JPH0585959A - Production of methylnaphthalene - Google Patents
Production of methylnaphthaleneInfo
- Publication number
- JPH0585959A JPH0585959A JP24890091A JP24890091A JPH0585959A JP H0585959 A JPH0585959 A JP H0585959A JP 24890091 A JP24890091 A JP 24890091A JP 24890091 A JP24890091 A JP 24890091A JP H0585959 A JPH0585959 A JP H0585959A
- Authority
- JP
- Japan
- Prior art keywords
- methylnaphthalene
- acid
- fraction
- distillation
- coal tar
- 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
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000011280 coal tar Substances 0.000 claims abstract description 11
- 238000004508 fractional distillation Methods 0.000 claims abstract description 10
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 18
- 238000004821 distillation Methods 0.000 abstract description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 12
- 239000010802 sludge Substances 0.000 abstract description 12
- -1 nitrogen-containing compound Chemical class 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- 230000007935 neutral effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 16
- 238000000605 extraction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-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
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000011084 recovery Methods 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はコールタールの分留によ
り得られるメチルナフタリン含有油からメチルナフタリ
ンを分離精製する方法に関する。TECHNICAL FIELD The present invention relates to a method for separating and purifying methylnaphthalene from a methylnaphthalene-containing oil obtained by fractional distillation of coal tar.
【０００２】[0002]
【従来技術とその課題】メチルナフタリンは、溶剤、染
色キャリアー、ビタミン、高性能樹脂等の原料等とし
て、各種業界で有用なものであり、その製造法の重要な
ひとつとしてコールタールの分留による方法が知られて
いる。しかるに、コールタールの分留により得られるメ
チルナフタリン含有油には、メチルナフタリンと沸点の
近接するキノリン、イソキノリン等の塩基性含窒素化合
物が含有されており、之等を除去すると共に、更に含有
されるビフェニル、ジメチルナフタリン類、アセナフテ
ン、ジベンゾフラン等を除去しなければ、高純度のメチ
ルナフタリンを得ることはできない。BACKGROUND OF THE INVENTION Methylnaphthalene is useful in various industries as a raw material for solvents, dye carriers, vitamins, high-performance resins, etc. The method is known. However, methylnaphthalene-containing oil obtained by fractional distillation of coal tar contains basic nitrogen-containing compounds such as quinoline and isoquinoline which have a boiling point close to that of methylnaphthalene. High-purity methylnaphthalene cannot be obtained without removing biphenyl, dimethylnaphthalene, acenaphthene, dibenzofuran, and the like.
【０００３】上記塩基性含窒素化合物の除去手段として
は、従来より、コールタール分留留分に酸を反応させて
上記塩基性含窒素化合物を水溶性塩として除去し、そし
てその後分留して分離精製されたメチルナフタリンを得
る方法が知られている。しかしながら、この方法では、
酸を反応させる場合にタール状のスラッジが多量に発生
し、これが操業性を低下させ、目的とするメチルナフタ
リンの回収率を低下させると共に、廃棄物処理の問題を
も伴うという欠点がある。更にメチルナフタリンを分離
精製する方法としては、メチルナフタリン含有油に共沸
剤としてポリアルキレングリコール類を混合して共沸蒸
留を行なう方法も知られている（特公昭６３−６５３１
号公報参照）が、この方法では多量の共沸剤を用いねば
ならない不利があると共に、共沸剤が分離精製したメチ
ルナフタリン内に混入するため、この共沸剤を上記メチ
ルナフタリンから分離して回収する工程が必要となる欠
点がある。As means for removing the basic nitrogen-containing compound, conventionally, a coal tar fractionated distillate is reacted with an acid to remove the basic nitrogen-containing compound as a water-soluble salt, and then fractionated. A method for obtaining separated and purified methylnaphthalene is known. However, with this method,
When the acid is reacted, a large amount of tar-like sludge is generated, which lowers the operability, lowers the recovery rate of the target methylnaphthalene, and has a problem of waste disposal. Further, as a method of separating and refining methylnaphthalene, a method of mixing methylnaphthalene-containing oil with polyalkylene glycol as an azeotropic agent and performing azeotropic distillation is also known (Japanese Patent Publication No. 63-6531).
However, this method has the disadvantage that a large amount of azeotropic agent must be used, and since the azeotropic agent is mixed in the separated and purified methylnaphthalene, the azeotropic agent must be separated from the methylnaphthalene. There is a drawback that a recovery process is required.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、上記従来
技術の欠点を解消して高純度のメチルナフタリンを効率
よく分離精製する手段を開発することを目的として鋭意
研究を重ねた結果、メチルナフタリン含有油を予め蒸留
した後、酸抽出を行なう時には、該酸抽出の際にスラッ
ジの発生を伴うことなく、塩基性含窒素化合物がみごと
に除去できるという新しい事実を発見し、ここに上記目
的に合致する手段の開発に成功した。Means for Solving the Problems The inventors of the present invention have conducted extensive studies for the purpose of developing a means for efficiently separating and purifying high-purity methylnaphthalene by solving the above-mentioned drawbacks of the prior art. When a methylnaphthalene-containing oil was previously distilled and then subjected to an acid extraction, a new fact was discovered that a basic nitrogen-containing compound can be finely removed without generating sludge during the acid extraction. We have succeeded in developing a means that matches the purpose.
【０００５】本発明は上記知見に基づいて完成されたも
のであり、その要旨とする所は、コールタールの分留に
より得られるメチルナフタリン含有油を蒸留して沸点２
００〜２９０℃の留分を得、次いでこれを酸抽出してキ
ノリン、イソキノリン等を除去して準精製メチルナフタ
リンを得、更にナフタリン等を分留して除去することを
特徴とするメチルナフタリン含有油からメチルナフタリ
ンを分離精製する精製メチルナフタリンの製造方法にあ
る。The present invention has been completed based on the above findings, and the gist of the present invention is to distill the methylnaphthalene-containing oil obtained by fractional distillation of coal tar to obtain a boiling point of 2
A distillate having a temperature of 0 to 290 ° C. is obtained, and then this is subjected to acid extraction to remove quinoline, isoquinoline and the like to obtain semi-purified methylnaphthalene, and further naphthalene and the like are fractionally distilled and removed. It is a method for producing purified methylnaphthalene by separating and purifying methylnaphthalene from oil.
【０００６】本発明方法によれば、上記の通り酸抽出に
先だって蒸留を行なうことに基づいて、酸抽出の際にス
ラッジの発生を伴うことなく、塩基性含窒素化合物を除
去でき、従ってスラッジ処理の必要もなく、またスラッ
ジによる目的物の回収率低下もなく、非常に高収率、高
純度で目的とするメチルナフタリンを分離することがで
きる。本発明方法によって、かかる優れた効果が奏し得
る理由は尚明らかではないが、酸抽出の際のスラッジの
発生は、メチルナフタリン含有油中に存在するインドー
ル等のオレフィン類が酸を触媒として重合することによ
ると考えられ、本発明によれば、このスラッジ発生要因
となるオレフィン類等が蒸留除去できるためと考えられ
る。いずれにせよ、本発明方法によれば、コールタール
の分留油よりメチルナフタリンを高収率、高純度で分離
でき、しかもこの方法では高価な共沸剤等を利用する必
要もない。従って本発明方法は工業的実施に適したもの
である。According to the method of the present invention, the basic nitrogen-containing compound can be removed without generating sludge during the acid extraction based on the fact that the distillation is performed prior to the acid extraction as described above. It is also possible to separate the target methylnaphthalene with a very high yield and a high purity without the need for the above, and without lowering the recovery rate of the target product due to sludge. Although the reason why such an excellent effect can be achieved by the method of the present invention is not yet clear, the generation of sludge during acid extraction is caused by the polymerization of olefins such as indole present in the methylnaphthalene-containing oil using the acid as a catalyst. It is considered that this is because, according to the present invention, the olefins and the like that cause the sludge can be removed by distillation. In any case, according to the method of the present invention, methylnaphthalene can be separated from a fractionated oil of coal tar with high yield and high purity, and this method does not require the use of an expensive azeotropic agent. Therefore, the method of the present invention is suitable for industrial practice.
【０００７】本発明方法において、被処理原料とするコ
ールタールの分留により得られるメチルナフタリン含有
油としては、通常の分留操作により得られる各種のもの
をいずれも利用できる。その代表例としては、約２００
〜３００℃の留分を例示できる。該代表的メチルナフタ
リン含有油の組成［ガスクロマトグラフ法による］は、
下記表１に示す通りである。In the method of the present invention, as the methylnaphthalene-containing oil obtained by fractional distillation of coal tar as a raw material to be treated, any of various oils obtained by ordinary fractional distillation operation can be used. A typical example is about 200
An example is a fraction of 300 ° C. The composition of the representative methylnaphthalene-containing oil [by gas chromatography] is
It is as shown in Table 1 below.
【０００８】[0008]
【表１】 [Table 1]
【０００９】本発明方法においては、上記メチルナフタ
リン含有油をまず蒸留して、沸点２００〜２９０℃の留
分を得る。この蒸留操作はよく知られている一般的方法
に従い、通常の蒸留装置、例えば多段蒸留塔等を用い
て、常圧乃至減圧下に行なうことができ、特に精留する
必要はない。またこの蒸留では通常２９０℃までの留
分、好ましくは沸点２００℃から２５０℃の留分を得る
のが適当である。斯くして得られる留分の代表的組成
は、上記と同一測定法による測定の結果、下記表２に示
す通りである。In the method of the present invention, the methylnaphthalene-containing oil is first distilled to obtain a fraction having a boiling point of 200 to 290 ° C. This distillation operation can be carried out according to a well-known general method using an ordinary distillation apparatus such as a multistage distillation column under atmospheric pressure or reduced pressure, and it is not necessary to carry out rectification. Further, in this distillation, it is suitable to obtain a fraction having a boiling point of up to 290 ° C., preferably a boiling point of 200 ° C. to 250 ° C. The representative composition of the thus obtained fraction is as shown in Table 2 below as a result of measurement by the same measurement method as above.
【００１０】[0010]
【表２】 [Table 2]
【００１１】次いで本発明方法においては、上記で得ら
れる留分を酸抽出する。この酸抽出操作は、従来行なわ
れている操作と実質的に異なる訳ではなく、一般には硫
酸、塩酸等の無機酸類を用いて行なうことができる。該
酸は濃酸でも希酸でもよく、その被処理留分に対する使
用割合も特に限定はない。Next, in the method of the present invention, the fraction obtained above is acid-extracted. This acid extraction operation is not substantially different from the operation conventionally performed, and can generally be performed using inorganic acids such as sulfuric acid and hydrochloric acid. The acid may be a concentrated acid or a dilute acid, and there is no particular limitation on the ratio of the acid to the fraction to be treated.
【００１２】上記酸抽出後、得られる油層、即ち中性留
分より常法に従い蒸留を行なうことにより、所望のメチ
ルナフタリンを収得できる。After the above-mentioned acid extraction, a desired methylnaphthalene can be obtained by distilling the obtained oil layer, that is, the neutral fraction according to a conventional method.
【００１３】[0013]
【実施例】以下、本発明を更に詳しく説明するため実施
例を挙げる。EXAMPLES Examples will be given below to explain the present invention in more detail.
【００１４】[0014]
【実施例１】前記表１に記載の組成を有するコールター
ルの分留によるメチルナフタリン含有留分（以下「％」
とあるはこの原料であるメチルナフタリン含有留分を１
００％とし、これに対する重量％を意味するものとす
る）を、理論段数５０段の蒸留塔を用いて還流比５（５
０ｍｍＨｇ）で蒸留を行ない、１２５℃から流出温度１
４５℃（常圧に換算すると、２００℃から流出温度２５
０℃に相当）までの留分を得た。その組成は前記表２に
示す通りである。Example 1 Methylnaphthalene-containing fraction (hereinafter “%”) obtained by fractional distillation of coal tar having the composition shown in Table 1 above.
There is 1 part of the methylnaphthalene-containing fraction that is the raw material.
00%, which means the weight% relative to this), using a distillation column with 50 theoretical plates and a reflux ratio of 5 (5
Distillation at 0 mmHg), and the outflow temperature from 125 ° C to 1
45 ° C (converted to atmospheric pressure, 200 ° C to outflow temperature 25
A fraction up to 0 ° C.) was obtained. Its composition is as shown in Table 2 above.
【００１５】上記で得られた蒸留留分を、３０％硫酸と
容量比３：２で混合し、４０℃で２時間攪拌後、静置分
離を行なった。この時の界面の分離状態は良好であり、
スラッジの発生は実質的に認められなかった。The distillation fraction obtained above was mixed with 30% sulfuric acid in a volume ratio of 3: 2, stirred at 40 ° C. for 2 hours, and then allowed to stand and separate. The separation state of the interface at this time is good,
Substantially no sludge generation was observed.
【００１６】上記で分離した油層（５１％）即ち準精製
メチルナフタリン（その前記測定法に従う組成を表３に
示す）を、理論段数５０段の蒸留塔を用いて還流比１０
（５０ｍｍＨｇ）で蒸留を行ない、１２５℃から流出温
度１４０℃の蒸留によってナフタリン等（８％）の軽量
分及びビフェニル、ジメチルナフタリン類、アセトナフ
テン、ジベンゾフラン等の重量分を除去して、目的とす
る精製メチルナフタリン（４３％）を得た。The oil layer (51%) separated above, that is, semi-purified methylnaphthalene (the composition according to the above-mentioned measuring method is shown in Table 3), was used in a distillation column having 50 theoretical plates and a reflux ratio of 10
Distillation at (50 mmHg) is performed to remove light weight components such as naphthalene (8%) and weight components such as biphenyl, dimethylnaphthalene, acetonaphthene, and dibenzofuran by distillation from 125 ° C. to an outlet temperature of 140 ° C. Purified methylnaphthalene (43%) was obtained.
【００１７】かくして得られた精製メチルナフタリンの
回収率は８１％であった。またこのもの前記測定法に従
う組成は、表４に示す通りであり、塩基性含窒素化合物
は完全に除去されており、また酸抽出によるメチルナフ
タリンのロスは実質的に認められなかった。The recovery rate of the purified methylnaphthalene thus obtained was 81%. The composition of this product according to the above-mentioned measurement method is as shown in Table 4, the basic nitrogen-containing compound was completely removed, and the loss of methylnaphthalene due to acid extraction was not substantially observed.
【００１８】[0018]
【実施例２】実施例１と同様にして蒸留を行なって得ら
れた留分を、６０％硫酸と容量比２：１で混合し、１０
分間攪拌後、静置分離を行なった。この時の界面の分離
状態は良好であり、スラッジの発生は実質的に認められ
なかった。即ち、硫酸濃度が高いと一般にはスラッジの
発生の可能性が高くなるが、本発明方法では高濃度の酸
に対しても、スラッジの発生がないことが確認された。Example 2 Distillation obtained in the same manner as in Example 1 was mixed with 60% sulfuric acid at a volume ratio of 2: 1 to obtain 10
After stirring for a minute, stationary separation was performed. At this time, the separated state of the interface was good, and the generation of sludge was not substantially observed. That is, it is generally confirmed that sludge is not likely to be generated even with a high concentration of acid in the method of the present invention, although the possibility of generation of sludge is generally high when the concentration of sulfuric acid is high.
【００１９】上記で分離した油層を実施例１と同様にし
て、目的とする精製メチルナフタリンを得た。このもの
は塩基性含窒素化合物が完全に除去されており、また酸
抽出によるメチルナフタリンのロスは実質的に認められ
なかった。The oil layer separated above was treated in the same manner as in Example 1 to obtain the desired purified methylnaphthalene. In this product, the basic nitrogen-containing compound was completely removed, and the loss of methylnaphthalene due to acid extraction was not substantially observed.
【００２０】[0020]
【比較例１】前記表１に記載のメチルナフタリン含有留
分を、４０％硫酸と容量比１００：４５で混合し、４０
℃で２時間攪拌後、静置分離を行なった。この時、界面
付近には多量のスラッジ（１０％）の発生が認められ
た。次いで油層（８５％）を理論段数５０段の蒸留塔を
用いて還流比５：１（５０ｍｍＨｇ）で蒸留を行ない、
１２５℃から流出温度１４０℃でナフタリン等（７％）
を除去し、更に１４０℃から流出温度１４５℃でビフェ
ニル、ジメチルナフタリン類、アセナフテン、ジベンゾ
フラン等を除去して、精製メチルナフタリン（４２％）
を得た。このものの組成を同様にして測定した結果は表
４に示す通りであり、メチルナフタリンの回収率は７６
％に止まった。Comparative Example 1 The methylnaphthalene-containing fraction shown in Table 1 above was mixed with 40% sulfuric acid at a volume ratio of 100: 45 to obtain 40
After stirring at 0 ° C. for 2 hours, stationary separation was performed. At this time, generation of a large amount of sludge (10%) was recognized near the interface. Next, the oil layer (85%) was distilled at a reflux ratio of 5: 1 (50 mmHg) using a distillation column having 50 theoretical plates.
Naphthalene etc. (7%) at 125 ° C to 140 ° C outflow temperature
Biphenyl, dimethylnaphthalene, acenaphthene, dibenzofuran, etc. are further removed at 140 ° C. to an outflow temperature of 145 ° C. to obtain purified methylnaphthalene (42%).
Got The composition of this product was measured in the same manner and the results are shown in Table 4. The recovery of methylnaphthalene was 76.
Stopped at%.
【００２１】[0021]
【表３】 [Table 3]
【００２２】[0022]
【表４】 [Table 4]
Claims (2)
ナフタリン含有油を蒸留して沸点２００〜２９０℃の留
分を得、次いでこれを酸抽出することを特徴とするメチ
ルナフタリン含有油からメチルナフタリンを分離精製す
る準精製メチルナフタリンの製造方法。1. A methylnaphthalene-containing oil obtained by distilling a methylnaphthalene-containing oil obtained by fractional distillation of coal tar to obtain a fraction having a boiling point of 200 to 290 ° C., which is then acid-extracted. A method for producing semi-purified methylnaphthalene for separating and purifying
ンを更に蒸留することを特徴とする精製メチルナフタリ
ンの製造方法。2. A method for producing purified methylnaphthalene, characterized in that the semi-purified methylnaphthalene obtained in claim 1 is further distilled.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24890091A JPH0585959A (en) | 1991-09-27 | 1991-09-27 | Production of methylnaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24890091A JPH0585959A (en) | 1991-09-27 | 1991-09-27 | Production of methylnaphthalene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0585959A true JPH0585959A (en) | 1993-04-06 |
Family
ID=17185109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24890091A Pending JPH0585959A (en) | 1991-09-27 | 1991-09-27 | Production of methylnaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0585959A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100393677C (en) * | 2005-06-30 | 2008-06-11 | 天津大学 | Method for extracting 1-methylnaphthalene and 2-methylnaphthalene from tar |
-
1991
- 1991-09-27 JP JP24890091A patent/JPH0585959A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100393677C (en) * | 2005-06-30 | 2008-06-11 | 天津大学 | Method for extracting 1-methylnaphthalene and 2-methylnaphthalene from tar |
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