JPS6041622A - Separation of p-xylene from p-xylene-containing mixture - Google Patents
Separation of p-xylene from p-xylene-containing mixtureInfo
- Publication number
- JPS6041622A JPS6041622A JP12505084A JP12505084A JPS6041622A JP S6041622 A JPS6041622 A JP S6041622A JP 12505084 A JP12505084 A JP 12505084A JP 12505084 A JP12505084 A JP 12505084A JP S6041622 A JPS6041622 A JP S6041622A
- Authority
- JP
- Japan
- Prior art keywords
- xylene
- compound
- metacyclophane
- containing mixture
- inclusion
- 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.)
- Granted
Links
Abstract
Description
【発明の詳細な説明】
本発明は、下記式
で表わされるメタシクロファンを利用したｐ −キシレ
ン含有混合物からのＰ−キシレンの分離法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for separating p-xylene from a p-xylene-containing mixture using metacyclophane represented by the following formula.
従来、Ｐ−キシレンの包接化合物に関しては、例えば
（１）トリー〇−チモチドとの包接体；アメリカン・ケ
ミカル働ンサアテイー
（Ａｍ＋ Ｃｈｅｍ、Ｓｏｃ、）
３７４７（１９５２）及び同２３３９（１９５８）参照
（１１） α−サイクｐデキストリンとの包接体；米国
特許第３，４５６，０２８明細１Ｆ参照ＯｉＤ 天然又
は合成ゼオライトとの包接体；特公昭３７−５１５５号
公報参照
本発明者らは、これら公知のＰ−キシレンの包接体とは
異なる包接体及びその利用について、種々研究した結果
本発明に到達した。Conventionally, regarding clathrate compounds of P-xylene, for example, (1) clathrates with tri-thymotide; see Am+ Chem, Soc. 3747 (1952) and 2339 (1958) ( 11) Inclusion complex with α-cyc p-dextrin; see US Pat. No. 3,456,028 Specification 1F OiD Inclusion complex with natural or synthetic zeolite; see Japanese Patent Publication No. 37-5155. The present invention was achieved as a result of various studies on inclusion bodies different from known inclusion bodies of P-xylene and their uses.
すなわち、本発明は下記式（Ｉ）
で表わされるメタシクロファンとＰ−キシレン含有混合
物とを接触せしめて、前記メタシクロファンＫＰ−キシ
レンを包接せしめた包接化合物を形成せしめ、該包接化
合物を分離し、該包接化合物からＰ−キシレンを分離回
収することを特徴とするＰ−キシレン含有混合物からの
Ｐ−キシレンの分離法である。That is, the present invention involves contacting metacyclophane represented by the following formula (I) with a P-xylene-containing mixture to form an inclusion compound containing the metacyclophane KP-xylene, and forming an inclusion compound containing the metacyclophane KP-xylene. This is a method for separating P-xylene from a mixture containing P-xylene, which is characterized by separating the compound and separating and recovering P-xylene from the clathrate compound.
かかる本発明において、前記メタシクロファンにＰ−キ
シレンが包接し、包接組成物を形成することは、従来全
く知られてなく、またこの現象に基いて、Ｐ−キシレン
含有混合物からＰ−キシレンを高選択率、高回収率で分
離し得ることができる。In the present invention, it has never been known that P-xylene is included in the metacyclophane to form an inclusion composition, and based on this phenomenon, P-xylene is included from a P-xylene-containing mixture. can be separated with high selectivity and high recovery rate.
以下本発明について詳述する。The present invention will be explained in detail below.
本発明のメタンクロファンは前記式ＣＩ）で表わされる
環状化合物であればよく、それは種々の製造法によって
得ることができる。例えばその製造法としては、
（ａ）ヘルベチ力、キミカ、γフタ（Ｈｅ ｌｖｅ ｔ
ｉ ｃａ。The methanecrophane of the present invention may be any cyclic compound represented by the above formula CI), and can be obtained by various production methods. For example, the manufacturing methods include (a) Helvet's force, Kimika, γ-futa (Helvet's force),
i ca.
Ｃｈｉｍｉｃａ Ａｃｔａ ） ５０巻Ｆ２５ｃｉｃｕ
ｌｕｓ ７（１９６７）Ｎｏ、２０４
（ｂ）シンセシス（Ｓｙｍｔｈｅｓｉｓ ） ４２４
（１９７４）等に記載されている。Chimica Acta) 50 volumes F25cicu
lus 7 (1967) No. 204 (b) Synthesis 424
(1974) and others.
本発明において、前記一般式ＣＩ）のメタシクＩｆｆフ
ァンとＰ−キシレンとの包接化合物を得るには種々の方
法が適用される。In the present invention, various methods can be applied to obtain the clathrate compound of metasic Iff fan and P-xylene of the general formula CI).
例えば、Ｐ−キシレン含有混合物中に前記メタシクロフ
ァンを添加してもよいし、また包接化を完全に行なわし
めるために上記の如くメタシクロファンを添加して得ら
れる混合物を加温し完全に溶解した溶液とし、これを冷
却して生じた結晶を分離することによっても得られる。For example, the metacyclophane may be added to a mixture containing P-xylene, or the mixture obtained by adding metacyclophane as described above may be heated to completely achieve inclusion. It can also be obtained by preparing a solution dissolved in water, cooling the solution, and separating the resulting crystals.
いずれの方法によっても容易にメタシクロファンにＰ−
キシレンが包接した包接化合物を得ることができる。Metacyclophane can be easily converted to P- by either method.
A clathrate compound containing xylene can be obtained.
前記式ＣＩ）のメタシクロファンの使用分は、Ｐ −−
１’−シレン含有混合物中の■〕−キシレン１モル当り
、０．０１〜１００モル、好ましくは０．１〜１０モル
、就中０．２〜２モルの割合が有利である。The amount of metacyclophane of formula CI) used is P --
Proportions of from 0.01 to 100 mol, preferably from 0.1 to 10 mol, in particular from 0.2 to 2 mol, are advantageous per mole of [1]-xylene in the mixture containing 1'-silene.
約述の如（してメタシクロファンにＰ−キシレンを包接
させる場合、一般に一５０〜３５０℃、好ましくは０〜
２００℃、特に２０〜１５０℃の範囲の温度で行なわれ
る。かくして形成された包接化合物をそれを含有する混
合物から分離するには、通常固液分離（例えば１過、遠
心分離、沈降等）によるか或は溶媒成分を蒸留により蒸
発除去する方法が好ましく利用出来る。As mentioned above, when P-xylene is included in metacyclophane, the temperature is generally -50 to 350°C, preferably 0 to 350°C.
It is carried out at a temperature of 200°C, especially in the range from 20 to 150°C. In order to separate the clathrate compound thus formed from a mixture containing it, it is usually preferable to use solid-liquid separation (for example, filtration, centrifugation, sedimentation, etc.) or to remove the solvent component by evaporation by distillation. I can do it.
いずれの方法であってもその繰作温夏は一５０〜１２０
℃、好ましくは０〜９０℃の範囲が望ましく・。No matter which method is used, the temperature for repeated cultivation is between 150 and 120.
℃, preferably in the range of 0 to 90℃.
本発明において、Ｐ−キシレンを分離する”Ｐ−キシレ
ン含有混合物”としては、Ｐ−キシレンを含有している
ものであればよ＜、ｐ−キシレン以外の成分として包接
化を阻害したり、生成した包接化合物から、Ｐ−キシレ
ンを容易に脱着したりしないものであればよく、殊に包
接化合物を容易に溶解したりしないものが好適である。In the present invention, the "P-xylene-containing mixture" from which P-xylene is separated may be one that contains P-xylene, or contains components other than p-xylene that inhibit inclusion. Any material may be used as long as it does not easily desorb P-xylene from the generated clathrate compound, and in particular, one that does not easily dissolve the clathrate compound is preferred.
Ｐ−キシレン含有混合物中のＰ−キシレンの含有量は、
Ｐ−キシレンの含有量が極めて低い場合であっても包接
化合物をイ５ることができるので、広い範囲でよい。例
えば、Ｐ−キシレン含有混合物としてＣ８芳香族炭化水
素類を用いた場合、これにメタシクロファンを添加し包
接化せしめることにより容易にＣ８芳香族炭化水素類か
らＰ−キシレン包接化合物を分離することができる。The content of P-xylene in the P-xylene-containing mixture is
Even if the content of P-xylene is extremely low, the clathrate compound can be removed, so a wide range may be used. For example, when C8 aromatic hydrocarbons are used as a P-xylene-containing mixture, the P-xylene clathrate compound can be easily separated from the C8 aromatic hydrocarbons by adding metacyclophane to clathrate it. can do.
″Ｃ８芳香族炭化水素類”とは、Ｏ−キシレンｍ−キシ
レン、Ｐ−キシレンの３種のキシレン類とエチルベンゼ
ンを意味し、これら４種の０８芳香族炭化水素類はそれ
らの沸点が極めて接近しており工業的に蒸留分離を行う
ことは非常に困難である。特にｍ−キシレンとＰ−キシ
レンとの沸点差は小さく通常の実験室的精密蒸留をもっ
てしても、これらを単離することは極めて難しい。"C8 aromatic hydrocarbons" means three types of xylenes, O-xylene, m-xylene, and P-xylene, and ethylbenzene, and these four types of 08 aromatic hydrocarbons have very close boiling points. Therefore, it is extremely difficult to carry out distillation separation industrially. In particular, the difference in boiling point between m-xylene and p-xylene is small and it is extremely difficult to isolate them even by ordinary laboratory precision distillation.
マタ、エチルベンゼンとＰ−キシレンとの沸点差も不さ
くこれらを蒸留分離するのは容易でない。However, the difference in boiling points between ethylbenzene and P-xylene is also small, making it difficult to separate them by distillation.
現在工業的には、Ｐ−キシレンの異常に高い融点を利用
した結晶化分離法、ＨＰ−ＢＦ、とｍ−キシレンの錯化
合物の形成を利用した分離法等が知られているが、いず
れも原料油の深冷化、結晶体の取扱い、装置の腐蝕等の
問題があった。Currently, industrially known methods include a crystallization separation method that utilizes the abnormally high melting point of P-xylene, and a separation method that utilizes the formation of a complex compound of HP-BF and m-xylene. There were problems such as deep cooling of raw oil, handling of crystals, and corrosion of equipment.
また近年ゼオライトによる吸着分離法が工業化されてい
る。この方法は結晶化分離法における共晶点と溶解度の
問題がないためＫＰ−キシレンの回収率の向上、ユーテ
ィリティーの改善。In recent years, adsorption separation methods using zeolites have been industrialized. Since this method does not have the problems of eutectic point and solubility in the crystallization separation method, it improves the recovery rate of KP-xylene and improves its utility.
装置の小屋化等が期待されている。しかしその反面、高
価な吸着剤の使用、経時的吸着能（装置能力）の低下、
複雑な脱着機構、脱着剤とキシレンの分離等の問題があ
り必ずしも有利なプロセスとは言えない。It is expected that the equipment will be converted into a shed. However, on the other hand, the use of expensive adsorbents, the decline in adsorption capacity (equipment capacity) over time,
It is not necessarily an advantageous process because of problems such as a complicated desorption mechanism and separation of the desorbent and xylene.
しかし本発明において使用するメタシクロファンは、そ
の性能もさることながら、まず安価に合成出来ること、
経済的なプロセスを自由に選択しうろことなどの有利な
点を有している。However, the metacyclophane used in the present invention has not only excellent performance, but also the fact that it can be synthesized at low cost.
It has advantages such as being able to freely choose economic processes.
またメタシクロファンとＰ−キシレンとの包接組成物は
、種々の方法により容易にＰ−キシレンを脱着させるこ
とが出来、純粋なＰ−キシレンを得ることが出来る。Further, in the inclusion composition of metacyclophane and P-xylene, P-xylene can be easily desorbed by various methods, and pure P-xylene can be obtained.
本発明においてメタシク＋：＋７７ノとＰ−キシレンと
の包接化合物からＰ−キシレンを分離スる場合には、種
々の方法が採用されるが、例えば（ａ）包接化合物を９
０〜３５０℃、好ましくは１２０〜２８０℃の範囲の温
度に加熱しＰ−キシレンを分離する方法、（ｂ）包接化
合物に、例えばｎ−へキサン、ベンゼン、シクロヘキサ
ン。In the present invention, when separating P-xylene from the clathrate compound of metasic+:+77 and P-xylene, various methods are employed, for example, (a) separating the clathrate compound from 9
A method for separating P-xylene by heating to a temperature in the range of 0 to 350°C, preferably 120 to 280°C, (b) inclusion compounds such as n-hexane, benzene, and cyclohexane.
アセトン等の溶媒を接触させてＰ−キシレンを分離する
方法等が有利に適用される。A method of separating P-xylene by bringing it into contact with a solvent such as acetone is advantageously applied.
以下本発明の包接化合物について説明すると、分離され
た結晶（包接化合物）を真空乾燥し、付着物を除いた後
分析した結果は次の通りであった。The clathrate compound of the present invention will be explained below. The isolated crystal (clathrate compound) was vacuum dried to remove deposits, and the results of analysis were as follows.
＋１１ 赤外分析；
メタシクロファン
３０５０〜２８５０．１６１０．１５９０゜１４９０
＋１４５５ １Ｌｏｓ’ｏ ＋８９０ ＋７９０ 。+11 Infrared analysis; Metacyclophane 3050-2850.1610.1590°1490
+1455 1 Los'o +890 +790.
７００、・４６０α−１
Ｐ−キシレン
３０５０〜２８５０ ＋１５１５．７９０．４８５ｃｍ
−’包接組成物
３０５０〜２８５０，１６１０．１５９０゜１５１５．
１４９０，１４５３，１０８０，８９０゜７９０ ＋７
００．４８５ ＋４６０ｃｍ ”従ってメタシクロファ
ン及びＰ−キシレンによる吸収（１５１５１４８５）以
外の吸収は認められなかった。700, 460α-1 P-xylene 3050-2850 +1515.790.485cm
-'Inclusion composition 3050-2850, 1610.1590°1515.
1490, 1453, 1080, 890°790 +7
00.485 +460cm ”Therefore, no absorption other than that due to metacyclophane and P-xylene (15151485) was observed.
（２） ガスクロ分析：
結晶（包接化合物）を力′スクμ分析したところ結晶中
に包接されているＰ−キシレンの他の成分に対する濃度
は約９５％以上であり、大部分がＰ−キシレンであるこ
とが關められた。(2) Gas chromatography analysis: When the crystal (clathrate compound) was subjected to force μ analysis, the concentration of P-xylene clathrated in the crystal relative to other components was approximately 95% or more, and the majority was P-xylene. It was suspected that it was xylene.
＋３１ 示差熱分析；
結晶（包接化合物）を示差熱分析したところ、９０〜１
１５℃において重量減少が認められ、その減少量から包
接率（Ｐ−キシレン／メタシクロファン＝０．９９Ｃモ
ル比）〕であることがわかった。この〕結果Ｐ−キシレ
ン：メタシクロファン中１１（モル比）テ包接している
ことを示している。+31 Differential thermal analysis; Differential thermal analysis of the crystal (clathrate compound) revealed that it was 90-1
A weight loss was observed at 15° C., and the amount of weight loss was found to be due to the inclusion ratio (P-xylene/metacyclophane = 0.99 C molar ratio). This result shows that P-xylene: 11 (molar ratio) is included in metacyclophane.
以上の結果は、実施例に示される如く、Ｐ−キシレン混
合物としてＰ−キシレン以外の他の成分が１種又はそれ
以上任意の割合で含有されていても、本発明の包接化合
物が得られ、このことは、メタシクロファンの使用によ
りＰ−キシレン含有混合物からＰ−キシレンを選択的に
包接させることが出来、分離させることが出来ることを
示している。The above results show that even if the P-xylene mixture contains one or more components other than P-xylene in arbitrary proportions, the clathrate compound of the present invention can be obtained. This shows that P-xylene can be selectively included and separated from a P-xylene-containing mixture by using metacyclophane.
以下実施例を揚げて本発明を詳述する。The present invention will be described in detail below with reference to Examples.
なお実施例中ｍｅとあるのはメタシクロファン、ｐｘと
あるのはＰ−キシレン、ｍｘとあるのはｍ−キシレン、
ＥＢとあるのはエチルベンゼンを示す。In the examples, "me" means metacyclophane, "px" means P-xylene, "mx" means m-xylene,
EB indicates ethylbenzene.
また実施例中選択度（八）は下記式に基づいて鍔出され
た値である。In addition, the selectivity (8) in Examples is a value determined based on the following formula.
実施例１
ｍｅ ０．０５部を０．５部ずつのＰＸ＋ｍｘ＋ＥＢに
各々室温で添加する。この時ＰＸだけが白濁するがｍｘ
＋ ＦＢは完全に溶解する。この液を各々８０℃まで
昇温し約２分間保持し各溶液を完全に溶解せしめてから
室温までさげるとＰＸ溶液のみから針状結晶が多量生成
する。他のｍＸ＋ＥＢ溶液は溶解状態であり長時間放置
しても結晶は生成しなかった。Example 1 0.05 part of me is added to 0.5 parts of each PX+mx+EB at room temperature. At this time, only PX becomes cloudy, but mx
+ FB is completely dissolved. When each of these solutions is heated to 80° C. and maintained for about 2 minutes to completely dissolve each solution, and then cooled to room temperature, a large amount of needle-shaped crystals are generated from only the PX solution. The other mX+EB solutions were in a dissolved state and no crystals were formed even after being left for a long time.
実施例２
ｍｅ ０．２部を、ＰＸ 、ｒｎＸ ＋ ＥＢ各々１部
の混合溶液３部に添加し、１００℃まで昇温し、完全に
溶解してから室温までさげると針状結晶が生成する。こ
の混合物を濾過し、得られた結晶な室温１００ ｍｌｌ
ｇｏｂｓで１時間乾燥し付着したキシレンを除去して、
０．２２部の白色、針状結晶を得た。この結゛晶の一部
をガスクｐで分析したところ、選択度はβＰＸ／ｍＸ−
２４．βＰＸ／ＥＢ＝ ６８であり、結晶中のＰＸ濃度
はＰＸ／ （ＰＸ＋ｍＸ＋Ｆ Ｂ ）＝０．９５なので
結晶中には、ｍＸ Ｔ ＥＢがほとんど含まれていない
ことがわかった。さらにこの結晶の赤外分析のデータは
、
３０５０〜２８５０．１６１０＋１５９０．１５１５゜
１４９０．１４５３，１０８０，８９０．７９０ ＋７
００＋４８５．４６０ロー１
でありｍｃによる吸収及びＰＸによる吸収（１５１５，
４８５）以外（ｍＸ ＋ ｅＢ ）の吸収は認められな
かった。Example 2 0.2 part of me is added to 3 parts of a mixed solution of 1 part each of PX, rnX + EB, heated to 100°C, completely dissolved, and then lowered to room temperature to form needle-shaped crystals. . This mixture was filtered, resulting in 100 ml of crystalline room temperature
Dry with gobs for 1 hour to remove attached xylene,
0.22 parts of white, needle-shaped crystals were obtained. When a part of this crystal was analyzed using Gask p, the selectivity was βPX/mX-
24. Since βPX/EB=68 and the PX concentration in the crystal is PX/(PX+mX+F B )=0.95, it was found that mX T EB was hardly contained in the crystal. Furthermore, the infrared analysis data of this crystal is: 3050~2850.1610+1590.1515°1490.1453,1080,890.790 +7
00+485.460 low 1, absorption by mc and absorption by PX (1515,
No absorption of (mX + eB) other than 485) was observed.
これらの結果から、この結晶にはキシレン類の付着物は
なくほとんど純粋なＰＸ包接体と考えられる。From these results, this crystal is considered to be an almost pure PX clathrate with no xylenes deposits.
次にこの白色針状結晶０．００８３部を示着熱天瓶によ
り分析したところ、９０〜１１５℃において０．００１
２部の重量減少が認められ、その減少量から包接率（ｐ
ｘ ＋ｍｘ＋ＦＢ ） ／ ｍｅ （モル比）＝ ０．
９９の値が得られた。Next, when 0.0083 part of this white needle-like crystal was analyzed using an indicative thermostat, it was found that 0.001 part at 90-115°C.
A weight loss of 2 parts was observed, and the inclusion rate (p
x+mx+FB)/me (molar ratio)=0.
A value of 99 was obtained.
実施例３
ｎｉｃＯ，２部をｐＸ＋ ｍＸ各々１部からなる混合溶
液２部に添加し、実施例２と同様な操作を行い、０．２
１部の白色針状結晶を得た。この結晶をガスクｐで分析
したところβｐｘ／ｍｘ＝１．９ の値が得られた。Example 3 2 parts of nicO was added to 2 parts of a mixed solution consisting of 1 part each of pX + mX, and the same operation as in Example 2 was performed to obtain 0.2 parts of nicO.
One part of white needle-like crystals was obtained. When this crystal was analyzed using gask p, a value of βpx/mx=1.9 was obtained.
実施例４〜９
ｍｅ ０．１部を下記の溶媒１．０部とｐｘ １．０部
の混合溶液に添加し、７０〜１３０℃で加熱溶解した後
、室温まで徐冷し、結晶を生成する、その結晶を室温で
吸引濾過により、溶液と分離した後室温０．３ｘ＋Ｈｇ
の減圧下で１時間乾燥する。かくして得られた白色結晶
を他の溶媒に溶かしてガスクロ分析を行い、分離係数β
ｐｘ／５ｏｌｖとして、下表に示す結果を得た。Examples 4 to 9 0.1 part of me was added to a mixed solution of 1.0 part of the following solvent and 1.0 part of px, and after heating and dissolving at 70 to 130°C, it was slowly cooled to room temperature to form crystals. After separating the crystals from the solution by suction filtration at room temperature,
Dry under reduced pressure for 1 hour. The white crystals thus obtained were dissolved in another solvent and subjected to gas chromatography analysis to determine the separation factor β.
The results shown in the table below were obtained as px/5olv.
実施例工０
実施例２で得られた白色針状結晶０．１部をメタノール
２部に添加し、１０℃で１０分攪拌１別して０．０９部
の白色針状結晶を得た。この結晶の一部をガスクロ分析
を行ったところ、ｐｘ／（ｐｘ＋ｍｘ ＋ＥＢ ） ＝
０．９４ であり、メタノールと接触する前と同様で
あった。Example 0 0.1 part of the white needle-like crystals obtained in Example 2 was added to 2 parts of methanol, and the mixture was stirred for 10 minutes at 10° C. to obtain 0.09 part of white needle-like crystals. When a part of this crystal was subjected to gas chromatography analysis, px/(px+mx +EB) =
0.94, which was the same as before contact with methanol.
実施例１１
実施例２と同様にして得られた白色針状結晶（組＃：：
（ｐｘ ＋ｍｘ ＋ＥＢ ）／ｍｃ＝ ０．９９ （
ｒｎｏ／／ｍｏ／’ ） 、ｐｘｌＣｐｘ＋ｍｘ十ＦＢ
） ＝ ０．９５ （ｍｏＩＶ／ｍｏＡ！ ））０．
２部にベンゼン１．０部を加え、封管に仕込み、１３０
℃まで加熱し、結晶を完全に溶解した後、室温まで冷却
し、再度針状結晶を形成させた。Example 11 White needle-like crystals obtained in the same manner as in Example 2 (set #::
(px +mx +EB)/mc= 0.99 (
rno//mo/'), pxlCpx+mxtenFB
) = 0.95 (moIV/moA!))0.
Add 1.0 part of benzene to 2 parts and place in a sealed tube, 130
After heating to ℃ to completely dissolve the crystals, the mixture was cooled to room temperature to form needle-shaped crystals again.
該混合物から、濾過によりケークを分離した残液、及び
該ケークを０．５部のベンゼンで洗浄した洗浄液との合
計（以後、Ｆ液という）は１．１部であった。The total amount of the residual liquid obtained by separating the cake from the mixture by filtration and the washing liquid obtained by washing the cake with 0.5 part of benzene (hereinafter referred to as liquid F) was 1.1 parts.
このＰ液をガスクロで分析した所Ｃｐｘ−１−ｍχ十Ｅ
Ｂ）／ベンゼン＝ ２．１ （ｗｔ％） 、 ｐｘ／（
ｐｘ＋ｍｘ＋ＥＢ）−０，９５（ｍｏＪ／ｍｏＪ ）
であった。かくしてｆ液からベンゼンを蒸発、除去する
ことによ０ｐｘ（微量のｍｘ ＋ ＥＢを含有）を８０
％の回収率で得ることができた。When this P liquid was analyzed by gas chromatography, Cpx-1-mχ1E
B)/benzene = 2.1 (wt%), px/(
px+mx+EB)-0,95(moJ/moJ)
Met. In this way, by evaporating and removing benzene from the f liquid, 0px (containing a trace amount of mx + EB) was reduced to 80
% recovery rate.
特許出肢人 帝人株式会社、ど−・ 〆・１・、・・Patent creator Teijin Ltd. 〆・１・、・・
Claims (1)
物とを接触せしめて、前記メタシクロファンにＰ−キシ
レンを包接せしめた包接化合物を形成せしめ、該包接化
合切を分離し、該包接化合物からＰ−キシレンを分離回
収することを特徴とするＰ−キシレン含有混合物からの
Ｐ−キシレンの分離法。[Scope of Claims] Metacyclophane represented by the following formula and a P-xylene-containing mixture are brought into contact to form an inclusion compound in which P-xylene is included in the metacyclophane, and the inclusion compound is 1. A method for separating P-xylene from a P-xylene-containing mixture, the method comprising separating the clathrate and recovering P-xylene from the clathrate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12505084A JPS6041622A (en) | 1984-06-20 | 1984-06-20 | Separation of p-xylene from p-xylene-containing mixture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12505084A JPS6041622A (en) | 1984-06-20 | 1984-06-20 | Separation of p-xylene from p-xylene-containing mixture |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12625975A Division JPS604805B2 (en) | 1975-10-22 | 1975-10-22 | Production method of clathrate compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6041622A true JPS6041622A (en) | 1985-03-05 |
| JPS6128647B2 JPS6128647B2 (en) | 1986-07-01 |
Family
ID=14900588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12505084A Granted JPS6041622A (en) | 1984-06-20 | 1984-06-20 | Separation of p-xylene from p-xylene-containing mixture |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6041622A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940832A (en) * | 1988-06-13 | 1990-07-10 | Tsutomu Miyashi | Process for separating 2,6-dimethylnaphthalene |
| KR100914024B1 (en) | 2008-06-12 | 2009-08-28 | 경희대학교 산학협력단 | Method for separation of p-xylene from xylene mixture by guanidinium 4-chlorophenethyl monosulfonate host |
| KR100916286B1 (en) | 2007-12-26 | 2009-09-10 | 경희대학교 산학협력단 | Selective separatin of xylene isomer from xylene mixture by inclusion using guanidinium biphenyl¡ª2,2¡¯¡ªdiyldimethanesulfonate host compound |
| KR100916287B1 (en) | 2007-12-26 | 2009-09-10 | 경희대학교 산학협력단 | Separation of xylene isomer from xylene mixture by selective inclusion using guanidinium ortho¡ªterphenyl 4,4¡¯¡ªdisulfonate host compound |
| KR100984798B1 (en) | 2008-06-12 | 2010-10-04 | 경희대학교 산학협력단 | Method for separation of p-xylene from xylene mixture by guanidinium 2-chlorophenethyl monosulfonate host |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62182744U (en) * | 1986-05-09 | 1987-11-19 | ||
| JPS62182754U (en) * | 1986-05-09 | 1987-11-19 |
-
1984
- 1984-06-20 JP JP12505084A patent/JPS6041622A/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4940832A (en) * | 1988-06-13 | 1990-07-10 | Tsutomu Miyashi | Process for separating 2,6-dimethylnaphthalene |
| KR100916286B1 (en) | 2007-12-26 | 2009-09-10 | 경희대학교 산학협력단 | Selective separatin of xylene isomer from xylene mixture by inclusion using guanidinium biphenyl¡ª2,2¡¯¡ªdiyldimethanesulfonate host compound |
| KR100916287B1 (en) | 2007-12-26 | 2009-09-10 | 경희대학교 산학협력단 | Separation of xylene isomer from xylene mixture by selective inclusion using guanidinium ortho¡ªterphenyl 4,4¡¯¡ªdisulfonate host compound |
| KR100914024B1 (en) | 2008-06-12 | 2009-08-28 | 경희대학교 산학협력단 | Method for separation of p-xylene from xylene mixture by guanidinium 4-chlorophenethyl monosulfonate host |
| KR100984798B1 (en) | 2008-06-12 | 2010-10-04 | 경희대학교 산학협력단 | Method for separation of p-xylene from xylene mixture by guanidinium 2-chlorophenethyl monosulfonate host |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6128647B2 (en) | 1986-07-01 |
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