JP3157253B2 - Method for separating 2,6-dimethylnaphthalene - Google Patents
Method for separating 2,6-dimethylnaphthaleneInfo
- Publication number
- JP3157253B2 JP3157253B2 JP05410092A JP5410092A JP3157253B2 JP 3157253 B2 JP3157253 B2 JP 3157253B2 JP 05410092 A JP05410092 A JP 05410092A JP 5410092 A JP5410092 A JP 5410092A JP 3157253 B2 JP3157253 B2 JP 3157253B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethylnaphthalene
- oil
- adsorption
- separating
- zeolite
- 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 - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
- C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ジメチルナフタレン異
性体混合物を含む原料油から、２,６-ジメチルナフタレ
ンを分離する方法に関する。この２,６-ジメチルナフタ
レンは酸化して２,６-ナフタレンジカルボン酸にされ、
耐熱性に優れた高性能ポリエステルの原料として有用で
ある。The present invention relates to a method for separating 2,6-dimethylnaphthalene from a feedstock containing a mixture of dimethylnaphthalene isomers. This 2,6-dimethylnaphthalene is oxidized to 2,6-naphthalenedicarboxylic acid,
It is useful as a raw material for high-performance polyester with excellent heat resistance.
【０００２】[0002]
【従来の技術】従来、２,６-または２,７-ジメチルナフ
タレンの共晶混合物から２,７-ジメチルナフタレンを選
択的に分離する方法(特公昭５２-９４５号公報)や、ジ
メチルナフタレン混合物をＹ型ゼオライトに接触させる
ことによって、２,６-ジメチルナフタレンの濃度を高
め、これを冷却晶析して２,６-ジメチルナフタレンを結
晶として分離する方法(特公昭４９-２７５７８号公報)
が知られている。2. Description of the Related Art Conventionally, a method of selectively separating 2,7-dimethylnaphthalene from a eutectic mixture of 2,6- or 2,7-dimethylnaphthalene (Japanese Patent Publication No. 52-945), a method of separating dimethylnaphthalene mixture, Is brought into contact with Y-type zeolite to increase the concentration of 2,6-dimethylnaphthalene, which is cooled and crystallized to separate 2,6-dimethylnaphthalene as crystals (Japanese Patent Publication No. 49-27578).
It has been known.
【０００３】ところで、Ｙ型ゼオライトを吸着カラムに
充填して流通方式により、ジメチルナフタレン異性体混
合物から２,６-ジメチルナフタレンを分離する場合、
２,６-ジメチルナフタレンが先に破過して流出し、続い
て２,６-ジメチルナフタレン以外のジメチルナフタレン
異性体が吸着により遅れて破過してくる。このとき２,
６-ジメチルナフタレンとそれ以外の化合物との破過時
間の差は長ければ長いほど、分離採取される留分中の
２,６-ジメチルナフタレンの純度、回収率が高くなり、
分離効率が良くなる。[0003] In the case where 2,6-dimethylnaphthalene is separated from a mixture of dimethylnaphthalene isomers by a Y-type zeolite packed in an adsorption column by a flow system,
2,6-Dimethylnaphthalene breaks through first and flows out, and subsequently, dimethylnaphthalene isomers other than 2,6-dimethylnaphthalene break through with a delay due to adsorption. At this time,
The longer the difference in breakthrough time between 6-dimethylnaphthalene and other compounds, the higher the purity and recovery of 2,6-dimethylnaphthalene in the fraction collected and separated,
Separation efficiency is improved.
【０００４】しかしながら、上記従来の方法は、ジメチ
ルナフタレン異性体混合物をそのままで、或いは脱着溶
媒で希釈して、ゼオライトと接触させるため、破過時間
の差が小さく、２,６-ジメチルナフタレンの純度、回収
率ともに低く、分離効率が悪いという問題があった。However, in the above-mentioned conventional method, the dimethylnaphthalene isomer mixture is brought into contact with zeolite as it is or diluted with a desorption solvent, so that the difference in breakthrough time is small, and the purity of 2,6-dimethylnaphthalene is small. However, both the recovery rates are low and the separation efficiency is poor.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、上記課題を
解決するもので、本発明の目的はジメチルナフタレン異
性体混合物から、高純度、高回収率で２,６-ジメチルナ
フタレンを分離する方法を提供することにある。SUMMARY OF THE INVENTION The present invention solves the above-mentioned problems, and an object of the present invention is to provide a method for separating 2,6-dimethylnaphthalene from a dimethylnaphthalene isomer mixture with high purity and high recovery. Is to provide.
【０００６】[0006]
【課題を解決するための手段】本発明者は、Ｙ型ゼオラ
イトを用いた２,６-ジメチルナフタレンの吸着分離方法
を疑似移動床などを使用した連続分離へ適用すべく、流
通方式の吸着カラム装置を用いて鋭意検討した結果、ジ
メチルナフタレン異性体混合物を含む原料油を吸着展開
する際、原料油の吸着展開を助長する補助溶剤、例え
ば、パラフィン系あるいはナフテン系炭化水素を吸着展
開時に添加することにより、目的物である２,６-ジメチ
ルナフタレンと他のジメチルナフタレン異性体類あるい
はその他の炭化水素類との分離効率を著しく高めること
ができることを見出し、本発明に至った。In order to apply the method of adsorbing and separating 2,6-dimethylnaphthalene using Y-type zeolite to continuous separation using a simulated moving bed or the like, the present inventor has developed a flow-type adsorption column. As a result of intensive studies using the apparatus, when adsorbing and developing a feedstock oil containing a dimethylnaphthalene isomer mixture, an auxiliary solvent that promotes the adsorption and spread of the feedstock oil, for example, a paraffinic or naphthenic hydrocarbon is added at the time of adsorption and development. As a result, the present inventors have found that the separation efficiency between 2,6-dimethylnaphthalene, which is the target substance, and other dimethylnaphthalene isomers or other hydrocarbons can be significantly increased, and the present invention has been accomplished.
【０００７】すなわち本発明は、２,６−ジメチルナフ
タレンに１,６−体、１,３−体、１,７−体および２,７
−体のジメチルナフタレンが混合されたジメチルナフタ
レン異性体混合物を含む原料油を、吸着展開を助長する
パラフィン系あるいはナフテン系炭化水素である補助溶
剤とともに、Ｙ型ゼオライトと流通方式の吸着カラム装
置を用いて接触させることを特徴とする２,６−ジメチ
ルナフタレンの分離方法である。That is, the present invention relates to 1,6-form, 1,3-form, 1,7-form and 2,7-form of 2,6-dimethylnaphthalene.
-A raw material oil containing a dimethylnaphthalene isomer mixture in which dimethylnaphthalene is mixed, using a Y-type zeolite and a flow-type adsorption column device together with an auxiliary solvent that is a paraffinic or naphthenic hydrocarbon that promotes adsorption development. 2. A method for separating 2,6-dimethylnaphthalene, comprising:
【０００８】上記本発明に云うジメチルナフタレン異性
体混合物を含む原料油とは、２,６−ジメチルナフタレ
ンに１,６−体、１,３−体、１,７−体および２,７−体
のジメチルナフタレンが混合されたものであり、これに
ジメチルナフタレン以外の成分を含んでいても良く、ま
たその混合比は特には問わないが、２,６−ジメチルナ
フタレンを１０％以上含有したものが好適である。この
原料油は石炭タール、流動接触分解プロセスのサイクル
油或いはナフサまたは灯油留分の脱水素環化油等を蒸留
精製する方法、ナフタレンのメチル化反応により合成す
る方法、メチルナフタレン及びポリメチルナフタレンの
不均化またはトランスメチル化反応により合成する方法
等により得られる。The feedstock oil containing a mixture of dimethylnaphthalene isomers according to the present invention refers to 1,6-form, 1,3-form, 1,7-form and 2,7-form in 2,6-dimethylnaphthalene. Of dimethylnaphthalene, and may contain components other than dimethylnaphthalene, and the mixing ratio thereof is not particularly limited, but those containing 2,6-dimethylnaphthalene of 10% or more are preferable. It is suitable. This raw material oil is obtained by distillation and purification of coal tar, cycle oil of fluid catalytic cracking process or dehydrocyclized oil of naphtha or kerosene fraction, method of synthesis by naphthalene methylation reaction, and method of methyl naphthalene and polymethyl naphthalene. It is obtained by a method of synthesizing by a disproportionation or transmethylation reaction or the like.
【０００９】一方、吸着展開を助長する補助溶剤として
は、パラフィン系あるいはナフテン系炭化水素、例えば
イソオクタン、ｎ-デカン、ｎ-ウンデカン、ｎ-ドデカ
ン、ｎ-トリデカン、シクロヘキサン、デカリン、メチ
ルシクロヘキサン、エチルシクロヘキサン、ジメチルシ
クロヘキサン、ジエチルシクロヘキサン、炭素数が８〜
１４のイソパラフィン等のいずれか一種あるいは二種以
上を混合したものを用いることができる。On the other hand, co-solvents for promoting adsorption development include paraffinic or naphthenic hydrocarbons such as isooctane, n-decane, n-undecane, n-dodecane, n-tridecane, cyclohexane, decalin, methylcyclohexane, ethyl Cyclohexane, dimethylcyclohexane, diethylcyclohexane, carbon number 8 ~
One of 14 isoparaffins or the like or a mixture of two or more of them can be used.
【００１０】また、Ｙ型ゼオライトとは天然のフォージ
ャサイトと類似の構造を有し、Na2O・Al2O3・3〜6SiO2・xH
2Oの組成を持つもので、ＮａＹ型のほか、このＮａＹ型
ゼオライトをアルカリ金属またはアルカリ土類金属の中
から選らばれた金属イオン、例えば、カリウム、リチウ
ム、ルビジウム、セシウム、バリウム、カルシウム、マ
グネシウム、ストロンチウム、ランタン等の金属イオン
のいずれか一種または二種以上で置換したＹ型ゼオライ
トを特に好適に用いることができる。このゼオライトは
これをそのまま用いても良く、またスチーム処理、アル
カリ処理、酸処理、イオン交換等を行なって用いても良
い。Moreover, having a structure similar to the natural faujasite and Y-type zeolite, Na 2 O · Al 2 O 3 · 3~6SiO 2 · xH
It has a composition of 2 O, and in addition to NaY type, this NaY type zeolite is a metal ion selected from alkali metals or alkaline earth metals, for example, potassium, lithium, rubidium, cesium, barium, calcium, magnesium Y-type zeolites substituted with one or more of metal ions such as strontium and lanthanum can be used particularly preferably. This zeolite may be used as it is, or may be used after performing steam treatment, alkali treatment, acid treatment, ion exchange and the like.
【００１１】本発明は、上記Ｙ型ゼオライトが充填され
た吸着層に、原料油を通液すると同時に前記補助溶剤を
通液するか、予め原料油に前記補助溶剤を添加して吸着
層に通液する方法により行なうことが好ましい。この場
合、前記補助溶剤は原料油中の２,６-ジメチルナフタレ
ン１容量に対して２〜５０倍容を用いると良い。According to the present invention, the feedstock oil is passed through the adsorbent layer filled with the Y-type zeolite, and at the same time, the auxiliary solvent is passed through the adsorbent layer. It is preferable to carry out by a method of liquid. In this case, the auxiliary solvent is preferably used in an amount of 2 to 50 times the volume of 2,6-dimethylnaphthalene in the feedstock oil.
【００１２】この原料油とゼオライトとの接触は、原料
油が液状であれば温度は低い方が良いが、特には、２５
〜２００℃の範囲で適宜選定すれば良い。The contact between the base oil and the zeolite is preferably performed at a lower temperature if the base oil is in a liquid state.
What is necessary is just to select suitably in the range of -200 degreeC.
【００１３】また、原料油をアロマ系の脱着溶剤、その
他の溶解し、これに上記補助溶剤を同時に通液するか、
予め原料油に添加して行っても良い。[0013] Further, the raw material oil is dissolved in an aroma-based desorbing solvent or other solvent, and the above-mentioned auxiliary solvent is simultaneously passed through the solution.
It may be added to the feedstock oil in advance.
【００１４】上記吸着分離後、２,６-ジメチルナフタレ
ン以外のゼオライトに吸着したジメチルナフタレン類を
脱着して再使用に供するため、脱着溶媒を通液するが、
本発明においては、この脱着溶媒としてパラフィン、ナ
フテン、アロマ系などの溶剤を用いることができるが、
脱着時間などの問題からアロマ系の溶剤、例えばベンゼ
ン、トルエン、キシレン、エチルベンゼン、ジエチルベ
ンゼンなどを用いることが好ましい。以下に、実施例に
より本発明を具体的に説明する。After the above adsorption separation, dimethylnaphthalenes adsorbed on zeolite other than 2,6-dimethylnaphthalene are desorbed in order to desorb and reuse the dimethylnaphthalene for reuse.
In the present invention, a solvent such as paraffin, naphthene, and aroma can be used as the desorption solvent.
It is preferable to use an aromatic solvent, for example, benzene, toluene, xylene, ethylbenzene, diethylbenzene, etc. from the viewpoint of the desorption time. Hereinafter, the present invention will be described specifically with reference to examples.
【００１５】[0015]
【実施例】 （実施例１〜５）吸着剤として、市販のＮａＹ型ゼオラ
イトを用い、これを内容積２７mｌのチューブ型カラム
（８mmφ×６００mm）へ充填して、吸着分離カラムと
し、これを外部から加熱して充填層の温度を１００℃に
保持した。EXAMPLES (Examples 1 to 5) A commercially available NaY-type zeolite was used as an adsorbent and packed into a tube column (8 mmφ × 600 mm) having an internal volume of 27 ml to form an adsorption separation column. To maintain the temperature of the packed bed at 100 ° C.
【００１６】次に、原料油として表１に示す組成のジメ
チルナフタレン異性体混合物を、吸着展開を助長する補
助溶剤であるイソオクタン、ｎ-デカン、ｎ-ウンデカ
ン、ｎ-ドデカン、またはｎ-トリデカンに溶解して１０
wt％の濃度の溶液を調製し、吸着剤容量に対する流量
(ＬＨＳＶ)を２.２ｈ-1として、上記吸着分離カラムへ
通液して吸着展開した。吸着分離層から流出する溶液を
フラクションコレクターにより分取し、各フラクション
溶液をガスクロマトグラフィーにより組成分析した。こ
の分析結果からジメチルナフタレン異性体類の吸着破過
曲線を作成して図１〜５に示した。また、吸着破過曲線
の任意の時間までの図上積分により求められる２,６-ジ
メチルナフタレンの純度及び回収率を計算し、回収率と
純度の関係を表２に示した。Next, a dimethylnaphthalene isomer mixture having the composition shown in Table 1 as a feed oil was added to isooctane, n-decane, n-undecane, n-dodecane or n-tridecane, which is a cosolvent for promoting adsorption development. Dissolve 10
Prepare a solution with a concentration of wt% and flow rate to the adsorbent volume.
(LHSV) was set to 2.2 h −1 , and the solution was passed through the adsorption separation column and adsorbed and developed. The solution flowing out of the adsorption separation layer was fractionated by a fraction collector, and the composition of each fraction solution was analyzed by gas chromatography. From this analysis result, adsorption breakthrough curves of dimethylnaphthalene isomers were prepared and shown in FIGS. Further, the purity and the recovery of 2,6-dimethylnaphthalene, which were obtained by integrating the adsorption breakthrough curve up to an arbitrary time on the diagram, were calculated, and the relationship between the recovery and the purity is shown in Table 2.
【００１７】（実施例６〜７）表１に示す組成の原料油
をデカリン、エチルシクロヘキサンに１０wt％濃度で溶
解した以外は実施例１〜５と同様に実施した。このとき
の吸着破過曲線を図６〜７に示し、２,６-ジメチルナフ
タレンの回収率と純度の関係を表２に示した。(Examples 6 to 7) The same procedures as in Examples 1 to 5 were carried out except that the raw material oil having the composition shown in Table 1 was dissolved in decalin and ethylcyclohexane at a concentration of 10% by weight. The adsorption breakthrough curves at this time are shown in FIGS. 6 and 7, and the relationship between the recovery and the purity of 2,6-dimethylnaphthalene is shown in Table 2.
【００１８】（比較例１〜２）表１に示す組成の原料油
をテトラリン、ｏ-キシレンに１０wt％で溶解した以外
は実施例１〜５と同様に実施した。この吸着破過曲線を
図８〜９に示し、２,６-ジメチルナフタレンの回収率と
純度の関係を表２に示した。(Comparative Examples 1 and 2) The same procedure as in Examples 1 to 5 was carried out except that the raw material oil having the composition shown in Table 1 was dissolved in tetralin and o-xylene at 10% by weight. The adsorption breakthrough curves are shown in FIGS. 8 and 9 and the relationship between the recovery and the purity of 2,6-dimethylnaphthalene is shown in Table 2.
【００１９】これらの結果から明らかなように、イソオ
クタン、ｎ-デカン、ｎ-ウンデカン、ｎ-ドデカン、ｎ-
トリデカン、デカリン、エチルシクロヘキサン等の吸着
展開を助長する補助溶剤を用いると、２,６-ジメチルナ
フタレンの純度および回収率を著しく高めることができ
る。As apparent from these results, isooctane, n-decane, n-undecane, n-dodecane, n-dodecane
The use of an auxiliary solvent such as tridecane, decalin, ethylcyclohexane or the like which promotes the development of adsorption can significantly increase the purity and recovery of 2,6-dimethylnaphthalene.
【００２０】[0020]
【表１】 [Table 1]
【表２】 [Table 2]
【００２１】[0021]
【発明の効果】本発明は、ジメチルナフタレン異性体混
合物中から、２,６-ジメチルナフタレンを効率良く、し
かも高純度で分離することができ、工業的意義が極めて
高いものである。Industrial Applicability According to the present invention, 2,6-dimethylnaphthalene can be efficiently separated from a mixture of dimethylnaphthalene isomers with high purity, and is extremely industrially significant.
図は、ジメチルナフタレン異性体類の吸着破過曲線を示
すもので、The figure shows the adsorption breakthrough curves of dimethylnaphthalene isomers.
【図１〜５】はイソオクタン、ｎ-デカン、ｎ-ウンデカ
ン、ｎ-ドデカン、ｎ-トリデカンを、1 to 5 are isooctane, n-decane, n-undecane, n-dodecane, n-tridecane,
【図６〜７】はデカリン、エチルシクロヘキサンを、6 and 7 show decalin and ethylcyclohexane,
【図８〜９】はテトラリン、ｏ-キシレンをそれぞれ補
助溶剤として用いた場合のものである。8 and 9 show the results when tetralin and o-xylene were used as auxiliary solvents, respectively.
Claims (2)
体、１,３−体、１,７−体および２,７−体のジメチル
ナフタレンが混合されたジメチルナフタレン異性体混合
物を含む原料油を、吸着展開を助長するパラフィン系あ
るいはナフテン系炭化水素である補助溶剤とともに、Ｙ
型ゼオライトと流通方式の吸着カラム装置を用いて接触
させることを特徴とする２,６−ジメチルナフタレンの
分離方法。(1) 1,6-dimethylnaphthalene has 1,6-
Oil containing a mixture of dimethylnaphthalene isomers in which 1,3-, 1,7- and 2,7-form dimethylnaphthalenes are mixed with paraffinic or naphthenic hydrocarbons that promote adsorption and development. With some co-solvent, Y
2. A method for separating 2,6-dimethylnaphthalene, wherein the zeolite is brought into contact with a zeolite using a flow-type adsorption column apparatus.
ル、流動接触分解プロセスのサイクル油或いはナフサま
たは灯油留分の脱水素環化油を蒸留精製する方法、ナフ
タレンのメチル化反応により合成する方法、メチルナフ
タレン及びポリメチルナフタレンの不均化またはトラン
スメチル化反応により合成する方法により得られるもの
であることを特徴とする２,６−ジメチルナフタレンの
分離方法。2. A method according to claim 1, wherein the raw material oil is a coal tar, a cycle oil of a fluid catalytic cracking process or a method for distilling and refining a dehydrocyclized oil of a naphtha or kerosene fraction, and a method for synthesizing a naphthalene by a methylation reaction. A method for separating 2,6-dimethylnaphthalene, which is obtained by a method of synthesizing methyl, naphthalene and polymethylnaphthalene by disproportionation or transmethylation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05410092A JP3157253B2 (en) | 1992-02-06 | 1992-02-06 | Method for separating 2,6-dimethylnaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05410092A JP3157253B2 (en) | 1992-02-06 | 1992-02-06 | Method for separating 2,6-dimethylnaphthalene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05213787A JPH05213787A (en) | 1993-08-24 |
| JP3157253B2 true JP3157253B2 (en) | 2001-04-16 |
Family
ID=12961202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05410092A Expired - Fee Related JP3157253B2 (en) | 1992-02-06 | 1992-02-06 | Method for separating 2,6-dimethylnaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3157253B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7576253B2 (en) | 2004-12-24 | 2009-08-18 | Mitsubishi Gas Chemical Company, Inc. | Method of separating dimethylnaphthalene isomers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006109667A1 (en) * | 2005-04-06 | 2006-10-19 | Mitsubishi Gas Chemical Company, Inc. | Method of purifying 2,7-dimethylnaphthalene |
-
1992
- 1992-02-06 JP JP05410092A patent/JP3157253B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7576253B2 (en) | 2004-12-24 | 2009-08-18 | Mitsubishi Gas Chemical Company, Inc. | Method of separating dimethylnaphthalene isomers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05213787A (en) | 1993-08-24 |
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