JP2874281B2 - Method for separating and purifying biphenyl-4,4'-diol - Google Patents
Method for separating and purifying biphenyl-4,4'-diolInfo
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- JP2874281B2 JP2874281B2 JP12665390A JP12665390A JP2874281B2 JP 2874281 B2 JP2874281 B2 JP 2874281B2 JP 12665390 A JP12665390 A JP 12665390A JP 12665390 A JP12665390 A JP 12665390A JP 2874281 B2 JP2874281 B2 JP 2874281B2
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- bpdo
- crude
- diol
- water
- biphenyl
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、ビフェニル−4,4′−ジオール（以下BPDO
と略記する）の分離精製方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to biphenyl-4,4'-diol (hereinafter referred to as BPDO).
Abbreviated as).
BPDOは、エンジニアリングプラスチックス特に液晶ポ
リマーのモノマーとして近年注目を集めており、又、高
分子材料の酸化防止剤としても有用な化合物である。BPDO has recently attracted attention as a monomer of engineering plastics, especially as a liquid crystal polymer, and is also a useful compound as an antioxidant for polymer materials.
BPDOの製造方法として、これまで幾つかの方法が提案
されている。例えば、 ビフェニル類を臭素化して加水分解する方法、 ビフェニル類をスルホン化してアルカリ溶融する方
法、 2,6−ジ−tert−ブチルフェノール類を酸化カップリ
ングして得られる、テトラ−tert−ブチルジフェノール
類を酸触媒下に脱アルキルする方法、 Ｐ−クロロフェノール類を脱ハロゲン二量化する方法 等が知られている。Several methods have been proposed for producing BPDO. For example, a method of brominating and hydrolyzing biphenyls, a method of sulfonating biphenyls and alkali-melting, and tetra-tert-butyldiphenol obtained by oxidative coupling of 2,6-di-tert-butylphenols There are known a method of dealkylating phenols in the presence of an acid catalyst, a method of dehalogenating P-chlorophenols, and the like.
これら各種製造方法から得られる粗製BPDO中には、い
ずれもアルカリ金属化合物、アルカリ土類金属化合物、
遷移金属化合物、アルミニウム化合物又はイオウ酸化物
等の、無機不純物が含まれている。具体的には、Na,K,C
a,Cu,Fe,Ni,Cr,Al等のハロゲン化物、酸化物もしくは硫
酸塩である。これら不純物の混入は、外観のみならずポ
リマーの重合性等に悪影響を及ぼすため、除去が必要で
ある。これら不純物の除去法については、BPDOが高融
点、高沸点物質であり、蒸留操作による精製は困難であ
る為、再結晶法による精製方法が幾つか提案されてい
る。In the crude BPDO obtained from these various production methods, all are alkali metal compounds, alkaline earth metal compounds,
It contains inorganic impurities such as transition metal compounds, aluminum compounds or sulfur oxides. Specifically, Na, K, C
a, a halide such as Cu, Fe, Ni, Cr and Al, an oxide or a sulfate. The incorporation of these impurities has an adverse effect not only on the appearance but also on the polymerizability of the polymer and the like, so it is necessary to remove them. Regarding a method for removing these impurities, BPDO is a substance having a high melting point and a high boiling point, and it is difficult to purify it by a distillation operation. Therefore, several purification methods by a recrystallization method have been proposed.
例えば、特開昭59−98027号公報には粗製BPDOを脂肪
族低級アルコール、ケトン類又は環状エーテルに溶解
後、この溶液に芳香族炭化水素類を加え、得られた溶液
を蒸留して上記アルコール、ケトン類又は環状エーテル
の大部分を留去してBPDOを析出させ、これを分離する方
法が開示されている。ところがこの方法では、水が存在
しないためBPDO中の不純物であるアルカリ金属化合物、
アルカリ土類金属化合物、遷移金属化合物、アルミニウ
ム化合物又はイオウ酸化物等は、ほとんど除去出来ずBP
DO類の純度が向上しないという問題点があった。For example, JP-A-59-98027 discloses that crude BPDO is dissolved in an aliphatic lower alcohol, a ketone or a cyclic ether, an aromatic hydrocarbon is added to this solution, and the obtained solution is distilled to obtain the above alcohol. A method is disclosed in which most of ketones or cyclic ethers are distilled off to precipitate BPDO, which is then separated. However, in this method, since there is no water, an alkali metal compound which is an impurity in BPDO,
Alkaline earth metal compounds, transition metal compounds, aluminum compounds or sulfur oxides can hardly be removed and BP
There was a problem that the purity of DOs did not improve.
又、特開平１−226841号公報には、粗製BPDOを、脂肪
族低級ケトン類及びアルコール類から選ばれる一種以上
の有機溶媒と水との混合溶媒に溶解し活性炭処理した
後、溶媒の一部を留去し得られる溶液を冷却して晶析を
行い、生成する結晶を分離する方法が開示されている。
ところがこの方法では、BTPDOの回収率が低く、加えて
晶析操作には冷却を必要とし長時間を要するという問題
点があり工業的に有利な方法とはいえなかった。In JP-A 1-226841, crude BPDO is dissolved in a mixed solvent of water and at least one organic solvent selected from aliphatic lower ketones and alcohols and activated carbon treatment, and then a part of the solvent is treated. There is disclosed a method of cooling a solution obtained by distilling off and crystallization to separate generated crystals.
However, this method has a problem that the recovery rate of BTPDO is low, and in addition, the crystallization operation requires cooling and requires a long time, and thus cannot be said to be an industrially advantageous method.
本発明の目的は、このように従来分離精製工程上繁雑
でかつ経済的にも問題があったBPDOの粉体としての分離
回収方法に於いて、簡単な操作により短時間で高純度か
つ色相の優れたBPDOを得ることが出来るBPDOの工業的プ
ロセスを開発することである。An object of the present invention is to provide a method for separating and recovering BPDO as a powder, which has conventionally been complicated and economically problematic in the separation and purification process, and has a simple operation to achieve high purity and hue in a short time. The purpose is to develop an industrial process of BPDO that can obtain excellent BPDO.
本発明者らは、前記の問題点を解決するために種々研
究を重ねた結果、本発明に到達したものである。The present inventors have conducted various studies in order to solve the above-mentioned problems, and as a result, have reached the present invention.
すなわち、本発明のBPDOの精製方法は、製造工程で得
られた粗製BPDOを有機溶媒に抽出し、抽出溶液を熱水中
に滴下し、同時に溶媒を留去しながらBPDOを水中に分散
した粉体として回収することを特徴とするBPDOの分離精
製方法にある。That is, the method for purifying BPDO of the present invention comprises extracting the crude BPDO obtained in the production step into an organic solvent, dropping the extracted solution into hot water, and dispersing the BPDO in water while simultaneously evaporating the solvent. A method for separating and purifying BPDO, characterized in that it is recovered as a body.
以下その詳細について説明する。 The details will be described below.
本発明によるBPDOの分離精製方法は、製造工程で得ら
れた粗製BPDOを有機溶媒に抽出し、抽出溶液を熱水中に
滴下し、同時に溶媒を留去しながらBPDOを水中に分散し
た粉体として取り上げることにより達成される。The method for separating and purifying BPDO according to the present invention comprises extracting the crude BPDO obtained in the production step into an organic solvent, dropping the extracted solution into hot water, and dispersing the BPDO in water while simultaneously distilling off the solvent. Achieved by taking up.
粗製BPDO中の無機不純物は、製法により含有成分が異
なるが、一般に臭素化ビフェニルの加水分解法では、N
a,K,Cu,Fe等のハロゲン化物や酸化物が、スルホン酸塩
のアルカリ溶融法では、Na,K,Ca,Fe等の硫酸塩、酸化物
が、フェノール類の酸化カップリング法では、Al,Cu,Na
等のハロゲン化物、酸化物、硫酸塩が含まれてくる。Inorganic impurities in crude BPDO have different components depending on the production method.In general, in the hydrolysis method of brominated biphenyl, N
a, K, Cu, Fe and other halides and oxides, in the alkali melting method of sulfonates, Na, K, Ca, Fe and other sulfates and oxides, in the oxidation coupling method of phenols, Al, Cu, Na
Halides, oxides and sulfates.
粗製BPDOは、多くはアルカリ性水溶液の形態で得られ
てくるため、酸を添加し酸性に戻して、水層から有機溶
媒に抽出する。Since crude BPDO is mostly obtained in the form of an alkaline aqueous solution, it is returned to acidic by adding an acid and extracted from the aqueous layer into an organic solvent.
本発明でいうBPDOを抽出する有機溶媒とは、BPDOを溶
解する良溶媒を指し、100℃以下で蒸留もしくは水との
共沸蒸留が出来るアルコール類又はケトン類が好まし
い。例えば、メタノール、エタノール、１−プロパノー
ル、２−プロパノール、１−ブタノール、２−ブタノー
ル、ｔ−ブタノール、アミルアルコール、シクロヘキサ
ノール、アセトン、メチルエチルケトン、ジエチルケト
ン、メチルイソブチルケトン、シクロヘキサノン等が挙
げられる。これらの溶媒の中でも、メチルエチルケト
ン、メチルイソブチルケトンはBPDOの溶解度が高く特に
好ましい溶媒である。The organic solvent for extracting BPDO in the present invention refers to a good solvent that dissolves BPDO, and is preferably an alcohol or ketone that can be distilled at 100 ° C. or lower or azeotropically distilled with water. Examples include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, amyl alcohol, cyclohexanol, acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, cyclohexanone, and the like. Among these solvents, methyl ethyl ketone and methyl isobutyl ketone are particularly preferred because of their high solubility of BPDO.
これら溶媒の使用量は、BPDOが溶解する量以上を用い
れば十分であり、溶剤の種類によっても異なるが、通常
BPDO溶液濃度で１〜50重量％程度である。The amount of these solvents used is sufficient if it is greater than or equal to the amount in which BPDO is dissolved, and varies depending on the type of solvent.
The concentration of the BPDO solution is about 1 to 50% by weight.
粗製BPDO抽出液に不溶解物が混在するときはこれを濾
過し、又、着色が著しいときは必要に応じて活性炭処理
することも出来る。活性炭の使用量は、BPDOに対し約0.
01〜50重量％程度が好ましい。活性炭処理の温度は室温
以上溶媒の沸点以下が好ましい。When insoluble matter is mixed in the crude BPDO extract, the insoluble matter can be filtered, and when the coloring is remarkable, activated carbon treatment can be performed if necessary. The amount of activated carbon used is about 0% for BPDO.
About 01 to 50% by weight is preferable. The temperature of the activated carbon treatment is preferably from room temperature to the boiling point of the solvent.
活性炭処理の方法としては、活性炭を粗製BPDO抽出液
に添加して接触させるか、活性炭を吸着塔に充填して粗
製BPDO抽出液を通液して接触させてもよく、その方法は
限定されない。もちろん粗製BPDO抽出液の着色分が少な
い場合には、活性炭処理を行うことなく次の操作に移っ
てもよい。The method of the activated carbon treatment may be such that activated carbon is added to the crude BPDO extract and brought into contact with the crude BPDO extract, or the activated carbon may be filled in an adsorption tower and passed through the crude BPDO extract and brought into contact, and the method is not limited. Of course, if the crude BPDO extract has a small amount of color, the next operation may be performed without performing the activated carbon treatment.
熱水の量は、脱溶媒終了後のBPDOのスラリー濃度によ
り決まり、スラリーとして取扱いが可能でかつ経済的に
有利な量が選ばれる。The amount of hot water is determined by the BPDO slurry concentration after the completion of the desolvation, and an amount that can be handled as a slurry and is economically advantageous is selected.
熱水の温度は、粗製BPDO抽出液の溶媒の沸点もしくは
水との共沸温度のいずれか以上であり、通常40〜100℃
程度である。脱溶媒中、脱溶媒槽内は、BPDOが水中に均
一に分散するように十分な撹拌を行っておくことが望ま
しい。The temperature of hot water is at least one of the boiling point of the solvent of the crude BPDO extract or the azeotropic temperature with water, and is usually 40 to 100 ° C.
It is about. During desolvation, it is desirable that sufficient stirring is performed in the desolvation tank so that BPDO is uniformly dispersed in water.
熱水中への粗製BPDO抽出液の添加方法としては、粗製
BPDO抽出液を加熱水面に滴下する方法や、口径や小さい
ノズルから加熱水面へ噴出させる方法が選ばれる。又、
熱水中への粗製BPDO抽出液の添加速度が有機溶媒の留出
速度より速いと、BPDOの固結により不純物を取り込む可
能性があるので、瞬時に有機溶媒を系外へ留出するため
に添加速度を有機溶媒の留出速度以下にすることが望ま
しい。As a method of adding the crude BPDO extract to hot water,
A method of dropping the BPDO extract on the heated water surface, or a method of ejecting the BPDO extract from the small-diameter nozzle to the heated water surface is selected. or,
If the rate of addition of the crude BPDO extract to hot water is faster than the rate of distilling out the organic solvent, impurities may be taken in due to the solidification of BPDO. It is desirable that the rate of addition be equal to or lower than the rate of distillation of the organic solvent.
本発明の方法は、通常常圧下で行われるが減圧下でも
実施可能である。The method of the present invention is generally carried out under normal pressure, but can also be carried out under reduced pressure.
粗製BPDO抽出液を上記熱水中に滴下し、同時に前述の
操作により脱溶媒を行うと、BPDOは短時間のうちに析出
し、水中に均一に分散した微粉体となる。従って析出し
たBPDO粉体は、そのスラリー液から慣用の方法で短時間
のうちに容易に分離回収が出来る。例えば、遠心分離、
吸引濾過、スプレードライ等により分離回収出来る。When the crude BPDO extract is dropped into the hot water and the solvent is removed by the above-described operation at the same time, the BPDO precipitates in a short time and becomes a fine powder uniformly dispersed in the water. Therefore, the precipitated BPDO powder can be easily separated and recovered from the slurry liquid by a conventional method in a short time. For example, centrifugation,
It can be separated and collected by suction filtration, spray drying, etc.
これらの方法により、BPDOを製造工程より得られた反
応液から微粉体として定量的に分離回収できる。According to these methods, BPDO can be quantitatively separated and recovered as fine powder from the reaction solution obtained from the production process.
こうして得られた精製BPDOの回収率は、非常に高くほ
ぼ定量的となる。又、得られた精製BPDOは粗製BPDOに含
まれていたアルカリ金属化合物、アルカリ土類金属化合
物、遷移金属化合物、アルミニウム化合物、イオウ酸化
物等の無機不純物をほとんど含まない高純度のもので、
色相もよく白色の結晶である。The recovery of the purified BPDO thus obtained is very high and almost quantitative. In addition, the obtained purified BPDO is of high purity containing almost no inorganic impurities such as alkali metal compounds, alkaline earth metal compounds, transition metal compounds, aluminum compounds and sulfur oxides contained in the crude BPDO,
It is a white crystal with good hue.
以上の説明から明らかなように本発明の方法によれ
ば、簡単な操作により短時間で、無機不純物を低減化し
た高純度かつ色相の優れたBPDOを工業的に有利な方法で
製造することが出来る。As is apparent from the above description, according to the method of the present invention, in a short time by a simple operation, it is possible to produce BPDO having high purity and excellent hue with reduced inorganic impurities in an industrially advantageous manner. I can do it.
以下、本発明を実施例により説明するが、本発明はこ
れらの実施例に限定されるものではない。Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to these examples.
実施例１ 4,4′−ジブロモビフェニルのアルカリ加水分解反応
によって得られた、粗製BPDO（Fe150ppm,Cu300ppm,Na15
00ppmを含有）14gをスラリー状で含む反応液にメチルエ
チルケトン200mlを加え抽出した。Example 1 Crude BPDO (Fe150ppm, Cu300ppm, Na15) obtained by alkaline hydrolysis of 4,4'-dibromobiphenyl
200 ml of methyl ethyl ketone was added to a reaction solution containing 14 g of a slurry (containing 00 ppm) in the form of a slurry, followed by extraction.
次いで、90℃に加熱した600mlの熱水中に上記抽出液
を、0.6/hrの滴下速度で滴下しながらメチルエチルケ
トンを連続的に留去した。蒸留時、BPDOは直ちに析出し
微粉体となって水中に均一に分散した。Subsequently, methyl ethyl ketone was continuously distilled off while dropping the above extract at a dropping rate of 0.6 / hr into 600 ml of hot water heated to 90 ° C. During the distillation, BPDO immediately precipitated and became fine powder, which was uniformly dispersed in water.
粗製BPDO抽出液の滴下終了後、得られたBPDOの水スラ
リーを濾過し、粉体を水２で洗浄して乾燥を行い、白
色の精製BPDO13.5gを得た。回収率は96.4％であり、精
製BPDOを分析したところ、純度99.9％,Fe5ppm,Cu5ppm,N
a10ppmであった。After the completion of the dropwise addition of the crude BPDO extract, the obtained water slurry of BPDO was filtered, and the powder was washed with water 2 and dried to obtain 13.5 g of white purified BPDO. The recovery rate was 96.4%. When the purified BPDO was analyzed, the purity was 99.9%, Fe5ppm, Cu5ppm, N
a was 10 ppm.
実施例２ 4,4′−ジブロモビフェニルのアルカリ加水分解反応
によって得られた、粗製BPDO（Fe200ppm,Cu350ppm,Na20
00ppmを含有）14gをスラリー状で含む反応液にメチルエ
チルケトン200mlを加え抽出し、粉末活性炭1.4gを加え
て30分間加熱還流した。加熱還流した後、室温まで冷却
して濾過し、活性炭及び粗製BPDO中の不溶解物を濾別し
た。Example 2 Crude BPDO (Fe200ppm, Cu350ppm, Na20) obtained by alkaline hydrolysis of 4,4'-dibromobiphenyl
200 ml of methyl ethyl ketone was added to the reaction solution containing 14 g of the slurry (containing 00 ppm) in the form of a slurry, followed by extraction. After heating under reflux, the mixture was cooled to room temperature and filtered, and insolubles in activated carbon and crude BPDO were separated by filtration.
次いで、90℃に加熱した600mlの熱水中に上記抽出液
を、0.4/hrの滴下速度で滴下しながらメチルエチルケ
トンを連続的に留去した。蒸留時、BPDOは直ちに析出し
微粉体となって水中に均一に分散した。Subsequently, methyl ethyl ketone was continuously distilled off while dropping the above-mentioned extract at a rate of 0.4 / hr into 600 ml of hot water heated to 90 ° C. During the distillation, BPDO immediately precipitated and became fine powder, which was uniformly dispersed in water.
粗製BPDO抽出液の滴下終了後、得られたBPDOの水スラ
リーを実施例１と同様に処理し、白色の精製BPDO13.4g
を得た。回収率は95.7％であり、精製BPDOを分析したと
ころ、純度99.9％,Fe6ppm,Cu4ppm,Na8ppmであった。After the completion of the dropwise addition of the crude BPDO extract, the obtained water slurry of BPDO was treated in the same manner as in Example 1 to obtain 13.4 g of white purified BPDO.
I got The recovery rate was 95.7%. When the purified BPDO was analyzed, the purity was 99.9%, Fe6ppm, Cu4ppm, and Na8ppm.
実施例３ 4,4′−ジブロモビフェニルのアルカリ加水分解反応
によって得られた、粗製BPDO（Fe150ppm,Cu300ppm,Na15
00ppmを含有）14gをスラリー状で含む反応液に１−ブタ
ノール300mlを加え抽出した。Example 3 Crude BPDO (Fe150ppm, Cu300ppm, Na15) obtained by alkaline hydrolysis of 4,4'-dibromobiphenyl
300 ml of 1-butanol was added to a reaction solution containing 14 g of a slurry (containing 00 ppm) and extracted.
次いで、100℃に加熱した600mlの熱水中に上記抽出液
を、0.6/hrの滴下速度で滴下しながらメチルエチルケ
トンを連続的に留去した。蒸留時、BPDOは直ちに析出し
微粉体となって水中に均一に分散した。Next, methyl ethyl ketone was continuously distilled off while dropping the above-mentioned extract at a dropping rate of 0.6 / hr into 600 ml of hot water heated to 100 ° C. During the distillation, BPDO immediately precipitated and became fine powder, which was uniformly dispersed in water.
粗製BPDO抽出液の滴下終了後、得られたBPDOの水スラ
リーを実施例１と同様に処理し、白色の精製BPDO13.4g
を得た。回収率は95.7％であり、精製BPDOを分析したと
ころ、純度99.9％,Fe5ppm,Cu7ppm,Na10ppmであった。After the completion of the dropwise addition of the crude BPDO extract, the obtained water slurry of BPDO was treated in the same manner as in Example 1 to obtain 13.4 g of white purified BPDO.
I got The recovery rate was 95.7%. When the purified BPDO was analyzed, the purity was 99.9%, Fe5ppm, Cu7ppm, and Na10ppm.
実施例４ ビフェニル−4,4′−ジスルホン酸ソーダ塩をアルカ
リ溶融することによって得られた黄色の粗製BPDO（Na25
00ppm,S3000ppmを含有）10gをスラリー状態で含む反応
液にメチルエチルケトン200mlを加え抽出した。Example 4 Yellow crude BPDO (Na25) obtained by alkaline melting of biphenyl-4,4'-disulfonic acid sodium salt
200 g of methyl ethyl ketone was added to a reaction solution containing 10 g of a slurry (containing 00 ppm and 3000 ppm of S) in the form of a slurry, followed by extraction.
次いで、90℃に加熱した600mlの熱水中に上記抽出液
を、0.4/hrの滴下速度で滴下しながらメチルエチルケ
トンを連続的に留去した。蒸留時、BPDOは直ちに析出し
微粉体となって水中に均一に分散した。Subsequently, methyl ethyl ketone was continuously distilled off while dropping the above-mentioned extract at a rate of 0.4 / hr into 600 ml of hot water heated to 90 ° C. During the distillation, BPDO immediately precipitated and became fine powder, which was uniformly dispersed in water.
粗製BPDO抽出液の滴下終了後、得られたBPDOの水スラ
リーを実施例１と同様に処理し、白色の精製BPDO9.6gを
得た。回収率は96.0％であり、精製BPDOを分析したとこ
ろ、純度99.8％,Na6ppm,S8ppmであった。After the completion of the dropwise addition of the crude BPDO extract, the obtained aqueous slurry of BPDO was treated in the same manner as in Example 1 to obtain 9.6 g of white purified BPDO. The recovery was 96.0%, and the purity of the purified BPDO was analyzed. As a result, the purity was 99.8%, Na6ppm, and S8ppm.
実施例５ 2,6−ジ−tert−ブチルフェノールの酸化カップリン
グ、脱ブチル化によって得られた粗製BPDO（Al120ppmを
含有）10gをスラリー状態で含む反応液にメチルエチル
ケトン200mlを加え抽出した。Example 5 200 ml of methyl ethyl ketone was added to a reaction solution containing 10 g of crude BPDO (containing 120 ppm of Al) obtained by oxidative coupling and debutylation of 2,6-di-tert-butylphenol in a slurry state, followed by extraction.
次いで、90℃に加熱した600mlの熱水中に上記抽出液
を、0.4/hrの滴下速度で滴下しながらメチルエチルケ
トンを連続的に留去した。蒸留時、BPDOは直ちに析出し
微粉体となって水中に均一に分散した。Subsequently, methyl ethyl ketone was continuously distilled off while dropping the above-mentioned extract at a rate of 0.4 / hr into 600 ml of hot water heated to 90 ° C. During the distillation, BPDO immediately precipitated and became fine powder, which was uniformly dispersed in water.
粗製BPDO抽出液の滴下終了後、得られたBPDOの水スラ
リーを実施例１と同様に処理し、白色の精製BPDO9.5gを
得た。回収率は95.0％であり、精製BPDOを分析したとこ
ろ純度99.8％,Al7ppmであった。After the completion of the dropping of the crude BPDO extract, the obtained aqueous slurry of BPDO was treated in the same manner as in Example 1 to obtain 9.5 g of white purified BPDO. The recovery was 95.0%, and the purity of the purified BPDO was analyzed, whereby the purity was 99.8% and Al was 7 ppm.
比較例 4,4′−ジブロモビフェニルのアルカリ加水分解反応
によって得られた、粗製BPDO（Fe200ppm,Cu250ppm,Na15
00ppmを含有）14gをスラリー状で含む反応液を、吸引濾
過により濾過した。Comparative Example Crude BPDO (Fe200ppm, Cu250ppm, Na15) obtained by alkaline hydrolysis of 4,4'-dibromobiphenyl
A reaction solution containing 14 g of a slurry (containing 00 ppm) was filtered by suction filtration.
次いで、濾過した湿結晶を水２で洗浄して乾燥を行
い、淡黄色のBPDO13.4gを得た。回収率は95.7％であ
り、BPDOを分析したところ、Fe35ppm,Cu52ppm,Na50ppm
であった。Next, the filtered wet crystals were washed with water 2 and dried to obtain 13.4 g of pale yellow BPDO. The recovery rate was 95.7%, and when BPDO was analyzed, Fe35ppm, Cu52ppm, Na50ppm
Met.
Claims (3)
体として分離回収する方法に於いて、製造工程で得られ
た粗製ビフェニル−4,4′−ジオールを有機溶媒に抽出
し、抽出溶液を熱水中に滴下し、同時に溶媒を留去しな
がらビフェニル−4,4′−ジオールを水中に分散した粉
体として回収することを特徴とするビフェニル−4,4′
−ジオールの分離精製方法。1. A method for purifying biphenyl-4,4'-diol and separating and recovering it as a powder, wherein the crude biphenyl-4,4'-diol obtained in the production step is extracted into an organic solvent and extracted. Biphenyl-4,4 'characterized by recovering biphenyl-4,4'-diol as a powder dispersed in water while dropping the solution into hot water and simultaneously distilling off the solvent.
-A method for separating and purifying a diol.
する有機溶媒として、100℃以下で蒸留もしくは水との
共沸蒸留が出来るアルコール類又はケトン類を用いる特
許請求の範囲第一項記載の分離精製方法。2. The method according to claim 1, wherein an alcohol or ketone which can be distilled at 100 ° C. or lower or azeotropically distilled with water is used as the organic solvent for extracting the crude biphenyl-4,4′-diol. Separation and purification method.
溶液を活性炭で処理する特許請求の範囲第一項記載の分
離精製方法。3. The method according to claim 1, wherein the crude biphenyl-4,4'-diol extraction solution is treated with activated carbon.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12665390A JP2874281B2 (en) | 1990-05-18 | 1990-05-18 | Method for separating and purifying biphenyl-4,4'-diol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12665390A JP2874281B2 (en) | 1990-05-18 | 1990-05-18 | Method for separating and purifying biphenyl-4,4'-diol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0426640A JPH0426640A (en) | 1992-01-29 |
| JP2874281B2 true JP2874281B2 (en) | 1999-03-24 |
Family
ID=14940542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12665390A Expired - Fee Related JP2874281B2 (en) | 1990-05-18 | 1990-05-18 | Method for separating and purifying biphenyl-4,4'-diol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2874281B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031484B (en) * | 2021-12-09 | 2024-04-02 | 宁夏清研高分子新材料有限公司 | Method for synthesizing 4,4' -biphenol |
-
1990
- 1990-05-18 JP JP12665390A patent/JP2874281B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0426640A (en) | 1992-01-29 |
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