JPH04266851A - Purification of aromatic dicarboxylic acid diphenyl ester - Google Patents
Purification of aromatic dicarboxylic acid diphenyl esterInfo
- Publication number
- JPH04266851A JPH04266851A JP2719791A JP2719791A JPH04266851A JP H04266851 A JPH04266851 A JP H04266851A JP 2719791 A JP2719791 A JP 2719791A JP 2719791 A JP2719791 A JP 2719791A JP H04266851 A JPH04266851 A JP H04266851A
- Authority
- JP
- Japan
- Prior art keywords
- dicarboxylic acid
- diphenyl ester
- weight
- acid diphenyl
- ester
- 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 11
- 239000004305 biphenyl Substances 0.000 title claims description 10
- 235000010290 biphenyl Nutrition 0.000 title claims description 10
- -1 aromatic dicarboxylic acid diphenyl ester Chemical class 0.000 title claims description 5
- 238000000746 purification Methods 0.000 title abstract description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- DOFDKNLHJKJCMO-UHFFFAOYSA-N diphenyl naphthalene-2,6-dicarboxylate Chemical compound C=1C=C2C=C(C(=O)OC=3C=CC=CC=3)C=CC2=CC=1C(=O)OC1=CC=CC=C1 DOFDKNLHJKJCMO-UHFFFAOYSA-N 0.000 claims abstract description 13
- HVSDTPCELAXJRF-UHFFFAOYSA-N phenyl 4-(4-phenoxycarbonylphenyl)benzoate Chemical compound C=1C=C(C=2C=CC(=CC=2)C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HVSDTPCELAXJRF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 21
- 238000001953 recrystallisation Methods 0.000 abstract description 10
- 239000013078 crystal Substances 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 5
- SZMFICGAHHWEAP-UHFFFAOYSA-N 4-(4-phenoxycarbonylphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(=O)OC=2C=CC=CC=2)C=C1 SZMFICGAHHWEAP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ITAMCOCNZJPJDF-UHFFFAOYSA-N 1-(6-aminopurin-9-yl)propan-2-yloxymethyl-phenoxyphosphinic acid Chemical compound C1=NC2=C(N)N=CN=C2N1CC(C)OCP(O)(=O)OC1=CC=CC=C1 ITAMCOCNZJPJDF-UHFFFAOYSA-N 0.000 description 2
- QDRPMFSBJVIWCI-UHFFFAOYSA-N C1=CC2=CC(C(=O)O)=CC=C2C=C1C(=O)OC1=CC=CC=C1 Chemical compound C1=CC2=CC(C(=O)O)=CC=C2C=C1C(=O)OC1=CC=CC=C1 QDRPMFSBJVIWCI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VOFXSGJWZPGHDR-UHFFFAOYSA-N dibutoxy(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](OCCCC)(OCCCC)C1=CC=CC=C1 VOFXSGJWZPGHDR-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 description 1
- UPEZEZWAFHMKIY-UHFFFAOYSA-N diphenyl naphthalene-1,2-dicarboxylate Chemical compound C=1C=C2C=CC=CC2=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 UPEZEZWAFHMKIY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、芳香族ジカルボン酸ジ
フェニルの精製方法に関し、詳しくは、特に、２，６−
ナフタレンジカルボン酸ジフェニルエステル及び４，４
’−ビフェニルジカルボン酸ジフェニルエステルの再結
晶による精製方法に関する。[Field of Industrial Application] The present invention relates to a method for purifying diphenyl aromatic dicarboxylate, and in particular, to a method for purifying diphenyl aromatic dicarboxylate.
naphthalene dicarboxylic acid diphenyl ester and 4,4
The present invention relates to a method for purifying '-biphenyldicarboxylic acid diphenyl ester by recrystallization.
【０００２】0002
【従来の技術】２，６−ナフタレンジカルボン酸ジフェ
ニルエステル及び４，４’−ビフェニルジカルボン酸ジ
フェニルエステルは、例えば、芳香族ポリエステルの製
造原料として有用であり、従来、対応する芳香族ジカル
ボン酸と過剰量のフェノールとのエステル化反応によつ
て製造されている。しかし、このようにして得られる上
記芳香族ジカルボン酸ジフェニルは、通常、着色が著し
いので、色相のすぐれた芳香族ポリエステルを製造する
には、重合原料である上記芳香族ジカルボン酸ジフェニ
ル自体も色相にすぐれることが要求される。[Prior Art] 2,6-naphthalene dicarboxylic acid diphenyl ester and 4,4'-biphenyl dicarboxylic acid diphenyl ester are useful, for example, as raw materials for producing aromatic polyesters, and conventionally, they have been used in combination with the corresponding aromatic dicarboxylic acid in excess. It is produced by an esterification reaction with a certain amount of phenol. However, the diphenyl aromatic dicarboxylate obtained in this way is usually markedly colored, so in order to produce an aromatic polyester with an excellent hue, the diphenyl aromatic dicarboxylate itself, which is a polymerization raw material, must also be colored. Excellence is required.
【０００３】一般に、芳香族ジカルボン酸ジアリールエ
ステルの精製方法としては、多くの場合、再結晶法が採
用されていいる。例えば、特公昭５５−４７０２７号公
報には、テレフタル酸ジアリールエステルの再結晶溶剤
として、炭素数９又は１０のアルキル置換ベンゼンやモ
ノクロロベンゼン、又はこれらの混合物を用いる方法が
提案されており、また、特公昭４６−３７５７４号公報
には、エチレングリコール又はジエチレングリコールの
モノエーテルを用いる方法が提案されている。また、特
公昭５９−３６６４４号公報には、再結晶溶剤として、
沸点１００〜２５０℃、融点２０℃以下の芳香族炭化水
素や活性水素を分子内にもたない含窒素塩基性化合物を
用いる方法が提案されている。更に、米国特許第 ４，
０２０，０９９号明細書には、炭化水素を主溶剤とする
ジメチルスルホキシドとの混合溶剤から、テレフタル酸
ジフェニルを再結晶させて精製する方法が提案されてい
る。[0003] Generally, as a method for purifying aromatic dicarboxylic acid diaryl esters, a recrystallization method is often adopted. For example, Japanese Patent Publication No. 55-47027 proposes a method using an alkyl-substituted benzene having 9 or 10 carbon atoms, monochlorobenzene, or a mixture thereof as a recrystallization solvent for terephthalic acid diaryl ester; Japanese Patent Publication No. 46-37574 proposes a method using monoether of ethylene glycol or diethylene glycol. In addition, in Japanese Patent Publication No. 59-36644, as a recrystallization solvent,
A method has been proposed in which a nitrogen-containing basic compound having a boiling point of 100 to 250°C and a melting point of 20°C or less and having no active hydrogen in its molecule is used. Additionally, U.S. Patent No. 4,
No. 020,099 proposes a method for purifying diphenyl terephthalate by recrystallizing it from a mixed solvent containing a hydrocarbon as the main solvent and dimethyl sulfoxide.
【０００４】しかし、従来、２，６−ナフタレンジカル
ボン酸ジフェニルエステル又は４，４’−ビフェニルジ
カルボン酸ジフェニルエステルを再結晶法にて工業的に
有利に精製する方法は知られていない。[0004] Hitherto, however, there has been no known method for industrially advantageous purification of 2,6-naphthalenedicarboxylic acid diphenyl ester or 4,4'-biphenyldicarboxylic acid diphenyl ester by recrystallization.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、高純度の２
，６−ナフタレンジカルボン酸ジフェニルエステル又は
４，４’−ビフェニルジカルボン酸ジフェニルエステル
の工業的に有利な再結晶による精製方法を提供すること
を目的とする。[Problems to be Solved by the Invention] The present invention provides highly purified
, 6-naphthalene dicarboxylic acid diphenyl ester or 4,4'-biphenyldicarboxylic acid diphenyl ester is provided with an industrially advantageous purification method by recrystallization.
【０００６】[0006]
【課題を解決するための手段】本発明による芳香族ジカ
ルボン酸ジフェニルの精製方法は、２，６−ナフタレン
ジカルボン酸ジフェニルエステル又は４，４’−ビフェ
ニルジカルボン酸ジフェニルエステルをジメチルスルホ
キシドから再結晶させることを特徴とする。２，６−ナ
フタレンジカルボン酸ジフェニルエステル及び４，４’
−ビフェニルジカルボン酸ジフェニルエステルは、通常
、それぞれ対応する芳香族ジカルボン酸とフェノールと
のエステル化反応によつて製造される。本発明の方法に
おいては、このような反応によつて得られる反応混合液
をそのままジメチルスルホキシドに加えてもよいが、上
記反応混合物から２，６−ナフタレンジカルボン酸ジフ
ェニルエステル又は４，４’−ビフェニルジカルボン酸
ジフェニルエステルを蒸留、減圧蒸留等の方法によつて
得られた粗反応生成物をジメチルスルホキシドに溶解さ
せるのが好ましい。[Means for Solving the Problems] A method for purifying diphenyl aromatic dicarboxylate according to the present invention includes recrystallizing 2,6-naphthalenedicarboxylic acid diphenyl ester or 4,4'-biphenyldicarboxylic acid diphenyl ester from dimethyl sulfoxide. It is characterized by 2,6-naphthalene dicarboxylic acid diphenyl ester and 4,4'
-Biphenyldicarboxylic acid diphenyl ester is usually produced by an esterification reaction between the corresponding aromatic dicarboxylic acid and phenol. In the method of the present invention, the reaction mixture obtained by such a reaction may be added to dimethyl sulfoxide as it is, but 2,6-naphthalene dicarboxylic acid diphenyl ester or 4,4'-biphenyl It is preferable to dissolve a crude reaction product obtained from dicarboxylic acid diphenyl ester by a method such as distillation or vacuum distillation in dimethyl sulfoxide.
【０００７】粗反応生成物は、通常、室温からジメチル
スルホキシドの沸点（１８９℃）、好ましくは５０〜１
５０℃の範囲でジメチルスルホキシドに溶解させる。ジ
メチルスルホキシドは、粗反応生成物１重量部に対して
、通常、１〜１００重量部、好ましくは５〜２０重量部
の範囲で用いられる。再結晶溶剤としてのジメチルスル
ホキシドは、必要に応じて、アルコール、ジオキサン、
エーテル、水、ジメチルホルムアミド、ハロゲン化アル
キル等の溶剤をジメチルスルホキシド１ｍｌに対して０
．０００１〜１ｍｌ程度含んでいてもよい。[0007] The crude reaction product is usually obtained from room temperature to the boiling point of dimethyl sulfoxide (189°C), preferably from 50 to 1
Dissolve in dimethyl sulfoxide at a temperature of 50°C. Dimethyl sulfoxide is generally used in an amount of 1 to 100 parts by weight, preferably 5 to 20 parts by weight, per 1 part by weight of the crude reaction product. Dimethyl sulfoxide as a recrystallization solvent can be used with alcohol, dioxane,
Add solvents such as ether, water, dimethylformamide, and alkyl halides to 1 ml of dimethyl sulfoxide.
．． It may contain about 0001 to 1 ml.
【０００８】再結晶は、通常、０〜７５℃、好ましくは
５〜４０℃の範囲の温度で行なわれる。[0008] Recrystallization is normally carried out at a temperature in the range of 0 to 75°C, preferably 5 to 40°C.
【０００９】[0009]
【実施例】以下に実施例を挙げて本発明を説明するが、
本発明はこれら実施例により何ら限定されるものではな
い。
参考例１
２，６−ナフタレンジカルボン酸３．０ｇ（０．０１４
モル）、フェノール２０．９ｇ（０．２２２モル）及び
ジフェニルジブトキシスズ２３ｍｇを混合し、２６０℃
で３時間攪拌した。得られた反応混合物からフェノール
を減圧下に留去して、粗反応生成物５．０ｇを得た。
参考例２
４，４’−ビフェニルジカルボン酸３．４ｇ（０．０１
４モル）、フェノール２１．１ｇ（０．２２４モル）及
びジフェニルジブトキシスズ２３ｍｇを混合し、２６０
℃で３時間攪拌した。得られた反応混合物からフェノー
ルを減圧下に留去して、粗反応生成物５．０ｇを得た。
実施例１
参考例１に記載した方法で得た２，６−ナフタレンジカ
ルボン酸ジフェニルエステル７７．２重量％、２，６−
ナフタレンジカルボン酸モノフェニルエステル２１．５
重量％及び２，６−ナフタレンジカルボン酸１．３重量
％からなり、ｂ値が１．８である混合物１０ｇにジメチ
ルスルホキシド５０ｍｌを加え、８０℃で溶解させた。
この溶液を２０℃に冷却して、結晶５ｇを得た。[Examples] The present invention will be explained below with reference to Examples.
The present invention is not limited in any way by these Examples. Reference example 1 2,6-naphthalenedicarboxylic acid 3.0g (0.014
20.9 g (0.222 mol) of phenol and 23 mg of diphenyldibutoxytin were mixed and heated at 260°C.
The mixture was stirred for 3 hours. Phenol was distilled off from the resulting reaction mixture under reduced pressure to obtain 5.0 g of a crude reaction product. Reference example 2 4,4'-biphenyl dicarboxylic acid 3.4 g (0.01
4 mol), 21.1 g (0.224 mol) of phenol and 23 mg of diphenyldibutoxytin were mixed, and 260
The mixture was stirred at ℃ for 3 hours. Phenol was distilled off from the resulting reaction mixture under reduced pressure to obtain 5.0 g of a crude reaction product. Example 1 77.2% by weight of 2,6-naphthalene dicarboxylic acid diphenyl ester obtained by the method described in Reference Example 1, 2,6-
Naphthalene dicarboxylic acid monophenyl ester 21.5
% by weight and 1.3% by weight of 2,6-naphthalene dicarboxylic acid with a b value of 1.8, 50 ml of dimethyl sulfoxide was added and dissolved at 80°C. This solution was cooled to 20° C. to obtain 5 g of crystals.
【００１０】得られた結晶の成分は、２，６−ナフタレ
ンジカルボン酸ジフェニルエステル９９．４重量％、２
，６−ナフタレンジカルボン酸モノフェニルエステル０
．３重量％及び２，６−ナフタレンジカルボン酸０．３
重量％からなり、ｂ値は０．２であつた。また、得られ
た結晶は、スケーリングすることなく、容易に分離する
ことができた。
実施例２
参考例２に記載した方法で得た４，４’−ビフェニルジ
カルボン酸ジフェニルエステル３１．２重量％、４，４
’−ビフェニルジカルボン酸モノフェニルエステル５５
．８重量％及び４，４’−ビフェニルジカルボン酸１３
．０重量％からなり、ｂ値が１．６である混合物１０ｇ
にジメチルスルホキシド１００ｍｌを加え、８０℃で溶
解させた。この溶液を２０℃に冷却して、結晶２ｇを得
た。The components of the obtained crystals were 99.4% by weight of 2,6-naphthalene dicarboxylic acid diphenyl ester;
,6-naphthalene dicarboxylic acid monophenyl ester 0
．． 3% by weight and 0.3% of 2,6-naphthalene dicarboxylic acid
% by weight, and the b value was 0.2. Furthermore, the obtained crystals could be easily separated without scaling. Example 2 4,4'-biphenyldicarboxylic acid diphenyl ester obtained by the method described in Reference Example 2, 31.2% by weight, 4,4
'-Biphenyldicarboxylic acid monophenyl ester 55
．． 8% by weight and 4,4'-biphenyldicarboxylic acid 13
．． 10 g of a mixture consisting of 0% by weight and a b value of 1.6
100 ml of dimethyl sulfoxide was added to the solution and dissolved at 80°C. This solution was cooled to 20° C. to obtain 2 g of crystals.
【００１１】得られた結晶の成分は、４，４’−ビフェ
ニルジカルボン酸ジフェニルエステル９９．５重量％、
４，４’−ビフェニルジカルボン酸モノフェニルエステ
ル０．３重量％及び４，４’−ビフェニルジカルボン酸
０．２重量％からなり、ｂ値は０．３であつた。また、
得られた結晶は、スケーリングすることなく、容易に分
離することができた。
実施例３
参考例１に記載した方法で得た２，６−ナフタレンジカ
ルボン酸ジフェニルエステル７７．２重量％、２，６−
ナフタレンジカルボン酸モノフェニルエステル２１．５
重量％及び２，６−ナフタレンジカルボン酸１．３重量
％からなり、ｂ値が１．８である混合物１０．２ｇにジ
メチルスルホキシド５０ｍｌ及びエタノール０．５ｍｌ
からなる混合溶剤を加え、８０℃で溶解させた。この溶
液を２０℃に冷却して、結晶５．５ｇを得た。The components of the obtained crystals were 99.5% by weight of 4,4'-biphenyldicarboxylic acid diphenyl ester;
It consisted of 0.3% by weight of 4,4'-biphenyldicarboxylic acid monophenyl ester and 0.2% by weight of 4,4'-biphenyldicarboxylic acid, and the b value was 0.3. Also,
The obtained crystals could be easily separated without scaling. Example 3 77.2% by weight of 2,6-naphthalene dicarboxylic acid diphenyl ester obtained by the method described in Reference Example 1, 2,6-
Naphthalene dicarboxylic acid monophenyl ester 21.5
% by weight and 1.3% by weight of 2,6-naphthalene dicarboxylic acid with a b value of 1.8, 50 ml of dimethyl sulfoxide and 0.5 ml of ethanol.
A mixed solvent consisting of was added and dissolved at 80°C. This solution was cooled to 20° C. to obtain 5.5 g of crystals.
【００１２】得られた結晶の成分は、２，６−ナフタレ
ンジカルボン酸ジフェニルエステル９９．５重量％、２
，６−ナフタレンジカルボン酸モノフェニルエステル０
．１重量％及び２，６−ナフタレンジカルボン酸０．４
重量％であつた。また、得られた結晶は、スケーリング
することなく、容易に分離することができた。
実施例４
参考例２に記載した方法で得た４，４’−ビフェニルジ
カルボン酸ジフェニルエステル３０．６重量％、４，４
’−ビフェニルジカルボン酸モノフェニルエステル５６
．４重量％及び４，４’−ビフェニルジカルボン酸１３
．０重量％からなり、ｂ値が である混合物９．
８ｇにジメチルスルホキシド５０ｍｌ及びジオキサン１
ｍｌからなる混合溶剤を加え、８０℃で溶解させた。こ
の溶液を２０℃に冷却して、結晶２．５ｇを得た。The components of the obtained crystals were 99.5% by weight of 2,6-naphthalene dicarboxylic acid diphenyl ester;
,6-naphthalene dicarboxylic acid monophenyl ester 0
．． 1% by weight and 0.4% of 2,6-naphthalene dicarboxylic acid
It was in weight%. Furthermore, the obtained crystals could be easily separated without scaling. Example 4 4,4'-biphenyldicarboxylic acid diphenyl ester obtained by the method described in Reference Example 2, 30.6% by weight, 4,4
'-Biphenyldicarboxylic acid monophenyl ester 56
．． 4% by weight and 4,4'-biphenyldicarboxylic acid 13
．． 9. A mixture consisting of 0% by weight and having a b value of 9.
8 g to 50 ml of dimethyl sulfoxide and 1 part of dioxane
ml of mixed solvent was added and dissolved at 80°C. This solution was cooled to 20° C. to obtain 2.5 g of crystals.
【００１３】得られた結晶の成分は、４，４’−ビフェ
ニルジカルボン酸ジフェニルエステル９９．３重量％、
４，４’−ビフェニルジカルボン酸モノフェニルエステ
ル０．６重量％及び４，４’−ビフェニルジカルボン酸
０．１重量％であつた。また、得られた結晶は、スケー
リングすることなく、容易に分離することができた。The components of the obtained crystals were 99.3% by weight of 4,4'-biphenyldicarboxylic acid diphenyl ester;
They were 0.6% by weight of 4,4'-biphenyldicarboxylic acid monophenyl ester and 0.1% by weight of 4,4'-biphenyldicarboxylic acid. Furthermore, the obtained crystals could be easily separated without scaling.
【００１４】[0014]
【発明の効果】以上のように、本発明の方法によれば、
ジメチルスルホキシドを溶剤として用いる再結晶法によ
つて、高純度で色相にすぐれる２，６−ナフタレンジカ
ルボン酸ジフェニルエステル又は４，４’−ビフェニル
ジカルボン酸ジフェニルエステルをを工業的に有利に得
ることができる。[Effects of the Invention] As described above, according to the method of the present invention,
2,6-naphthalenedicarboxylic acid diphenyl ester or 4,4'-biphenyldicarboxylic acid diphenyl ester with high purity and excellent color can be obtained industrially advantageously by a recrystallization method using dimethyl sulfoxide as a solvent. can.
Claims (1)
ルエステル又は４，４’−ビフェニルジカルボン酸ジフ
ェニルエステルをジメチルスルホキシドから再結晶させ
ることを特徴とする芳香族ジカルボン酸ジフェニルエス
テルの精製方法。1. A method for purifying aromatic dicarboxylic acid diphenyl ester, which comprises recrystallizing 2,6-naphthalenedicarboxylic acid diphenyl ester or 4,4'-biphenyldicarboxylic acid diphenyl ester from dimethyl sulfoxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2719791A JPH04266851A (en) | 1991-02-21 | 1991-02-21 | Purification of aromatic dicarboxylic acid diphenyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2719791A JPH04266851A (en) | 1991-02-21 | 1991-02-21 | Purification of aromatic dicarboxylic acid diphenyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04266851A true JPH04266851A (en) | 1992-09-22 |
Family
ID=12214366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2719791A Pending JPH04266851A (en) | 1991-02-21 | 1991-02-21 | Purification of aromatic dicarboxylic acid diphenyl ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04266851A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5397440A (en) * | 1993-04-16 | 1995-03-14 | Hoechst Aktiengesellschaft | Isolation of dimethyl 4,4'-biphenyldicarboxylate |
| US6420298B1 (en) | 1999-08-31 | 2002-07-16 | Exxonmobil Oil Corporation | Metallocene catalyst compositions, processes for making polyolefin resins using such catalyst compositions, and products produced thereby |
-
1991
- 1991-02-21 JP JP2719791A patent/JPH04266851A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5397440A (en) * | 1993-04-16 | 1995-03-14 | Hoechst Aktiengesellschaft | Isolation of dimethyl 4,4'-biphenyldicarboxylate |
| US6420298B1 (en) | 1999-08-31 | 2002-07-16 | Exxonmobil Oil Corporation | Metallocene catalyst compositions, processes for making polyolefin resins using such catalyst compositions, and products produced thereby |
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