JPH06247882A - P-divinylbenzene composition - Google Patents
P-divinylbenzene compositionInfo
- Publication number
- JPH06247882A JPH06247882A JP6134093A JP6134093A JPH06247882A JP H06247882 A JPH06247882 A JP H06247882A JP 6134093 A JP6134093 A JP 6134093A JP 6134093 A JP6134093 A JP 6134093A JP H06247882 A JPH06247882 A JP H06247882A
- Authority
- JP
- Japan
- Prior art keywords
- divinylbenzene
- paradivinylbenzene
- organic solvent
- composition
- polymerization inhibitor
- 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.)
- Withdrawn
Links
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 5
- 238000002425 crystallisation Methods 0.000 claims abstract description 5
- 230000008025 crystallization Effects 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 238000000746 purification Methods 0.000 claims abstract description 5
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 238000013329 compounding Methods 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- DSNHSQKRULAAEI-UHFFFAOYSA-N 1,4-Diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1 DSNHSQKRULAAEI-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- -1 methanol and ethanol Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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】本発明はパラジビニルベンゼン組
成物に係り、詳しくは安定性が優れ、使用に便利なパラ
ジビニルベンゼン組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a paradivinylbenzene composition, and more particularly to a paradivinylbenzene composition which has excellent stability and is convenient to use.
【０００２】[0002]
【従来の技術】パラジビニルベンゼンは二重結合を２つ
有しているため各種樹脂の架橋剤として有用であり、イ
オン交換樹脂等の他、各種樹脂の改質原料として使用さ
れている。そして、より機能的に使用するため高純度品
が望まれている。パラジビニルベンゼンはパラジエチル
ベンゼンを脱水素することにより製造できる（特開昭６
２−４５５４２号公報）。しかし、パラジビニルベンゼ
ンは反応性が高く、重合してポリマーとなりやすいた
め、高濃度のパラジビニルベンゼンを回収したとしても
保存安定性が悪く、使用するまでに長時間を要する場合
には、高純度品としての優位性が小さい。更に、高濃度
のパラジビニルベンゼンは融点が３１℃前後と高く、重
合防止剤等の配合が困難であるだけでなく、効果も小さ
い。BACKGROUND OF THE INVENTION Paradivinylbenzene is useful as a cross-linking agent for various resins because it has two double bonds, and is used as a raw material for modifying various resins in addition to ion exchange resins and the like. A high-purity product is desired for more functional use. Paradivinylbenzene can be produced by dehydrogenating paradiethylbenzene (Japanese Patent Laid-Open No. Sho 6-62)
2-45542). However, since paradivinylbenzene is highly reactive and tends to polymerize to form a polymer, storage stability is poor even if high concentration paradivinylbenzene is recovered, and when it takes a long time to use it, it is highly purified. Little advantage as a product. Furthermore, high-concentration paradivinylbenzene has a high melting point of around 31 ° C., which makes it difficult to compound a polymerization inhibitor and the like and has a small effect.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、安定
性が優れ、且つ使用性の優れたパラジビニルベンゼン組
成物を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a paradivinylbenzene composition having excellent stability and usability.
【０００４】[0004]
【課題を解決するための手段】本発明者は、上記のよう
な課題を解決するため、パラジビニルベンゼンに、特定
の有機溶媒を添加すれば、パラジビニルベンゼンの保存
中又は輸送中の重合を抑制でき、しかも用途に応じて容
易に使用可能な状態にしうるとの知見のもとに研究を行
い、本発明を完成した。すなわち、本発明は、ジエチル
ベンゼンを脱水素して得られた反応混合物を、蒸留及び
／又は晶析を含む精製処理して得られたパラジビニルベ
ンゼン含有量が８０ｗｔ％以上のジビニルベンゼン１０
０重量部に対して、１０〜７０重量部の常温液体の酸ア
ミド類及びアルカノ−ル類から選ばれる有機溶媒、並び
に重合防止剤を配合してなるパラジビニルベンゼン組成
物である。In order to solve the above-mentioned problems, the present inventor has proposed that when a specific organic solvent is added to paradivinylbenzene, the polymerization of paradivinylbenzene during storage or transportation can be performed. The present invention has been completed by conducting research based on the finding that it can be suppressed and can be easily used depending on the application. That is, according to the present invention, the reaction mixture obtained by dehydrogenating diethylbenzene is subjected to a purification treatment including distillation and / or crystallization to obtain divinylbenzene 10 having a paradivinylbenzene content of 80 wt% or more.
A paradivinylbenzene composition comprising 10 to 70 parts by weight of an organic solvent selected from acid amides and alkanols at room temperature, and a polymerization inhibitor, relative to 0 parts by weight.
【０００５】パラジビニルベンゼン含有量が８０重量％
以上のジビニルベンゼンは、パラ異性体含有量が高いジ
エチルベンゼンを脱水素して、蒸留及び／又は晶析を含
む精製処理することにより得られ、このような精製処理
は公知である。Paradivinylbenzene content of 80% by weight
The above-mentioned divinylbenzene is obtained by dehydrogenating diethylbenzene having a high content of para isomers and subjecting it to a purification treatment including distillation and / or crystallization, and such a purification treatment is known.
【０００６】本発明でジビニルベンゼンに配合する有機
溶媒は、常温液体の酸アミド類及びアルカノ−ル類から
選ばれる有機溶媒である。酸アミド類としては、ホルム
アミド、ホルムエチルアミド、ホルムジメチルアミド、
アセトジメチルアミド、アセトエチルアミド、アセトジ
エチルアミド等が挙げられる。これらは、１種であって
も２種以上の混合物であってもよい。The organic solvent blended with divinylbenzene in the present invention is an organic solvent selected from acid amides and alkanols which are liquid at room temperature. The acid amides include formamide, formethylamide, formdimethylamide,
Acetodimethylamide, acetoethylamide, acetodiethylamide and the like can be mentioned. These may be one kind or a mixture of two or more kinds.
【０００７】アルカノ−ル類としては、メタノ−ル、エ
タノ−ル等の低級アルコ−ルやヘキサノ−ル、オクタノ
−ル等の高級アルコ−ルが挙げられるが、炭素数６〜８
の高級アルコ−ルが好ましい。これらは非重合性のもの
が好ましく、非重合性であれば、常温液体であるため、
使用に当たってこれを配合したまま使用しても重合等を
行っても重合反応等に不都合を及ぼすことはない。ま
た、重合反応等を行ったのち、これを分離することも可
能である。更に、有機溶媒としてジビニルベンゼンに比
較して低沸点の溶媒や低凝固点の有機溶媒を選択すれ
ば、蒸留、晶析等の手段により容易に分離でき、高濃度
のジビニルベンゼンとすることが容易である。また、こ
のようにして分離された有機溶媒は、必要により再使用
することができる。Examples of the alkanols include lower alcohols such as methanol and ethanol, and higher alcohols such as hexanole and octanole, which have 6 to 8 carbon atoms.
The higher alcohols are preferred. These are preferably non-polymerizable, and if non-polymerizable, they are liquids at room temperature,
In use, even if it is used as it is blended or polymerized, it does not adversely affect the polymerization reaction. It is also possible to separate this after carrying out a polymerization reaction and the like. Furthermore, if a solvent having a lower boiling point than that of divinylbenzene or an organic solvent having a low freezing point is selected as the organic solvent, it can be easily separated by means such as distillation or crystallization, and a high concentration of divinylbenzene can be easily obtained. is there. The organic solvent thus separated can be reused if necessary.
【０００８】これらの有機溶媒に共通することは、ジビ
ニルベンゼンと相溶性がよく、ジビニルベンゼンの重合
を防止する効果が有することである。有機溶媒の使用量
は、ジビニルベンゼン１００重量部に対して１０〜７０
重量部、好ましくは３０〜５０重量部である。有機溶媒
の使用量が少ないと実用に耐える重合防止効果を奏する
ことができない。一方、多過ぎると分離する際の効率が
悪く、また、容積が大きくなるので保存効率も悪くなる
のに対して、重合防止効果はさほど増進しない。Common to these organic solvents is that they are compatible with divinylbenzene and have the effect of preventing the polymerization of divinylbenzene. The amount of the organic solvent used is 10 to 70 with respect to 100 parts by weight of divinylbenzene.
Parts by weight, preferably 30 to 50 parts by weight. If the amount of the organic solvent used is small, it is not possible to obtain a polymerization-preventing effect that is practical. On the other hand, if the amount is too large, the separation efficiency is poor and the storage efficiency is poor because the volume is large.
【０００９】上記有機溶媒を配合するだけでも、重合防
止効果はあるが、使用するまでの期間がある場合は、よ
り重合防止効果が高いことが望まれる。したがって、本
発明では、更に重合防止剤を配合する。好適には、重合
防止剤としてｔ−ブチルカテコールを配合する。有機溶
媒と重合防止剤とを併用すると、それぞれを単独で配合
したときの重合防止効果の和より更に大きな効果が得ら
れる。重合防止剤の使用量は、重合防止剤や溶媒の種類
にもよるが一般に５００〜５０００ｐｐｍ程度が効果的
である。Even if only the above-mentioned organic solvent is added, the polymerization inhibitory effect can be obtained. However, when there is a period before use, it is desired that the polymerization inhibitory effect is higher. Therefore, in the present invention, a polymerization inhibitor is further added. Suitably, t-butyl catechol is blended as a polymerization inhibitor. When the organic solvent and the polymerization inhibitor are used in combination, a larger effect can be obtained than the sum of the polymerization prevention effects when they are individually blended. Although the amount of the polymerization inhibitor used depends on the type of the polymerization inhibitor and the solvent, generally about 500 to 5000 ppm is effective.
【００１０】[0010]
実施例〜３、比較例１〜４ パラ異性体含有量が９７重量％のジエチルベンゼンを脱
水素し、得られた脱水素油を蒸留及び晶析してパラ異性
体含有量９７重量％で、濃度９９重量％のジビニルベン
ゼンを回収した。得られたパラジビニルベンゼンに対し
て表１に示す有機溶媒及びｔ−ブチルカテコール（ＴＢ
Ｃ）を配合し、均一に混合したのち、２０℃に保たれた
室内に放置し、ポリマーの生成量を測定した。有機溶媒
の種類、ジビニルベンゼン１００重量部に対する有機溶
媒及びＴＢＣの配合量並びに一定時間経過後のポリマー
の生成量を表１に示す。Examples 3 to 3, Comparative Examples 1 to 4 Diethylbenzene having a para isomer content of 97 wt% was dehydrogenated, and the resulting dehydrogenated oil was distilled and crystallized to give a para isomer content of 97 wt% and a concentration of 99. Weight percent divinylbenzene was recovered. With respect to the obtained paradivinylbenzene, the organic solvents and t-butylcatechol (TB
C) was blended and uniformly mixed, and then left in a room kept at 20 ° C. to measure the amount of polymer produced. Table 1 shows the kinds of the organic solvent, the blending amounts of the organic solvent and TBC with respect to 100 parts by weight of divinylbenzene, and the production amount of the polymer after a certain period of time.
【００１１】[0011]
【表１】 注）DMA はジメチルアセトアミド、2EH は2-エチルヘキ
サノ−ル、Sty はスチレン、Tol はトルエンを示し、Ge
l は、ゲル化を示す。[Table 1] Note) DMA is dimethylacetamide, 2EH is 2-ethylhexanol, Sty is styrene, Tol is toluene, Ge
l indicates gelation.
【００１２】[0012]
【発明の効果】本発明のパラジビニルベンゼン組成物
は、安定性が優れるので長期間の保存、輸送に耐えるこ
とができる。また、容易に高純度のパラジビニルベンゼ
ンとすることができるので、使いやすさの点でも優れ
る。INDUSTRIAL APPLICABILITY The paradivinylbenzene composition of the present invention has excellent stability and can withstand long-term storage and transportation. In addition, since it can be easily made into highly pure paradivinylbenzene, it is also excellent in ease of use.
Claims (2)
反応混合物を、蒸留及び／又は晶析を含む精製処理して
得られたパラジビニルベンゼン含有量が８０ｗｔ％以上
のジビニルベンゼン１００重量部に対して、１０〜７０
重量部の常温液体の酸アミド類及びアルカノ−ル類から
選ばれる有機溶媒、並びに重合防止剤を配合してなるパ
ラジビニルベンゼン組成物。1. A reaction mixture obtained by dehydrogenating diethylbenzene is subjected to a purification treatment including distillation and / or crystallization to obtain 100 parts by weight of divinylbenzene having a paradivinylbenzene content of 80 wt% or more. 10-70
A paradivinylbenzene composition obtained by blending parts by weight of an organic solvent selected from acid amides and alkanols that are liquid at room temperature, and a polymerization inhibitor.
る請求項１記載のパラジビニルベンゼン組成物。2. The paradivinylbenzene composition according to claim 1, wherein the polymerization inhibitor is t-butylcatechol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6134093A JPH06247882A (en) | 1993-02-26 | 1993-02-26 | P-divinylbenzene composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6134093A JPH06247882A (en) | 1993-02-26 | 1993-02-26 | P-divinylbenzene composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06247882A true JPH06247882A (en) | 1994-09-06 |
Family
ID=13168308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6134093A Withdrawn JPH06247882A (en) | 1993-02-26 | 1993-02-26 | P-divinylbenzene composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06247882A (en) |
-
1993
- 1993-02-26 JP JP6134093A patent/JPH06247882A/en not_active Withdrawn
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Withdrawal of application because of no request for examination |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20000509 |