JPS62178534A - Purification of bisphenol compound - Google Patents
Purification of bisphenol compoundInfo
- Publication number
- JPS62178534A JPS62178534A JP1789886A JP1789886A JPS62178534A JP S62178534 A JPS62178534 A JP S62178534A JP 1789886 A JP1789886 A JP 1789886A JP 1789886 A JP1789886 A JP 1789886A JP S62178534 A JPS62178534 A JP S62178534A
- Authority
- JP
- Japan
- Prior art keywords
- bisphenols
- mixed solvent
- bisphenol compound
- purified
- bis
- 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
- 229930185605 Bisphenol Natural products 0.000 title claims abstract description 29
- -1 bisphenol compound Chemical class 0.000 title abstract description 6
- 238000000746 purification Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 13
- 239000012046 mixed solvent Substances 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 24
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 6
- 150000002576 ketones Chemical class 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002989 phenols Chemical class 0.000 abstract description 4
- 239000008096 xylene Substances 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 238000001953 recrystallisation Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000012264 purified product Substances 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RKSBPFMNOJWYSB-UHFFFAOYSA-N 3,3-Bis(4-hydroxyphenyl)pentane Chemical compound C=1C=C(O)C=CC=1C(CC)(CC)C1=CC=C(O)C=C1 RKSBPFMNOJWYSB-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は各種重合体の原料として有用なビスフェノール
類の精製方法に関し、詳しくは高純度の精製品を効率よ
く得る方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for purifying bisphenols useful as raw materials for various polymers, and more particularly to a method for efficiently obtaining purified products of high purity.
ポリカーボネート樹脂、エポキシ樹脂などの原料として
用いられるビスフェノール類は通常、フェノール類とケ
トンとを酸性触媒の存在下に反応させることによって製
造されている。Bisphenols used as raw materials for polycarbonate resins, epoxy resins, and the like are usually produced by reacting phenols and ketones in the presence of an acidic catalyst.
しかしながら、このようにして得られるビスフェノール
類には異性体をはじめとして種々の不純物が含まれてい
る。それ故、この粗製ビスフェノール類は適当な手段で
精製したのち各種用途に供される。ビスフェノール類の
精製方法としては、精留による方法と再結晶による方法
が知られており、主として後者の方法が採用されている
。However, the bisphenols obtained in this way contain various impurities including isomers. Therefore, these crude bisphenols are purified by appropriate means and then used for various purposes. As a method for purifying bisphenols, a method using rectification and a method using recrystallization are known, and the latter method is mainly employed.
再結晶によるビスフェノール類の精製方法として、たと
えば米国特許第４．３００．０００号明細書に水とメタ
ノールの混合物を用いて行なう方法が開示されている。As a method for purifying bisphenols by recrystallization, for example, US Pat. No. 4,300,000 discloses a method using a mixture of water and methanol.
しかし、この方法により得られるビスフェノール類は製
品純度が十分ではない。また、特開昭６０−４８９４１
号公報にはケトンと芳香族炭化水素よりなる混合溶媒を
用いて行なう方法が記載されているが、この方法は溶媒
効率が十分でないという問題があった。However, the bisphenols obtained by this method do not have sufficient product purity. Also, JP-A-60-48941
Although the publication describes a method using a mixed solvent consisting of a ketone and an aromatic hydrocarbon, this method has a problem in that the solvent efficiency is insufficient.
本発明は、これら従来法の欠点を解消したビスフェノー
ル類の精製方法の提供を特徴とする特許である。The present invention is a patent that is characterized by providing a method for purifying bisphenols that eliminates the drawbacks of these conventional methods.
すなわち本発明は、粗製ビスフェノール類を精製するに
あたり、アルコール類と芳香族炭化水素よりなる混合溶
媒を用いて再結晶させることを特徴とするビスフェノー
ル類の精製法である。That is, the present invention is a method for purifying bisphenols, which is characterized by recrystallizing crude bisphenols using a mixed solvent consisting of alcohols and aromatic hydrocarbons.
前述した如く、ビスフェノール類はフェノール類とケト
ンとを酸性触媒の存在下で反応させることによって得ら
れるが、本発明の方法は任意のビスフェノール類に適用
できる。ビスフェノール類を例示すると、２，２−ビス
（４−ヒドロキシフェニル）プロパン、ビス（４−ヒド
ロキシフェニル）メタン、１．１−ビス（４−ヒドロキ
シフェニル）エタン、３，３−ビス（４−ヒドロキシフ
ェニル）ペンタン、１−フェニル−１，１−ビス（４−
オキシフェニル）エタン、４．４”−ジヒドロキシテト
ラフェニルメタン、１．２−ビス（４−ヒドロキシフェ
ニル）エタン、１．６−ビス（４−ヒドロキシフェニル
）ヘキサン、１．１−ビス（４−ヒドロキシフェニル）
シクロヘキサン、２．２−ビス（３−メチル−４−ヒド
ロキシフェニル）プロパンなどを挙げることができる。As mentioned above, bisphenols can be obtained by reacting phenols and ketones in the presence of an acidic catalyst, but the method of the present invention can be applied to any bisphenols. Examples of bisphenols include 2,2-bis(4-hydroxyphenyl)propane, bis(4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)ethane, and 3,3-bis(4-hydroxyphenyl). phenyl)pentane, 1-phenyl-1,1-bis(4-
oxyphenyl)ethane, 4.4”-dihydroxytetraphenylmethane, 1.2-bis(4-hydroxyphenyl)ethane, 1.6-bis(4-hydroxyphenyl)hexane, 1.1-bis(4-hydroxy phenyl)
Examples include cyclohexane and 2,2-bis(3-methyl-4-hydroxyphenyl)propane.
これらビスフェノール類の製造の際に異性体が副生ずる
ほか、原料に由来する未反応フェノール類やケトン縮合
物などの不純物が含まれている。In addition to isomers produced as by-products during the production of these bisphenols, they also contain impurities such as unreacted phenols and ketone condensates derived from raw materials.
そこで、このような粗製ビスフェノールを精製するにあ
たり、本発明ではアルコール類と芳香族炭化水素よりな
る混合溶媒を用いて再結晶させるのである。ここで、ア
ルコール類としては炭素数１〜１０個、好ましくは１〜
５個の脂肪族飽和アルコールが好適に用いられ、とりわ
けメタノール。Therefore, in order to purify such crude bisphenol, in the present invention, it is recrystallized using a mixed solvent consisting of alcohols and aromatic hydrocarbons. Here, the alcohol has 1 to 10 carbon atoms, preferably 1 to 10 carbon atoms.
Five aliphatic saturated alcohols are preferably used, especially methanol.
エタノール、プロパツール、ブタノールなどが好ましい
。なお、本発明においては、後述するように、混合溶媒
中のアルコール類は留去し、必要に応じ再使用するので
、組合せる芳香族炭化水素よりも沸点の低いアルコール
類を選択することが必要である。Ethanol, propatool, butanol, etc. are preferred. In addition, in the present invention, as described later, the alcohols in the mixed solvent are distilled off and reused as necessary, so it is necessary to select alcohols with a lower boiling point than the aromatic hydrocarbons to be combined. It is.
次に、芳香族炭化水素としてはベンゼンやアルキル置換
ベンゼン類が好適に用いられ、置換基としてのアルキル
基は炭素数１〜５個、好ましくは１〜３個であり、アル
キル基の数は１〜３個で、複数個の場合は同一であって
も異なったものであってもよい。好適な具体例はベンゼ
ン、トルエン。Next, as the aromatic hydrocarbon, benzene and alkyl-substituted benzenes are preferably used, and the alkyl group as a substituent has 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms, and the number of alkyl groups is 1. ~3 pieces, and in the case of multiple pieces, they may be the same or different. Preferred specific examples are benzene and toluene.
キシレン、エチルベンゼンなどである。These include xylene and ethylbenzene.
アルコール類と芳香族炭化水素よりなる混合溶媒は、体
積比でアルコール類５〜９に対し芳香族炭化水素５〜１
の割合で配合して用いる。その理由は、アルコール類の
割合が多すぎると、生成物の純度が低下し、一方芳香族
炭化水素の割合が多いと、ビスフェノール類の収率が低
下するからである。The mixed solvent consisting of alcohols and aromatic hydrocarbons has a volume ratio of 5 to 9 alcohols to 5 to 1 aromatic hydrocarbons.
It is used by mixing in the ratio of The reason is that if the proportion of alcohols is too high, the purity of the product will decrease, while if the proportion of aromatic hydrocarbons is too high, the yield of bisphenols will decrease.
粗製ビスフェノール類はこの混合溶媒に溶解させたのち
再結晶させるが、別法としてビスフェノール類を混合溶
媒を形成する一方の物質、たとえばアルコール類に溶解
させた後、他方の物質を加えてもよい。The crude bisphenols are dissolved in this mixed solvent and then recrystallized, but alternatively, the bisphenols may be dissolved in one substance forming the mixed solvent, such as an alcohol, and then the other substance is added.
ビスフェノール類を再結晶化させる方法としては、常圧
もしくは減圧下、好ましくは３００〜５１１Ｈｇ程度の
減圧下にアルコール類を留去してビスフェノール類を析
出させ、次いで濾別する方法が好ましい。この方法によ
ると、不純物は芳香族炭化水素に移行し、高純度に精製
されたビスフェノール類が得られる。As a method for recrystallizing bisphenols, it is preferable to precipitate bisphenols by distilling off alcohols under normal pressure or reduced pressure, preferably about 300 to 511 Hg, and then filtering them out. According to this method, impurities are transferred to aromatic hydrocarbons, and highly purified bisphenols are obtained.
本発明によれば、純度９９．０〜９９．９％という高純
度のビスフェノール類を効率よく製造することができる
。しかも、溶媒効率が良いので、実用性に冨む方法であ
る。得られたビスフェノール類はポリカーボネート樹脂
、エポキシ樹脂などの重合体の原料として有用である。According to the present invention, highly pure bisphenols with a purity of 99.0 to 99.9% can be efficiently produced. Moreover, since the solvent efficiency is good, this method is highly practical. The obtained bisphenols are useful as raw materials for polymers such as polycarbonate resins and epoxy resins.
次に、本発明を実施例により詳しく説明する。 Next, the present invention will be explained in detail with reference to examples.
実施例１
０−クレゾール９７．２ ｇ （０，９モル）に対して
アセトン１７．４ ｇ （０，３モル）と触媒としての
メルカプト酢酸１ｍＡを加え、６０℃に昇温してから塩
化水素ガスを吹き込みながら攪拌して１０時間反応させ
た。Example 1 17.4 g (0.3 mol) of acetone and 1 mA of mercaptoacetic acid as a catalyst were added to 97.2 g (0.9 mol) of 0-cresol, and after raising the temperature to 60°C, hydrogen chloride was added. The mixture was stirred and reacted for 10 hours while blowing gas.
生成した結晶を温水により３回洗浄して２．２−ビス（
３−メチル−４−ヒドロキシフェニル）プロパンの粗製
品（純度９１．７％）を得た。The formed crystals were washed three times with warm water to obtain 2,2-bis(
A crude product of 3-methyl-4-hydroxyphenyl)propane (purity 91.7%) was obtained.
次に、この粗製品をメタノール１２０ｍｊ２に溶解した
のちキシレン３９ｍ１を加えて混合した。しかる後、１
０ ｍｍ ｌ ｇの減圧下にメタノールを全量留去した
。この結果、２．２−ビス（３−メチル−４−ヒドロキ
シフェニル）プロパンが白色結晶として析出した。Next, this crude product was dissolved in 120 mj2 of methanol, and then 39 m1 of xylene was added and mixed. After that, 1
The entire amount of methanol was distilled off under reduced pressure of 0 mm lg. As a result, 2,2-bis(3-methyl-4-hydroxyphenyl)propane was precipitated as white crystals.
得られた結晶を濾別したのち乾燥した。精製品の収量は
４４．５ｇであり、収率は５７．９％、純度９９．８％
であった。この場合の溶媒効率は２９．６％であった。The obtained crystals were filtered and then dried. The yield of purified product was 44.5g, yield 57.9%, purity 99.8%
Met. The solvent efficiency in this case was 29.6%.
実施例２
フェノール８４．７ ｇ （０，９モル）に対して３−
ペンタノン２５．８ ｇ （０，３ｇモル）と触媒とし
てのメルカプト酢酸１ｍｌを加え、以下実施例１と同様
にして反応を行ない粗製３．３−ビス（４−ヒドロキシ
フェニル）ペンタン（純度９３．４％）を得た。Example 2 3- for 84.7 g (0.9 mol) of phenol
25.8 g (0.3 g mol) of pentanone and 1 ml of mercaptoacetic acid as a catalyst were added, and the reaction was carried out in the same manner as in Example 1 to obtain crude 3.3-bis(4-hydroxyphenyl)pentane (purity 93.4). %) was obtained.
次に、アルコール類としてエタノールを使用したほかは
実施例１と同様にして精製３．３−ビス（４−ヒドロキ
シフェニル）ペンタン４５．７ ｇを得た。この精製品
の収率は５９．５％、純度９９．１％であった。また、
この場合の溶媒効率は３０．５％であつた。Next, 45.7 g of purified 3.3-bis(4-hydroxyphenyl)pentane was obtained in the same manner as in Example 1 except that ethanol was used as the alcohol. The yield of this purified product was 59.5% and the purity was 99.1%. Also,
The solvent efficiency in this case was 30.5%.
実施例３
フェノール８４．７ ｇ （０，９モル）に対してアセ
トフェノン３６ ｇ （０，３モル）と触媒としてのメ
ルカプト酢酸１ ｍ ｌを加え、以下実施例１と同様に
して反応ヲ行ない粗製１−フェニル−１，１−ビス（４
−ヒドロキシフェニル）エタンを得た。この粗製品の純
度９２．８％であった。Example 3 To 84.7 g (0.9 mol) of phenol, 36 g (0.3 mol) of acetophenone and 1 ml of mercaptoacetic acid as a catalyst were added, and the reaction was carried out in the same manner as in Example 1 to obtain a crude product. 1-phenyl-1,1-bis(4
-hydroxyphenyl)ethane was obtained. The purity of this crude product was 92.8%.
粗製品の精製にあたって、メタノール１２０ｍｊ２とキ
シレン５Ｑｍｊ！を用いて実施例１と同様の操作を行な
い精製された１−フェニル−１，１−ビス（４−ヒドロ
キシフェニル）エタン４５．３ ｇを得た。In purifying the crude product, 120mj2 of methanol and 5Qmj of xylene were used! 45.3 g of purified 1-phenyl-1,1-bis(4-hydroxyphenyl)ethane was obtained by carrying out the same operation as in Example 1.
精製品の収率は５２．１％であり、純度は９９．３％で
あった。また、この場合の溶媒効率は２５．２％であっ
た。The yield of the purified product was 52.1%, and the purity was 99.3%. Moreover, the solvent efficiency in this case was 25.2%.
比較例１
実施例１と同様にして得られた粗製２．２−ビス（３−
メチル−４−ヒドロキシフェニル）プロパンをメチルイ
ソブチルケトン３０ｍ１とトルエン２８０ｍ１ｌよりな
る混合溶媒を用いて実施例１と同様にして精製した。Comparative Example 1 Crude 2.2-bis(3-
Methyl-4-hydroxyphenyl)propane was purified in the same manner as in Example 1 using a mixed solvent consisting of 30 ml of methyl isobutyl ketone and 280 ml of toluene.
精製品の収量は４３ｇ、純度は９９．３％であった。The yield of the purified product was 43 g, and the purity was 99.3%.
また、このときの溶媒効率は１３．９％であった。Moreover, the solvent efficiency at this time was 13.9%.
比較例２
実施例１と同様にして得られた粗製２，２−ビス（３−
メチル−４−ヒドロキシフェニル）プロパンを水１００
ｍｊ＋とメタノール１００ｍｊ！の混合溶媒を用いて実
施例１と同様にして精製した。Comparative Example 2 Crude 2,2-bis(3-
Methyl-4-hydroxyphenyl)propane to 100% water
mj+ and methanol 100mj! Purification was performed in the same manner as in Example 1 using a mixed solvent of
精製品の収量は４５ｇ、純度は９７．５％であった。The yield of the purified product was 45 g, and the purity was 97.5%.
また、この場合の溶媒効率は２２．５％であった。Moreover, the solvent efficiency in this case was 22.5%.
Claims (2)
コール類と芳香族炭化水素よりなる混合溶媒を用いて再
結晶させることを特徴とするビスフェノール類の精製法
。(1) A method for purifying bisphenols, which comprises recrystallizing crude bisphenols using a mixed solvent of alcohols and aromatic hydrocarbons.
が、体積比で前者：後者＝５〜９：５〜１の混合物であ
る特許請求の範囲第１項記載の方法。(2) The method according to claim 1, wherein the mixed solvent consisting of an alcohol and an aromatic hydrocarbon is a mixture in a volume ratio of the former to the latter = 5 to 9:5 to 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1789886A JPS62178534A (en) | 1986-01-31 | 1986-01-31 | Purification of bisphenol compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1789886A JPS62178534A (en) | 1986-01-31 | 1986-01-31 | Purification of bisphenol compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62178534A true JPS62178534A (en) | 1987-08-05 |
Family
ID=11956551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1789886A Pending JPS62178534A (en) | 1986-01-31 | 1986-01-31 | Purification of bisphenol compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62178534A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05294871A (en) * | 1992-04-14 | 1993-11-09 | Nippon Steel Chem Co Ltd | Production of bisphenol a |
| WO2003076378A1 (en) * | 2002-03-13 | 2003-09-18 | Mitsubishi Chemical Corporation | Process for producing bisphenol a |
| NL1026555C2 (en) * | 2003-07-03 | 2006-09-27 | Honshu Chemical Industry Co | Process for the preparation of high purity 1,1-bis (4-hydroxypheny) cyclohexanes. |
| WO2008010526A1 (en) * | 2006-07-19 | 2008-01-24 | Nipponkayaku Kabushikikaisha | 1,1-bis(4-hydroxyphenyl)-1-phenylethane and thermal recording material using the same |
| JP2008290983A (en) * | 2007-05-25 | 2008-12-04 | Api Corporation | Granular powder of bisphenol compound and method for producing the same |
| JP2017200913A (en) * | 2016-04-28 | 2017-11-09 | 三菱ケミカル株式会社 | Method for producing bisphenol compound |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4885561A (en) * | 1972-02-17 | 1973-11-13 | ||
| JPS4948545A (en) * | 1972-05-02 | 1974-05-10 |
-
1986
- 1986-01-31 JP JP1789886A patent/JPS62178534A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4885561A (en) * | 1972-02-17 | 1973-11-13 | ||
| JPS4948545A (en) * | 1972-05-02 | 1974-05-10 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05294871A (en) * | 1992-04-14 | 1993-11-09 | Nippon Steel Chem Co Ltd | Production of bisphenol a |
| WO2003076378A1 (en) * | 2002-03-13 | 2003-09-18 | Mitsubishi Chemical Corporation | Process for producing bisphenol a |
| JPWO2003076378A1 (en) * | 2002-03-13 | 2005-07-07 | 三菱化学株式会社 | Method for producing bisphenol A |
| NL1026555C2 (en) * | 2003-07-03 | 2006-09-27 | Honshu Chemical Industry Co | Process for the preparation of high purity 1,1-bis (4-hydroxypheny) cyclohexanes. |
| WO2008010526A1 (en) * | 2006-07-19 | 2008-01-24 | Nipponkayaku Kabushikikaisha | 1,1-bis(4-hydroxyphenyl)-1-phenylethane and thermal recording material using the same |
| US8216970B2 (en) | 2006-07-19 | 2012-07-10 | Nipponkayaku Kabushikikaisha | 1,1-bis(4-hydroxyphenyl)-1-phenylethane and thermal recording material for recording the same |
| JP2008290983A (en) * | 2007-05-25 | 2008-12-04 | Api Corporation | Granular powder of bisphenol compound and method for producing the same |
| JP2017200913A (en) * | 2016-04-28 | 2017-11-09 | 三菱ケミカル株式会社 | Method for producing bisphenol compound |
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