JPH0796512B2 - Aralkyl ether purification method - Google Patents
Aralkyl ether purification methodInfo
- Publication number
- JPH0796512B2 JPH0796512B2 JP8804489A JP8804489A JPH0796512B2 JP H0796512 B2 JPH0796512 B2 JP H0796512B2 JP 8804489 A JP8804489 A JP 8804489A JP 8804489 A JP8804489 A JP 8804489A JP H0796512 B2 JPH0796512 B2 JP H0796512B2
- Authority
- JP
- Japan
- Prior art keywords
- aralkyl ether
- aralkyl
- aromatic aldehyde
- xylene
- sodium bisulfite
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 Aralkyl ether Chemical compound 0.000 title claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 17
- 238000000746 purification Methods 0.000 title description 3
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 18
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 15
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 15
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- DAJPMKAQEUGECW-UHFFFAOYSA-N 1,4-bis(methoxymethyl)benzene Chemical group COCC1=CC=C(COC)C=C1 DAJPMKAQEUGECW-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- LHKUVIRLOYVRHW-UHFFFAOYSA-N 4-(methoxymethyl)benzaldehyde Chemical compound COCC1=CC=C(C=O)C=C1 LHKUVIRLOYVRHW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ULBFBRPHDKBYQM-UHFFFAOYSA-N 2-(propoxymethyl)benzaldehyde Chemical compound CCCOCC1=CC=CC=C1C=O ULBFBRPHDKBYQM-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- REKVGPTYHRAVGP-UHFFFAOYSA-N 1,2-dimethyl-3-propan-2-yloxybenzene Chemical group CC(C)OC1=CC=CC(C)=C1C REKVGPTYHRAVGP-UHFFFAOYSA-N 0.000 description 1
- OXVZEOYNXOZOFP-UHFFFAOYSA-N 1,2-dimethyl-3-propoxybenzene Chemical group CCCOC1=CC=CC(C)=C1C OXVZEOYNXOZOFP-UHFFFAOYSA-N 0.000 description 1
- VSZHMZHUNQBLCO-UHFFFAOYSA-N 1,3-dimethyl-2-propan-2-yloxybenzene Chemical group CC(C)OC1=C(C)C=CC=C1C VSZHMZHUNQBLCO-UHFFFAOYSA-N 0.000 description 1
- ORWYJYFTKGSHEU-UHFFFAOYSA-N 1,3-dimethyl-2-propoxybenzene Chemical group CCCOC1=C(C)C=CC=C1C ORWYJYFTKGSHEU-UHFFFAOYSA-N 0.000 description 1
- WGJIHRZEAYNAEJ-UHFFFAOYSA-N 1,4-dimethyl-2-propan-2-yloxybenzene Chemical group CC(C)OC1=CC(C)=CC=C1C WGJIHRZEAYNAEJ-UHFFFAOYSA-N 0.000 description 1
- ZPKBFIQHUKPFJG-UHFFFAOYSA-N 1,4-dimethyl-2-propoxybenzene Chemical group CCCOC1=CC(C)=CC=C1C ZPKBFIQHUKPFJG-UHFFFAOYSA-N 0.000 description 1
- ORFMUMKOCXSUCB-UHFFFAOYSA-N 2-(ethoxymethyl)benzaldehyde Chemical compound CCOCC1=CC=CC=C1C=O ORFMUMKOCXSUCB-UHFFFAOYSA-N 0.000 description 1
- GPWBSZYCZARIHN-UHFFFAOYSA-N 2-(methoxymethyl)benzaldehyde Chemical compound COCC1=CC=CC=C1C=O GPWBSZYCZARIHN-UHFFFAOYSA-N 0.000 description 1
- SMWZOTWAZCCTLX-UHFFFAOYSA-N 3-(ethoxymethyl)benzaldehyde Chemical compound CCOCC1=CC=CC(C=O)=C1 SMWZOTWAZCCTLX-UHFFFAOYSA-N 0.000 description 1
- BQWQTLKHBHLJAQ-UHFFFAOYSA-N 3-(methoxymethyl)benzaldehyde Chemical compound COCC1=CC=CC(C=O)=C1 BQWQTLKHBHLJAQ-UHFFFAOYSA-N 0.000 description 1
- ARTRGEPZDFYZBS-UHFFFAOYSA-N 3-(propan-2-yloxymethyl)benzaldehyde Chemical compound CC(C)OCC1=CC=CC(C=O)=C1 ARTRGEPZDFYZBS-UHFFFAOYSA-N 0.000 description 1
- LRQHUVSUJCYZGD-UHFFFAOYSA-N 3-(propoxymethyl)benzaldehyde Chemical compound CCCOCC1=CC=CC(C=O)=C1 LRQHUVSUJCYZGD-UHFFFAOYSA-N 0.000 description 1
- GDNCBNMUXKLEGG-UHFFFAOYSA-N 4-(ethoxymethyl)benzaldehyde Chemical compound CCOCC1=CC=C(C=O)C=C1 GDNCBNMUXKLEGG-UHFFFAOYSA-N 0.000 description 1
- MDEBVGMOLFOALU-UHFFFAOYSA-N 4-(propan-2-yloxymethyl)benzaldehyde Chemical compound CC(C)OCC1=CC=C(C=O)C=C1 MDEBVGMOLFOALU-UHFFFAOYSA-N 0.000 description 1
- DXXXEQFCKKKIIY-UHFFFAOYSA-N 4-(propoxymethyl)benzaldehyde Chemical compound CCCOCC1=CC=C(C=O)C=C1 DXXXEQFCKKKIIY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は高純度アラルキルエーテルの精製方法に関す
る。更に詳しくは芳香族アルデヒドを0.1重量％以上含
有するアラルキルエーテルを精製する方法において、40
℃以下で該アルデヒドの２〜50倍モルの亜硫酸水素ナト
リウムと該アラルキルエーテルとを接触させる事を特徴
とするアラルキルエーテルの精製方法である。アラルキ
ルエーテルは、耐熱性、特に耐酸化劣化性の優れたフェ
ノールアラルキル樹脂（商品名ザイロック）の原料とな
る重要な物質である。TECHNICAL FIELD The present invention relates to a method for purifying high-purity aralkyl ether. More specifically, in the method for purifying an aralkyl ether containing 0.1% by weight or more of an aromatic aldehyde,
A method for purifying an aralkyl ether, which comprises contacting sodium bisulfite in an amount of 2 to 50 times the molar amount of the aldehyde with the aralkyl ether at a temperature of not more than 0 ° C. Aralkyl ether is an important substance as a raw material of a phenol aralkyl resin (trade name: Zyloc), which is excellent in heat resistance, particularly resistance to oxidative deterioration.
アラルキルエーテルは自動酸化を受けやすく、保存中に
芳香族アルデヒドに変質する。また、アラルキルジクロ
ライドとアルコールを原料とし、アラルキルエーテルを
製造する場合、アラルキルジクロライド中に含有する不
純物、例えばα，α，α′−トリクロルキシレンからア
ルコキシメチルベンズアルデヒド（芳香族アルデヒド）
が副生し、しかもこの芳香族アルデヒドが、アラルキル
エーテルと沸点が近い為に精製が難しく、高純度のアラ
ルキルエーテルの製造が難しいのが現状である。Aralkyl ethers are susceptible to autoxidation and transform into aromatic aldehydes during storage. When aralkyl ether is produced from aralkyl dichloride and alcohol as raw materials, impurities contained in aralkyl dichloride, for example, α, α, α'-trichloroxylene to alkoxymethylbenzaldehyde (aromatic aldehyde)
However, since the aromatic aldehyde has a boiling point close to that of aralkyl ether, it is difficult to purify the aromatic aldehyde, and it is difficult to produce high-purity aralkyl ether.
この芳香族アルデヒドは、樹脂製造時に分子量調節を難
しくする他、色相に悪影響を与える事から、従来より高
純度のアラルキルエーテルの工業的精製法の確立が望ま
れていた。Since this aromatic aldehyde makes it difficult to control the molecular weight during resin production and adversely affects the hue, it has been desired to establish an industrial purification method of aralkyl ether having a higher purity than ever before.
本発明の目的は、芳香族アルデヒドを含まないアラルキ
ルエーテルの工業的精製法を提供する事にある。An object of the present invention is to provide an industrial purification method of aralkyl ether containing no aromatic aldehyde.
本発明者らは、上記目的を達成する為鋭意検討し、本発
明に至った。The present inventors have earnestly studied to achieve the above-mentioned object, and arrived at the present invention.
即ち本発明は、芳香族アルデヒドを0.1重量％以上含有
するアラルキルエーテルを精製する方法において、40℃
以下で該アルデヒドの２〜50倍モルの亜硫酸水素ナトリ
ウムと該アラルキルエーテルとを接触させる事を特徴と
するアラルキルエーテルの精製方法である。That is, the present invention is a method for purifying an aralkyl ether containing 0.1% by weight or more of an aromatic aldehyde, at 40 ° C.
The method for purifying aralkyl ether is characterized in that the aralkyl ether is contacted with sodium bisulfite in an amount of 2 to 50 times the molar amount of the aldehyde and the aralkyl ether.
以下、本発明を更に詳細に説明する。Hereinafter, the present invention will be described in more detail.
本発明で言うアラルキルエーテルとしては、例えば、
α，α′−ジメトキシ−ｐ−キシレン、α，α′−ジメ
トキシ−ｏ−キシレン、α，α′−ジメトキシ−ｍ−キ
シレン、α，α′−ジエトキシ−ｐ−キシレン、α，
α′−ジエトキシ−ｏ−キシレン、α，α′−ジエトキ
シ−ｍ−キシレン、α，α′−ジ（１−プロポキシ）−
ｐ−キシレン、α，α′−ジ（１−プロポキシ）−ｏ−
キシレン、α，α′−ジ（１−プロポキシ）−ｍ−キシ
レン、α，α′−ジ（２−プロポキシ）−ｐ−キシレ
ン、α，α′−ジ（２−プロポキシ）−ｏ−キシレン、
α，α′−ジ（２−プロポキシ）−ｍ−キシレンであ
る。また、芳香族アルデヒドとしては、ｐ−メトキシメ
チルベンズアルデヒド、ｏ−メトキシメチルベンズアル
デヒド、ｍ−メトキシメチルベンズアルデヒド、ｐ−メ
チルベンズアルデヒド、ｏ−メチルベンズアルデヒド、
ｍ−メチルベンズアルデヒド、ｐ−エトキシメチルベン
ズアルヒド、ｏ−エトキシメチルベンズアルヒド、ｍ−
エトキシメチルベンズアルヒド、ｐ−１−プロポキシメ
チルベンズアルデヒド、ｏ−１−プロポキシメチルベン
ズアルデヒド、ｍ−１−プロポキシメチルベンズアルデ
ヒド、ｐ−２−プロポキシメチルベンズアルデヒド、ｏ
−２−プロポキシメチルベンズアルデヒド、ｍ−２−プ
ロポキシメチルベンズアルデヒドが、代表的な例であ
る。Examples of the aralkyl ether referred to in the present invention include, for example:
α, α′-dimethoxy-p-xylene, α, α′-dimethoxy-o-xylene, α, α′-dimethoxy-m-xylene, α, α′-diethoxy-p-xylene, α,
α'-diethoxy-o-xylene, α, α'-diethoxy-m-xylene, α, α'-di (1-propoxy)-
p-xylene, α, α′-di (1-propoxy) -o-
Xylene, α, α′-di (1-propoxy) -m-xylene, α, α′-di (2-propoxy) -p-xylene, α, α′-di (2-propoxy) -o-xylene,
It is α, α'-di (2-propoxy) -m-xylene. As the aromatic aldehyde, p-methoxymethylbenzaldehyde, o-methoxymethylbenzaldehyde, m-methoxymethylbenzaldehyde, p-methylbenzaldehyde, o-methylbenzaldehyde,
m-methylbenzaldehyde, p-ethoxymethylbenzaldehyde, o-ethoxymethylbenzaldehyde, m-
Ethoxymethylbenzaldehyde, p-1-propoxymethylbenzaldehyde, o-1-propoxymethylbenzaldehyde, m-1-propoxymethylbenzaldehyde, p-2-propoxymethylbenzaldehyde, o
2-propoxymethylbenzaldehyde and m-2-propoxymethylbenzaldehyde are typical examples.
本発明は、芳香族アルデヒドを含むアラルキルエーテル
と、亜硫酸水素ナトリウムとを接触させる事により達成
される。亜硫酸水素ナトリウムは、固体でも水溶液でも
効果大であるが、接触時間等から固体の場合は、溶解度
以上の水を添加し溶解させて用いた方がより効果的であ
る。水溶液は、通常35％前後が市販されているが、必要
に応じて希釈してもかまわない。The present invention can be achieved by bringing aralkyl ether containing an aromatic aldehyde into contact with sodium bisulfite. Sodium bisulfite is effective both as a solid and an aqueous solution, but in the case of a solid due to contact time and the like, it is more effective to add water having a solubility or higher and dissolve it. About 35% of the aqueous solution is usually on the market, but it may be diluted if necessary.
亜硫酸水素ナトリウムの使用量は、芳香族アルデヒドに
対し２〜50倍モルが好適である。更に好ましくは、３〜
40倍モルである。上述の上限値を越える場合には必要以
上に亜硫酸水素ナトリウムを使用する事となり好ましく
ない。下限値未満の場合には芳香族アルデヒドの除去効
果が不充分であり好ましくない。The amount of sodium bisulfite used is preferably 2 to 50 times mol of the aromatic aldehyde. More preferably 3 to
40 times the mole. If the above upper limit is exceeded, sodium bisulfite will be used more than necessary, which is not preferable. If it is less than the lower limit, the effect of removing the aromatic aldehyde is insufficient, which is not preferable.
芳香族アルデヒドを含むアラルキルエーテルと、亜硫酸
水素ナトリウムとを接触させる時の温度は40℃以下が好
適である。更に好ましくは、35℃以下である。上述の上
限値を越える場合には、芳香族アルデヒドの除去効果が
不充分であり好ましくない。また必要以上に低温で接触
させても効果は変わらない。The temperature at which the aralkyl ether containing an aromatic aldehyde and sodium bisulfite are brought into contact with each other is preferably 40 ° C. or lower. More preferably, it is 35 ° C or lower. When the amount exceeds the above upper limit, the effect of removing the aromatic aldehyde is insufficient, which is not preferable. Further, the effect does not change even if they are contacted at a temperature lower than necessary.
本発明は、アラルキルエーテル（油層）と亜硫酸水素ナ
トリウム水溶液とを接触させる必要がある為、通常は撹
拌をおこなう。圧力は、常圧または加圧が好ましい。接
触時間は、亜硫酸水素ナトリウムの過剰率、反応温度、
反応機の形状と容量、撹拌機の種類と撹拌数、アラルキ
ルエーテル仕込量、水量により変わりうるもので一概に
は規定できないが、10分以上接触させれば効果は充分で
ある。In the present invention, since it is necessary to bring the aralkyl ether (oil layer) into contact with the sodium hydrogen sulfite aqueous solution, stirring is usually performed. The pressure is preferably normal pressure or increased pressure. The contact time depends on the excess ratio of sodium bisulfite, the reaction temperature,
It may vary depending on the shape and capacity of the reactor, the type and number of stirrers, the charged amount of aralkyl ether, and the amount of water, but cannot be specified unconditionally, but contacting for 10 minutes or more is sufficient for the effect.
アラルキルエーテル中に含有される芳香族アルデヒドと
亜硫酸水素ナトリウムを接触させた後に高純度のアラル
キルエーテルのみを得る方法としては次の様な方法をと
る事ができる。アラルキルエーテル中に含有される芳香
族アルデヒドと、亜硫酸水素ナトリウムを接触させた後
に静置すれば分液するので、水層のみを除去するだけ
で、高純度のアラルキルエーテルが得られる。更に、水
層を除去した後、若干含まれる水を、蒸留法又は吸着除
去法等の方法で除けば、水分を含まないアラルキルエー
テルが得られる。As a method for obtaining only high-purity aralkyl ether after bringing the aromatic aldehyde contained in the aralkyl ether into contact with sodium hydrogen sulfite, the following method can be employed. The aromatic aldehyde contained in the aralkyl ether and sodium bisulfite are brought into contact with each other, and then allowed to stand to cause liquid separation, so that only a water layer is removed to obtain a highly pure aralkyl ether. Further, after removing the water layer, water containing a little is removed by a method such as a distillation method or an adsorption removal method to obtain a water-free aralkyl ether.
以下実施例、比較例で本発明を更に詳細に説明する。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples.
実施例１ 撹拌機、還流冷却器を備えたガラス製の反応機に、1.5
重量％のｐ−メトキシメチルベンズアルデヒドを含む、
純度98％重量％のアラルキルエーテルを100g仕込んだ
後、亜硫酸水素ナトリウムを10.4gと追加水を100g添加
した。20℃で20分間撹拌した後10分間静置した。上層を
ガスクロマトグラフィーで分析した。その結果、ｐ−メ
トキシメチルベンズアルデヒドが0.03重量％まで低下で
きた。Example 1 A glass reactor equipped with a stirrer and reflux condenser was charged with 1.5
Containing p-methoxymethylbenzaldehyde in weight percent,
After charging 100 g of aralkyl ether having a purity of 98% by weight, 10.4 g of sodium bisulfite and 100 g of additional water were added. The mixture was stirred at 20 ° C for 20 minutes and then left standing for 10 minutes. The upper layer was analyzed by gas chromatography. As a result, p-methoxymethylbenzaldehyde could be reduced to 0.03% by weight.
実施例２〜７、比較例１ 実施例１と同様にして、撹拌機、還流冷却器を備えたガ
ラス製の反応機に、第１表に示す粗アラルキルエーテル
を仕込んだ後、亜硫酸水素ナトリウムを第１表に示す様
に添加した。第１表に示す温度で20分間撹拌した後10分
間静置した。上層をガスクロマトグラフィーで分析し
た。結果を第１表に示す。Examples 2 to 7 and Comparative Example 1 In the same manner as in Example 1, a glass reactor equipped with a stirrer and a reflux condenser was charged with the crude aralkyl ether shown in Table 1, and sodium bisulfite was added. It was added as shown in Table 1. After stirring at the temperature shown in Table 1 for 20 minutes, the mixture was allowed to stand for 10 minutes. The upper layer was analyzed by gas chromatography. The results are shown in Table 1.
以上の様に本発明は、アラルキルエーテル中に存在し
て、樹脂製造時に分子量調節を難しくし、樹脂の色相に
悪影響を与える芳香族アルデヒドを、工業的に除去でき
る優れた方法である。しかも亜硫酸水素ナトリウムは安
価であり、コスト的にも有利である。INDUSTRIAL APPLICABILITY As described above, the present invention is an excellent method capable of industrially removing an aromatic aldehyde which is present in an aralkyl ether and which makes it difficult to control the molecular weight during resin production and adversely affects the hue of the resin. Moreover, sodium bisulfite is inexpensive and advantageous in terms of cost.
Claims (2)
るアラルキルエーテルを精製する方法において、40℃以
下で該アルデヒドの２〜50倍モルの亜硫酸水素ナトリウ
ムと該アラルキルエーテルとを接触させる事を特徴とす
るアラルキルエーテルの精製方法。1. A method for purifying an aralkyl ether containing 0.1% by weight or more of an aromatic aldehyde, which comprises contacting the aralkyl ether with sodium bisulfite in an amount of 2 to 50 times the molar amount of the aldehyde at 40 ° C. or lower. A method for purifying aralkyl ether.
シ−ｐ−キシレンである請求項１記載のアラルキルエー
テルの精製方法。2. The method for purifying an aralkyl ether according to claim 1, wherein the aralkyl ether is α, α′-dimethoxy-p-xylene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8804489A JPH0796512B2 (en) | 1989-04-10 | 1989-04-10 | Aralkyl ether purification method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8804489A JPH0796512B2 (en) | 1989-04-10 | 1989-04-10 | Aralkyl ether purification method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02268128A JPH02268128A (en) | 1990-11-01 |
| JPH0796512B2 true JPH0796512B2 (en) | 1995-10-18 |
Family
ID=13931830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8804489A Expired - Lifetime JPH0796512B2 (en) | 1989-04-10 | 1989-04-10 | Aralkyl ether purification method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0796512B2 (en) |
-
1989
- 1989-04-10 JP JP8804489A patent/JPH0796512B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02268128A (en) | 1990-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1198446A (en) | Process of manufacturing diaryl esters of dicarboxylic acids | |
| JPH08295654A (en) | Method for purifying aniline | |
| JPH0796512B2 (en) | Aralkyl ether purification method | |
| JPS5883028A (en) | Preparation of polytetramethylene glycol | |
| GB2030566A (en) | Preparation of 4,4'-dihydroxy- diphenylsulphone | |
| EP3983368B1 (en) | Process for the production of diacyl peroxides | |
| JP2002363132A (en) | Method for producing 2,2,4-trimethyl-1,3-pentanediol diisobutyrate | |
| JPS63303937A (en) | Manufacture of propynol | |
| SU1740365A1 (en) | Method of m-phenoxyphenol synthesis | |
| US4532352A (en) | Separation of aniline and p-fluoroaniline | |
| JPS5926615B2 (en) | Recovery method of trifluoromethanesulfonic acid | |
| JPH0796511B2 (en) | Method for producing aralkyl ether | |
| JP4752300B2 (en) | Process for producing N-ethyl-N- (2-methylphenyl) -2-butenamide | |
| JP2750761B2 (en) | Separation method of substituted aromatic isomers using inclusion complex | |
| JPS6150958A (en) | Method of purifying 4,4'-dihydroxydiphenylsulfone | |
| JPS5814413B2 (en) | How to remove aluminum components | |
| JPH02275834A (en) | Production of highly purified alkoxymethylbenzaldehyde | |
| JPS6169736A (en) | Production of tetralin derivative | |
| JP4930668B2 (en) | Process for producing dihydroxydiphenylsulfone isomer mixture | |
| JPH09316027A (en) | Acrylic acid purification method | |
| JPH0768160B2 (en) | Method for producing alkoxymethylbenzaldehyde | |
| JPS5984832A (en) | Preparation of high-purity 2,5-xylenol | |
| JP3159522B2 (en) | Method for producing high-purity m-phenylenediamine | |
| JPS61215357A (en) | Separation of p-fluoroaniline | |
| EP3983370A1 (en) | Process for the production of diacyl peroxides |