JPS63150232A - Production of diphenyl - Google Patents
Production of diphenylInfo
- Publication number
- JPS63150232A JPS63150232A JP29613786A JP29613786A JPS63150232A JP S63150232 A JPS63150232 A JP S63150232A JP 29613786 A JP29613786 A JP 29613786A JP 29613786 A JP29613786 A JP 29613786A JP S63150232 A JPS63150232 A JP S63150232A
- Authority
- JP
- Japan
- Prior art keywords
- diphenyl
- fraction
- azeotropic
- diethylene glycol
- distillation
- 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.)
- Pending
Links
- 235000010290 biphenyl Nutrition 0.000 title claims abstract description 79
- 239000004305 biphenyl Substances 0.000 title claims abstract description 79
- 125000006267 biphenyl group Chemical group 0.000 title claims abstract description 79
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 238000004821 distillation Methods 0.000 claims abstract description 17
- 238000009835 boiling Methods 0.000 claims abstract description 10
- 239000011280 coal tar Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000001953 recrystallisation Methods 0.000 claims abstract description 5
- 238000002425 crystallisation Methods 0.000 abstract description 11
- 238000010533 azeotropic distillation Methods 0.000 abstract description 9
- 230000008025 crystallization Effects 0.000 abstract description 8
- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical class C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 abstract description 7
- 238000001816 cooling Methods 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 4
- 235000020971 citrus fruits Nutrition 0.000 abstract description 2
- 150000002475 indoles Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 238000000151 deposition Methods 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- -1 indoles Chemical class 0.000 abstract 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical class C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical class C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
この発明は、ジフェニルの製造方法に関するもので、ジ
フェニル含有留分から共沸蒸留により濃縮したジフェニ
ル留分を晶析および再結晶することにより高純度ジフェ
ニルを回収する方法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a method for producing diphenyl, in which high purity is obtained by crystallizing and recrystallizing a diphenyl fraction concentrated by azeotropic distillation from a diphenyl-containing fraction. The present invention relates to a method for recovering diphenyl.
［従来技術］
ジフェニルは、染色キャリヤー、柑橘類の防黴剤、熱、
媒体およびその原料、感圧紙の顕色剤であるバラフェニ
ルフェノールの原料あるいはエンジニアリングプラスチ
ック原料として有用である。[Prior art] Diphenyl is used as a dye carrier, as a fungicide for citrus fruits, as a heat,
It is useful as a medium and its raw material, as a raw material for rose phenylphenol, which is a color developer for pressure-sensitive paper, and as a raw material for engineering plastics.
ジフェニルは、ベンゼンの熱重合法により高純度（９９
％以上）の製品が合成されている。一方、コールタール
や石油系の熱分解油など炭化水素の高温熱処理によって
生成する留分中にも含まれていることが知られている。Diphenyl is produced with high purity (99%) by thermal polymerization of benzene.
% or more) of products have been synthesized. On the other hand, it is also known to be contained in fractions produced by high-temperature heat treatment of hydrocarbons such as coal tar and petroleum-based pyrolysis oil.
これらの原料からジフェニルを分離する方法としては、
ジフェニルを含む炭化水素留分をジフェニル含有量６０
重量％以上で、かつβ−メチルナフタリン／ジフェニル
の重量比０．１５以下になるように蒸留してジフェニル
留分を得、ついでこれを連続的に晶析させてジフェニル
を分離回収する方法（特開昭５７−９８２２１号公報）
が提案されている。The method for separating diphenyl from these raw materials is as follows:
Hydrocarbon fraction containing diphenyl has a diphenyl content of 60
% by weight or more and a weight ratio of β-methylnaphthalene/diphenyl of 0.15 or less to obtain a diphenyl fraction, which is then continuously crystallized to separate and recover diphenyl (special method). Publication No. 57-98221)
is proposed.
しかし、特開昭５７−９８２２１号公報の方法は、濃縮
したジフェニル留分の連続晶析によって高純度のジフェ
ニルを回収するためには、ジフェニル含有量を６０重量
％以上に濃縮すると共に、連続晶析で除去し難いβ−メ
チルナフタリン含有量を一定量以下になるよう蒸留によ
り調製する必要がある。However, in the method of JP-A-57-98221, in order to recover high-purity diphenyl by continuous crystallization of the concentrated diphenyl fraction, the diphenyl content must be concentrated to 60% by weight or more, and continuous crystallization must be performed. It is necessary to reduce the content of β-methylnaphthalene, which is difficult to remove by distillation, to a certain amount or less.
しかしながら、コールタールを蒸留して得られるジフェ
ニル留分は、ジフェニルと沸点の近接した多数の不純物
を多量に含んでいる。代表的な不純物は、メチルナフタ
リン類、ジメチルナフタリン類、エチルナフタリン類、
キノリン、イソキノリンなどの塩基類およびインドール
であり、特にジフェニル（沸点２５５℃）と沸点の接近
したインドール（沸点２５４℃）は、蒸留によって分離
することは殆ど不可能である。このため、β−メチルナ
フタリン含有量を一定量以下に調製しても、連続晶析に
際し融点が５３℃のインドールがジフェニル（融点７１
℃）と共に晶析するため、特開昭５７−９８２２１号公
報の方法は、コールタールからのジフェニル含有留分に
適用するためには、前以てインドールを除去しなければ
、高純度のジフェニルを製造することは不可能である。However, the diphenyl fraction obtained by distilling coal tar contains a large amount of many impurities whose boiling points are close to that of diphenyl. Typical impurities are methylnaphthalenes, dimethylnaphthalenes, ethylnaphthalenes,
Bases such as quinoline and isoquinoline and indoles, especially indole (boiling point 254°C), which has a boiling point close to diphenyl (boiling point 255°C), are almost impossible to separate by distillation. For this reason, even if the content of β-methylnaphthalene is adjusted below a certain level, indole with a melting point of 53°C is converted to diphenyl (melting point 71°C) during continuous crystallization.
℃), the method of JP-A-57-98221 cannot be applied to diphenyl-containing fractions from coal tar unless indole is removed in advance. It is impossible to manufacture.
［解決しようとする問題点］
この発明は、コールタールを蒸留して得られるジフェニ
ル含有留分から共沸蒸留および晶析によって、高純度の
ジフェニルを高収率で回収できる方法を提供するもので
ある。[Problems to be Solved] The present invention provides a method for recovering high-purity diphenyl in high yield from a diphenyl-containing fraction obtained by distilling coal tar by azeotropic distillation and crystallization. .
［発明の詳細な
説明
グリコールを蒸留に付し、ジフェニルとジエチレングリ
コールとの共沸留分を留取し、ついでこの留分を冷却し
て析出する結晶物を分離し、該結晶−物を溶剤を使用し
て再結晶することを特徴とするジフェニルの製造方法で
ある。[Detailed Description of the Invention] Glycol is subjected to distillation, an azeotropic fraction of diphenyl and diethylene glycol is distilled off, and this fraction is then cooled to separate the precipitated crystals. This is a method for producing diphenyl, which is characterized by recrystallizing the diphenyl.
この発明における原料のジフェニル含有留分としては、
沸点２２０〜２８０℃のコールタール留分、すなわちナ
フタリン油、洗浄油等が挙げられるが、これらを回分蒸
留、連続蒸留またはこれらの組み合わせによって蒸留し
て得たものが好適である。The diphenyl-containing fraction of the raw material in this invention is as follows:
Coal tar fractions having a boiling point of 220 to 280°C, ie, naphthalene oil, washing oil, etc., can be mentioned, but those obtained by distilling these by batch distillation, continuous distillation, or a combination thereof are preferable.
この発明において、ジフェニル含有留分にジエチレング
リコールを添加して蒸留するのは、ジエチレングリコー
ルがジフェニルと共沸し、原料中に共存するエチルナフ
タリン以外の不純物であるメチルナフタリン類、ジメチ
ルナフタリン類、キノリン類、インドールその他の有機
化合物と共沸しない温度域が存在することを見い出し、
これを利用せんがためである。その温度は常圧下２３２
〜２３３℃にある。In this invention, diethylene glycol is added and distilled to the diphenyl-containing fraction because diethylene glycol is azeotroped with diphenyl, and impurities other than ethylnaphthalene coexisting in the raw material, such as methylnaphthalenes, dimethylnaphthalenes, and quinolines, We discovered that there is a temperature range that does not azeotrope with indole and other organic compounds.
This is to make use of this. Its temperature is 232℃ under normal pressure.
~233°C.
この発明においては、エチルナフタリン類はジエチレン
グリコールとの共沸蒸留によって、ジフェニルと同じ温
度域で留出してくるので、ジフェニル留分中に残留する
が、融点がジフェニルに比較してきわめて低く、１−エ
チルナフタリンでは一１５℃、２−エチルナフタリンは
一７０℃であり、次いで行われる冷却晶析によって殆ど
が除去される。In this invention, ethylnaphthalene is distilled out in the same temperature range as diphenyl through azeotropic distillation with diethylene glycol, so it remains in the diphenyl fraction, but its melting point is extremely low compared to diphenyl, and 1- For ethylnaphthalene, the temperature is -15°C, and for 2-ethylnaphthalene, it is -70°C, and most of it is removed by subsequent cooling crystallization.
また、ジフェニルと沸点のきわめて近いインドールは、
前記ジフェニルとジエチレングリコールとが共沸する２
３２〜２３３℃では共沸しないため、容易に除去される
。Indole, which has a boiling point very similar to diphenyl,
2 where the diphenyl and diethylene glycol are azeotropic
Since it does not azeotrope at 32 to 233°C, it is easily removed.
ジフェニル含有留分に対するジエチレングリコールの添
加量は、本発明者等の行った実験結果に５一
よれば、コールタール蒸留時のカットする温度によって
異なるが、ジフェニル含有留分中のジフェニル量の０．
７〜１．３重量倍、好ましくは０．９〜１．０重量倍が
適当である。According to the experimental results conducted by the present inventors, the amount of diethylene glycol added to the diphenyl-containing fraction varies depending on the cutting temperature during coal tar distillation.
A suitable amount is 7 to 1.3 times by weight, preferably 0.9 to 1.0 times by weight.
なお、ジフェニル含有留分が、ジエチレングリコールと
ジフェニルとの共沸温度より低い温度域で留出する成分
、例えば２２４〜２２６℃で共沸するメチルナフタリン
類を含有する場合は、前以て任意の方法（精密蒸留、共
沸蒸留、抽出等）によって、これらの成分を除去したの
ちジエチレングリコールを添加してジフェニルとの共沸
蒸留を行うのが有利である。In addition, if the diphenyl-containing fraction contains a component that distills out at a temperature lower than the azeotropic temperature of diethylene glycol and diphenyl, for example, methylnaphthalenes that azeotropically boil at 224 to 226°C, it can be prepared by any method in advance. It is advantageous to remove these components by (precision distillation, azeotropic distillation, extraction, etc.) and then add diethylene glycol and carry out the azeotropic distillation with diphenyl.
また、ジフェニル含有留分へのジエチレングリコールの
添加方法は、蒸留塔へ装入する前に添加してもよく、蒸
留塔へ別々に装入し塔内で混合せしめることもできる。Furthermore, diethylene glycol may be added to the diphenyl-containing fraction before being charged into the distillation column, or may be separately charged into the distillation column and mixed within the column.
ジエチレングリコールとジフェニルとの共沸留分は、冷
却してジフェニル結晶物を析出させたのち、遠心濾過し
てジフェニル結晶物を分離する。The azeotropic fraction of diethylene glycol and diphenyl is cooled to precipitate diphenyl crystals, and then centrifugally filtered to separate the diphenyl crystals.
この冷却−晶析工程では、前工程で留取したジエヂレン
クリコールとジフェニル共沸留分に随伴してきたエチル
ナフタリン類や若干量のジメチルナフタリン類が、融点
差により除去される。In this cooling-crystallization step, ethylnaphthalenes and a small amount of dimethylnaphthalenes that have accompanied the dielene glycol and diphenyl azeotropic fraction distilled in the previous step are removed due to the difference in melting point.
結晶物を析出させる温度は、０〜１０℃、好ましくは５
℃前後でよい。また、冷却−晶析方法は、ハツチ式ある
いは連続式のいずれでもよい。The temperature at which the crystalline substance is precipitated is 0 to 10°C, preferably 5°C.
Around ℃ is fine. Further, the cooling-crystallization method may be either a hatch type or a continuous type.
この工程で得られるジフェニル結晶は、ジエチレングリ
コールが付着しているので除去するのが得策である。そ
の除去方法としては、種々の方法が考えられるが、適当
な溶剤を用い、その溶剤中で再結晶せしめてジフェニル
を分離回収するのが有利である。使用する再結晶溶剤と
しては、メタノール、エタノール、プロパツール等の炭
素数１〜３のアルコール類、ヘキサン、ヘプタン等の脂
肪族炭化水素等が好ましい。溶剤の使用量は、多い方が
高純度となるが、回収率が低下するので、ジフェニル結
晶物に対して１〜６重量倍、好ましくは２〜４重量倍程
度がよい。Since the diphenyl crystals obtained in this step have diethylene glycol attached to them, it is advisable to remove them. Various methods can be considered for its removal, but it is advantageous to use a suitable solvent and recrystallize in the solvent to separate and recover diphenyl. Preferred examples of the recrystallization solvent used include alcohols having 1 to 3 carbon atoms such as methanol, ethanol, and propatool, and aliphatic hydrocarbons such as hexane and heptane. The higher the amount of solvent used, the higher the purity, but the lower the recovery rate, so the amount is preferably about 1 to 6 times, preferably about 2 to 4 times the weight of the diphenyl crystals.
この再結晶は、通常の方法、すなわち加熱溶解−冷却晶
析の方法で行うことができる。ジフェニル結晶物を加熱
溶解させる温度は、４０〜５０℃が適当である。また、
溶解させたジフェニルと再結晶溶剤の均一溶液を冷却し
て精製結晶物を析出させる温度は、０〜１０℃、好まし
くは５℃前後が適当て゛ある。This recrystallization can be performed by a conventional method, that is, a heating melting-cooling crystallization method. The appropriate temperature for heating and dissolving the diphenyl crystal is 40 to 50°C. Also,
The temperature at which the homogeneous solution of dissolved diphenyl and recrystallization solvent is cooled to precipitate purified crystals is 0 to 10°C, preferably around 5°C.
なお、ジエチレングリコールとジフェニルとの共沸留分
から冷却晶析で分離されたジエチレングリコールは、回
収して共沸蒸留工程へ循環使用するのが経済的に有利で
ある。Note that it is economically advantageous to recover diethylene glycol separated from the azeotropic fraction of diethylene glycol and diphenyl by cooling crystallization and recycle it to the azeotropic distillation step.
また、この発明における蒸留操作は、通常の蒸留塔によ
り、常圧あるいは減圧で実施される。Further, the distillation operation in the present invention is carried out using a conventional distillation column at normal pressure or reduced pressure.
実施例
コールタールを蒸留して得られるナフタリン油からナフ
タリンを回収後の釜残油を蒸留し、沸点範囲２４６〜２
５６℃の留分を留取した。その組成は第１表に原料油と
して示す。Example After recovering naphthalene from naphthalene oil obtained by distilling coal tar, the residual oil in the pot was distilled to obtain a boiling point range of 246 to 2.
A fraction at 56°C was collected. Its composition is shown in Table 1 as raw oil.
第１表の原料油６００ｇに対し、ジエチレングリコール
４００ｇを添加し、理論段数約５０段のヘリパック充填
式蒸留装置を用い、常圧下、還流比２０で蒸留を行い、
留出温度２３２〜２３３℃でジエチレングリコールとジ
フェニルとの共沸物４７１．９ｇを留取した。400 g of diethylene glycol was added to 600 g of the raw material oil shown in Table 1, and distillation was carried out under normal pressure at a reflux ratio of 20 using a Helipak packed distillation apparatus with approximately 50 theoretical plates.
471.9 g of an azeotrope of diethylene glycol and diphenyl was distilled off at a distillation temperature of 232 to 233°C.
ジフェニル共沸留分を５℃まで冷却して結晶物を析出さ
せ、遠心濾過機を用いてジフェニル結晶１６４．０ ｇ
を取得した。このジフェニル結晶を５０℃でメタノール
４８６．０ｇに溶解させたのち、５℃まで冷却してジフ
ェニルを再結晶させ、遠心濾過したのり真空乾燥して精
製ジフェニル１１８．４ｇを回収した。The diphenyl azeotropic fraction was cooled to 5°C to precipitate crystals, and 164.0 g of diphenyl crystals were obtained using a centrifugal filter.
obtained. The diphenyl crystals were dissolved in 486.0 g of methanol at 50° C., then cooled to 5° C. to recrystallize the diphenyl, centrifugally filtered, and dried in vacuum to recover 118.4 g of purified diphenyl.
この精製ジフェニルは、第１表に示すとおり純度９９．
８％で、収率は原料油中のジフェニルを基準として６１
％であった。As shown in Table 1, this purified diphenyl has a purity of 99.
8%, the yield is 61% based on diphenyl in the feedstock.
%Met.
以下余白
比較例
実施例で留取したジフェニル含有留分５００ｇを実施例
と同じ蒸留装置を使用し、常圧下、還流比２０で精密蒸
留し、留出温度２４８〜２５５℃のジフェニル留分２９
６ 、５ ｇを得た。その組成は第２表に示す。Comparative Examples Below, 500 g of the diphenyl-containing fraction distilled in the example was precisely distilled under normal pressure at a reflux ratio of 20 using the same distillation apparatus as in the example, and the diphenyl fraction 29 with a distillation temperature of 248 to 255 °C
6.5 g was obtained. Its composition is shown in Table 2.
このジフェニル留分を５℃まで冷却して結晶物を析出さ
せ、遠心濾過機を用いて第２表に示す組成のジフェニル
結晶１５３．０ｇを得た。このジフェニル結晶を５０℃
でメタノール４６０ｇに溶解したのち、５℃まで冷却し
てジフェニルを再結晶させ、遠心濾過したのち真空乾燥
し、第２表に示す組成の精製ジフェニル４２．２ ｇを
回収した。This diphenyl fraction was cooled to 5° C. to precipitate crystals, and a centrifugal filter was used to obtain 153.0 g of diphenyl crystals having the composition shown in Table 2. This diphenyl crystal was heated to 50°C.
After dissolving in 460 g of methanol, the diphenyl was recrystallized by cooling to 5° C., centrifugally filtered, and vacuum dried to recover 42.2 g of purified diphenyl having the composition shown in Table 2.
この精製ジフェニルの純度は９８．６％、収率は２５．
８％で、実施例に比較し、純度、収率共に劣っていた。The purity of this purified diphenyl is 98.6%, and the yield is 25%.
8%, both purity and yield were inferior to Examples.
以下余白
［発明の効果］
前記したとおりこの発明によれば、ジフェニル含有留分
から共沸蒸留と晶析を組み合わせることにより、通常の
蒸留では分離不可能なインドールを除去することができ
、高純度のジフェニルを高収率で回収することができる
。[Effects of the Invention] As described above, according to the present invention, by combining azeotropic distillation and crystallization from a diphenyl-containing fraction, indole that cannot be separated by normal distillation can be removed, resulting in high purity. Diphenyl can be recovered in high yield.
Claims (2)
留に付し、ジフェニルとジエチレングリコールとの共沸
留分を留取し、該留分を冷却して析出する結晶物を分離
し、結晶物を溶剤の存在下再結晶することを特徴とする
ジフェニルの製造方法。(1) Diphenyl-containing fraction and diethylene glycol are subjected to distillation, an azeotropic fraction of diphenyl and diethylene glycol is distilled, the fraction is cooled and the precipitated crystals are separated, and the crystals are removed in the presence of a solvent. A method for producing diphenyl, which comprises sub-recrystallization.
のコールタール留分である特許請求の範囲第１項記載の
ジフェニルの製造方法。(2) Diphenyl-containing fraction has a boiling point range of 220-280℃
The method for producing diphenyl according to claim 1, which is a coal tar fraction of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29613786A JPS63150232A (en) | 1986-12-11 | 1986-12-11 | Production of diphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29613786A JPS63150232A (en) | 1986-12-11 | 1986-12-11 | Production of diphenyl |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63150232A true JPS63150232A (en) | 1988-06-22 |
Family
ID=17829628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29613786A Pending JPS63150232A (en) | 1986-12-11 | 1986-12-11 | Production of diphenyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63150232A (en) |
-
1986
- 1986-12-11 JP JP29613786A patent/JPS63150232A/en active Pending
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