JPH08310979A - Purification of vinyl monomer - Google Patents
Purification of vinyl monomerInfo
- Publication number
- JPH08310979A JPH08310979A JP14536395A JP14536395A JPH08310979A JP H08310979 A JPH08310979 A JP H08310979A JP 14536395 A JP14536395 A JP 14536395A JP 14536395 A JP14536395 A JP 14536395A JP H08310979 A JPH08310979 A JP H08310979A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- vinyl
- adsorbent
- vinyl monomer
- 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- Withdrawn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
- 239000000178 monomer Substances 0.000 title abstract description 51
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title abstract description 27
- 229920002554 vinyl polymer Polymers 0.000 title abstract description 27
- 238000000746 purification Methods 0.000 title description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 25
- 239000003112 inhibitor Substances 0.000 abstract description 21
- 239000003463 adsorbent Substances 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 10
- 229920000642 polymer Polymers 0.000 abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000741 silica gel Substances 0.000 abstract description 5
- 229910002027 silica gel Inorganic materials 0.000 abstract description 5
- 238000001179 sorption measurement Methods 0.000 abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002808 molecular sieve Substances 0.000 abstract description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract description 4
- 238000002834 transmittance Methods 0.000 abstract description 4
- 229910021536 Zeolite Inorganic materials 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 239000004927 clay Substances 0.000 abstract description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003456 ion exchange resin Substances 0.000 abstract description 3
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 3
- 239000010457 zeolite Substances 0.000 abstract description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000013522 chelant Substances 0.000 abstract description 2
- 239000011162 core material Substances 0.000 abstract description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000012856 packing Methods 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 238000007654 immersion Methods 0.000 abstract 1
- 238000005470 impregnation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical class [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ビニル系モノマー、特
にアクリル系などのモノマー中に含まれている重合禁止
剤を除去してビニル系モノマーを精製する方法に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for purifying a vinyl-based monomer by removing a polymerization inhibitor contained in a vinyl-based monomer, particularly an acrylic-based monomer.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】ビニル
系モノマー、特に市販アクリル系モノマー中には保存中
の重合を防止するため、ハイドロキノン、アルキル置換
フェノール等の重合禁止剤が通常３０〜２００ｐｐｍ程
度の多量含まれている。このような重合禁止剤が含まれ
たアクリル系モノマーは、これを重合して透明ポリマー
を得ようとする場合、重合禁止剤により着色し、可視光
を吸収するためポリマーの光透過性が低下する。このた
め、モノマー中の重合禁止剤を除去し、精製したモノマ
ーを用いて重合を行うことが望まれる。BACKGROUND OF THE INVENTION In order to prevent polymerization during storage in vinyl monomers, especially commercial acrylic monomers, polymerization inhibitors such as hydroquinone and alkyl-substituted phenols are usually used in an amount of about 30 to 200 ppm. It contains a large amount of. When an acrylic monomer containing such a polymerization inhibitor is polymerized to obtain a transparent polymer, it is colored by the polymerization inhibitor and absorbs visible light, so that the light transmittance of the polymer decreases. . Therefore, it is desired to remove the polymerization inhibitor from the monomer and carry out the polymerization using the purified monomer.
【０００３】このようなモノマーの精製法としては、蒸
留法、アルカリ抽出法等があるが、蒸留法は低沸点のア
クリル系モノマーには有効であるものの、高沸点モノマ
ーの場合は重合禁止剤が一緒に留出して精製物の純度を
悪くしたり、あるいはアクリル系モノマーが留出せず、
蒸留不可能になる。また、蒸留温度が高くなると、蒸留
中に重合が始まり、危険である。一方、アルカリ抽出法
は、精製効果が劣り、高純度のモノマーを得難いという
問題がある。As a method for purifying such a monomer, there are a distillation method, an alkali extraction method and the like. Although the distillation method is effective for a low boiling point acrylic monomer, a polymerization inhibitor is used for a high boiling point monomer. Distilled together to deteriorate the purity of the purified product, or acrylic monomer does not distill,
It cannot be distilled. Further, if the distillation temperature becomes high, polymerization will start during the distillation, which is dangerous. On the other hand, the alkali extraction method has a problem that the purification effect is poor and it is difficult to obtain a high-purity monomer.
【０００４】本発明は上記事情に鑑みなされたもので、
ビニル系モノマー中の重合禁止剤を容易かつ確実に除去
し得るビニル系モノマーの精製法を提供することを目的
とする。The present invention has been made in view of the above circumstances.
It is an object of the present invention to provide a method for purifying a vinyl-based monomer capable of easily and surely removing a polymerization inhibitor in the vinyl-based monomer.
【０００５】[0005]
【課題を解決するための手段及び作用】本発明者は、上
記目的を達成するため鋭意検討を行った結果、アクリル
系モノマー等のビニル系モノマーをアルミナ、シリカゲ
ル、モレキュラーシーブ、活性炭、イオン交換樹脂、キ
レート樹脂、ゼオライト、酸性白土等の吸着剤で処理す
ることにより、ビニル系モノマー中のハイドロキノン、
アルキル置換フェノール等の重合禁止剤を効率よく除去
することができ、特に吸着剤としてアルミナ、シリカゲ
ルなどを用いた場合、重合禁止剤をより効果的に除去し
得ることを知見し、本発明をなすに至った。Means for Solving the Problems and Actions The inventors of the present invention have conducted extensive studies to achieve the above-mentioned object, and as a result, vinyl-based monomers such as acrylic-based monomers were changed to alumina, silica gel, molecular sieves, activated carbon, ion exchange resins. , Chelating resin, zeolite, hydroquinone in vinyl monomers by treatment with an adsorbent such as acid clay
It was found that the polymerization inhibitor such as an alkyl-substituted phenol can be efficiently removed, and particularly when alumina, silica gel or the like is used as the adsorbent, the polymerization inhibitor can be removed more effectively, and the present invention is made. Came to.
【０００６】従って、本発明は、重合禁止剤を含有する
ビニル系モノマーを吸着剤で処理して、上記ビニル系モ
ノマー中の重合禁止剤を吸着除去することを特徴とする
ビニル系モノマーの精製法を提供する。Therefore, according to the present invention, a method for purifying a vinyl monomer, which comprises treating a vinyl monomer containing a polymerization inhibitor with an adsorbent to adsorb and remove the polymerization inhibitor from the vinyl monomer. I will provide a.
【０００７】以下、本発明につき更に詳しく説明する
と、本発明のビニル系モノマーの精製法は、該モノマー
を吸着剤で処理して該モノマー中の重合禁止剤を除去す
るものである。The present invention will be described in more detail below. In the method for purifying a vinyl monomer of the present invention, the polymerization inhibitor in the monomer is removed by treating the monomer with an adsorbent.
【０００８】ここで、処理の対象となるビニル系モノマ
ーは、ハイドロキノン類、アルキル置換フェノール類等
の重合禁止剤が通常１ｐｐｍ以上含有されているもの
で、本発明は特にかかる重合禁止剤を多量に、即ち１０
ｐｐｍ以上、特に５０ｐｐｍ以上、とりわけ１００ｐｐ
ｍ以上含むアクリル系モノマー、あるいはスチレン系、
酢酸ビニル系、アクリロニトリル系、フッ化エチレン系
モノマーの処理に有効に採用される。なお、アクリル系
モノマーとしては、アクリル酸、メタクリル酸、これら
アクリル酸やメタクリル酸と炭素数１〜２０の一価アル
コールとのエステルなどに好適に用いられるが、とりわ
けアクリル酸又はメタクリル酸と炭素数８〜２０の一価
アルコールとの高沸点エステルの処理には特に好適であ
る。Here, the vinyl-based monomer to be treated usually contains 1 ppm or more of a polymerization inhibitor such as hydroquinones and alkyl-substituted phenols, and the present invention particularly uses such a polymerization inhibitor in a large amount. I.e. 10
ppm or more, especially 50 ppm or more, especially 100 pp
acrylic monomer containing m or more, or styrene,
It is effectively used for treating vinyl acetate, acrylonitrile, and fluorinated ethylene monomers. The acrylic monomer is preferably used as acrylic acid, methacrylic acid, esters of these acrylic acids or methacrylic acids with monohydric alcohols having 1 to 20 carbon atoms, and particularly acrylic acid or methacrylic acid and carbon numbers. It is particularly suitable for treating high boiling esters with 8-20 monohydric alcohols.
【０００９】上記ビニル系モノマーを処理する吸着剤と
しては、アルミナ、シリカゲル、モレキュラーシーブ、
活性炭、イオン交換樹脂、キレート樹脂、ゼオライト及
び酸性白土が好適であり、中でもアルミナ、シリカゲ
ル、活性炭、モレキュラーシーブスが重合禁止剤の除去
効果が最も高く、好ましく用いられる。As the adsorbent for treating the vinyl monomer, alumina, silica gel, molecular sieve,
Activated carbon, ion exchange resin, chelate resin, zeolite and acid clay are preferable, and among them, alumina, silica gel, activated carbon, and molecular sieves have the highest effect of removing the polymerization inhibitor and are preferably used.
【００１０】上記吸着剤の平均粒径は適宜選定される
が、５０〜５００メッシュ、特に１００〜３００メッシ
ュであることが好ましい。またこれらの細粒をある形状
に成型加工したものも用いることができる。The average particle size of the adsorbent is appropriately selected, but is preferably 50 to 500 mesh, particularly 100 to 300 mesh. Further, those obtained by molding and processing these fine particles into a certain shape can also be used.
【００１１】上記吸着剤を用いた吸着処理法としては、
ビニル系モノマーに吸着剤を含浸する浸漬法、吸着剤を
カラムに充填し、これにビニル系モノマーを通すカラム
吸着法などを採用することができる。この場合、ビニル
系モノマーはそのまま吸着剤で処理してもよく、また必
要に応じてヘキサン等の有機溶媒で希釈したり、有機溶
媒をキャリヤー液として用いることもできる。なお、処
理温度は０〜１５０℃とすることができ、モノマーの粘
度により適宜選択すればよいが、通常は室温で十分であ
る。As an adsorption treatment method using the above adsorbent,
A dipping method in which a vinyl-based monomer is impregnated with an adsorbent, a column adsorption method in which the adsorbent is packed in a column, and the vinyl-based monomer is passed through the column can be adopted. In this case, the vinyl-based monomer may be directly treated with an adsorbent, or may be diluted with an organic solvent such as hexane, or the organic solvent may be used as a carrier liquid, if necessary. The treatment temperature may be 0 to 150 ° C. and may be appropriately selected depending on the viscosity of the monomer, but room temperature is usually sufficient.
【００１２】このような処理により、ビニル系モノマー
中の重合禁止剤量はもとの量の５０％以下に低減し、こ
のように重合禁止剤量が低減した精製モノマーは、これ
を用いて透明ポリマーを重合した場合、ポリマーの着色
が可及的に減少し、光透過率が高いものであり、従って
このポリマーは光伝送チューブの、コア材として有効で
ある。なお、この精製モノマーを用いて重合する方法
は、公知の方法でよい。By such a treatment, the amount of the polymerization inhibitor in the vinyl-based monomer is reduced to 50% or less of the original amount, and the purified monomer having the reduced amount of the polymerization inhibitor is transparent by using the same. When the polymer is polymerized, the coloration of the polymer is reduced as much as possible and the light transmittance is high, and thus the polymer is effective as the core material of the light transmission tube. The method of polymerizing using this purified monomer may be a known method.
【００１３】[0013]
【実施例】以下、実施例と比較例を示し、本発明を具体
的に説明するが、本発明は下記の実施例に制限されるも
のではない。EXAMPLES The present invention will be described below in detail with reference to examples and comparative examples, but the present invention is not limited to the following examples.
【００１４】〔実施例〕内径３ｃｍで下部がくびれたガ
ラス管内に脱脂綿を詰め、この上に表１に示す吸着剤１
０ｇを充填し、更にその上に脱脂綿を詰めて吸着剤を使
用した。これに重合禁止剤としてメトキシハイドロキノ
ン（ＭＥＨＱ）１００ｐｐｍを含むアクリル系モノマー
ＳＬＭＡ（メタクリル酸と炭素数１２及び１３の脂肪族
一価アルコールとのエステル）１００ｇを通過させて処
理し、流出液中のＭＥＨＱの量を下記方法で測定した。
結果を表１に示す。ＭＥＨＱ測定方法 ２ｇのＳＬＭＡを３ｇの氷酢酸で溶解し、これに飽和亜
硝酸ナトリウム液０．５ｍｌを添加して呈色させ、４２
０ｎｍの吸収強度を測定した。この値をＭＥＨＱ含量既
知のデータ（検量線）と比較し、ＨＥＨＱ含量（ｐｐ
ｍ）を求めた。[Example] A glass tube having an inner diameter of 3 cm and a constricted lower part was filled with absorbent cotton, and the adsorbent 1 shown in Table 1 was placed thereon.
0 g was filled, and absorbent cotton was used by further packing absorbent cotton on it. 100 g of an acrylic monomer SLMA (ester of methacrylic acid and an aliphatic monohydric alcohol having a carbon number of 12 and 13) containing 100 ppm of methoxyhydroquinone (MEHQ) as a polymerization inhibitor was passed through this and treated to obtain MEHQ in the effluent. Was measured by the following method.
The results are shown in Table 1. MEHQ measurement method 2 g of SLMA was dissolved in 3 g of glacial acetic acid, and 0.5 ml of saturated sodium nitrite solution was added thereto to cause coloration.
The absorption intensity at 0 nm was measured. This value is compared with the MEHQ content known data (calibration curve), and the HEHQ content (pp
m) was calculated.
【００１５】次に上記流出液（精製モノマー）を直径６
ｍｍ、長さ５０ｃｍのＦＥＰ（四フッ化エチレン−六フ
ッ化プロピレン共重合体）チューブに入れ、重合開始剤
としてベンゾイルパーオキサイドをアクリルモノマー１
００重量部に対して０．５重量部使用して７０℃で３時
間重合した後、得られた重合物の４２０ｎｍの透過率を
測定した。結果を表１に併記する。Next, the effluent (purified monomer) was treated with a diameter of 6
mm, length 50 cm FEP (tetrafluoroethylene-hexafluoropropylene copolymer) tube, benzoyl peroxide as a polymerization initiator acrylic monomer 1
After using 0.5 part by weight with respect to 00 parts by weight for polymerization for 3 hours at 70 ° C., the transmittance of the obtained polymer at 420 nm was measured. The results are also shown in Table 1.
【００１６】[0016]
【表１】 [Table 1]
【００１７】[0017]
【発明の効果】本発明のビニル系モノマーの精製法によ
れば、ビニル系モノマー中の重合禁止剤を効率よく容易
かつ確実に除去してビニル系モノマーを精製することが
できる。According to the method for purifying a vinyl-based monomer of the present invention, the vinyl-based monomer can be purified by efficiently and easily and surely removing the polymerization inhibitor in the vinyl-based monomer.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 69/15 Ｃ０７Ｃ 69/15 69/54 9546−4Ｈ 69/54 Ｚ 253/34 253/34 255/08 255/08 Ｃ０８Ｆ 2/00 ＭＡＤ Ｃ０８Ｆ 2/00 ＭＡＤ // Ｂ０１Ｊ 20/08 Ｂ０１Ｊ 20/08 Ａ 20/10 20/10 Ｄ 20/18 20/18 Ｂ 20/20 20/20 Ｂ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical display location C07C 69/15 C07C 69/15 69/54 9546-4H 69/54 Z 253/34 253/34 255 / 08 255/08 C08F 2/00 MAD C08F 2/00 MAD // B01J 20/08 B01J 20/08 A 20/10 20/10 D 20/18 20/18 B 20/20 20/20 B
Claims (4)
を吸着剤で処理して、上記ビニル系モノマー中の重合禁
止剤を吸着除去することを特徴とするビニル系モノマー
の精製法。1. A method for purifying a vinyl-based monomer, which comprises treating a vinyl-based monomer containing a polymerization inhibitor with an adsorbent to adsorb and remove the polymerization inhibitor in the vinyl-based monomer.
ン系、酢酸ビニル系、アクリロニトリル系又はフッ化エ
チレン系モノマーである請求項１記載の精製法。2. The purification method according to claim 1, wherein the vinyl-based monomer is an acrylic-based, styrene-based, vinyl acetate-based, acrylonitrile-based, or fluorinated ethylene-based monomer.
ル酸と炭素数１〜２０の一価アルコールとのエステルで
ある請求項２記載の精製法。3. The purification method according to claim 2, wherein the acrylic monomer is an ester of (meth) acrylic acid and a monohydric alcohol having 1 to 20 carbon atoms.
キュラーシーブ、活性炭、イオン交換樹脂、キレート樹
脂、ゼオライト及び酸性白土から選ばれるものである請
求項１，２又は３記載の精製法。4. The purification method according to claim 1, wherein the adsorbent is selected from alumina, silica gel, molecular sieve, activated carbon, ion exchange resin, chelate resin, zeolite and acid clay.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14536395A JPH08310979A (en) | 1995-05-19 | 1995-05-19 | Purification of vinyl monomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14536395A JPH08310979A (en) | 1995-05-19 | 1995-05-19 | Purification of vinyl monomer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08310979A true JPH08310979A (en) | 1996-11-26 |
Family
ID=15383480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14536395A Withdrawn JPH08310979A (en) | 1995-05-19 | 1995-05-19 | Purification of vinyl monomer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08310979A (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6046357A (en) * | 1998-10-02 | 2000-04-04 | Celanese International Corporation | Stabilization and transport of α,β-unsaturated carboxylic acid and removal of stabilizer |
| JP2002284737A (en) * | 2001-03-26 | 2002-10-03 | Mitsubishi Rayon Co Ltd | Method for diminishing n-oxyl compound |
| JP2004107341A (en) * | 2002-08-30 | 2004-04-08 | Mitsubishi Rayon Co Ltd | Method for treating easily polymerizable material |
| WO2004052819A3 (en) * | 2002-12-06 | 2004-08-05 | Basf Ag | Method for reducing mehq content in acrylic acid |
| JP2005289840A (en) * | 2004-03-31 | 2005-10-20 | Dainippon Ink & Chem Inc | Purification method of N-isopropylacrylamide |
| JP2006087306A (en) * | 2004-09-21 | 2006-04-06 | Kao Corp | Hydroxyhydroquinone-eliminating method |
| WO2007110058A1 (en) * | 2006-03-29 | 2007-10-04 | Kemet Electronics Corporation | Method for purifying a monomer solution and method for producing an electric component, comprising said purification method |
| JP2007291041A (en) * | 2006-04-27 | 2007-11-08 | Osaka Organic Chem Ind Ltd | Method for producing adamantyl (meth)acrylate compound |
| WO2008074522A1 (en) | 2006-12-18 | 2008-06-26 | Evonik Röhm Gmbh | Method for the adsorptive purification of alkyl methacrylates |
| WO2009130986A1 (en) * | 2008-04-25 | 2009-10-29 | 旭硝子株式会社 | Method for purifying tetrafluoroethylene |
| WO2009142616A1 (en) * | 2007-12-21 | 2009-11-26 | Celanese International Corporation | Process for making low color polyvinyl alcohol |
| US20120074354A1 (en) * | 2009-06-08 | 2012-03-29 | Basf Se | Method for the restabilization of (meth)acrylic monomers |
| WO2013080967A1 (en) * | 2011-11-28 | 2013-06-06 | 旭化成ケミカルズ株式会社 | Method for purifying 1,3-butadiene |
| WO2013113034A1 (en) * | 2012-01-28 | 2013-08-01 | Optmed, Inc. | Purification of 1, 1 - disubstituted ethylene compounds |
| JP2013189415A (en) * | 2012-03-15 | 2013-09-26 | Mitsubishi Rayon Co Ltd | Production method of polytetramethylene ether glycol di(meth)acrylate |
| JP2016196442A (en) * | 2015-04-06 | 2016-11-24 | 株式会社メニコン | Method and apparatus for purifying polymerizable unsaturated monomer |
| JP2017527680A (en) * | 2014-09-22 | 2017-09-21 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | Process for producing an improved reactive monomer |
| CN107778197A (en) * | 2016-08-29 | 2018-03-09 | 中国石油化工股份有限公司 | A kind of method of purification of acrylonitrile |
| WO2022004508A1 (en) * | 2020-06-30 | 2022-01-06 | 東洋スチレン株式会社 | Styrene-based resin composition and molded article thereof |
-
1995
- 1995-05-19 JP JP14536395A patent/JPH08310979A/en not_active Withdrawn
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6207859B1 (en) | 1998-10-02 | 2001-03-27 | Celanese International Corporation | Stabilization and transport of α, β-unsaturated carboxylic acid and removal of stabilizer |
| US6046357A (en) * | 1998-10-02 | 2000-04-04 | Celanese International Corporation | Stabilization and transport of α,β-unsaturated carboxylic acid and removal of stabilizer |
| JP4705257B2 (en) * | 2001-03-26 | 2011-06-22 | 三菱レイヨン株式会社 | Method for reducing N-oxyl compounds |
| JP2002284737A (en) * | 2001-03-26 | 2002-10-03 | Mitsubishi Rayon Co Ltd | Method for diminishing n-oxyl compound |
| JP2004107341A (en) * | 2002-08-30 | 2004-04-08 | Mitsubishi Rayon Co Ltd | Method for treating easily polymerizable material |
| WO2004052819A3 (en) * | 2002-12-06 | 2004-08-05 | Basf Ag | Method for reducing mehq content in acrylic acid |
| JP2005289840A (en) * | 2004-03-31 | 2005-10-20 | Dainippon Ink & Chem Inc | Purification method of N-isopropylacrylamide |
| JP2006087306A (en) * | 2004-09-21 | 2006-04-06 | Kao Corp | Hydroxyhydroquinone-eliminating method |
| WO2007110058A1 (en) * | 2006-03-29 | 2007-10-04 | Kemet Electronics Corporation | Method for purifying a monomer solution and method for producing an electric component, comprising said purification method |
| JP2007291041A (en) * | 2006-04-27 | 2007-11-08 | Osaka Organic Chem Ind Ltd | Method for producing adamantyl (meth)acrylate compound |
| DE102006060161A1 (en) * | 2006-12-18 | 2008-06-26 | Evonik Röhm Gmbh | Process for the adsorptive purification of alkyl methacrylates |
| TWI424987B (en) * | 2006-12-18 | 2014-02-01 | Evonik Roehm Gmbh | Method for adsorbing and purifying alkyl methacrylate |
| US8324424B2 (en) | 2006-12-18 | 2012-12-04 | Evonik Röhm Gmbh | Method for the adsorptive purification of alkyl methacrylates |
| WO2008074522A1 (en) | 2006-12-18 | 2008-06-26 | Evonik Röhm Gmbh | Method for the adsorptive purification of alkyl methacrylates |
| AU2007334808B2 (en) * | 2006-12-18 | 2012-10-04 | Evonik Rohm Gmbh | Method for the adsorptive purification of alkyl methacrylates |
| WO2009142616A1 (en) * | 2007-12-21 | 2009-11-26 | Celanese International Corporation | Process for making low color polyvinyl alcohol |
| US8247626B2 (en) | 2008-04-25 | 2012-08-21 | Asahi Glass Company, Limited | Method for purifying tetrafluoroethylene |
| CN102015594A (en) * | 2008-04-25 | 2011-04-13 | 旭硝子株式会社 | Method for purifying tetrafluoroethylene |
| WO2009130986A1 (en) * | 2008-04-25 | 2009-10-29 | 旭硝子株式会社 | Method for purifying tetrafluoroethylene |
| JP5531952B2 (en) * | 2008-04-25 | 2014-06-25 | 旭硝子株式会社 | Method for purifying tetrafluoroethylene |
| US20120074354A1 (en) * | 2009-06-08 | 2012-03-29 | Basf Se | Method for the restabilization of (meth)acrylic monomers |
| US9422221B2 (en) * | 2009-06-08 | 2016-08-23 | Basf Se | Method for the restabilization of (meth)acrylic monomers |
| WO2013080967A1 (en) * | 2011-11-28 | 2013-06-06 | 旭化成ケミカルズ株式会社 | Method for purifying 1,3-butadiene |
| US9676683B2 (en) | 2011-11-28 | 2017-06-13 | Asahi Kasei Chemicals Corporation | Method for purifying 1,3-butadiene |
| JP5684924B2 (en) * | 2011-11-28 | 2015-03-18 | 旭化成ケミカルズ株式会社 | Method for purifying 1,3-butadiene |
| US8829225B2 (en) | 2012-01-28 | 2014-09-09 | Optmed, Inc. | Purification of 1,1-disubstituted ethylene |
| US20130310594A1 (en) * | 2012-01-28 | 2013-11-21 | Optmed, Inc. | 1,1-disubstituted ethylene process |
| WO2013113034A1 (en) * | 2012-01-28 | 2013-08-01 | Optmed, Inc. | Purification of 1, 1 - disubstituted ethylene compounds |
| JP2013189415A (en) * | 2012-03-15 | 2013-09-26 | Mitsubishi Rayon Co Ltd | Production method of polytetramethylene ether glycol di(meth)acrylate |
| JP2017527680A (en) * | 2014-09-22 | 2017-09-21 | エボニック デグサ ゲーエムベーハーＥｖｏｎｉｋ Ｄｅｇｕｓｓａ ＧｍｂＨ | Process for producing an improved reactive monomer |
| JP2016196442A (en) * | 2015-04-06 | 2016-11-24 | 株式会社メニコン | Method and apparatus for purifying polymerizable unsaturated monomer |
| CN107778197A (en) * | 2016-08-29 | 2018-03-09 | 中国石油化工股份有限公司 | A kind of method of purification of acrylonitrile |
| WO2022004508A1 (en) * | 2020-06-30 | 2022-01-06 | 東洋スチレン株式会社 | Styrene-based resin composition and molded article thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH08310979A (en) | Purification of vinyl monomer | |
| US5314974A (en) | Method for producing a spherical acrylonitrile crosslinked copolymer | |
| US5288850A (en) | Process for removing metals from vinylphenol polymers | |
| JP3363968B2 (en) | Sulfur-containing poly (meth) acrylate and method for producing the same | |
| JP2003246810A5 (en) | ||
| US4497710A (en) | Substrate for liquid chromatography and process for isolating and purifying fat-soluble substance by the liquid chromatography on the substrate | |
| CA1287946C (en) | Removal of vinylpyrrolidone from vinylpyrrolidone polymers | |
| JPH0331306A (en) | Production of water absorbing resin | |
| JP6247657B2 (en) | Method and apparatus for purifying polymerizable unsaturated monomer | |
| JP2914075B2 (en) | Method for producing (meth) acrylic acid ester | |
| JP3916353B2 (en) | (Meth) acrylic acid ester purification method | |
| JP2002509533A (en) | How to prohibit the polymerization of vinyl monomers | |
| JP2002194022A (en) | Method for purifying (meth) acrylate ester, (meth) acrylate ester and (meth)acrylic resin | |
| CN101067009A (en) | Method for eliminating solvent from pearl polymer | |
| US2836615A (en) | Methylene blue removal from acrylic monomers | |
| JP4442845B2 (en) | Resist monomer and purification method thereof | |
| JPH061749A (en) | Method for purifying (meth) acrylic acid ester | |
| JP2001288146A (en) | Method for purifying (meth)acrylic acid ester | |
| JP2006328264A (en) | Production method for acrylic adhesive | |
| JPH08313735A (en) | Optical transmission tube | |
| JP2716713B2 (en) | Method for producing non-hydrated soft lens | |
| JPH05310637A (en) | Purification of @(3754/24)meth)acrylic ester | |
| JP2005266794A (en) | Plastic lens and manufacturing method thereof | |
| JP2000016965A (en) | Production of hydroxyalkylacrylic ester or methacrylic acid ester modified with caprolactone | |
| US4375558A (en) | Purification of methacrylamidopropyltrimethyl-ammonium chloride with nonionic organic resins |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20040317 |