JP2849324B2 - Method for producing unsaturated dimer of α-methylstyrenes - Google Patents
Method for producing unsaturated dimer of α-methylstyrenesInfo
- Publication number
- JP2849324B2 JP2849324B2 JP6023097A JP2309794A JP2849324B2 JP 2849324 B2 JP2849324 B2 JP 2849324B2 JP 6023097 A JP6023097 A JP 6023097A JP 2309794 A JP2309794 A JP 2309794A JP 2849324 B2 JP2849324 B2 JP 2849324B2
- Authority
- JP
- Japan
- Prior art keywords
- methylstyrenes
- methylstyrene
- sulfonic acid
- acid compound
- dimer
- 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
-
- 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)
Description
【０００１】[0001]
【産業上の利用分野】本発明はＳＢＲなどの共重合体製
造時における分子量調節剤等として好適に用いられるα
−メチルスチレン類の不飽和二量体の製造法に関する。BACKGROUND OF THE INVENTION The present invention relates to an .alpha.-type compound which is suitably used as a molecular weight regulator in the production of a copolymer such as SBR.
The present invention relates to a process for producing unsaturated dimers of methylstyrenes.
【０００２】[0002]
【従来の技術】ＡＢＳ樹脂、ＡＳ樹脂、ポリスチレン、
ＳＢＲなどの共重合体製造時において分子量調節剤とし
てこれまで四塩化炭素やドデシルメルカプタン類が用い
られてきた。しかしながら、四塩化炭素は、オゾン層破
壊物質として１９９２年のモントリオール国際会議で１
９９５年末までに全廃することが確定しており、またド
デシルメルカプタン類は、取り扱い時及び使用時の臭気
公害が指摘されており、その使用が制限されるに至って
いる。そこで、これらの代替品としてα−メチルスチレ
ン類の不飽和二量体、特に１−ペンテン体が使用される
ようになってきているが、１−ペンテン体を選択性よく
工業的に製造する方法は現在のところ見当らない。2. Description of the Related Art ABS resin, AS resin, polystyrene,
Carbon tetrachloride and dodecyl mercaptans have been used as molecular weight regulators during the production of copolymers such as SBR. However, carbon tetrachloride was one of the ozone depleting substances at the 1992 Montreal International Conference.
It has been confirmed that it will be completely abolished by the end of 995, and it has been pointed out that dodecyl mercaptans are subject to odor pollution during handling and use, and their use has been restricted. Therefore, unsaturated dimers of α-methylstyrenes, particularly 1-pentenes, have come to be used as substitutes for these. However, a method for industrially producing 1-pentenes with high selectivity. Is not currently available.
【０００３】α−メチルスチレン類の不飽和二量体を製
造する従来公知の方法としては、例えば、特公昭４１−
６３３５号公報に、α−メチルスチレン類を酸触媒の存
在下に反応させて、α−メチルスチレン類の二量体を製
造する方法が記載されている。この方法においては、不
飽和二量体の精製は、酸触媒を濾過により除去した後、
あるいは水洗により中和した後、蒸留することにより行
われている。Conventionally known methods for producing unsaturated dimers of α-methylstyrenes include, for example, Japanese Patent Publication No.
No. 6335 describes a method for producing α-methylstyrene dimers by reacting α-methylstyrenes in the presence of an acid catalyst. In this method, the purification of the unsaturated dimer is carried out after removing the acid catalyst by filtration.
Alternatively, it is carried out by neutralization by washing with water and then distillation.
【０００４】しかしながら、この方法により得られた不
飽和二量体は、初期には問題がないが、保存安定性が悪
く、保存中に着色するという問題がある。However, the unsaturated dimer obtained by this method has no problem at the beginning, but has poor storage stability and has a problem of coloring during storage.
【０００５】[0005]
【発明が解決しようとする課題】本発明はα−メチルス
チレン類から保存安定性に優れたα−メチルスチレン類
の不飽和二量体を生産性よく製造することができるα−
メチルスチレン類の不飽和二量体の製造法を提供するこ
とを目的とする。DISCLOSURE OF THE INVENTION The present invention relates to an α-methylstyrene which can produce an unsaturated dimer of an α-methylstyrene having excellent storage stability with good productivity.
An object of the present invention is to provide a method for producing an unsaturated dimer of methylstyrenes.
【０００６】[0006]
【課題を解決するための手段】本発明者らは前記目的を
達成するために鋭意研究を行った結果、反応液にアルカ
リを共存させｐＨを８以上にしてから蒸留精製すること
により、保存安定性に優れたα−メチルスチレン類の不
飽和二量体を生産性よく製造できることを見出し、この
知見に基づいて本発明を完成するに至った。Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above object. As a result, the reaction solution was made to coexist with an alkali and the pH was adjusted to 8 or higher, and then purified by distillation to obtain a stable solution. It has been found that unsaturated dimers of α-methylstyrenes having excellent properties can be produced with high productivity, and the present invention has been completed based on this finding.
【０００７】すなわち、本発明はα−メチルスチレン類
をスルホン酸化合物水溶液の存在下に反応させた後、触
媒であるスルホン酸化合物を除去し、反応液にアルカリ
を共存させｐＨを８以上にしてから蒸留精製することを
特徴とするα−メチルスチレン類の不飽和二量体の製造
法を提供するものである。That is, according to the present invention, after reacting α-methylstyrenes in the presence of an aqueous solution of a sulfonic acid compound, the sulfonic acid compound as a catalyst is removed, and the pH is adjusted to 8 or higher by coexisting an alkali in the reaction solution. And a process for producing an unsaturated dimer of α-methylstyrenes, characterized in that the dimer is purified by distillation.
【０００８】本発明の製造法は、α−メチルスチレン類
をスルホン酸化合物水溶液の存在下に反応させる反応段
階と、反応液からスルホン酸化合物を除去し、次いでア
ルカリ共存下で反応液を蒸留精製する精製段階の２段階
からなる。The production method of the present invention comprises a reaction step of reacting α-methylstyrenes in the presence of an aqueous solution of a sulfonic acid compound, a step of removing the sulfonic acid compound from the reaction solution, and then purifying the reaction solution by distillation in the presence of an alkali. Purification step.
【０００９】まず、本発明の製造法における反応段階に
ついて説明する。First, the reaction steps in the production method of the present invention will be described.
【００１０】α−メチルスチレン類の二量体としては、
α−メチルスチレンの二量体を例にとれば、１種の飽和
二量体、すなわち、１，１，３−トリメチル−３−フェ
ニルインダン（ＳＤ１）と２種の不飽和二量体、すなわ
ち、２，４−ジフェニル−４−メチル−１−ペンテン
（ＵＤ１）と２，４−ジフェニル−４−メチル−２−ペ
ンテン（ＵＤ２）があるが、本発明の方法によれば、α
−メチルスチレン（ＡＭＳ）から飽和二量体を実質的に
生成させずに、保存安定性に優れた不飽和二量体を選択
性よく製造することができる。特に不飽和二量体のう
ち、２，４−ジフェニル−４−メチル−１−ペンテンを
選択性よく製造することができる。例えば、１−ペンテ
ン体の割合を蒸留精製前であっても９０％以上とするこ
とが可能である。The dimers of α-methylstyrenes include:
Taking a dimer of α-methylstyrene as an example, one kind of saturated dimer, ie, 1,1,3-trimethyl-3-phenylindane (SD1) and two kinds of unsaturated dimer, ie, , 2,4-diphenyl-4-methyl-1-pentene (UD1) and 2,4-diphenyl-4-methyl-2-pentene (UD2). According to the method of the present invention, α
-An unsaturated dimer having excellent storage stability can be produced with high selectivity without substantially generating a saturated dimer from methylstyrene (AMS). In particular, among unsaturated dimers, 2,4-diphenyl-4-methyl-1-pentene can be produced with high selectivity. For example, the ratio of the 1-pentene compound can be 90% or more even before purification by distillation.
【００１１】本発明において用いられるα−メチルスチ
レン類としては、例えばα−メチルスチレン、ｍ−又は
ｐ−メチル−α−メチルスチレン、ｍ−又はｐ−エチル
−α−メチルスチレン、ｍ−又はｐ−イソプロピル−α
−メチルスチレン等が挙げられ、特にα−メチルスチレ
ンが好ましい。The α-methylstyrenes used in the present invention include, for example, α-methylstyrene, m- or p-methyl-α-methylstyrene, m- or p-ethyl-α-methylstyrene, m- or p-methylstyrene. -Isopropyl-α
-Methylstyrene and the like, and α-methylstyrene is particularly preferred.
【００１２】本発明において触媒として用いられるスル
ホン酸化合物水溶液としては、例えばトルエンスルホン
酸、フェノールスルホン酸、メタンスルホン酸、エタン
スルホン酸、ベンゼンスルホン酸、ナフタリン−α−ス
ルホン酸、ナフタリン−β−スルホン酸等のスルホン酸
化合物の水溶液が用いられ、特にｐ−トルエンスルホン
酸の水溶液が好ましい。The aqueous solution of a sulfonic acid compound used as a catalyst in the present invention includes, for example, toluenesulfonic acid, phenolsulfonic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, naphthalene-α-sulfonic acid, naphthalene-β-sulfone. An aqueous solution of a sulfonic acid compound such as an acid is used, and an aqueous solution of p-toluenesulfonic acid is particularly preferable.
【００１３】α−メチルスチレン類とスルホン酸化合物
水溶液の重量比は特に限定されないが、好ましくは２
０：８０〜９９：１とする。α−メチルスチレン類とス
ルホン酸化合物水溶液の重量比が５０：５０〜９５：５
の範囲内にある場合には、反応系の状態がα−メチルス
チレン類の連続相中にスルホン酸化合物水溶液が分散し
ている状態となり、α−メチルスチレン類の不飽和二量
体への選択率が向上する。α−メチルスチレン類の量が
上記範囲より少なくなると反応系の状態がスルホン酸化
合物水溶液の連続相中にα−メチルスチレン類の分散相
が分散している状態となり、α−メチルスチレン類の不
飽和二量体への選択率が低下し、スルホン酸化合物水溶
液の量が上記範囲より少なくなると反応時間が長くな
る。α−メチルスチレン類とスルホン酸化合物水溶液と
の重量比の好ましい範囲は６０：４０〜８５：１５であ
る。The weight ratio of the α-methylstyrene to the aqueous solution of the sulfonic acid compound is not particularly limited, but is preferably 2%.
0:80 to 99: 1. The weight ratio between the α-methylstyrenes and the aqueous sulfonic acid compound solution is 50:50 to 95: 5.
In the case of being within the range, the state of the reaction system becomes a state in which the aqueous solution of the sulfonic acid compound is dispersed in the continuous phase of α-methylstyrene, and the selection of the unsaturated dimer of α-methylstyrene is performed. The rate is improved. If the amount of α-methylstyrene is less than the above range, the state of the reaction system is such that the dispersed phase of α-methylstyrene is dispersed in the continuous phase of the aqueous sulfonic acid compound solution, and When the selectivity to the saturated dimer decreases and the amount of the sulfonic acid compound aqueous solution is less than the above range, the reaction time increases. The preferred range of the weight ratio between the α-methylstyrenes and the aqueous sulfonic acid compound solution is 60:40 to 85:15.
【００１４】また、上記スルホン酸化合物水溶液中のス
ルホン酸化合物の濃度は、好ましくは３０〜７０重量％
とする。スルホン酸化合物の濃度が３０重量％未満では
反応時間が長くなり、濃度が７０重量％を超えるとスル
ホン酸化合物が水に溶けにくくなり、反応系中に析出す
ることがある。The concentration of the sulfonic acid compound in the aqueous sulfonic acid compound solution is preferably 30 to 70% by weight.
And If the concentration of the sulfonic acid compound is less than 30% by weight, the reaction time will be prolonged. If the concentration exceeds 70% by weight, the sulfonic acid compound will be less soluble in water and may precipitate in the reaction system.
【００１５】反応温度は、好ましくは４０〜９０℃とす
る。４０℃未満では反応が進みにくくなることがあり、
９０℃を超えると選択率が低下することがある。反応時
間は０．５〜２４時間とすることが好ましい。反応圧力
は常圧又は加圧条件下で好適に行われる。[0015] The reaction temperature is preferably 40 to 90 ° C. If the temperature is lower than 40 ° C., the reaction may be difficult to proceed,
If it exceeds 90 ° C., the selectivity may decrease. The reaction time is preferably set to 0.5 to 24 hours. The reaction pressure is suitably performed under normal pressure or under pressurized conditions.
【００１６】α−メチルスチレンとスルホン酸化合物水
溶液との攪拌は、十分に行うことが好ましい。α−メチ
ルスチレンとスルホン酸化合物水溶液の重量比が５０：
５０〜９５：５の範囲内にある場合には、十分な攪拌に
よって、α−メチルスチレンの連続相中にスルホン酸化
合物水溶液相が分散した状態で反応が進み、１−ペンテ
ン体の選択率が向上する。It is preferable that the stirring of the α-methylstyrene and the aqueous solution of the sulfonic acid compound is sufficiently performed. The weight ratio of α-methylstyrene to the aqueous solution of the sulfonic acid compound is 50:
When the ratio is in the range of 50 to 95: 5, the reaction proceeds in a state where the aqueous solution of the sulfonic acid compound is dispersed in the continuous phase of α-methylstyrene by sufficient stirring, and the selectivity of the 1-pentene compound is lowered improves.
【００１７】次に、上記反応段階に続く精製段階につい
て説明する。Next, the purification step following the above reaction step will be described.
【００１８】精製段階におけるスルホン酸化合物の除去
は、例えば、上記反応段階で得られた反応液を室温に冷
却した後、静置して分液させ、上層の反応液（油層）を
取り出す方法によって好適に行われる。次いで得られた
上層の反応液（油層）にアルカリを加えてｐＨを８以
上、好ましくは９〜１１として蒸留精製を行うことによ
り保存安定性に優れたα−メチルスチレンの不飽和二量
体精製物が得られる。ｐＨが８未満で蒸留を行うと保存
安定性に劣るα−メチルスチレン類の不飽和二量体が得
られる。The removal of the sulfonic acid compound in the purification step is carried out, for example, by cooling the reaction solution obtained in the above reaction step to room temperature, allowing it to stand still and separating it, and taking out the upper reaction solution (oil layer). It is preferably performed. Then, an alkali is added to the obtained upper layer reaction solution (oil layer) to adjust the pH to 8 or more, preferably 9 to 11, to carry out distillation purification, thereby purifying unsaturated dimer of α-methylstyrene having excellent storage stability. Things are obtained. When distillation is performed at a pH of less than 8, unsaturated dimers of α-methylstyrenes having poor storage stability can be obtained.
【００１９】触媒としてスルホン酸化合物を用いた場
合、水洗、中和などで反応液をｐＨ７の中性にすれば、
蒸留時にα−メチルスチレン類の不飽和二量体が分解や
異性化することはない。しかしｐＨ８未満で蒸留した場
合は、得られる精製物の保存安定性が劣る。これは、反
応液が見かけ上中性になった段階でも、微量の遊離スル
ホン酸が反応液中に残っているためと思われる。すなわ
ち、微量の遊離スルホン酸では蒸留中にα−メチルスチ
レン類の不飽和二量体の分解や異性化を引き起こすには
至らないものの、保存期間が長期にわたるに従い影響が
現れ、保存安定性を悪化させるものと思われる。反応液
をｐＨ８以上にすることによって初めて、反応液中の遊
離スルホン酸の量が保存安定性に影響すら及ぼさない程
の量にまで減少するものと思われる。但し、保存安定性
が悪化する直接の原因が、遊離スルホン酸が精製物中に
残存することにあるかどうかは明らかではない。すなわ
ち、保存安定性の悪化が、蒸留後の精製物にまで遊離ス
ルホン酸が残っているために起こるものなのかというこ
とに関しては明らかではない。When a sulfonic acid compound is used as a catalyst, if the reaction solution is neutralized to pH 7 by washing with water, neutralizing, or the like,
During the distillation, the unsaturated dimer of α-methylstyrenes does not decompose or isomerize. However, when the distillation is performed at a pH lower than 8, the storage stability of the obtained purified product is poor. This is probably because a small amount of free sulfonic acid remained in the reaction solution even when the reaction solution became apparently neutral. In other words, a trace amount of free sulfonic acid does not cause decomposition or isomerization of the unsaturated dimer of α-methylstyrenes during distillation, but the effect appears as the storage period becomes longer and the storage stability deteriorates. It seems to cause. It is thought that the amount of free sulfonic acid in the reaction solution is reduced to an amount that does not affect the storage stability even when the reaction solution is adjusted to pH 8 or higher. However, it is not clear whether the direct cause of the deterioration of storage stability is that the free sulfonic acid remains in the purified product. That is, it is not clear whether the storage stability is deteriorated because free sulfonic acid remains even in the purified product after distillation.
【００２０】この精製段階で行われる蒸留法は特に制限
はないが、好ましくは減圧蒸留により行われる。特に条
件に制限はないが、減圧度５〜５０ｍｍＨｇ、温度１２
０〜２３０℃で行うことが好ましい。The distillation method performed in this purification step is not particularly limited, but is preferably performed by distillation under reduced pressure. The conditions are not particularly limited, but the degree of pressure reduction is 5 to 50 mmHg and the temperature is 12
It is preferably performed at 0 to 230 ° C.
【００２１】アルカリとしては、Ｋ2ＣＯ3、Ｎａ2Ｃ
Ｏ3、Ｋ3ＰＯ4、Ｎａ3ＰＯ4などのように弱酸と強塩基
の組み合わせからなる塩が好ましく用いられる。特に、
Ｋ2ＣＯ3が好ましく用いられる。As the alkali, K 2 CO 3 , Na 2 C
Salts composed of a combination of a weak acid and a strong base, such as O 3 , K 3 PO 4 , and Na 3 PO 4, are preferably used. In particular,
K 2 CO 3 is preferably used.
【００２２】[0022]
【実施例】以下、本発明を実施例に基づいて詳細に説明
するが、本発明はこれに限定されるものではない。The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples.
【００２３】実施例１ α−メチルスチレン（ＡＭＳ）８０．０ｇに、ｐ−トル
エンスルホン酸（ＰＴＳ）一水和物１２．０ｇを水８．
０ｇに溶解して調製したｐ−トルエンスルホン酸一水和
物の６０重量％水溶液２０．０ｇを加え、攪拌羽根で約
３００ｒｐｍでよくかきまぜながら７０℃まで昇温し
た。このときＰＴＳ一水和物水溶液／ＡＭＳ（重量比）
は２０／８０であり、反応系はＡＭＳ連続相中にＰＴＳ
水溶液分散相が分散された状態であることが観察され
た。次いで、そのまま７０℃で１４時間攪拌を続けてα
−メチルスチレンの転換率が９０％になるまで反応を進
めた。Example 1 12.0 g of p-toluenesulfonic acid (PTS) monohydrate was added to 80.0 g of α-methylstyrene (AMS) and 80.0 g of water.
Then, 20.0 g of a 60% by weight aqueous solution of p-toluenesulfonic acid monohydrate prepared by dissolving in 0 g was added, and the temperature was raised to 70 ° C. while stirring well at about 300 rpm with a stirring blade. At this time, PTS monohydrate aqueous solution / AMS (weight ratio)
Is 20/80, and the reaction system is PTS in the AMS continuous phase.
It was observed that the aqueous dispersion phase was in a dispersed state. Then, stirring was continued for 14 hours at 70 ° C.
The reaction proceeded until the conversion of methylstyrene was 90%.
【００２４】上記で得られた反応液を室温に冷却した
後、静置し分液を行い、分液した上層の反応液（油層）
を取り出した。この反応液（油層）１００ｇに対して２
５％Ｋ2ＣＯ3水溶液０．２８ｇを加え中和し、反応液の
ｐＨを１１とした。これを直接減圧蒸留（減圧度７ｍｍ
Ｈｇ、温度１２０〜２２０℃）してα−メチルスチレン
の不飽和二量体精製品を得た。精製品中にはＡＭＳモノ
マーや飽和二量体は含まれておらず、不飽和二量体への
選択率は１００％であり、そのうち２，４−ジフェニル
−４−メチル−１−ペンテンへの選択率は９７％と優れ
たものであった。得られた精製品の保存安定性の評価結
果を表１に示す。After the reaction solution obtained above is cooled to room temperature, it is allowed to stand still to perform liquid separation, and the separated upper layer reaction solution (oil layer)
Was taken out. 100 g of this reaction solution (oil layer)
The reaction solution was neutralized by adding 0.28 g of a 5% K 2 CO 3 aqueous solution to adjust the pH of the reaction solution to 11. This is directly distilled under reduced pressure (decompression degree 7 mm
Hg, temperature: 120 to 220 ° C.) to obtain a purified unsaturated dimer of α-methylstyrene. The purified product does not contain AMS monomer or saturated dimer, and the selectivity to unsaturated dimer is 100%, of which 2,4-diphenyl-4-methyl-1-pentene The selectivity was as excellent as 97%. Table 1 shows the results of evaluating the storage stability of the obtained purified product.
【００２５】実施例２、３及び比較例１、２ 実施例１において、加えるアルカリを変えて蒸留時のｐ
Ｈを表１に示すように変え、実施例１と同様に反応を行
なった。得られた精製品の保存安定性の評価結果を表１
に示す。反応液のｐＨを本発明の範囲内にして蒸留精製
を行った場合には、保存安定性に優れた不飽和二量体が
得られている。Examples 2 and 3 and Comparative Examples 1 and 2 In Example 1, the alkali added was changed and the p during distillation was changed.
The reaction was carried out in the same manner as in Example 1 except that H was changed as shown in Table 1. Table 1 shows the evaluation results of the storage stability of the obtained purified products.
Shown in When distillation purification was performed with the pH of the reaction solution within the range of the present invention, an unsaturated dimer having excellent storage stability was obtained.
【００２６】[0026]
【表１】 [Table 1]
【００２７】保存安定性の評価は、サンプルを６０℃の
雰囲気下に放置し、色相をＡＳＴＭＤ−１２０９に準拠
して測定することにより行った。The storage stability was evaluated by leaving the sample in an atmosphere at 60 ° C. and measuring the hue according to ASTM D-1209.
【００２８】[0028]
【発明の効果】本発明により、α−メチルスチレン類か
ら保存安定性に優れたα−メチルスチレン類の不飽和二
量体を選択率よく、生産性良く製造することが可能とな
った。According to the present invention, it has become possible to produce an unsaturated dimer of α-methylstyrene having excellent storage stability from α-methylstyrene with good selectivity and high productivity.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 西澤 ▲広▼ 千葉県市原市五井南海岸14番地 五井化 成株式会社 (56)参考文献 特開 平３−203995（ＪＰ，Ａ) 特開 昭52−36651（ＪＰ，Ａ) 特開 平３−258733（ＪＰ，Ａ) 特公 昭41−6335（ＪＰ，Ｂ１) (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 15/50 C07C 7/04 C07C 2/26──────────────────────────────────────────────────続 き Continuation of front page (72) Inventor Nishizawa ▲ Hiro ▼ Goi Kasei Co., Ltd., 14 Goi South Coast, Ichihara City, Chiba Prefecture (56) References JP-A-3-203995 (JP, A) JP-A Sho 52 -36651 (JP, A) JP-A-3-258733 (JP, A) JP-B-41-6335 (JP, B1) (58) Fields investigated (Int. Cl. 6 , DB name) C07C 15/50 C07C 7/04 C07C 2/26
Claims (4)
物水溶液の存在下に反応させた後、触媒であるスルホン
酸化合物を除去し、反応液にアルカリを共存させｐＨを
８以上にしてから蒸留精製することを特徴とするα−メ
チルスチレン類の不飽和二量体の製造法。1. After reacting α-methylstyrenes in the presence of an aqueous solution of a sulfonic acid compound, the sulfonic acid compound as a catalyst is removed, and the reaction solution is coexisted with an alkali to adjust the pH to 8 or more, followed by distillation and purification. A process for producing an unsaturated dimer of α-methylstyrenes.
レンである請求項１記載のα−メチルスチレン類の不飽
和二量体の製造法。2. The process for producing an unsaturated dimer of α-methylstyrene according to claim 1, wherein the α-methylstyrene is α-methylstyrene.
らなる塩である請求項１又は２記載のα−メチルスチレ
ン類の不飽和二量体の製造法。3. The method for producing an unsaturated dimer of α-methylstyrenes according to claim 1, wherein the alkali is a salt comprising a combination of a weak acid and a strong base.
又は３記載のα−メチルスチレン類の不飽和二量体の製
造法。4. The method according to claim 1, wherein the alkali is K 2 CO 3.
Or a method for producing an unsaturated dimer of α-methylstyrenes according to 3 above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6023097A JP2849324B2 (en) | 1994-01-25 | 1994-01-25 | Method for producing unsaturated dimer of α-methylstyrenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6023097A JP2849324B2 (en) | 1994-01-25 | 1994-01-25 | Method for producing unsaturated dimer of α-methylstyrenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08176028A JPH08176028A (en) | 1996-07-09 |
| JP2849324B2 true JP2849324B2 (en) | 1999-01-20 |
Family
ID=12100953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6023097A Expired - Fee Related JP2849324B2 (en) | 1994-01-25 | 1994-01-25 | Method for producing unsaturated dimer of α-methylstyrenes |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2849324B2 (en) |
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1994
- 1994-01-25 JP JP6023097A patent/JP2849324B2/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| JPH08176028A (en) | 1996-07-09 |
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