JPS6379858A - Purification of acrylic acid or methacrylic acid dialkylaminoethyl ester - Google Patents
Purification of acrylic acid or methacrylic acid dialkylaminoethyl esterInfo
- Publication number
- JPS6379858A JPS6379858A JP22211686A JP22211686A JPS6379858A JP S6379858 A JPS6379858 A JP S6379858A JP 22211686 A JP22211686 A JP 22211686A JP 22211686 A JP22211686 A JP 22211686A JP S6379858 A JPS6379858 A JP S6379858A
- Authority
- JP
- Japan
- Prior art keywords
- ester
- acrylic acid
- active carbon
- meth
- dialkylaminoethyl
- 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
- 150000002148 esters Chemical class 0.000 title claims abstract description 29
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000000746 purification Methods 0.000 title description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000000126 substance Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- 238000011437 continuous method Methods 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract 7
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 229920006158 high molecular weight polymer Polymers 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- -1 dialkylamino alcohol Chemical compound 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- DJLHXXNSHHGFLB-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;n-methylmethanamine Chemical compound CNC.CCOC(=O)C(C)=C DJLHXXNSHHGFLB-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005956 quaternization reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920006317 cationic polymer Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZMVHTLOQSTVDFE-UHFFFAOYSA-N methanol;methyl 2-methylprop-2-enoate Chemical compound OC.COC(=O)C(C)=C ZMVHTLOQSTVDFE-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明はアクリル酸ジアルキルアミノエチルエステルま
たはメタクリル酸ジアルキルアミノエチルエステル（以
下、（メタ）アクリル酸ジアルキルアミノエチルエステ
ルとする）の精製法に関するものである。詳しくは、こ
れら（メタ）アクリル酸ジアルキルアミノエチルエステ
ルを中和塩または四級塩とし、さらに重合して、高分子
量の良好な水溶性を有する重合体を得るのに適した（メ
タ）アクリル酸ジアルキルアミノエチルエステルの精製
法に関するものである。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a method for purifying acrylic acid dialkylaminoethyl ester or methacrylic acid dialkylaminoethyl ester (hereinafter referred to as (meth)acrylic acid dialkylaminoethyl ester). It is. Specifically, these (meth)acrylic acid dialkylaminoethyl esters are converted into neutralized salts or quaternary salts, and further polymerized to obtain (meth)acrylic acid suitable for obtaining a polymer having a high molecular weight and good water solubility. This invention relates to a method for purifying dialkylaminoethyl ester.
（メタ）アクリル酸ジアルキルアミノエチルエステルは
、塩酸、硫酸などの鉱酸で中和するか、塩化メチル、ジ
メチル硫酸などのアルキル化剤と反応せしめることによ
り中和塩または四級塩とし、こめ中和塩または四級塩の
単独重合、あるいはアクリルアミド等の共重合体は、カ
チオン系高分子凝集剤、繊維処理剤、紙加工剤等として
広く用いられている。(Meth)acrylic acid dialkylaminoethyl ester is made into a neutralized salt or quaternary salt by neutralizing it with a mineral acid such as hydrochloric acid or sulfuric acid, or by reacting it with an alkylating agent such as methyl chloride or dimethyl sulfuric acid. Homopolymers of Japanese salts or quaternary salts, or copolymers of acrylamide and the like are widely used as cationic polymer flocculants, fiber processing agents, paper processing agents, and the like.
（従来の技術）
凝集剤として使用するためには、高分子量でしかも水溶
性が良好であることが望ましい。ところが（メタ）アク
リル酸ジアルキルアミノエチルエステルに含まれる不純
物は、重合の際、連鎖移動剤として作用し得られる重合
体の分子量を低下させたり、架橋剤となって重合体の水
溶性を低下させる原因となる。（メタ）アクリル酸ジア
ルキルアミノエチルエステルの精製は、一般に減圧蒸留
により行われる。(Prior Art) In order to use it as a flocculant, it is desirable to have a high molecular weight and good water solubility. However, impurities contained in (meth)acrylic acid dialkylaminoethyl ester act as a chain transfer agent during polymerization, reducing the molecular weight of the resulting polymer, or act as a crosslinking agent, reducing the water solubility of the polymer. Cause. Purification of (meth)acrylic acid dialkylaminoethyl ester is generally performed by vacuum distillation.
また、中和して水溶性の塩とした後、水溶性の非極性溶
剤と接触させて不純物を抽出する方法も知られている。Also known is a method in which impurities are extracted by neutralizing the salt to make it a water-soluble salt and then bringing it into contact with a water-soluble non-polar solvent.
（発明が解決しようとする問題点）
しかし、（メタ）アクリル酸ジアルキルアミノエチルエ
ステルと不純物の沸点は近く、不純物を蒸留のみで精度
良く分離するには、多くの蒸留段数及び還流比を必要と
する。しかし、（メタ）アクリル酸ジアルキルアミノエ
チルエステルは重合しやすい化合物であり、厳しい蒸留
条件で長時間蒸留操作を行うことは、系内での重合物の
析出、蒸留収率の低下等を引き起こし、工業的には好ま
しくない。また（メタ）アクリル酸ジアルキルアミノエ
チルエステルを中和塩として水に不溶性の非極性溶剤と
接触させて不純物を抽出除去する方法は、抽出効率が悪
く、また、使用した多量の溶剤の回収が必要で、製造工
程が煩雑となる。(Problem to be solved by the invention) However, the boiling points of (meth)acrylic acid dialkylaminoethyl ester and impurities are close to each other, and a large number of distillation stages and reflux ratio are required to accurately separate impurities by distillation alone. do. However, (meth)acrylic acid dialkylaminoethyl ester is a compound that easily polymerizes, and performing distillation operations for a long time under severe distillation conditions may cause precipitation of polymers in the system, decrease in distillation yield, etc. Industrially unfavorable. In addition, the method of extracting and removing impurities by contacting (meth)acrylic acid dialkylaminoethyl ester as a neutralized salt with a water-insoluble non-polar solvent has poor extraction efficiency and requires the recovery of a large amount of the solvent used. This makes the manufacturing process complicated.
（問題を解決するための手段）
本発明者らは、前述の精製法の欠点を解決し、高分子量
でかつ水溶性が良好な重合体を製造するに適した、（メ
タ）アクリル酸ジアルキルアミノエチルエステルの精製
法について鋭意検討した結果、（メタ）アクリル酸ジア
ルキルアミノエチルエステルの精製に際し、活性炭で処
理することにより品質良好な（メタ）アクリル酸ジアル
キルアミノエチルエステルが得られることを見出し、本
発明を完成するに至った。(Means for Solving the Problem) The present inventors have solved the drawbacks of the above-mentioned purification method, and have developed a dialkylamino (meth)acrylate suitable for producing a polymer having a high molecular weight and good water solubility. As a result of intensive studies on purification methods for ethyl ester, we discovered that (meth)acrylic acid dialkylaminoethyl ester of good quality could be obtained by treating it with activated carbon when purifying (meth)acrylic acid dialkylaminoethyl ester. The invention was completed.
すなわち、本発明は、一般式
（式中、Ｒ＋は水素原子またはメチル基、Ｒ２及びＲ３
は炭素数１〜２のアルキル基を示す）で表される（メタ
）アクリル酸ジアルキルアミノエチルエステルの精製に
際し、活性炭で処理することを特徴とする（メタ）アク
リル酸ジアルキルアミノエチルエステルの精製法。That is, the present invention provides a method using the general formula (wherein R+ is a hydrogen atom or a methyl group, R2 and R3
represents an alkyl group having 1 to 2 carbon atoms) A method for purifying (meth)acrylic acid dialkylaminoethyl ester, which comprises treating the dialkylaminoethyl (meth)acrylate with activated carbon. .
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明の方法により精製される（メタ）アクリル酸ジア
ルキルアミノエチルエステルは、一般式（式中、Ｒ，は
水素原子またはメチル基、Ｒ２及びＲ３は炭素数１〜２
のアルキル基を示す）で表される（メタ）アクリル酸ジ
アルキルアミンエチルエステルであり、具体的には、ア
クリル酸ジメチルアミノエチル、メタクリル酸ジメチル
アミノエチル、アクリル酸ジエチルアミノエチル、メタ
クリル酸ジエチルアミノエチルなどが挙げられる。 こ
れら（メタ）アクリル酸ジアルキルアミノエチルエステ
ルの合成は、一般に（メタ）アクリル酸のジアルキルア
ミノアルコールによるエステル化、あるいは（メタ）ア
クリル酸の低級アルキルエステルとジアルキルアミノア
ルコールのエステル交換反応により行われる。前記のご
とく合成した（メタ）アクリル酸ジアルキルアミノエチ
ルエステル含有液は、低沸点成分を除去した後、通常、
まず、減圧蒸留により精製する。蒸留は通常の方法によ
り行うことが可能である０例えば、理論段数４〜２０段
の蒸留塔を用いて、還流比０．１〜４程度の連続または
回分蒸留により行う、減圧蒸留により得られる（メタ）
アクリル酸ジアルキルアミノエチルエステルの純度は、
−ｉに９７．０〜９９．９％で、含まれる主な不純物は
（メタ）アクリル酸、（メタ）アクリル酸の低級アルキ
ルエステル、ジアルキルアミノアルコール及び（メタ）
アクリル酸エステル類の不飽和結合部へアルコール類が
付加した化合物などである。その他にも数種類の微量の
不純物が含まれる０次に不純物を含有する前記の純度９
７．０〜９９．９％の（メタ）アクリル酸ジアルキルア
ミノエチルエステルを活性炭で処理する。The (meth)acrylic acid dialkylaminoethyl ester purified by the method of the present invention has the general formula (wherein, R is a hydrogen atom or a methyl group, and R2 and R3 have 1 to 2 carbon atoms.
It is a (meth)acrylic acid dialkylamine ethyl ester represented by (representing an alkyl group of Can be mentioned. The synthesis of these (meth)acrylic acid dialkylaminoethyl esters is generally carried out by esterification of (meth)acrylic acid with a dialkylamino alcohol, or by transesterification of a lower alkyl ester of (meth)acrylic acid and a dialkylamino alcohol. The (meth)acrylic acid dialkylaminoethyl ester-containing liquid synthesized as described above is usually treated after removing low-boiling components.
First, it is purified by vacuum distillation. Distillation can be carried out by a conventional method.For example, it can be obtained by continuous or batch distillation using a distillation column with 4 to 20 theoretical plates at a reflux ratio of about 0.1 to 4, or by vacuum distillation. Meta)
The purity of acrylic acid dialkylaminoethyl ester is
-i is 97.0 to 99.9%, and the main impurities contained are (meth)acrylic acid, lower alkyl esters of (meth)acrylic acid, dialkylamino alcohol, and (meth)acrylic acid.
These include compounds in which alcohols are added to the unsaturated bonds of acrylic esters. The above-mentioned purity 9 contains 0-order impurities that also contain trace amounts of several other impurities.
7.0-99.9% (meth)acrylic acid dialkylaminoethyl ester is treated with activated carbon.
活性炭処理の方法には、活性炭を充填した塔に処理液を
流す連続法、または処理液に活性炭を添加して処理した
後、活性炭を濾過、遠心分離等により分離除去す回分法
がある１本発明の方法ではいずれの方法も用いることが
できる。使用する活性炭は、市販の種々のものがそのま
ま使用可能である。There are two methods for activated carbon treatment: a continuous method in which the treated liquid is passed through a column filled with activated carbon, and a batch method in which activated carbon is added to the treated liquid and then separated and removed by filtration, centrifugation, etc. Either method can be used in the method of the invention. Various commercially available activated carbons can be used as they are.
活性炭の使用量は、（メタ）アクリル酸ジアルキルアミ
ノエチルの０．１〜５重量％が好ましい。The amount of activated carbon used is preferably 0.1 to 5% by weight of dialkylaminoethyl (meth)acrylate.
処理温度は、（メタ）アクリル酸ジアルキルアミノエチ
ルの凝固点から沸点まで可能であるが、エステルの安定
性を考慮すると０〜１００℃の範囲が好ましい、活性炭
により除去される不純物の知見については明らかではな
いが、極＜微量のエチレングリコールジメタクリレート
等のジビニル化合物が含まれており、これらの除去効果
が考えられる。The treatment temperature can range from the freezing point to the boiling point of dialkylaminoethyl (meth)acrylate, but considering the stability of the ester, a range of 0 to 100°C is preferable.It is unclear what impurities are removed by activated carbon. However, it contains extremely small amounts of divinyl compounds such as ethylene glycol dimethacrylate, and is thought to have the effect of removing them.
（実施例） 以下、実施例により本発明の方法を具体的に説明する。(Example) Hereinafter, the method of the present invention will be specifically explained with reference to Examples.
実施例１
（合成及び蒸留）
攪拌機、温度計及び理論段数１０段の分留塔を備えた内
容積１１のフラスコに、ジメチルアミノエタノール１７
８ｇ、メタクリル酸メチル６００ ｇ 、ナトリウムメ
トキシド３．０ｇ、重合禁止剤としてフェノチアジン１
．５ｇを仕込み、圧力３００ｍｄｇで攪拌しながら加熱
還流した。生成するメタノールをメタノール−メタクリ
ル酸メチル共沸混合物として留去して反応を進めた。６
時間で反応は終了し、過剰に仕込んだメタクリル酸メチ
ルを留去後、さらに圧力５ ｍｍＨｇ、分留塔塔頂温度
５６〜５８℃でメタクリル酸ジメチルアミンエチルエス
テルを留去させた。得られたメタクリル酸ジメチルアミ
ノエチルエステルは２８０ ｇで純度は９９．２％であ
った。Example 1 (Synthesis and distillation) Into a flask with an internal volume of 11 equipped with a stirrer, a thermometer, and a fractionating column with 10 theoretical plates, 17 mL of dimethylaminoethanol was added.
8 g, methyl methacrylate 600 g, sodium methoxide 3.0 g, phenothiazine 1 as a polymerization inhibitor
．． 5 g was charged and heated to reflux while stirring at a pressure of 300 mdg. The reaction proceeded by distilling off the generated methanol as a methanol-methyl methacrylate azeotrope. 6
The reaction was completed in a few hours, and after distilling off the excess methyl methacrylate, dimethylamine methacrylate ethyl ester was further distilled off at a pressure of 5 mmHg and a fractionation column top temperature of 56 to 58°C. The obtained dimethylaminoethyl methacrylate weighed 280 g and had a purity of 99.2%.
（活性炭処理）
上記のメタクリル酸ジメチルアミノエチルエステルに、
粉状活性炭（ツルミコールＰＣ）５．６ｇを加え、室温
にて３０分間撹拌した後、活性炭を減圧濾過により分離
した。得られたメタクリル酸ジメチルアミノエチルエス
テルは２７．２ｇで純度は９９．４％であった。(Activated carbon treatment) To the above methacrylic acid dimethylaminoethyl ester,
After adding 5.6 g of powdered activated carbon (Tsurumicol PC) and stirring at room temperature for 30 minutes, the activated carbon was separated by vacuum filtration. The obtained dimethylaminoethyl methacrylate weighed 27.2 g and had a purity of 99.4%.
（四級化及び重合）
１１ガラス製耐圧四ンロフラスコに、前記の如く活性炭
処理したメタクリル酸ジメチルアミノエチルエステル２
２０ ｇ 、水７３ｇを仕込み、３０℃で塩化メチルを
吹き込みながら、圧力ＩＫｇ／ｃｄで５時間反応させた
０反応終了後、過剰に吹き込んだ塩化メチルを除去して
四級アンモニウム塩水溶液を得た。この四級アンモニウ
ム塩水溶液２５０ｇをアクリルアミド３６０ｇと通常の
方法により共重合させた。得られた重合体は、乾燥、粉
砕して粒状とした。重合体の０．１重世％水溶液は、溶
解性良好で不活性のゲルは認められなかった。また、そ
の粒度は２３０ｃｐｓ（１重量％水溶液、食塩１．１重
世％添加、２５℃にてＢ型粘度計で測定）と十分高分子
量の重合体であった。(Quaternization and Polymerization) 11 In a pressure-resistant four-ringed glass flask, dimethylaminoethyl methacrylate 2 was treated with activated carbon as described above.
After the completion of the reaction, the excess methyl chloride was removed to obtain a quaternary ammonium salt aqueous solution. . 250 g of this aqueous quaternary ammonium salt solution was copolymerized with 360 g of acrylamide by a conventional method. The obtained polymer was dried and ground into granules. A 0.1% aqueous solution of the polymer had good solubility and no inert gel was observed. Further, the particle size was 230 cps (measured using a B-type viscometer at 25° C. in a 1% aqueous solution, 1.1% sodium chloride added, and a B-type viscometer), indicating that the polymer had a sufficiently high molecular weight.
比較例
実施例１と同様の合成及び蒸留を行い、活性炭処理を行
わず実施例１と同様に四級化及び重合を行った。得られ
た重合体は水に対して不溶性であヮた。Comparative Example Synthesis and distillation were performed in the same manner as in Example 1, and quaternization and polymerization were performed in the same manner as in Example 1 without performing activated carbon treatment. The obtained polymer was highly insoluble in water.
実施例２
（活性炭処理）
実施例１と同様の方法で合成及びＮ留を行い、純度９９
．２％のメタクリル酸ジメチルアミノエチルエステルを
得た。内径２０ｍｍ、長さ５００ｍ５のガラス管に粒状
活性Ｒ（ツルミコールＧＬ−３０）を充填し前記メタク
リル酸ジメチルアミノエチルを流速６ ｍ／）ｌｒで流
した。処理後のメタクリル酸ジメチルアミンエチルエス
テルの純度は９９．４％であった。Example 2 (Activated carbon treatment) Synthesis and N distillation were performed in the same manner as in Example 1, and the purity was 99.
．． 2% of methacrylic acid dimethylaminoethyl ester was obtained. A glass tube with an inner diameter of 20 mm and a length of 500 m5 was filled with granular active R (Tulmicol GL-30), and the dimethylaminoethyl methacrylate was allowed to flow at a flow rate of 6 m/lr. The purity of dimethylamine methacrylate ethyl ester after treatment was 99.4%.
（四級化及び重合）
前記の如く得られたメタクリル酸ジメチルアミンエチル
エステルを、実施例Ｉと同様の方法で四級化及び重合を
行った。得られた重合体の０．１重量％水溶液は、溶解
性良好で不溶性のゲルは認められなかった。また、その
粘度は２３５ｃｐｓ （実施例１と同様の方法で測定）
と、十分な高分子量の重合体であった。(Quaternization and Polymerization) The dimethylamine methacrylate ethyl ester obtained above was quaternized and polymerized in the same manner as in Example I. The obtained 0.1% by weight aqueous solution of the polymer had good solubility and no insoluble gel was observed. In addition, its viscosity is 235 cps (measured in the same manner as Example 1)
It was a polymer with a sufficiently high molecular weight.
（発明の効果）
本発明の方法により精製したメタクリル酸ジメチルアミ
ノエチルエステルは、カチオン系高分子凝集剤、繊維処
理剤、紙加工剤等の用途に好適な品質のものであった。(Effects of the Invention) The dimethylaminoethyl methacrylate ester purified by the method of the present invention was of a quality suitable for use as a cationic polymer flocculant, a fiber treatment agent, a paper processing agent, and the like.
特許出願人 三井東圧化学株式会社手続補正書印発
）
昭和６２年３月２０日Patent applicant: Mitsui Toatsu Kagaku Co., Ltd. Procedural amendment (sealed) March 20, 1986
Claims (1)
Ｒ＿３は炭素数１〜２のアルキル基を示す）で表される
アクリル酸ジアルキルアミノエチルエステルまたはメタ
クリル酸ジアルキルアミノエチルエステルの精製に際し
、活性炭で処理することを特徴とするアクリル酸ジアル
キルアミノエチルエステルまたはメタクリル酸ジアルキ
ルアミノエチルエステルの精製法。[Claims] 1) Represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. A method for purifying acrylic acid dialkylaminoethyl ester or methacrylic acid dialkylaminoethyl ester, which comprises treating the acrylic acid dialkylaminoethyl ester or methacrylic acid dialkylaminoethyl ester with activated carbon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22211686A JPH0745446B2 (en) | 1986-09-22 | 1986-09-22 | Method for purifying dialkylaminoethyl ester of acrylic acid or methacrylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22211686A JPH0745446B2 (en) | 1986-09-22 | 1986-09-22 | Method for purifying dialkylaminoethyl ester of acrylic acid or methacrylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6379858A true JPS6379858A (en) | 1988-04-09 |
| JPH0745446B2 JPH0745446B2 (en) | 1995-05-17 |
Family
ID=16777402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22211686A Expired - Lifetime JPH0745446B2 (en) | 1986-09-22 | 1986-09-22 | Method for purifying dialkylaminoethyl ester of acrylic acid or methacrylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0745446B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01230610A (en) * | 1988-03-11 | 1989-09-14 | Kohjin Co Ltd | Cationic polymer |
| JP2006028080A (en) * | 2004-07-15 | 2006-02-02 | Osaka Organic Chem Ind Ltd | Method of purifying (meth)acrylic ester |
-
1986
- 1986-09-22 JP JP22211686A patent/JPH0745446B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01230610A (en) * | 1988-03-11 | 1989-09-14 | Kohjin Co Ltd | Cationic polymer |
| JP2006028080A (en) * | 2004-07-15 | 2006-02-02 | Osaka Organic Chem Ind Ltd | Method of purifying (meth)acrylic ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0745446B2 (en) | 1995-05-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2386538B1 (en) | N-(1-hydroxyethyl)carboxamide compound and process for producing same | |
| RU2757390C2 (en) | Preparation of n,n-(di)alkylaminoalkyl(meth)acrylamide or n,n-(di)alkylaminoalkyl(meth)acrylate and their quaternary ammonium salts as flocculating auxiliary substances and gel-forming agents | |
| EP0419654A1 (en) | Water-soluble cationic polymer | |
| JPS62158237A (en) | Synthesis of (meth)acrylic acid anhydride | |
| JPS6379858A (en) | Purification of acrylic acid or methacrylic acid dialkylaminoethyl ester | |
| JPS606351B2 (en) | Production method of cationic vinyl monomer aqueous solution | |
| JP3274258B2 (en) | Method for producing N-monosubstituted- (meth) acrylamide | |
| JPH0459308B2 (en) | ||
| US5587515A (en) | Method of manufacturing N-monosubstituted (meth)acrylamides | |
| JP3674966B2 (en) | Method for producing highly polymerizable monomer | |
| JP3044694B2 (en) | Purification method of glycidyl methacrylate | |
| JP2886990B2 (en) | Method for producing unsaturated quaternary ammonium salt | |
| JP2793045B2 (en) | Process for producing alkylaminoalkyl esters of acrylic acid or methacrylic acid and quaternary salts thereof | |
| WO1988006152A1 (en) | Process for preparing unsaturated quaternary ammonium salts | |
| JP3365430B2 (en) | Method for producing N-vinylformamide polymer | |
| JPS62201852A (en) | Purification of alkylaminoalkyl acrylate or methacrylate | |
| JP2705827B2 (en) | Method for producing unsaturated quaternary ammonium salt | |
| JPS6244538B2 (en) | ||
| JPS63230714A (en) | Production of cationic polymer | |
| JP2837279B2 (en) | Method for producing unsaturated quaternary ammonium salts | |
| JP2872813B2 (en) | Method for producing unsaturated quaternary ammonium salt | |
| JPH03135945A (en) | Quaternary ammonium salt and production thereof | |
| JP2007504264A (en) | Production method of (meth) acrylate diammonium salt and use as monomer for polymer synthesis | |
| JPH0283358A (en) | Production of unsaturated carboxylic acid amide | |
| JPH0443902B2 (en) |