers and the content ratio of the fluorinated alcohol in the lower layer becomes a certain level or more. Is preferred.
含フッ素アルコールおよび水を含有する混合液への酸の添加は、常圧、常温で行えばよく、通常、温度制御等をする必要はない。添加した酸が上記混合液と均一に混ざるよう撹拌翼等で混合する。
２層分離させるためには、これを静置すればよいが、遠心分離器等を用いて分離させてもかまわない。静置して２層分離させる場合、静置時間は、各層の厚さや界面の面積にもよるが、３〜１２時間程度とすればよい。The acid may be added to the mixed solution containing the fluorinated alcohol and water at normal pressure and normal temperature, and it is usually unnecessary to control the temperature. Mix with a stirring blade or the like so that the added acid is uniformly mixed with the mixture.
In order to separate the two layers, this may be left still, but may be separated using a centrifuge or the like. When the two layers are allowed to stand, the standing time may be about 3 to 12 hours, although it depends on the thickness of each layer and the area of the interface.
本発明における２層分離工程で得られる下層中の含フッ素アルコールの含有割合は８０質量％以上が好ましく、特には９０質量％以上、さらには９２質量％以上であるのが好ましい。上記含フッ素アルコールの含有割合が大きいほど、次工程で蒸留を実施する場合の負荷が小さくなるので好ましい。 The content ratio of the fluorinated alcohol in the lower layer obtained in the two-layer separation step in the present invention is preferably 80% by mass or more, particularly 90% by mass or more, more preferably 92% by mass or more. The larger the content ratio of the fluorinated alcohol, the more preferable because the load in carrying out distillation in the next step is reduced.
本発明における２層分離工程で得られる上層には、通常、１０〜３０質量％程度の含フッ素アルコールが含まれるが、この上層中の含フッ素アルコールについては、得られた上層を、次のバッチの２層分離工程において用いる酸の一部として繰り返し利用することにより有効に回収できる。 The upper layer obtained in the two-layer separation step in the present invention usually contains about 10 to 30% by mass of fluorinated alcohol. For the fluorinated alcohol in this upper layer, the obtained upper layer is used in the next batch. It can be effectively recovered by repeatedly using it as part of the acid used in the two-layer separation step.
本発明においては、上記２層分離させる工程で得られた下層をさらに蒸留する蒸留工程を有することが好ましい。これにより、下層中の水をさらに除去し、水分濃度の小さい含フッ素アルコールを得ることができる。
蒸留条件は特に限定されず、通常の多段蒸留で水を除去できる。本発明における２層分離工程で得られる下層は水の含有割合が小さいため、この蒸留工程に要する時間は短時間ですむ。In this invention, it is preferable to have the distillation process which further distills the lower layer obtained at the process of carrying out the said 2 layer separation. Thereby, the water in a lower layer can be removed further and a fluorinated alcohol with a small water concentration can be obtained.
Distillation conditions are not particularly limited, and water can be removed by ordinary multistage distillation. Since the lower layer obtained in the two-layer separation step in the present invention has a small water content, the time required for this distillation step is short.
蒸留工程においては、上記下層を蒸留すること等により、水分濃度が１０００ｐｐｍ以下の含フッ素アルコールを得ることが好ましい。これは、含フッ素アルコールを情報記憶媒体に用いる色素の溶媒として用いる場合、水分濃度は低い方が好ましいためである。水分濃度は特には５００ｐｐｍ以下、さらには２００ｐｐｍ以下とするのが好ましい。上記水分濃度とするため、本発明においては、蒸留工程の後に、さらに、好ましくはゼオライト等の乾燥剤を用いて含フッ素アルコール中の水分を除去する工程を設けてもよい。 In the distillation step, it is preferable to obtain a fluorinated alcohol having a water concentration of 1000 ppm or less by, for example, distilling the lower layer. This is because when the fluorinated alcohol is used as a solvent for the dye used in the information storage medium, it is preferable that the moisture concentration is low. The water concentration is particularly preferably 500 ppm or less, and more preferably 200 ppm or less. In order to obtain the water concentration, in the present invention, a step of removing water in the fluorinated alcohol may be provided after the distillation step, preferably using a desiccant such as zeolite.
以下、本発明を、実施例（例１〜３）を参照して説明する。
［例１］
ＴＦＰＯ ５０ｇ、脱イオン水 １５ｇを分液ロートに入れて振とうさせたところ、両者は完全に混ざり合い、均一な混合液となった。これに９６質量％の濃硫酸 １１．５ｇをゆっくり滴下し、振とうさせた後、３時間静置したところ混合液は２層分離した。なお、上記濃硫酸の添加量を、混合液中の水に対するプロトン（Ｈ＋）のモル比に換算すると０．２７である。分離した上層と下層を分取したところ、上層 ２４．６ｇ、下層 ４９．８ｇが得られた。上層および下層におけるＴＦＰＯの濃度をＮＭＲにて定量したところ、上層のＴＦＰＯ濃度は２４．５質量％、下層のＴＦＰＯ濃度は９３．７質量％であった。ＮＭＲの測定条件を以下に示す。Hereinafter, the present invention will be described with reference to Examples (Examples 1 to 3).
[Example 1]
When 50 g of TFPO and 15 g of deionized water were placed in a separatory funnel and shaken, the two were completely mixed and a uniform mixture was obtained. To this, 11.5 g of 96% by mass concentrated sulfuric acid was slowly added dropwise, and after shaking, the mixture was allowed to stand for 3 hours. In addition, it is 0.27 when the addition amount of the said concentrated sulfuric acid is converted into the molar ratio of the proton (H <+> ) with respect to the water in a liquid mixture. When the separated upper layer and lower layer were separated, 24.6 g of the upper layer and 49.8 g of the lower layer were obtained. When the concentration of TFPO in the upper layer and the lower layer was quantified by NMR, the TFPO concentration in the upper layer was 24.5% by mass, and the TFPO concentration in the lower layer was 93.7% by mass. NMR measurement conditions are shown below.
＜ＮＭＲ測定条件＞
測定装置：日本電子社製 ＥＣＰ−４００、
測定核：１Ｈ、
測定法：シングルパルス法、
測定溶媒：なし（試料のみを試験管に採取）、
測定温度：室温、
試料管外径：５ｍｍ。<NMR measurement conditions>
Measuring device: ECP-400 manufactured by JEOL Ltd.
Measuring nucleus: 1 H,
Measurement method: Single pulse method,
Measurement solvent: None (only sample is collected in a test tube),
Measurement temperature: room temperature,
Sample tube outer diameter: 5 mm.
［例２］
９６質量％濃硫酸の滴下量を９ｇとした以外は例１と同様にして、ＴＦＰＯと脱イオン水の混合、分離を行った。なお、上記濃硫酸の添加量を、混合液中の水に対するプロトン（Ｈ＋）のモル比に換算すると０．２１である。静置後、混合液は２層分離し、上層２３．０ｇ、下層５０．７ｇが得られ、上層のＴＦＰＯ濃度は１８．３質量％、下層のＴＦＰＯ濃度は９３．４質量％であった。[Example 2]
TFPO and deionized water were mixed and separated in the same manner as in Example 1 except that the amount of 96 mass% concentrated sulfuric acid added was 9 g. In addition, it is 0.21 when the addition amount of the said concentrated sulfuric acid is converted into the molar ratio of the proton (H <+> ) with respect to the water in a liquid mixture. After standing, the mixed solution was separated into two layers to obtain 23.0 g of the upper layer and 50.7 g of the lower layer, the TFPO concentration of the upper layer was 18.3% by mass, and the TFPO concentration of the lower layer was 93.4% by mass.
［例３］
９６質量％濃硫酸の滴下量を４．５ｇとした以外は例１と同様にして、ＴＦＰＯと脱イオン水の混合、分離を行った。なお、上記濃硫酸の添加量を、混合液中の水に対するプロトン（Ｈ＋）のモル比に換算すると０．１１である。静置後、混合液は２層分離し、上層１５．７ｇ、下層５３．７ｇが得られ、上層のＴＦＰＯ濃度は１５．５質量％、下層のＴＦＰＯ濃度は９０．０質量％であった。[Example 3]
TFPO and deionized water were mixed and separated in the same manner as in Example 1 except that the amount of 96 mass% concentrated sulfuric acid added was 4.5 g. In addition, when the addition amount of the said concentrated sulfuric acid is converted into the molar ratio of the proton (H <+> ) with respect to the water in a liquid mixture, it is 0.11. After standing, the mixed solution was separated into two layers to obtain 15.7 g of the upper layer and 53.7 g of the lower layer, the TFPO concentration of the upper layer was 15.5% by mass, and the TFPO concentration of the lower layer was 90.0% by mass.
本発明の含フッ素アルコールの回収方法は、ＣＤ−ＲやＤＶＤ−Ｒの製造工程で発生する廃液から含フッ素アルコールを回収し、再利用するプロセスとして有用である。
なお、２００５年２月１５日に出願された日本特許出願２００５−３７８８８号の明細書、特許請求の範囲、図面及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。The method for recovering fluorine-containing alcohol of the present invention is useful as a process for recovering and reusing fluorine-containing alcohol from waste liquid generated in the production process of CD-R and DVD-R.
It should be noted that the entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2005-37888 filed on February 15, 2005 are cited herein as disclosure of the specification of the present invention. Incorporated.
Claims (10)
Ｈ−（ＣＲｆＦＣＦ２）ｎ−ＣＲ１Ｒ２−ＯＨ・・・式１The fluorinated alcohol is represented by the following formula 1 (wherein R f is a fluorine atom or a polyfluoroalkyl group having 1 to 4 carbon atoms, R 1 and R 2 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, n Is an integer of 1 to 4.). The method for recovering a fluorinated alcohol according to claim 1.
H- (CR f FCF 2) n -CR 1 R 2 -OH ··· Formula 1
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| JP2007503631A JP5082843B2 (en) | 2005-02-15 | 2006-02-09 | Method for recovering fluorine-containing alcohol |
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| JP2007503631A JP5082843B2 (en) | 2005-02-15 | 2006-02-09 | Method for recovering fluorine-containing alcohol |
| PCT/JP2006/302260 WO2006087964A1 (en) | 2005-02-15 | 2006-02-09 | Method for recovering fluorine-containing alcohol |
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| JP2007503631A Expired - Fee Related JP5082843B2 (en) | 2005-02-15 | 2006-02-09 | Method for recovering fluorine-containing alcohol |
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| Country | Link |
|---|---|
| JP (1) | JP5082843B2 (en) |
| CN (1) | CN101119950B (en) |
| TW (1) | TW200639144A (en) |
| WO (1) | WO2006087964A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718630B (en) * | 2012-06-11 | 2014-07-02 | 中昊晨光化工研究院 | Tetrafluoropropanol rectification purifying method |
| CN111892502A (en) * | 2020-09-11 | 2020-11-06 | 安徽灵达高新材料有限公司 | Efficient separation method of mixture of acrylic ester and methanol |
| CN113979838B (en) * | 2021-08-04 | 2023-09-29 | 浙江巨圣氟化学有限公司 | Method for refining tetrafluoropropanol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0459020A (en) * | 1990-06-20 | 1992-02-25 | Central Glass Co Ltd | Method for recoverying fluorine-containing alcohol |
| JP2001187755A (en) * | 1999-04-20 | 2001-07-10 | Daikin Ind Ltd | Method for recovering fluorine-based solvent |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5233098A (en) * | 1990-05-30 | 1993-08-03 | Central Glass Company, Limited | Method for removing and recovering fluorinated alcohol from waste gas |
| TW499414B (en) * | 1999-04-20 | 2002-08-21 | Daikin Ind Ltd | Method for recovering fluorine-containing solvents |
-
2006
- 2006-02-09 CN CN2006800047567A patent/CN101119950B/en not_active Expired - Fee Related
- 2006-02-09 WO PCT/JP2006/302260 patent/WO2006087964A1/en not_active Application Discontinuation
- 2006-02-09 JP JP2007503631A patent/JP5082843B2/en not_active Expired - Fee Related
- 2006-02-15 TW TW095105094A patent/TW200639144A/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0459020A (en) * | 1990-06-20 | 1992-02-25 | Central Glass Co Ltd | Method for recoverying fluorine-containing alcohol |
| JP2001187755A (en) * | 1999-04-20 | 2001-07-10 | Daikin Ind Ltd | Method for recovering fluorine-based solvent |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI359805B (en) | 2012-03-11 |
| JPWO2006087964A1 (en) | 2008-07-03 |
| CN101119950A (en) | 2008-02-06 |
| TW200639144A (en) | 2006-11-16 |
| WO2006087964A1 (en) | 2006-08-24 |
| CN101119950B (en) | 2010-09-15 |
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