JPH0454142A - Method for separating phenolic compound - Google Patents
Method for separating phenolic compoundInfo
- Publication number
- JPH0454142A JPH0454142A JP16259290A JP16259290A JPH0454142A JP H0454142 A JPH0454142 A JP H0454142A JP 16259290 A JP16259290 A JP 16259290A JP 16259290 A JP16259290 A JP 16259290A JP H0454142 A JPH0454142 A JP H0454142A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- phenol
- phenolic
- exchange resin
- 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.)
- Granted
Links
- 150000002989 phenols Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 19
- -1 phenol compound Chemical class 0.000 claims abstract description 23
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000002378 acidificating effect Effects 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims abstract description 6
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 claims abstract description 6
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims abstract description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 6
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims abstract description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims abstract description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 6
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims abstract description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 4
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940074360 caffeic acid Drugs 0.000 claims abstract description 3
- 235000004883 caffeic acid Nutrition 0.000 claims abstract description 3
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940074391 gallic acid Drugs 0.000 claims abstract description 3
- 235000004515 gallic acid Nutrition 0.000 claims abstract description 3
- 229960005219 gentisic acid Drugs 0.000 claims abstract description 3
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 claims abstract description 3
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229960001553 phloroglucinol Drugs 0.000 claims abstract description 3
- 229940079877 pyrogallol Drugs 0.000 claims abstract description 3
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 4
- RMTXUPIIESNLPW-UHFFFAOYSA-N 1,2-dihydroxy-3-(pentadeca-8,11-dienyl)benzene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1O RMTXUPIIESNLPW-UHFFFAOYSA-N 0.000 claims description 2
- QARRXYBJLBIVAK-UEMSJJPVSA-N 3-[(8e,11e)-pentadeca-8,11-dienyl]benzene-1,2-diol;3-[(8e,11e)-pentadeca-8,11,14-trienyl]benzene-1,2-diol;3-[(8e,11e,13e)-pentadeca-8,11,13-trienyl]benzene-1,2-diol;3-[(e)-pentadec-8-enyl]benzene-1,2-diol;3-pentadecylbenzene-1,2-diol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O.CCCCCC\C=C\CCCCCCCC1=CC=CC(O)=C1O.CCC\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.C\C=C\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.OC1=CC=CC(CCCCCCC\C=C\C\C=C\CC=C)=C1O QARRXYBJLBIVAK-UEMSJJPVSA-N 0.000 claims description 2
- IYROWZYPEIMDDN-UHFFFAOYSA-N 3-n-pentadec-8,11,13-trienyl catechol Natural products CC=CC=CCC=CCCCCCCCC1=CC=CC(O)=C1O IYROWZYPEIMDDN-UHFFFAOYSA-N 0.000 claims description 2
- DQTMTQZSOJMZSF-UHFFFAOYSA-N urushiol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DQTMTQZSOJMZSF-UHFFFAOYSA-N 0.000 claims description 2
- 150000007965 phenolic acids Chemical class 0.000 claims 2
- 235000009048 phenolic acids Nutrition 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 abstract description 11
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 11
- 239000003513 alkali Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 abstract description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N beta-resorcylic acid Natural products OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000007796 conventional method Methods 0.000 abstract description 2
- MNUOZFHYBCRUOD-UHFFFAOYSA-N hydroxyphthalic acid Natural products OC(=O)C1=CC=CC(O)=C1C(O)=O MNUOZFHYBCRUOD-UHFFFAOYSA-N 0.000 abstract 2
- AMKYESDOVDKZKV-UHFFFAOYSA-N o-orsellinic acid Chemical compound CC1=CC(O)=CC(O)=C1C(O)=O AMKYESDOVDKZKV-UHFFFAOYSA-N 0.000 abstract 2
- HGEFWFBFQKWVMY-DUXPYHPUSA-N 2,4-dihydroxy-trans cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1O HGEFWFBFQKWVMY-DUXPYHPUSA-N 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- 238000001179 sorption measurement Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000011069 regeneration method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- 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］
本発明は溶液中のフェノール化合物の分離方法に関する
。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for separating phenolic compounds in solution.
［従来の技術］
溶液中からフェノール化合物を分離回収する方法として
は、従来活性炭による吸着法がある。活性炭法において
吸着したフェノール化合物を回収する方法としては蒸気
等による熱再生法やアルカリによって溶離回収するアル
カリ再生法が用いられる。[Prior Art] As a method for separating and recovering phenolic compounds from a solution, there is a conventional adsorption method using activated carbon. In the activated carbon method, the adsorbed phenol compound can be recovered by a thermal regeneration method using steam or the like, or an alkali regeneration method in which the phenol compound is eluted and recovered using an alkali.
また場合によっては、フェノール化合物を溶解すること
のできる有機溶媒により洗浄抽出する溶媒再生法が採ら
れることもある。In some cases, a solvent regeneration method may be used in which washing and extraction are performed using an organic solvent that can dissolve the phenol compound.
さらにはフェノール化合物をその酸性を利用し塩基性イ
オン交換樹脂にイオン交換させ吸着するイオン交換法が
ある。この場合においても吸着したフェノール化合物を
回収するにはアルカリ再生法が用いられる。Furthermore, there is an ion exchange method in which a phenol compound is ion-exchanged and adsorbed onto a basic ion exchange resin by utilizing its acidity. Even in this case, the alkaline regeneration method is used to recover the adsorbed phenol compound.
［発明が解決しようとする課題］
従前の活性炭法やイオン交換法の欠点はその溶離方法の
不十分性にある。つまり熱再生法には蒸気のような高レ
ベルの熱エネルギーが多量に必要でありエネルギーの損
失が大きい。[Problems to be Solved by the Invention] A drawback of the conventional activated carbon method and ion exchange method lies in the insufficiency of their elution methods. In other words, the heat regeneration method requires a large amount of high-level thermal energy such as steam, resulting in large energy losses.
アルカリ溶離法ではフェノール化合物はフェノキシトと
して回収されるためこれを元のフェノール型とするため
には回収液に酸を加え塩とフェノールとしたのちフェノ
ール化合物を回収するという複雑な工程を要する。さら
にフェノール化合物にはアルカリ性雰囲気において不安
定な物質が多く製品品質上問題となることがある。In the alkaline elution method, the phenol compound is recovered as phenoxyte, so in order to return it to its original phenol form, a complicated process is required in which acid is added to the recovered solution to form salt and phenol, and then the phenol compound is recovered. Furthermore, many phenolic compounds are unstable in an alkaline atmosphere, which may cause problems in terms of product quality.
さらに溶媒再生法においては高価な有機溶媒を多量に使
用することのほか 引火危険性のある有ｌｌ溶媒を保存
使用するという安全上の問題も発生する。Furthermore, in the solvent regeneration method, not only a large amount of expensive organic solvent is used, but also a safety problem arises in that a flammable solvent is stored and used.
本発明はフェノール化合物を塩型に調整した強酸性カチ
オン交換樹脂に吸着させることにより）気や 酸、アル
カリを使用することなしにフェノール化合物を効率的に
分離することを目的とするものである。The purpose of the present invention is to efficiently separate phenolic compounds without using air, acids, or alkalis (by adsorbing phenolic compounds on a strongly acidic cation exchange resin prepared in a salt form).
［課題を解決するための手段］
本発明者等はこれらの課題を解決するために塩型に調製
した強酸性イオン交換樹脂を吸着剤としてフェノール化
合物を含む溶液を処理することにより該フェノール化合
物を選択的に吸着できることを見出し本発明を完成した
。すなわち、本発明は、フェノール化合物を含有する溶
液を塩型に調整した強酸性カチオン交換樹脂に接触せし
め、該フェノール化合物を吸着させることを特徴とする
フェノール化合物の分離方法を提供するものである。[Means for Solving the Problems] In order to solve these problems, the present inventors treated a solution containing a phenol compound using a strongly acidic ion exchange resin prepared in a salt form as an adsorbent, thereby removing the phenol compound. The present invention was completed by discovering that selective adsorption can be achieved. That is, the present invention provides a method for separating a phenol compound, which is characterized by bringing a solution containing a phenol compound into contact with a strongly acidic cation exchange resin prepared in a salt form, and adsorbing the phenol compound.
本発明における強酸性イオン交換樹脂としては、スチレ
ン−ジビニルベンゼン共重体のスルホン化物が用いられ
る。イオン交換樹脂にはゲル型とマクロポーラス型があ
るがどちらの形態のものも本発明に供することができる
。この種の強酸性イオン交換樹脂はレバチソ）Ｓ１００
、同５１０９、同ＭＤ３１３６ Ｂ、同ＴＳＷ４０、同
５ＰＩＩ２（以上バイエル社製）、ダイヤイオン５ＫＩ
Ｂ、同ＰＫ２０８、同ＰＫ２１２（三菱化成社製）、ダ
ウエックスＨＣＲ−５１５０Ｗｘ１．５ＤＷＸ２（ダウ
ケミカル社製）、アンバーライトｌＲ１２０、同ｌＲ１
２２、同２００Ｃ（以上ロームアンドハース社製）など
各種の商標で市販されているものがいずれも好適に使用
可能である。これら強酸性イオン交換樹脂を本目的に供
するには塩型に調製しておく必要がある。この塩橋とし
てはＬｉ、Ｎａ、に、Ｃａ、Ｃｕ、Ｐｂなどのうちから
一種または二種以上が適宜用いられる。イオン交換樹脂
を塩型とするには公知のごとくＨ型のイオン交換樹脂を
目的塩の水酸化物例えば水酸化ナトリウム、水酸化カリ
ウムあるいは目的塩のハロゲン化塩、硫酸塩などの水溶
液と接触処理すればよい。As the strongly acidic ion exchange resin in the present invention, a sulfonated product of styrene-divinylbenzene copolymer is used. Ion exchange resins include gel type and macroporous type, and either type can be used in the present invention. This type of strongly acidic ion exchange resin is Rebatiso) S100.
, 5109, MD3136 B, TSW40, 5PII2 (manufactured by Bayer), Diaion 5KI
B, PK208, PK212 (manufactured by Mitsubishi Kasei), DOWEX HCR-5150Wx1.5DWX2 (manufactured by Dow Chemical), Amberlite 1R120, 1R1
Any of those commercially available under various trademarks such as No. 22 and No. 200C (manufactured by Rohm and Haas) can be suitably used. In order to use these strongly acidic ion exchange resins for this purpose, it is necessary to prepare them in a salt form. As this salt bridge, one or more of Li, Na, Ca, Cu, Pb, etc. can be used as appropriate. In order to convert the ion exchange resin into a salt type, as is known, the H type ion exchange resin is contacted with an aqueous solution of a target salt hydroxide such as sodium hydroxide, potassium hydroxide, or a target salt such as a halide or sulfate. do it.
本発明における吸着操作の一例としては塩型イオン交換
樹脂をカラムに充填し被処理液を上向流あるいは下向流
により通液するカラム式があげられるほかバッチ式によ
っても差し支えない、カラム操作時の流体速度には制限
はないが、通常ＳＶ（ｈｒ−’ ）０． １〜Ｉ ００
の範囲、好ましくは０゜３〜６０ （ｈｒ−’ ）の範
囲である。An example of the adsorption operation in the present invention is a column type in which a column is filled with a salt-type ion exchange resin and the liquid to be treated is passed through the column in an upward or downward flow, and a batch type is also acceptable. There is no limit to the fluid velocity of SV(hr-'), but it is usually SV(hr-')0. 1~I 00
, preferably in the range of 0°3 to 60 (hr-').
本発明によって吸着したフェノール化合物を溶離するた
めには特殊な溶離剤は必要とせず該フェノール化合物を
吸着したイオン交換樹脂に水を接触させることにより簡
単に溶離することができるが都合により有Ｉ！溶剤、あ
るいは有機溶剤と水の混合物などを使用することも可能
である。In order to elute the adsorbed phenol compound according to the present invention, no special eluent is required, and the phenol compound can be easily eluted by bringing water into contact with the ion exchange resin that has adsorbed it. It is also possible to use a solvent or a mixture of an organic solvent and water.
上記の吸着溶離方法を実施するための操作温度に制限は
ないが通常０°Ｃ〜１００″Ｃの範囲で操作される。ま
た吸着時の操作温度と溶離時の操作温度は同一であって
も同一でなくても良いが相対的に低温で吸着する方が高
い吸着容量を得ることができ高温で溶離する方が熔離剤
量を低減できるので有利である。There is no limit to the operating temperature for carrying out the above adsorption/elution method, but it is usually operated in the range of 0°C to 100''C.Also, even if the operating temperature during adsorption and the operating temperature during elution are the same, Although they do not have to be the same, it is advantageous to adsorb at a relatively low temperature because a higher adsorption capacity can be obtained, and to elute at a higher temperature because the amount of eluent can be reduced.
本発明を適用できるフェノール化合物はフェノール類、
多価フェノール類ならびにこれらの置換誘導体でありフ
ェノール、カテコール、レゾルシン、ヒドロキノン、オ
ルシン、ウルシオール、ピロガロール、フロログルシン
、ヒドロキシヒドロキノン、サリチル酸、オキシ安息香
酸、プロトカテチュ酸、ゲンチシン酸、レゾルシル酸、
オルセリン酸、カフェー酸、ウンベル酸、没食子酸、オ
キシフタル酸 ならびにこれらのアルキル誘導体、なら
びにアセチル化誘導体などが例示される。Phenolic compounds to which the present invention can be applied include phenols,
Polyhydric phenols and their substituted derivatives such as phenol, catechol, resorcinol, hydroquinone, orcine, urushiol, pyrogallol, phloroglucin, hydroxyhydroquinone, salicylic acid, oxybenzoic acid, protocatechuic acid, gentisic acid, resorcylic acid,
Examples include orceric acid, caffeic acid, umbelic acid, gallic acid, oxyphthalic acid, their alkyl derivatives, and acetylated derivatives.
またこれらのフェノール化合物を含有する溶液は、特に
限定するものではないが、水または水を主体とする溶媒
の溶液が好ましい。このうち、該フェノール化合物の濃
度は、限定的ではないが、通常、０．００１〜２Ｑｗｔ
、％程度である。Further, the solution containing these phenol compounds is not particularly limited, but a solution of water or a solvent mainly composed of water is preferable. Among these, the concentration of the phenol compound is usually 0.001 to 2 Qwt, although it is not limited.
, about %.
以下に実施例で本発明の詳細な説明する。以下において
％は溶液中の重量基準濃度である。溶液中の組成成分分
析には液体クロマトグラフィーを用いた。The present invention will be explained in detail below using Examples. In the following, percentages are weight-based concentrations in solution. Liquid chromatography was used to analyze the composition of the solution.
実施例１
直径１６．０ｍｍのカラムにバイエル社製強酸性陽イオ
ン交換樹脂レバチッ）ＴＳＷ４０に型を高さ５００ｍｍ
まで充填しジャケットに温水を流通させ温度を維持する
ようにした。 被処理原液であるフェノール化合物溶液
としてはフェノール１．０％ Ｎ ａ ｚｓ Ｏａ
１％の組成を持つ水溶液を用いた。Example 1 A column with a diameter of 16.0 mm was molded with a strong acidic cation exchange resin (Levachi) TSW40 manufactured by Bayer AG to a height of 500 mm.
The temperature was maintained by filling the tank up to 100 ml and circulating hot water through the jacket. The phenol compound solution used as the stock solution to be treated was phenol 1.0% Na zs Oa.
An aqueous solution with a composition of 1% was used.
上記カラムを３０°Ｃに保ち原液をＳ Ｖ ２ （ｈｒ
）の流速で下向流により４００ｍ１供給しカラム出口よ
り処理液４００ｍ１を得た。処理液の組成はフェノール
０．０１％以下、Ｎ ａ ｚｓ Ｏ４０，９２％であっ
た。The above column was kept at 30°C and the stock solution was heated to SV 2 (hr
) at a flow rate of 400 ml was supplied in a downward flow, and 400 ml of the treated liquid was obtained from the column outlet. The composition of the treatment liquid was 0.01% or less of phenol and 40.92% of N azs O.
上記吸着操作に引続きカラム温度を３０°Ｃに保ち槽動
剤として純水をＳＶ２の流速で下向流により４００ｍ１
供給しカラム出口より溶離液４００ｍ１を得た。溶離液
の組成はフェノール０．９６％ Ｎａ、ｓＯ，０，０６
％であった。Following the above adsorption operation, the column temperature was kept at 30°C, and pure water was added as a tank moving medium to 400 ml by downward flow at a flow rate of SV2.
400 ml of eluent was obtained from the column outlet. The composition of the eluent is phenol 0.96% Na, sO, 0.06%
%Met.
実施例２
被処理原液であるフェノール化合物溶液としてはヒドロ
キノン１．５％ シクロヘキサノール１．５％の組成を
持つ水溶液を用いた。Example 2 An aqueous solution having a composition of 1.5% hydroquinone and 1.5% cyclohexanol was used as the phenol compound solution as the stock solution to be treated.
実施例１の強酸性陽イオン交換樹脂をバイエル社製レバ
チットＭＤＳ１３６８Ｎａ型に替えさらの？８離時のカ
ラム温度を６０°Ｃとし他は同し条件として次の結果を
得た。The strongly acidic cation exchange resin in Example 1 was replaced with Levacit MDS1368Na type manufactured by Bayer. The following results were obtained under the same conditions except that the column temperature at the time of separation was 60°C.
処理液中濃度 溶離液中濃度
ヒドロキノン ０．０１％ １．３４％シクロヘ
キサノール １．４３％ ０．０９％これから明らかな
ごとく、フェノール化合物たるヒドロキノンは本発明の
カチオン交換樹脂により効果的に吸着分離されているの
に対し、しからざる化合物のシクロヘキサノールは実質
的に、吸着分離されないのである。Concentration in treatment solution Concentration in eluent Hydroquinone 0.01% 1.34% Cyclohexanol 1.43% 0.09% As is clear from this, hydroquinone, a phenolic compound, is effectively adsorbed and separated by the cation exchange resin of the present invention. On the other hand, the unwanted compound cyclohexanol is virtually not adsorbed and separated.
実施例３〜７
実施例２と同じカラム条件で原液として表１に示すフェ
ノール化合物を含む溶液を用い他は同し条件で吸着処理
した結果を表１に示す。Examples 3 to 7 Table 1 shows the results of adsorption treatment under the same column conditions as in Example 2, using solutions containing the phenolic compounds shown in Table 1 as stock solutions, and with the other conditions being the same.
［発明の効果および産業上の利用可能性］本発明の方法
によれば、従来のイオン交換法のように強塩基性の雰囲
気に物質を曝すことなく選択的な吸着が可能でありさら
には活性炭法、イオン交換法などの従来技術では達成さ
れなかった溶離剤としての酸、アルカリあるいは水蒸気
を使用することなしに目的のフェノール化合物を効果的
に分離することができるので好適である。[Effects of the invention and industrial applicability] According to the method of the present invention, selective adsorption is possible without exposing the substance to a strong basic atmosphere as in the conventional ion exchange method, and furthermore, it is possible to adsorb substances selectively using activated carbon. This method is suitable because the target phenol compound can be effectively separated without using an acid, alkali, or water vapor as an eluent, which has not been achieved with conventional techniques such as the method and the ion exchange method.
表１Table 1
Claims (4)
た強酸性カチオン交換樹脂に接触せしめ、該フェノール
化合物を吸着させることを特徴とするフェノール化合物
の分離方法。(1) A method for separating phenolic compounds, which comprises bringing a solution containing a phenol compound into contact with a strongly acidic cation exchange resin prepared in a salt form to adsorb the phenol compound.
ゾルシン、ヒドロキノン、オルシン、ウルシオール、ピ
ロガロール、フロログルシン、ヒドロキシヒドロキノン
およびそれらの誘導体である特許請求の範囲第１項記載
の分離方法。(2) The separation method according to claim 1, wherein the phenolic compound is phenol, catechol, resorcinol, hydroquinone, orcine, urushiol, pyrogallol, phloroglucin, hydroxyhydroquinone, and derivatives thereof.
の誘導体である特許請求の範囲第１項記載の分離方法。(3) The separation method according to claim 1, wherein the phenolic compound is a phenolic acid or a derivative thereof.
プロトカテチュ酸、ゲンチシン酸、レゾルシル酸、オル
セリン酸、カフェー酸、ウンベル酸、没食子酸、オキシ
フタル酸およびそれらの誘導体である特許請求の範囲第
３項記載の分離方法。(4) Phenolic acids include salicylic acid, oxybenzoic acid,
The separation method according to claim 3, which is protocatechuic acid, gentisic acid, resorcilic acid, orceric acid, caffeic acid, umbelic acid, gallic acid, oxyphthalic acid, and derivatives thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16259290A JP2866711B2 (en) | 1990-06-22 | 1990-06-22 | Method for separating phenolic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16259290A JP2866711B2 (en) | 1990-06-22 | 1990-06-22 | Method for separating phenolic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0454142A true JPH0454142A (en) | 1992-02-21 |
| JP2866711B2 JP2866711B2 (en) | 1999-03-08 |
Family
ID=15757522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16259290A Expired - Lifetime JP2866711B2 (en) | 1990-06-22 | 1990-06-22 | Method for separating phenolic compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2866711B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998042651A1 (en) * | 1997-03-21 | 1998-10-01 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids |
| KR100357023B1 (en) * | 1999-08-05 | 2002-10-18 | 학교법인고려중앙학원 | Composition of Separator and Method of Separation for Hydroquinone and Benzoquinone |
| JP2006308415A (en) * | 2005-04-28 | 2006-11-09 | Kao Corp | Measurement method of amount of hydroxyhydroquinone |
| JP2007054058A (en) * | 2005-07-29 | 2007-03-08 | Kao Corp | Method for producing coffee composition |
| JP2007054057A (en) * | 2005-07-29 | 2007-03-08 | Kao Corp | Method for producing coffee composition |
| JP2007195458A (en) * | 2006-01-26 | 2007-08-09 | T Hasegawa Co Ltd | Method for producing tea extract processed product improved in flavor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100469751C (en) * | 2006-07-24 | 2009-03-18 | 乐山三江生化科技有限公司 | Process of rectifying gallic acid through eliminating metal impurity in small amount |
-
1990
- 1990-06-22 JP JP16259290A patent/JP2866711B2/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998042651A1 (en) * | 1997-03-21 | 1998-10-01 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Process for separating and purifying alkali metal salts of hydroxynaphthalenecarboxylic acids |
| KR100357023B1 (en) * | 1999-08-05 | 2002-10-18 | 학교법인고려중앙학원 | Composition of Separator and Method of Separation for Hydroquinone and Benzoquinone |
| JP2006308415A (en) * | 2005-04-28 | 2006-11-09 | Kao Corp | Measurement method of amount of hydroxyhydroquinone |
| JP2007054058A (en) * | 2005-07-29 | 2007-03-08 | Kao Corp | Method for producing coffee composition |
| JP2007054057A (en) * | 2005-07-29 | 2007-03-08 | Kao Corp | Method for producing coffee composition |
| JP4667318B2 (en) * | 2005-07-29 | 2011-04-13 | 花王株式会社 | Method for producing coffee composition |
| JP4667317B2 (en) * | 2005-07-29 | 2011-04-13 | 花王株式会社 | Method for producing coffee composition |
| JP2007195458A (en) * | 2006-01-26 | 2007-08-09 | T Hasegawa Co Ltd | Method for producing tea extract processed product improved in flavor |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2866711B2 (en) | 1999-03-08 |
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