JPH0224575B2 - - Google Patents
Info
- Publication number
- JPH0224575B2 JPH0224575B2 JP4487585A JP4487585A JPH0224575B2 JP H0224575 B2 JPH0224575 B2 JP H0224575B2 JP 4487585 A JP4487585 A JP 4487585A JP 4487585 A JP4487585 A JP 4487585A JP H0224575 B2 JPH0224575 B2 JP H0224575B2
- Authority
- JP
- Japan
- Prior art keywords
- membrane
- separation
- water
- pervaporation
- tertiary amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000012528 membrane Substances 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 19
- 150000003512 tertiary amines Chemical class 0.000 claims description 11
- 239000005062 Polybutadiene Substances 0.000 claims description 9
- 229920002857 polybutadiene Polymers 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 238000000926 separation method Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000005373 pervaporation Methods 0.000 description 12
- 239000012466 permeate Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005597 polymer membrane Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012510 hollow fiber Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- -1 polytetrafluoroethylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Landscapes
- Separation Using Semi-Permeable Membranes (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ポリブタジエンに三級アミンをブレ
ンドしてなる水−有機酸混合物を分離するための
分離膜に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a separation membrane for separating a water-organic acid mixture formed by blending polybutadiene with a tertiary amine.
従来、分離膜で区割された二つの室の供給液側
（一次側）に分離されるべき液体混合物を供給し
透過液側（二次側）を減圧にするか、又は不活性
ガスを流すことによつて低蒸気圧に保ち、膜との
親和性の大きな成分を二次側に蒸気として優先的
に透過させるパーベーパレーシヨン法（浸透気化
法）で水−有機液体混合物を分離する方法が実施
されており、このようなパーベーパレーシヨン法
により水−有機液体混合物を分離した実験例が
種々報告されている。具体的には、米国特許第
2953502号にはセルロースアセテート膜やポリビ
ニルアルコール系膜を用いて共沸混合液体を分離
した実験例、Journal of Applied Polymer
Science vol、26（1981）の3223ページにはグラフ
ト化ポリビニルアルコール膜を用いて水−メタノ
ール混合液体を分離した実験例などが報告されて
いる。
Conventionally, the liquid mixture to be separated is supplied to the feed liquid side (primary side) of two chambers separated by a separation membrane, and the pressure is reduced on the permeate side (secondary side), or an inert gas is passed. A method of separating a water-organic liquid mixture by the pervaporation method, which maintains a low vapor pressure and allows components with high affinity with the membrane to preferentially permeate as vapor to the secondary side. has been carried out, and various experimental examples have been reported in which water-organic liquid mixtures were separated by such pervaporation methods. Specifically, U.S. Patent No.
No. 2953502 includes an experimental example of separating azeotropic liquids using cellulose acetate membranes and polyvinyl alcohol membranes, Journal of Applied Polymer
Science Vol. 26 (1981), page 3223, reports on an experimental example in which a water-methanol mixed liquid was separated using a grafted polyvinyl alcohol membrane.
パーベーパレーシヨン法は、従来の逆浸透法の
ように浸透圧による濃度的な制限がないため低濃
度の液体混合物の分離と限定されることなく、全
ての範囲の濃度の液体混合物の分離が可能である
こと、また従来の蒸留法では分離の困難な共沸混
合物や沸点の接近した溶媒異性体（たとえばオル
トとパラ異性体、シスとトランス異性体）の分離
が可能などの特徴を有しているため、非常に有用
な分離方法であると考えられている。
Unlike conventional reverse osmosis, the pervaporation method is not limited to the concentration by osmotic pressure, so it is not limited to the separation of liquid mixtures with low concentrations, but can separate liquid mixtures with a whole range of concentrations. It also has the characteristics of being able to separate azeotropic mixtures and solvent isomers with close boiling points (for example, ortho and para isomers, cis and trans isomers) that are difficult to separate using conventional distillation methods. It is considered to be a very useful separation method.
しかしながら、従来のパーベーパレーシヨン用
膜を水−有機酸混合物の分離に用いることは、酸
による膜の劣化等により、事実上困難である。
又、シリコン、ポリオレフイン、ポリテトラフル
オロエチレン等の耐薬品性に優れた素材を膜に用
いても、混合液体が高分子膜を一回通過すること
による分離の割合、すなわち、分離係数が小さい
ため、目的とする濃度まで分離または濃縮するに
は、非常に多数の膜を透過させる必要があり、
又、とくに、高分子膜を透過する透過速度〔一般
に、単位膜表面積及び単位時間当りの透過量、す
なわちＱ（Kg／m2hr）で表示する〕が実用性のあ
る高い値となつたとき、分離係数αが非常に低く
なつてしまうため、やはり実用化は困難である。 However, it is practically difficult to use conventional pervaporation membranes to separate water-organic acid mixtures due to deterioration of the membrane due to acid.
Furthermore, even if a material with excellent chemical resistance such as silicone, polyolefin, or polytetrafluoroethylene is used for the membrane, the rate of separation of the mixed liquid after passing through the polymer membrane once, that is, the separation coefficient, is small. , in order to separate or concentrate to the desired concentration, it is necessary to pass through a large number of membranes.
In addition, especially when the permeation rate through a polymer membrane (generally expressed as the amount of permeation per unit membrane surface area and unit time, that is, Q (Kg/m 2 hr)) reaches a high value that is practical. , the separation coefficient α becomes very low, so it is still difficult to put it into practical use.
分離係数αA Bは、膜透過後のＡ成分のＢ成分に
対する重量比WA／WBを膜透過前のＡ成分のＢ
成分に対する重量比WA／WBで除した値、
αA B＝透過液中のWA／WB／被透過液中のWA／WB
で定義されるが、本発明の目的は水−有機液体混
合物をパーベーパレーシヨン法で分離するにあた
り、大きい透過速度のもとで、かかる分離係数の
高い耐酸劣化性に優れた膜を得ることにある。 Separation coefficient α A B is the weight ratio WA/WB of component A to component B after permeation through the membrane.
The value divided by the weight ratio WA/WB of the components, α A B = WA/WB in permeate/WA/WB in permeate, is defined as α A B = WA/WB in permeate liquid; The objective is to obtain a membrane with a high separation coefficient and excellent acid deterioration resistance under a high permeation rate when performing separation by vaporization.
本発明者らは、鋭意検討し、ポリブタジエンに
有機酸と親和性のある三級アミンをブレンドして
得られる膜が上記目的を達成する膜であることを
見出し、本発明に到達した。すなわち本発明は、
ポリブタジエンに三級アミンを１〜50重量％ブレ
ンドしてなる混合液分離用の膜である。
The present inventors have made extensive studies and have discovered that a film obtained by blending polybutadiene with a tertiary amine that has an affinity for organic acids is a film that achieves the above object, and has arrived at the present invention. That is, the present invention
This is a membrane for separating mixed liquids made by blending polybutadiene with 1 to 50% by weight of tertiary amine.
本発明の膜は、ポリブタジエンに第三級アミン
〔（R1）3N、R1：炭化水素基〕をブレンドして得
られるが、このような第三級アミンとしては、炭
素数が４〜18の炭化水素基をもつものが好まし
く、炭素数６〜12の炭化水素基をもつものがさら
に好ましい。具体的には、トリヘキシルアミン、
トリオクチルアミン、トリラウリルアミン等があ
げられる。 The membrane of the present invention is obtained by blending polybutadiene with a tertiary amine [(R 1 ) 3 N, R 1 : hydrocarbon group]. Those having 18 hydrocarbon groups are preferred, and those having 6 to 12 carbon atoms are more preferred. Specifically, trihexylamine,
Examples include trioctylamine and trilaurylamine.
又、本発明の膜は、ポリブタジエンに三級アミ
ンを１〜50重量％ブレンドして得ることができる
が、三級アミンの量が少なすぎると本発明の効果
が小さく、又多すぎると機械的強度に劣るので20
〜40重量％の範囲でブレンドするのが好ましい。 Furthermore, the membrane of the present invention can be obtained by blending polybutadiene with 1 to 50% by weight of tertiary amine, but if the amount of tertiary amine is too small, the effect of the present invention will be small, and if it is too large, the mechanical 20 because the strength is inferior
It is preferred to blend in a range of ~40% by weight.
本発明の膜は、ポリブタジエンをトルエン等の
有機溶媒に溶解し、三級アミンを加えて均一溶液
とし、ガラス板上等にキヤストすることにより容
易に得ることができる。このブレンド膜は非多孔
質の均質スキンレス構造の膜であり、通常は平板
状（平膜形状）で用いられるが、その他円筒状あ
るいは中空繊維状にして単位容積あたりの膜面積
を大きくして用いてもよい。 The membrane of the present invention can be easily obtained by dissolving polybutadiene in an organic solvent such as toluene, adding a tertiary amine to form a homogeneous solution, and casting the solution on a glass plate or the like. This blend membrane is a membrane with a non-porous, homogeneous skinless structure, and is usually used in the form of a flat plate (flat membrane shape), but it can also be used in the form of a cylinder or hollow fibers to increase the membrane area per unit volume. May be used.
本発明の膜によつて分離することのできる水−
有機酸混合物としては、液状であればいかなる水
−有機酸混合物でもよいが、具体的には水／ギ
酸、水／酢酸、水／プロピオン酸、水／酢酸等を
あげることができる。 Water that can be separated by the membrane of the invention -
The organic acid mixture may be any water-organic acid mixture as long as it is liquid, and specific examples include water/formic acid, water/acetic acid, water/propionic acid, water/acetic acid, and the like.
本発明に用いられるパーベーパレーシヨン装置
は特に限定されることなく従来公知の装置が用い
られ、かかる装置を常法の条件で運転して液体混
合物を分離することができる。パーベーパレーシ
ヨンを行なうにあたり、供給液側と透過液側の圧
力差については大きければ大きいほど効果的であ
るが、工業的に実施するには、0.5〜１気圧の圧
力差を設けることが好適である。また供給液側の
圧力は大気圧あるいはその近傍の圧力が好まし
く、透過液側の圧力は透過成分の蒸気圧以下の減
圧に保つことが好ましい。透過液側を減圧に保つ
方法としては真空に引いて減圧にするか、構成成
分と反応しないガスを流して低蒸気圧に保つなど
の方法がある。分離温度は分離すべき有機液体混
合物の共沸温度以下の温度が適当である。液体混
合物の分離にあたり、膜を１回通過させるだけで
は、目的の濃度が得られない場合には、同様なパ
ーベーパレーシヨン装置を連続に設置して多数回
通過させたり、蒸留と組み合せたりして目的の濃
度にまで濃縮分離することができる。 The pervaporation device used in the present invention is not particularly limited, and any conventionally known device can be used, and such a device can be operated under conventional conditions to separate a liquid mixture. When performing pervaporation, the larger the pressure difference between the feed liquid side and the permeate side, the more effective it is, but for industrial implementation, it is preferable to provide a pressure difference of 0.5 to 1 atmosphere. It is. The pressure on the feed liquid side is preferably at or near atmospheric pressure, and the pressure on the permeate side is preferably maintained at a reduced pressure below the vapor pressure of the permeate component. Methods for maintaining the permeate side at reduced pressure include drawing a vacuum to reduce the pressure, or flowing a gas that does not react with the constituent components to maintain a low vapor pressure. The separation temperature is suitably a temperature below the azeotropic temperature of the organic liquid mixture to be separated. When separating a liquid mixture, if the desired concentration cannot be obtained by passing it through the membrane once, similar pervaporation equipment can be installed in series and passed multiple times, or it can be combined with distillation. can be concentrated and separated to the desired concentration.
本発明の膜を用いてパーベーパレーシヨンで水
−有機酸混合物を分離することにより、高い分離
係数を維持しつつ、大きい透過速度で効率よく処
理することができるが、かかる効果は従来の知見
からは全く予想しがたいことである。かかる効果
を生ずる理由は必らずしも明らかではないが、膜
中の三級アミンが有機酸と錯体を作ることにある
と推察される。
By separating a water-organic acid mixture by pervaporation using the membrane of the present invention, it is possible to efficiently treat the water-organic acid mixture at a high permeation rate while maintaining a high separation coefficient. This is completely unpredictable. Although the reason for this effect is not necessarily clear, it is presumed that the tertiary amine in the film forms a complex with the organic acid.
以下、実施例により本発明を具体的に説明する
が、本発明はこれらにより何ら制限されるもので
はない。
EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these in any way.
実施例
ポリブタジエン10ｇをトルエン90ｇに溶解した
ポリブタジエンのトルエン溶液に、トリラウリル
アミンをポリマーに対して40重量％加え、均一溶
液とした後、ガラス板上にキヤストし、膜厚90μ
ｍの均質ブレンド膜を得た。該膜をパーベーパレ
ーシヨン装置（有効膜面積7.0cm2）に装着し、酢
酸濃度2.6重量％の水−酢酸混合液を60℃で供給
し、透過液側を真空ポンプにて１mmHgに吸引し、
パーベーパレーシヨン法により分離を行つた。膜
を透過した成分の酢酸濃度（酢酸が優先透過）は
ガスクロマトグラフにて分析し、透過した成分の
量は、透過成分を凝縮させて定量した。パーベー
パレーシヨンを開始して６時間後の分離係数
αAcOH H2Oは4.02、透過速度は15.5ｇ／m2・hrであつ
た。Example: To a toluene solution of polybutadiene in which 10 g of polybutadiene was dissolved in 90 g of toluene, 40% by weight of trilaurylamine was added to the polymer to make a homogeneous solution, and then cast on a glass plate to form a film with a thickness of 90μ.
A homogeneous blend film of m was obtained. The membrane was attached to a pervaporation device (effective membrane area 7.0 cm 2 ), a water-acetic acid mixture with an acetic acid concentration of 2.6% by weight was supplied at 60°C, and the permeate side was sucked to 1 mmHg with a vacuum pump. ,
Separation was performed by pervaporation method. The acetic acid concentration of the components that permeated the membrane (acetic acid permeated preferentially) was analyzed using a gas chromatograph, and the amount of permeated components was determined by condensing the permeated components. Six hours after starting pervaporation, the separation coefficient α AcOH H2O was 4.02 and the permeation rate was 15.5 g/m 2 ·hr.
比較例
トリラウリルアミンを含まないポリブタジエン
膜を用いた以外は実施例と全く同様にして、水−
酢酸混合液のパーベーパレーシヨン分離を行つ
た。分離係数αAcOH H2O（水が優先透過）は0.42、透過
速度は9.2ｇ／m2・hrであつた。Comparative Example Water-
Pervaporation separation of the acetic acid mixture was performed. The separation coefficient α AcOH H2O (water preferentially permeates) was 0.42, and the permeation rate was 9.2 g/m 2 ·hr.
以上の結果から、本発明の膜は水−有機酸混合
液系において優れた性能を示す膜であることが明
らかである。 From the above results, it is clear that the membrane of the present invention exhibits excellent performance in a water-organic acid mixed liquid system.
本発明の膜を用いれば、酸による劣化を生ずる
ことなく、従来の膜を用いた分離方法にくらべて
高い分離係数を維持しつつ、大きい透過速度で水
−有機酸混合物を効率よく処理することができ
る。このため、分離システムのコンパクト化、処
理能力の増大、低コスト化が図られ、本発明は化
学工業などの分離精製プロセスの短縮化や省エネ
ルギー化への膜分離方法の実用化に有効であり、
産業上の有用性が極めて大きいものである。
By using the membrane of the present invention, it is possible to efficiently treat a water-organic acid mixture at a high permeation rate while maintaining a higher separation coefficient than separation methods using conventional membranes without causing deterioration due to acid. Can be done. Therefore, the separation system can be made more compact, its processing capacity can be increased, and costs can be reduced, and the present invention is effective in practical application of membrane separation methods for shortening separation and purification processes in the chemical industry and saving energy.
It has extremely great industrial utility.
Claims (1)
ブレンドしてなる混合液分離用の膜。 ２ 該三級アミンが（R1）3N（Ｒ：炭素数が４〜
18の炭化水素基）である特許請求の範囲第１項記
載の膜。 ３ 該三級アミンが（R1）3N（R1：炭素数が６〜
12の炭化水素基）である特許請求の範囲第１項記
載の膜。[Claims] 1. 1 to 50% by weight of tertiary amine in polybutadiene
A membrane for separating mixed liquids made by blending. 2 The tertiary amine is (R 1 ) 3 N (R: carbon number is 4 to
18 hydrocarbon groups). 3 The tertiary amine is (R 1 ) 3 N (R 1 : carbon number is 6 to
12 hydrocarbon groups) according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4487585A JPS61204009A (en) | 1985-03-08 | 1985-03-08 | Membrane for separating liquid mixture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4487585A JPS61204009A (en) | 1985-03-08 | 1985-03-08 | Membrane for separating liquid mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61204009A JPS61204009A (en) | 1986-09-10 |
| JPH0224575B2 true JPH0224575B2 (en) | 1990-05-30 |
Family
ID=12703666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4487585A Granted JPS61204009A (en) | 1985-03-08 | 1985-03-08 | Membrane for separating liquid mixture |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61204009A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0446572U (en) * | 1990-08-23 | 1992-04-21 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9283523B2 (en) * | 2012-05-25 | 2016-03-15 | Pbi Performance Products, Inc. | Acid resistant PBI membrane for pervaporation dehydration of acidic solvents |
-
1985
- 1985-03-08 JP JP4487585A patent/JPS61204009A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0446572U (en) * | 1990-08-23 | 1992-04-21 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61204009A (en) | 1986-09-10 |
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