JPH1180043A - Production of meta-terphenyl - Google Patents
Production of meta-terphenylInfo
- Publication number
- JPH1180043A JPH1180043A JP9245745A JP24574597A JPH1180043A JP H1180043 A JPH1180043 A JP H1180043A JP 9245745 A JP9245745 A JP 9245745A JP 24574597 A JP24574597 A JP 24574597A JP H1180043 A JPH1180043 A JP H1180043A
- Authority
- JP
- Japan
- Prior art keywords
- terphenyl
- weight
- reaction
- isomerization
- aluminum chloride
- 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
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、ｏ−ターフェニ
ル、ｐ−ターフェニル又はこれらターフェニル類を含有
する混合物から、酸触媒による異性化反応によりｍ−タ
ーフェニルを製造する方法に関するものである。The present invention relates to a method for producing m-terphenyl from o-terphenyl, p-terphenyl or a mixture containing these terphenyls by an acid-catalyzed isomerization reaction. .
【０００２】[0002]
【従来の技術】ｍ−ターフェニルは、熱媒体や感熱紙増
感剤として有用であるため、効率よく経済的に有利な製
造方法の開発が望まれている。ｍ−ターフェニルの製造
方法としては、ベンゼンを７００〜９００℃で熱縮合さ
せて生成するビフェニル、ｏ−ターフェニル、ｍ−ター
フェニル、ｐ−ターフェニルの混合物を精密蒸留して、
ｍ−ターフェニルを得る方法が知られている。しかしな
がら、ベンゼンによる熱縮合生成混合物には、通常ｍ−
ターフェニルが１０重量％程度しか含まれていないた
め、これを増産しようとすると他の併産物も多量に副生
するという問題がある。2. Description of the Related Art Since m-terphenyl is useful as a heat medium and a thermal paper sensitizer, it is desired to develop an efficient and economically advantageous production method. As a method for producing m-terphenyl, a mixture of biphenyl, o-terphenyl, m-terphenyl, and p-terphenyl produced by thermally condensing benzene at 700 to 900 ° C. is subjected to precision distillation.
Methods for obtaining m-terphenyl are known. However, the heat condensation product mixture with benzene usually contains m-
Since only about 10% by weight of terphenyl is contained, there is a problem in that an attempt to increase the production thereof produces a large amount of other by-products.
【０００３】これらの問題を解決するために、ベンゼン
の熱縮合反応で副生するｏ−ターフェニル、ｐ−ターフ
ェニル及びｍ−ターフェニルを含む混合物を異性化し、
ｍ−ターフェニルを製造する方法が報告されている。例
えば、ｐ−ターフェニル、ｏ−ターフェニルをルイス酸
触媒の存在下でｍ−ターフェニルに異性化する方法（米
国特許２３６３２０９号）、ｐ−ターフェニルを固定化
された固体酸触媒によりｍ−ターフェニルに異性化する
方法（仏国特許１３４５０２１号）などが知られてい
る。しかし、いずれもｍ−体の異性化選択率が悪く、１
段の異性化反応で高純度のｍ−ターフェニルを得ること
ができないため、異性化後に蒸留精製する必要がある。
また、異性化の反応温度が高く、特別な設備仕様を施す
必要があり、経済性の問題がある。[0003] In order to solve these problems, a mixture containing o-terphenyl, p-terphenyl and m-terphenyl by-produced in the thermal condensation reaction of benzene is isomerized,
A method for producing m-terphenyl has been reported. For example, a method of isomerizing p-terphenyl or o-terphenyl to m-terphenyl in the presence of a Lewis acid catalyst (U.S. Pat. No. 2,363,209), m-terphenyl is immobilized on a solid acid catalyst having p-terphenyl immobilized thereon. A method of isomerizing to terphenyl (French Patent 1345021) is known. However, in each case, the isomerization selectivity of the m-isomer was poor and 1
Since high-purity m-terphenyl cannot be obtained by the isomerization reaction of the stage, it is necessary to purify by distillation after isomerization.
In addition, the reaction temperature for isomerization is high, and it is necessary to provide special equipment specifications, and there is an economic problem.
【０００４】[0004]
【発明が解決しようとする課題】したがって、本発明の
目的は、ｏ−ターフェニル、ｐ−ターフェニル又はこれ
らを含有する混合物を、酸触媒の存在下に温和な条件で
異性化反応させ、ｍ−ターフェニルを選択的に効率よく
製造できる方法を提供することにある。Accordingly, it is an object of the present invention to provide an isomerization reaction of o-terphenyl, p-terphenyl or a mixture containing them under mild conditions in the presence of an acid catalyst. -To provide a method for selectively and efficiently producing terphenyl.
【０００５】[0005]
【課題を解決するための手段】すなわち、本発明は、ｏ
−ターフェニル、ｐ−ターフェニル又はこれらを含有す
る混合物を、ターフェニル類に対し０．１〜５重量％の
塩化アルミニウム触媒の存在下、反応温度８０〜１５０
℃、０．５時間以上異性化反応させることを特徴とする
ｍ−ターフェニルの製造方法である。That is, the present invention provides an o
-Terphenyl, p-terphenyl or a mixture containing them in the presence of 0.1-5% by weight of aluminum chloride catalyst, based on terphenyls, at a reaction temperature of 80-150.
This is a method for producing m-terphenyl, wherein the isomerization reaction is carried out at 0.5 ° C. for 0.5 hours or more.
【０００６】本発明で使用する原料は、ｏ−ターフェニ
ル又はｐ−ターフェニル単独でもよく、またｏ−ターフ
ェニル、ｍ−ターフェニル、ｐ−ターフェニルの２種又
は３種の混合物でもよい。 ｏ−ターフェニル、ｍ−ター
フェニル、ｐ−ターフェニルの混合物の混合割合は特に
限定されるものでないが、 高い選択率で高純度のｍ−タ
−フェニルを得るためには、ｐ−ターフェニルの割合が
低いものが好ましい。また、ターフェニル類以外の成
分、例えばビフェニルなどを含有してもよい。The raw material used in the present invention may be o-terphenyl or p-terphenyl alone, or may be a mixture of two or three of o-terphenyl, m-terphenyl and p-terphenyl. The mixing ratio of the mixture of o-terphenyl, m-terphenyl and p-terphenyl is not particularly limited, but in order to obtain m-ter-phenyl with high selectivity and high purity, p-terphenyl is required. Is preferred. Further, components other than terphenyls, for example, biphenyl and the like may be contained.
【０００７】原料のターフェニル類に対する塩化アルミ
ニウム触媒の使用量は、反応温度によって異なるが、原
料ターフェニル類に対し使用量が増えるほどｐ−体への
異性化速度は増加するため、高純度のｍ−ターフェニル
を得ることが難しくなる。また、使用量が少ないと異性
化速度が遅くなり、ｍ−ターフェニルの生産性が悪くな
る。したがって、ｍ−ターフェニルを高濃度でかつ生産
性よく製造するため、塩化アルミニウム触媒の使用量は
０．１〜５重量％、好ましくは０．２〜２重量％であ
る。 ここで、ターフェニル類の量は、原料中のｏ−、ｍ
−及びｐ−ターフェニルの合計量を意味する。The amount of the aluminum chloride catalyst to be used for the starting terphenyls varies depending on the reaction temperature. It becomes difficult to obtain m-terphenyl. On the other hand, if the amount used is small, the isomerization rate becomes slow, and the productivity of m-terphenyl becomes poor. Therefore, in order to produce m-terphenyl at a high concentration and with good productivity, the amount of the aluminum chloride catalyst used is 0.1 to 5% by weight, preferably 0.2 to 2% by weight. Here, the amount of terphenyls is determined based on o- and m in the raw material.
Means the total amount of-and p-terphenyl.
【０００８】本発明の異性化反応の条件は、原料ターフ
ェニル類の異性体比率と目的生成物のｍ−ターフェニル
の純度、収率によって適宜条件を選定することができ
る。反応温度は、原料が液状になる温度以上であればよ
いが、ｍ−ターフェニルへの異性化選択性を高めるには
８０〜１５０℃が好ましい。反応温度が高いほど異性化
速度は増加するが、ｐ−ターフェニルの平衡組成比率が
上昇し好ましくない。反応時間は、塩化アルミニウム触
媒量、反応温度によって変わるが、通常０．５〜４８時
間、好ましくは１〜１０時間、反応圧力は、減圧、常
圧、加圧のいずれでもよい。反応形式は、回分式、連続
式又は半回分式のいずれの方法でもよい。The conditions for the isomerization reaction of the present invention can be appropriately selected depending on the isomer ratio of the starting terphenyls and the purity and yield of the target product, m-terphenyl. The reaction temperature may be higher than the temperature at which the raw material becomes liquid, but is preferably from 80 to 150 ° C. in order to enhance the isomerization selectivity to m-terphenyl. Although the isomerization rate increases as the reaction temperature increases, the equilibrium composition ratio of p-terphenyl increases, which is not preferable. The reaction time varies depending on the amount of the aluminum chloride catalyst and the reaction temperature, but is usually 0.5 to 48 hours, preferably 1 to 10 hours, and the reaction pressure may be any of reduced pressure, normal pressure, and increased pressure. The reaction format may be any of a batch system, a continuous system, and a semi-batch system.
【０００９】ターフェニル類の異性化反応は、温度が高
いほどｐ−体への異性化速度が増加し、ｐ−ターフェニ
ルの平衡組成が上昇して、ｍ−ターフェニルの収量が減
る。本発明によれば、酸強度の高い塩化アルミニウム触
媒を使用することで、ｍ−体への異性化に有利となる低
い反応温度で異性化させることができ、ｍ−ターフェニ
ルの選択率を高くすることができる。In the isomerization reaction of terphenyls, the higher the temperature, the higher the rate of isomerization to p-isomer, the higher the equilibrium composition of p-terphenyl, and the lower the yield of m-terphenyl. According to the present invention, by using an aluminum chloride catalyst having a high acid strength, it is possible to isomerize at a low reaction temperature which is advantageous for isomerization to the m-form, and the selectivity of m-terphenyl is increased. can do.
【００１０】このようにして、ｏ−ターフェニル、ｐ−
ターフェニル又はこれらを含有する混合物を塩化アルミ
ニウム触媒の存在下で、温和な条件でｍ−ターフェニル
に異性化させることができる。また、原料であるターフ
ェニル類の異性体比率によっては、１段で高純度のｍ−
ターフェニルが得られるが、ｍ−ターフェニルの純度が
低いものは、必要に応じて精密蒸留等の公知の方法によ
り高純度ｍ−ターフェニルに精製することができる。Thus, o-terphenyl, p-
Terphenyl or a mixture containing them can be isomerized to m-terphenyl under mild conditions in the presence of an aluminum chloride catalyst. Also, depending on the isomer ratio of the terphenyls as the raw material, high purity m-
Terphenyl can be obtained, but those with low purity of m-terphenyl can be purified to high purity m-terphenyl by a known method such as precision distillation, if necessary.
【００１１】[0011]
【実施例】以下、実施例及び比較例により本発明を具体
的に説明する。The present invention will be specifically described below with reference to examples and comparative examples.
【００１２】実施例１〜５で使用した原料ターフェニル
の組成（重量％）は、次のとおりであった。 ビフェニル ： ０．９０％ ｏ−ターフェニル ： ９１．８２％ ｍ−ターフェニル ： ５．４８％ ｐ−ターフェニル ： ０．０２％ その他 ： １．７８％The composition (% by weight) of the starting terphenyl used in Examples 1 to 5 was as follows. Biphenyl: 0.90% o-terphenyl: 91.82% m-terphenyl: 5.48% p-terphenyl: 0.02% Others: 1.78%
【００１３】実施例１ 原料ターフェニル１０２０ｇを８０℃に加熱し、１３０
℃に昇温して溶解させた後、撹袢しながら塩化アルミニ
ウム１０．２ｇ（１．０重量％）を加え１３０℃で３時
間加熱して異性化反応を行った。反応終了後、常温まで
冷却し、水及び２３％苛性ソーダ水溶液で洗浄した反応
生成物をガスクロマトグラフィ−で分析した結果、ｏ−
ターフェニル０．３８重量％、ｍ−ターフェニル９１．
３３重量％、ｐ−ターフェニル６．０８重量％であっ
た。Example 1 1020 g of the raw material terphenyl was heated to 80 ° C.
After the temperature was raised to 0 ° C to dissolve, 10.2 g (1.0% by weight) of aluminum chloride was added with stirring, and the mixture was heated at 130 ° C for 3 hours to perform an isomerization reaction. After completion of the reaction, the reaction product was cooled to room temperature, and the reaction product washed with water and a 23% aqueous sodium hydroxide solution was analyzed by gas chromatography.
Terphenyl 0.38% by weight, m-terphenyl
33% by weight and 6.08% by weight of p-terphenyl.
【００１４】実施例２ 反応温度を１００℃、反応時間５時間とした以外は、実
施例１と同様に異性化反応を行った結果、反応生成物は
ｏ−ターフェニル１．７８重量％、ｍ−ターフェニル９
５．０８重量％、ｐ−ターフェニル１．０５重量％であ
った。Example 2 The isomerization reaction was carried out in the same manner as in Example 1 except that the reaction temperature was 100 ° C. and the reaction time was 5 hours. As a result, the reaction product was 1.78% by weight of o-terphenyl, m -Terphenyl 9
It was 5.08% by weight and 1.05% by weight of p-terphenyl.
【００１５】実施例３ 塩化アルミニウムの使用量を７．６５ｇ（０．７５重量
％）、反応時間５時間とした以外は、実施例１と同様に
異性化反応を行った結果、反応生成物はｏ−ターフェニ
ル０．９１重量％、ｍ−ターフェニル９３．１５重量
％、ｐ−ターフェニル２．７２重量％であった。Example 3 The isomerization reaction was carried out in the same manner as in Example 1 except that the amount of aluminum chloride used was 7.65 g (0.75% by weight) and the reaction time was 5 hours. The content was 0.91% by weight of o-terphenyl, 93.15% by weight of m-terphenyl, and 2.72% by weight of p-terphenyl.
【００１６】実施例４ 塩化アルミニウムの使用量を５．１ｇ（０．５重量
％）、反応時間５時間とした以外は、実施例１と同様に
異性化反応を行った結果、反応生成物はｏ−ターフェニ
ル１７．２４重量％、ｍ−ターフェニル７９．３０重量
％、ｐ−ターフェニル０．９５重量％であった。Example 4 The isomerization reaction was carried out in the same manner as in Example 1 except that the amount of aluminum chloride used was 5.1 g (0.5% by weight) and the reaction time was 5 hours. The content was 17.24% by weight of o-terphenyl, 79.30% by weight of m-terphenyl, and 0.95% by weight of p-terphenyl.
【００１７】実施例５ 塩化アルミニウムの使用量を７．６５ｇ（０．７５重量
％）とした以外は、実施例１と同様に異性化反応を行っ
た。この反応液組成の時間変化をガスクロマトグラフィ
−で分析した結果を図１に示す。Example 5 An isomerization reaction was carried out in the same manner as in Example 1 except that the amount of aluminum chloride used was 7.65 g (0.75% by weight). FIG. 1 shows the result of analyzing the change over time of the composition of the reaction solution by gas chromatography.
【００１８】実施例６ 原料ターフェニルとしてｏ−ターフェニル８３．７７重
量％、ｍ−ターフェニル９．６１重量％、ｐ−ターフェ
ニル４．４５重量％であるものを使用した以外は、実施
例１と同様に異性化反応を行った結果、反応生成物はｏ
−ターフェニル６．５５重量％、ｍ−ターフェニル８
４．１６重量％、ｐ−ターフェニル６．１７重量％であ
った。Example 6 Example 8 was repeated except that the starting terphenyl used was 83.77% by weight of o-terphenyl, 9.61% by weight of m-terphenyl, and 4.45% by weight of p-terphenyl. As a result of performing the isomerization reaction in the same manner as in 1, the reaction product was o
6.55% by weight of terphenyl, m-terphenyl 8
4.16% by weight and 6.17% by weight of p-terphenyl.
【００１９】比較例 比較例で使用した原料ターフェニルの組成（重量％）は
次のとおりであった。 ｏ−ターフェニル ： ６０．００％ ｍ−ターフェニル ： １５．００％ ｐ−ターフェニル ： ２５．００％ オ−トクレーブに、原料ターフェニル１０２０ｇと酸触
媒として活性白土（日本活性白土製Ｋ−５００）２０４
ｇ（２０重量％）を入れ、撹袢しながら常圧、２３０℃
で４時間加熱した。冷却後、触媒を濾過分離し、反応生
成物をガスクロマトグラフィーで分析した結果、ｏ−タ
ーフェニル６．３１重量％、ｍ−ターフェニル６８．０
３重量％、ｐ−ターフェニル２５．０４重量％であっ
た。Comparative Example The composition (% by weight) of the starting terphenyl used in the comparative example was as follows. o-Terphenyl: 60.00% m-Terphenyl: 15.00% p-Terphenyl: 25.00% In an autoclave, 1020 g of a raw material terphenyl and activated clay as an acid catalyst (K-500 manufactured by Nippon Activated Shirato) ) 204
g (20% by weight), while stirring, at normal pressure, 230 ° C.
For 4 hours. After cooling, the catalyst was separated by filtration and the reaction product was analyzed by gas chromatography. As a result, 6.31% by weight of o-terphenyl and 68.0% of m-terphenyl were obtained.
3% by weight and 25.04% by weight of p-terphenyl.
【００２０】[0020]
【発明の効果】本発明によれば、ｏ−ターフェニル、ｐ
−ターフェニル又はこれらを含有する混合物を塩化アル
ミニウム触媒の存在下、温和な条件で異性化反応させる
ことで、熱媒体や感熱紙増感剤として有用な高純度のｍ
−ターフェニルを一段で効率よく製造することができ
る。According to the present invention, o-terphenyl, p
-Terphenyl or a mixture containing these isomerized under mild conditions in the presence of an aluminum chloride catalyst to obtain a high-purity m useful as a heat medium or a thermal paper sensitizer.
-Terphenyl can be efficiently produced in one step.
【図１】実施例５における反応液組成の時間変化を示す
グラフである。FIG. 1 is a graph showing the change over time of the composition of a reaction solution in Example 5.
Claims (1)
はこれらを含有する混合物を、ターフェニル類に対し
０．１〜５重量％の塩化アルミニウム触媒の存在下、反
応温度８０〜１５０℃、０．５時間以上異性化反応させ
ることを特徴とするｍ−ターフェニルの製造方法。1. An o-terphenyl, a p-terphenyl or a mixture containing these, is reacted at a reaction temperature of 80 to 150 ° C. in the presence of 0.1 to 5% by weight of an aluminum chloride catalyst based on terphenyls. A method for producing m-terphenyl, wherein the isomerization reaction is performed for 5 hours or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24574597A JP3984687B2 (en) | 1997-09-10 | 1997-09-10 | Method for producing m-terphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24574597A JP3984687B2 (en) | 1997-09-10 | 1997-09-10 | Method for producing m-terphenyl |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1180043A true JPH1180043A (en) | 1999-03-23 |
| JP3984687B2 JP3984687B2 (en) | 2007-10-03 |
Family
ID=17138174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24574597A Expired - Fee Related JP3984687B2 (en) | 1997-09-10 | 1997-09-10 | Method for producing m-terphenyl |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3984687B2 (en) |
-
1997
- 1997-09-10 JP JP24574597A patent/JP3984687B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3984687B2 (en) | 2007-10-03 |
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