JPH1171346A - Purification of n-methyl-2-pyrolidone - Google Patents
Purification of n-methyl-2-pyrolidoneInfo
- Publication number
- JPH1171346A JPH1171346A JP24962297A JP24962297A JPH1171346A JP H1171346 A JPH1171346 A JP H1171346A JP 24962297 A JP24962297 A JP 24962297A JP 24962297 A JP24962297 A JP 24962297A JP H1171346 A JPH1171346 A JP H1171346A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrrolidone
- purifying
- resin
- substance
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、N−メチル−2−
ピロリドンの精製方法に関し、特に、N−メチル−2−
ピロリドンを酸性物質で処理することによってN−メチ
ル−2−ピロリドン中の不純物を除去する方法に関する
ものである。TECHNICAL FIELD The present invention relates to N-methyl-2-
Regarding the method for purifying pyrrolidone, in particular, N-methyl-2-
The present invention relates to a method for removing impurities in N-methyl-2-pyrrolidone by treating pyrrolidone with an acidic substance.
【0002】[0002]
【従来の技術】N−メチル−2−ピロリドン(以下、N
MPと略することがある。)は各種の工業プロセスで溶
剤、溶媒として使用され、近時ますますその需要は増加
しつつある。特に種々のポリマーの溶媒としては、その
溶解力で、ポリフッ化ビニリデン系樹脂の極性溶媒とし
て用いられ、プリント配線板用、多孔質膜用、医療用
品、塗料用等の用途が注目されている。2. Description of the Related Art N-methyl-2-pyrrolidone (hereinafter referred to as N-methyl-2-pyrrolidone)
It may be abbreviated as MP. ) Is used as a solvent in various industrial processes, and its demand is increasing more and more recently. In particular, as a solvent for various polymers, due to its dissolving power, it is used as a polar solvent for polyvinylidene fluoride-based resins, and is attracting attention for uses such as printed wiring boards, porous membranes, medical supplies, and paints.
【0003】NMPは、主としてγ−ブチロラクトンと
アミン類との反応により合成されるが、このような方法
で合成されたNMPは放置しておくと黄色に着色する欠
点を有している。特にポリマーの溶媒として用いる場合
には、この着色はそのままポリマーに着色を与え非常に
好ましくない。[0003] NMP is mainly synthesized by the reaction of γ-butyrolactone with amines, but the NMP synthesized by such a method has a drawback that it is colored yellow when left unattended. In particular, when used as a solvent for a polymer, this coloring gives the polymer a color as it is, which is very undesirable.
【0004】これまで、経時着色の少ないNMPを製造
する方法として、特公昭47−22225号公報には、
N−置換−α−ピロリドンを過マンガン酸カリウム等の
酸化剤と混合して経時着色を起こす物質を取り除く方法
が記載され、特開平6−228088号公報及び特開平
6−228089号公報にはピロリドン類の蒸留精製を
3回行い、その蒸留条件を組合せることにより、経時着
色の少ないピロリドン類を得る方法が記載されている。
しかしながら、いずれの方法もポリフッ化ビニリデン樹
脂等の樹脂を溶解させた時に着色のない極微量の不純物
を除去することを目的としていない方法であり、特に、
前者の方法では、酸化剤と混合した後、50〜100℃
に加温し、次に酸化剤と分離させるために濾過及び蒸留
する工程が必要になり、コストアップが避けられない。
後者の方法では、蒸留を3回も行うためコストアップは
避けられないという問題点を有していた。Until now, Japanese Patent Publication No. 47-22225 discloses a method for producing NMP with little coloring over time.
A method is described in which N-substituted-α-pyrrolidone is mixed with an oxidizing agent such as potassium permanganate to remove substances that cause coloration with time. It describes a method of obtaining pyrrolidones with less coloring with time by performing distillation purification of the compounds three times and combining the distillation conditions.
However, none of the methods is intended to remove a trace amount of impurities without coloring when a resin such as polyvinylidene fluoride resin is dissolved.
In the former method, after mixing with an oxidizing agent, 50 to 100 ° C.
, And then a filtration and distillation step is required to separate the oxidizing agent from the oxidizing agent, which inevitably increases the cost.
The latter method has a problem that the cost is unavoidable because distillation is performed three times.
【0005】[0005]
【発明が解決しようとする課題】本発明の目的は、少な
い工程及び簡便な操作により、フッ化ビニリデン樹脂等
を溶解させた時に、着色を起こさないN−メチル−2−
ピロリドンの精製方法を提供することにある。SUMMARY OF THE INVENTION It is an object of the present invention to provide an N-methyl-2-methyl-2-nitrate which does not cause coloring when a vinylidene fluoride resin or the like is dissolved by a small number of steps and simple operations.
An object of the present invention is to provide a method for purifying pyrrolidone.
【0006】[0006]
【課題を解決するための手段】本発明者らは、上記課題
を解決すべく、鋭意研究を重ねた結果、N−メチル−2
−ピロリドンにフッ化ビニリデン樹脂を溶解させたとき
に着色を起こす原因となる物質は、N−メチル−2−ピ
ロリドン中に不純物として微量に含まれる塩基性物質で
あることをつきとめ、さらにこの塩基性物質は酸性物質
と接触させることにより中和除去されること、または多
孔質物質により吸着され除去されることを見出し、本発
明に到達した。すなわち、本発明は、N−メチル−2−
ピロリドンを酸性物質又は多孔性物質で処理することを
特徴とするN−メチル−2−ピロリドンの精製方法であ
る。Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, have found that N-methyl-2
-The substance causing coloring when the vinylidene fluoride resin is dissolved in pyrrolidone is found to be a basic substance contained in N-methyl-2-pyrrolidone in a trace amount as an impurity. The inventors have found that the substance is neutralized and removed by contact with an acidic substance, or that the substance is adsorbed and removed by a porous substance, and arrived at the present invention. That is, the present invention relates to N-methyl-2-
A method for purifying N-methyl-2-pyrrolidone, comprising treating pyrrolidone with an acidic substance or a porous substance.
【0007】本発明の好ましい態様は以下の通りであ
る。 酸性物質が有機酸、固体酸又はイオン交換樹脂である
前記N−メチル−2−ピロリドンの精製方法。 酸性物質がパラトルエンスルホン酸である前記N−メ
チル−2−ピロリドンの精製方法。 酸性物質が、陽イオン交換樹脂である前記N−メチル
−2−ピロリドンの精製方法。 多孔性物質が、活性炭である前記N−メチル−2−ピ
ロリドンの精製方法。The preferred embodiments of the present invention are as follows. The method for purifying N-methyl-2-pyrrolidone, wherein the acidic substance is an organic acid, a solid acid, or an ion exchange resin. The method for purifying N-methyl-2-pyrrolidone wherein the acidic substance is paratoluenesulfonic acid. The method for purifying N-methyl-2-pyrrolidone, wherein the acidic substance is a cation exchange resin. The method for purifying N-methyl-2-pyrrolidone, wherein the porous substance is activated carbon.
【0008】[0008]
【発明の実施の形態】本発明において、N−メチル−2
−ピロリドンは、γ−ブチロラクトンとアンモニア又は
アミン類等の反応により得られたものが主として対象と
なるがどのような方法で得られたものでも良い。このN
MP中の不純物、主に塩基性物質を酸性物質と接触させ
るか、多孔性物質により吸着させて除去する。DETAILED DESCRIPTION OF THE INVENTION In the present invention, N-methyl-2
-Pyrrolidone is mainly obtained by reacting γ-butyrolactone with ammonia or amines, but may be obtained by any method. This N
The impurities in the MP, mainly a basic substance, are removed by contacting with an acidic substance or by adsorbing with a porous substance.
【0009】本発明において、酸性物質としては、有機
酸、無機酸、イオン交換樹脂、固体酸等がある。In the present invention, examples of the acidic substance include an organic acid, an inorganic acid, an ion exchange resin, and a solid acid.
【0010】有機酸としては、一般式RCOOHで表わ
されるカルボン酸、一般式RSO3Hで表わされるスル
ホン酸、及び一般式RSO2Hで表わされるスルフィン
酸(但し、いずれの一般式においてもRは水素又は有機
化合物を表わす。)が挙げられる。特に、N−メチル−
2−ピロリドンによく溶け、N−メチル−2−ピロリド
ンと沸点が離れていて、蒸留分離しやすい物質が好まし
いことからパラトルエンスルホン酸が好ましい。As the organic acid, a carboxylic acid represented by the general formula RCOOH, a sulfonic acid represented by the general formula RSO 3 H, and a sulfinic acid represented by the general formula RSO 2 H (where R is Represents hydrogen or an organic compound). In particular, N-methyl-
Paratoluenesulfonic acid is preferred because it is preferably a substance that is well soluble in 2-pyrrolidone, has a boiling point apart from N-methyl-2-pyrrolidone, and is easily separated by distillation.
【0011】無機酸としては、塩酸、リン酸等が挙げら
れる。Examples of the inorganic acid include hydrochloric acid and phosphoric acid.
【0012】イオン交換樹脂としては、陽イオン交換樹
脂、陰イオン交換樹脂共に効果があるが、陽イオン交換
樹脂がその効果から好ましい。As the ion exchange resin, both a cation exchange resin and an anion exchange resin are effective, but a cation exchange resin is preferred from the viewpoint of the effect.
【0013】固体酸としてはゼオライト、シリカ、アル
ミナ等が挙げられる。Examples of the solid acid include zeolite, silica, alumina and the like.
【0014】多孔性物質としては、活性炭、モレキュラ
シーブス等が挙げられ、それらの中でも活性炭が特に好
ましい。Examples of the porous substance include activated carbon, molecular sieves and the like. Among them, activated carbon is particularly preferred.
【0015】本発明において、N−メチル−2−ピロリ
ドンを酸性物質又は多孔性物質で処理する際の温度は−
21℃〜120℃であり、常温で行うことができる。−
21℃未満ではN−メチル−2−ピロリドンは凝固し処
理できず、120℃を超えるとN−メチル−2−ピロリ
ドンそのものが分解しはじめ黄色く変色するので好まし
くない。In the present invention, the temperature at which N-methyl-2-pyrrolidone is treated with an acidic substance or a porous substance is as follows:
21 ° C. to 120 ° C., which can be performed at room temperature. −
If the temperature is lower than 21 ° C., N-methyl-2-pyrrolidone solidifies and cannot be processed. If the temperature exceeds 120 ° C., N-methyl-2-pyrrolidone itself starts to decompose and discolors yellow.
【0016】本発明において、N−メチル−2−ピロリ
ドンを酸性物質又は多孔質物質で処理する方法は、N−
メチル−2−ピロリドン中に処理物質を加えて撹拌する
回分式の方法、N−メチル−2−ピロリドンを固体物質
等の固体床で流通処理する連続方式のどちらも使用する
ことができる。In the present invention, the method for treating N-methyl-2-pyrrolidone with an acidic substance or a porous substance comprises the steps of:
Either a batch method in which a treatment substance is added to methyl-2-pyrrolidone and stirring, or a continuous method in which N-methyl-2-pyrrolidone is flow-treated on a solid bed of a solid substance or the like can be used.
【0017】上記のような処理方法によって得られたN
−メチル−2−ピロリドンはフッ化ビニリデン樹脂を溶
解させても着色せず、ポリマーの溶媒としてその溶解能
を十分発揮できるものである。The N obtained by the processing method as described above
-Methyl-2-pyrrolidone does not become colored even when the vinylidene fluoride resin is dissolved, and can sufficiently exhibit its dissolving ability as a polymer solvent.
【0018】[0018]
【実施例】以下、本発明を実施例により詳細に説明す
る。本実施例における試験方法は以下の通りである。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail with reference to embodiments. The test method in this example is as follows.
【0019】(1)ガードナーカラーの測定:JIS
K 0071に準拠し、米国Orbeco−Helli
ge社製“Daylite”comparator i
lluminatorを用いて測定した。(1) Measurement of Gardner color: JIS
K 0071, Orbeco-Helli, USA
Ge “Daylight” comparator i
It measured using the luminator.
【0020】比較例1 未処理のN−メチル−2−ピロリドン(純度99.8
%)88gに、12gのフッ化ビニリデン樹脂を溶解さ
せた。この溶液を色相をガードナーカラーで測定したと
ころ、18であった。Comparative Example 1 Untreated N-methyl-2-pyrrolidone (purity 99.8)
%) Of 88 g was dissolved with 12 g of vinylidene fluoride resin. The hue of this solution was measured by Gardner color to find that it was 18.
【0021】比較例2 ステンレス製コイル(3mmφ、長さ4mm)を充填し
た精留塔(内径16mmφ、長さ200mm)を装備し
た蒸留装置を用い、比較例1で使用したものと同じN−
メチル−2−ピロリドン(純度99.8%)を約20m
mHgの減圧下、毎時25g程度の速度で蒸留した。得
られたN−メチル−2−ピロリドンから88gをとり、
それに12gのフッ化ビニリデン樹脂を溶解させた。こ
の溶液の色相をガードナーカラーで測定したところ、7
であった。Comparative Example 2 Using a distillation apparatus equipped with a rectification column (inner diameter 16 mmφ, length 200 mm) packed with a stainless steel coil (3 mmφ, length 4 mm), the same N-type as that used in Comparative Example 1 was used.
About 20 m of methyl-2-pyrrolidone (purity 99.8%)
Distillation was performed at a rate of about 25 g / hour under reduced pressure of mHg. Take 88 g from the obtained N-methyl-2-pyrrolidone,
12 g of vinylidene fluoride resin was dissolved therein. When the hue of this solution was measured by Gardner color, it was 7
Met.
【0022】実施例1 比較例1で使用したものと同じN−メチル−2−ピロリ
ドン(純度99.8%)500gにパラトルエンスルホ
ン酸1水和物0.096gを溶解させた。その後、精留
塔を装備しない蒸留装置を用い、約20mmHgの減圧
下、毎時50g程度の速度でN−メチル−2−ピロリド
ンを蒸留した。得られたN−メチル−2−ピロリドンか
ら88gをとり、それに12gのフッ化ビニリデン樹脂
を溶解させた。この溶液の色相をガードナーカラーで測
定したところ、1であった。Example 1 0.096 g of paratoluenesulfonic acid monohydrate was dissolved in 500 g of the same N-methyl-2-pyrrolidone (purity 99.8%) as used in Comparative Example 1. Thereafter, N-methyl-2-pyrrolidone was distilled at a rate of about 50 g / hour under a reduced pressure of about 20 mmHg using a distillation apparatus not equipped with a rectification column. 88 g was taken from the obtained N-methyl-2-pyrrolidone, and 12 g of vinylidene fluoride resin was dissolved therein. When the hue of this solution was measured by Gardner color, it was 1.
【0023】実施例2 比較例1で使用したものと同じN−メチル−2−ピロリ
ドン(純度99.8%)100gに陽イオン交換樹脂
(アンバーリスト15)を0.5g加え、室温で5時間
撹拌した後、陽イオン交換樹脂を濾別した。得られたN
−メチル−2−ピロリドンから88gをとり、それに1
2gのフッ化ビニリデン樹脂を溶解させた。この溶液の
色相をガードナーカラーで測定したところ、1であっ
た。Example 2 0.5 g of a cation exchange resin (Amberlyst 15) was added to 100 g of the same N-methyl-2-pyrrolidone (purity 99.8%) as used in Comparative Example 1, and the mixture was allowed to stand at room temperature for 5 hours. After stirring, the cation exchange resin was filtered off. N obtained
88 g from -methyl-2-pyrrolidone,
2 g of vinylidene fluoride resin was dissolved. When the hue of this solution was measured by Gardner color, it was 1.
【0024】実施例3 比較例1で使用したものと同じN−メチル−2−ピロリ
ドン(純度99.8%)100gにシリカ・アルミナを
0.5g加え、室温で5時間撹拌した後、シリカ・アル
ミナを濾別した。得られたN−メチル−2−ピロリドン
から88gをとり、それに12gのフッ化ビニリデン樹
脂を溶解させた。この溶液の色相をガードナーカラーで
測定したところ、1であった。Example 3 0.5 g of silica / alumina was added to 100 g of N-methyl-2-pyrrolidone (purity 99.8%) same as that used in Comparative Example 1, and the mixture was stirred at room temperature for 5 hours. The alumina was filtered off. 88 g was taken from the obtained N-methyl-2-pyrrolidone, and 12 g of vinylidene fluoride resin was dissolved therein. When the hue of this solution was measured by Gardner color, it was 1.
【0025】実施例4 比較例1で使用したものと同じN−メチル−2−ピロリ
ドン(純度99.8%)100gにプロトン型ゼオライ
トYを0.5g加え、室温で5時間撹拌した後、プロト
ン型ゼオライトYを濾別した。得られたN−メチル−2
−ピロリドンから88gをとり、それに12gのフッ化
ビニリデン樹脂を溶解させた。この溶液の色相をガード
ナーカラーで測定したところ、1であった。Example 4 To 100 g of the same N-methyl-2-pyrrolidone (purity: 99.8%) as used in Comparative Example 1, 0.5 g of proton type zeolite Y was added, and the mixture was stirred at room temperature for 5 hours. The zeolite Y was filtered off. N-methyl-2 obtained
88 g were taken from pyrrolidone, into which 12 g of vinylidene fluoride resin were dissolved. When the hue of this solution was measured by Gardner color, it was 1.
【0026】実施例5 比較例1に使用したものと同じN−メチル−2−ピロリ
ドン(純度99.8%)100gに活性炭を0.5g加
え、室温で5時間撹拌した後、活性炭を濾別した。得ら
れたN−メチル−2−ピロリドンから88gをとり、そ
れに12gのフッ化ビニリデン樹脂を溶解させた。この
溶液の色相をガードナーカラーで測定したところ、1で
あった。Example 5 0.5 g of activated carbon was added to 100 g of N-methyl-2-pyrrolidone (purity: 99.8%) same as that used in Comparative Example 1, and the mixture was stirred at room temperature for 5 hours. did. 88 g was taken from the obtained N-methyl-2-pyrrolidone, and 12 g of vinylidene fluoride resin was dissolved therein. When the hue of this solution was measured by Gardner color, it was 1.
【0027】実施例6 図1に示すような流通系装置を組み、反応管内3に乾燥
重量にして8.3g(N−メチル−2−ピロリドンによ
り膨潤させた場合、約20mlになった)の陽イオン交
換樹脂を入れた。反応管の下方より未処理N−メチル−
2−ピロリドン用フィードタンク1よりポンプ2により
比較例1で使用したものと同じN−メチル−2−ピロリ
ドンを1時間に300mlづつ流通させた。(LHSV
=15)流通を開始して2時間後、60時間後のN−メ
チル−2−ピロリドンをそれぞれ88gを処理後N−メ
チル−2−ピロリドン受器4より採取し、それに12g
のフッ化ビニリデン樹脂を溶解させた。これら2つの溶
液の色相をガードナーカラーで測定したところ、両者と
も1であった。Example 6 A flow system as shown in FIG. 1 was assembled, and 8.3 g (about 20 ml when swollen with N-methyl-2-pyrrolidone) of a dry weight in a reaction tube 3 was obtained. Cation exchange resin was charged. Untreated N-methyl-
The same N-methyl-2-pyrrolidone as used in Comparative Example 1 was passed from the 2-pyrrolidone feed tank 1 by the pump 2 at a rate of 300 ml per hour. (LHSV
= 15) After 2 hours and 60 hours from the start of distribution, 88 g of each of N-methyl-2-pyrrolidone was treated and collected from the N-methyl-2-pyrrolidone receiver 4 and then 12 g.
Of vinylidene fluoride resin was dissolved. When the hues of these two solutions were measured by Gardner color, they were 1 both.
【0028】実施例、比較例から明らかなように、N−
メチル−2−ピロリドンをパラトルエンスルホン酸のよ
うな有機酸、陽イオン交換樹脂のようなイオン交換樹
脂、シリカ・アルミナ及びゼオライトのような固体酸、
及び活性炭のような多孔性物質で処理することによっ
て、フッ化ビニリデン樹脂のような樹脂を着色させる不
純物を除去できることが分かる。As is clear from the examples and comparative examples, N-
Methyl-2-pyrrolidone with an organic acid such as paratoluenesulfonic acid, an ion exchange resin such as a cation exchange resin, a solid acid such as silica-alumina and zeolite;
Further, it can be seen that by treating with a porous substance such as activated carbon, impurities that color a resin such as vinylidene fluoride resin can be removed.
【0029】[0029]
【発明の効果】本発明の方法によると、フッ化ビニリデ
ン樹脂溶解時の着色の原因となるNMP中の塩基性物質
が、酸性物質に中和される、または多孔質物質に吸着さ
れる。そのため、処理後のNMPにフッ化ビニリデン樹
脂を溶解させても着色しない。According to the method of the present invention, a basic substance in NMP which causes coloring during the dissolution of a vinylidene fluoride resin is neutralized by an acidic substance or adsorbed by a porous substance. For this reason, even if the vinylidene fluoride resin is dissolved in the NMP after the treatment, no coloring occurs.
【図1】本発明を実施する際のフローシートの1例であ
る。FIG. 1 is an example of a flow sheet when implementing the present invention.
1 未処理 N−メチル−2−ピロリドン用フィード
タンク 2 ポンプ 3 反応管 4 処理後N−メチル−2−ピロリドン受器Reference Signs List 1 Untreated feed tank for N-methyl-2-pyrrolidone 2 Pump 3 Reaction tube 4 N-methyl-2-pyrrolidone receiver after treatment
───────────────────────────────────────────────────── フロントページの続き (72)発明者 稲垣 裕之 埼玉県入間郡大井町西鶴ヶ岡一丁目3番1 号 東燃株式会社総合研究所内 (72)発明者 丹羽 正 埼玉県入間郡大井町西鶴ヶ岡一丁目3番1 号 東燃株式会社総合研究所内 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Hiroyuki Inagaki 1-3-1, Nishitsurugaoka, Oi-machi, Iruma-gun, Saitama Prefecture Tonen Co., Ltd. (72) Inventor Tadashi Niwa Nishi-Tsuruga, Oi-machi, Iruma-gun, Saitama 1-3-1 Oka Inside Tonen Research Institute
Claims (1)
又は多孔性物質で処理することを特徴とするN−メチル
−2−ピロリドンの精製方法。1. A method for purifying N-methyl-2-pyrrolidone, comprising treating N-methyl-2-pyrrolidone with an acidic substance or a porous substance.
Priority Applications (1)
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JP24962297A JPH1171346A (en) | 1997-08-29 | 1997-08-29 | Purification of n-methyl-2-pyrolidone |
Applications Claiming Priority (1)
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JP24962297A JPH1171346A (en) | 1997-08-29 | 1997-08-29 | Purification of n-methyl-2-pyrolidone |
Publications (1)
Publication Number | Publication Date |
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JPH1171346A true JPH1171346A (en) | 1999-03-16 |
Family
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JP24962297A Pending JPH1171346A (en) | 1997-08-29 | 1997-08-29 | Purification of n-methyl-2-pyrolidone |
Country Status (1)
Country | Link |
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JP (1) | JPH1171346A (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2003512145A (en) * | 1999-10-15 | 2003-04-02 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | Treatment of extraction solvents to remove acidic contaminants |
WO2005092851A1 (en) * | 2004-03-03 | 2005-10-06 | Lyondell Chemical Technology, L.P. | Method for purifying n-methyl-2-pyrrolidone |
CN102001986A (en) * | 2010-12-23 | 2011-04-06 | 上海化学试剂研究所 | Method for improving quality of industrial N-methylpyrrolidone |
JP2012062301A (en) * | 2010-09-17 | 2012-03-29 | Shanghai Chemical Reagent Research Inst | Method for producing high-purity n-methyl-2-pyrrolidone |
JP2013018747A (en) * | 2011-07-12 | 2013-01-31 | Japan Organo Co Ltd | Nmp purification system in electrode production process |
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CN103145599A (en) * | 2011-12-07 | 2013-06-12 | 巴斯夫欧洲公司 | Method for purifying n-alkyl substituted pyrrolidones through hydration |
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JP2014144938A (en) * | 2013-01-30 | 2014-08-14 | Japan Organo Co Ltd | NMP purification system |
JP2014144936A (en) * | 2013-01-30 | 2014-08-14 | Japan Organo Co Ltd | Nmp purification system and nmp purification method |
JP2014144937A (en) * | 2013-01-30 | 2014-08-14 | Japan Organo Co Ltd | NMP purification system |
JP2015518079A (en) * | 2012-05-29 | 2015-06-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Method for producing high performance thermoplastics with improved intrinsic color |
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1997
- 1997-08-29 JP JP24962297A patent/JPH1171346A/en active Pending
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2003512145A (en) * | 1999-10-15 | 2003-04-02 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | Treatment of extraction solvents to remove acidic contaminants |
JP4892150B2 (en) * | 1999-10-15 | 2012-03-07 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | Treatment of extraction solvents to remove acidic contaminants |
WO2005092851A1 (en) * | 2004-03-03 | 2005-10-06 | Lyondell Chemical Technology, L.P. | Method for purifying n-methyl-2-pyrrolidone |
JP2007526921A (en) * | 2004-03-03 | 2007-09-20 | ライオンデル ケミカル テクノロジー、 エル.ピー. | Method for purifying N-methyl-2-pyrrolidone |
JP2012062301A (en) * | 2010-09-17 | 2012-03-29 | Shanghai Chemical Reagent Research Inst | Method for producing high-purity n-methyl-2-pyrrolidone |
CN102001986A (en) * | 2010-12-23 | 2011-04-06 | 上海化学试剂研究所 | Method for improving quality of industrial N-methylpyrrolidone |
JP2013018747A (en) * | 2011-07-12 | 2013-01-31 | Japan Organo Co Ltd | Nmp purification system in electrode production process |
JP2013018748A (en) * | 2011-07-12 | 2013-01-31 | Japan Organo Co Ltd | Nmp purification system in electrode production process |
CN103145599A (en) * | 2011-12-07 | 2013-06-12 | 巴斯夫欧洲公司 | Method for purifying n-alkyl substituted pyrrolidones through hydration |
EP2602246A1 (en) * | 2011-12-07 | 2013-06-12 | Basf Se | Method for purifying N-alkyl substituted pyrrolidones |
EP2602247A1 (en) * | 2011-12-07 | 2013-06-12 | Basf Se | Method for purifying N-alkyl substituted pyrrolidones through hydration |
JP2013119551A (en) * | 2011-12-07 | 2013-06-17 | Basf Se | Method for purifying n-alkyl substituted pyrrolidone through hydrogenation |
JP2015518079A (en) * | 2012-05-29 | 2015-06-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Method for producing high performance thermoplastics with improved intrinsic color |
US9255069B2 (en) | 2012-11-22 | 2016-02-09 | Basf Se | Process for purifying N-alkylpyrrolidones |
US9923194B2 (en) | 2012-11-22 | 2018-03-20 | Basf Se | Process for purifying N-alkylpyrrolidones |
JP2014144938A (en) * | 2013-01-30 | 2014-08-14 | Japan Organo Co Ltd | NMP purification system |
JP2014144936A (en) * | 2013-01-30 | 2014-08-14 | Japan Organo Co Ltd | Nmp purification system and nmp purification method |
JP2014144937A (en) * | 2013-01-30 | 2014-08-14 | Japan Organo Co Ltd | NMP purification system |
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