JPS61186346A - Production of 4,4-bis(4-hdyroxyphenyl)pentanoic acid - Google Patents
Production of 4,4-bis(4-hdyroxyphenyl)pentanoic acidInfo
- Publication number
- JPS61186346A JPS61186346A JP60027244A JP2724485A JPS61186346A JP S61186346 A JPS61186346 A JP S61186346A JP 60027244 A JP60027244 A JP 60027244A JP 2724485 A JP2724485 A JP 2724485A JP S61186346 A JPS61186346 A JP S61186346A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mercaptan
- alkyl
- bis
- pentanoic acid
- 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
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の目的〕
（産業上の利用分野）
本発明は４，４−ビス（４−ヒドロキシフェニル）ペン
タン酸の製造に関するものであるｏ４，４−ビス（４−
ヒドロキシフェニル）ペンタン酸は、高分子添加剤例え
ばポリカーボネートの改質剤等に用いられる有用な化合
物である。Detailed Description of the Invention [Object of the Invention] (Industrial Application Field) The present invention relates to the production of 4,4-bis(4-hydroxyphenyl)pentanoic acid, o4,4-bis(4-
Hydroxyphenyl)pentanoic acid is a useful compound used as a polymeric additive, such as a modifier for polycarbonate.
（従来の技術）
４．４−ビス（４−ヒドロキシフェニル）ペンタン酸ｆ
ｔ製造する方法として従来、硫酸あるいは塩酸等の鉱酸
の存在下、レプリン酸と７エノールとを縮合せしめる方
法（米国特許第２９７１０２５号。(Prior art) 4.4-bis(4-hydroxyphenyl)pentanoic acid f
A conventional method for producing t is a method of condensing leplic acid and 7 enol in the presence of a mineral acid such as sulfuric acid or hydrochloric acid (US Pat. No. 2,971,025).
英国特許第７６８２０６号）、塩酸の存在下、レプ号）
あるいはメチルメルカプタンを用いる方法（特公昭４１
−５９３０号）等が知られている０（発明が解決しよう
とする問題点）
前記従来法における反応は
（１） 特に触媒物質等を用いない場合、収率が低い
０
（２）触媒物質としてメルカプト酢酸を用いた場合、樹
脂状生成物の収量を低くするため、長時間反応させる必
要があり、また副反応生成物の割合も多く、分離のため
に結晶化操作を必要とする。British Patent No. 768206), in the presence of hydrochloric acid, Rep. No. 768206)
Alternatively, a method using methyl mercaptan (Special Publication Publication No. 41)
-5930) etc. (Problems to be Solved by the Invention) The reaction in the conventional method is (1) The yield is low, especially when no catalyst substance is used. (2) As a catalyst substance, When mercaptoacetic acid is used, it is necessary to carry out the reaction for a long time in order to reduce the yield of the resinous product, and the proportion of side reaction products is also high, requiring a crystallization operation for separation.
（３）触媒物質としてメチルメルカプタンを用いた場合
、低沸物質のため取り扱いが困難なうえ、加圧下での反
応をしいられる。さらに悪臭対策も必要となる１、
等の欠点を有し、いずれも工業的に有利な方法とはいえ
ない。(3) When methyl mercaptan is used as a catalyst substance, it is difficult to handle because it is a low-boiling substance, and the reaction must be carried out under pressure. In addition, these methods have drawbacks such as 1, which requires countermeasures against bad odors, and neither method can be said to be industrially advantageous.
本発明は、上記従来法の欠点を排除するため触媒物質と
してアルキルメルカプクンを用い、鉱酸の存在下、フェ
ノールとレプリン酸を縮合させ、高収率で４，４−ビス
（４−ヒドロキシフェニル）ペンタン酸を工業的に製造
する方法を提供するものである。In order to eliminate the drawbacks of the above-mentioned conventional methods, the present invention uses alkyl mercapkun as a catalyst material to condense phenol and lepuric acid in the presence of mineral acid, resulting in a high yield of 4,4-bis(4-hydroxyphenyl ) Provides a method for industrially producing pentanoic acid.
（問題点を解決するための手段）
本発明の要旨は、鉱酸の存在下、フェノールとレプリン
酸とを縮合せしめる際、触媒物質として一般式ＲＳＨ（
ここにＲはＣ５〜Ｃ２Ｇのアルキル基を示す）で表わさ
れるアルキルメルカプクンを使用することを特徴とする
４、４−４ｘｉ’ス（４−ヒドロキシフェニル）ペンタ
ン酸の製造法である。(Means for Solving the Problems) The gist of the present invention is to use the general formula RSH (
This is a method for producing 4,4-4xi'-(4-hydroxyphenyl)pentanoic acid, which is characterized by using an alkylmercapkun represented by R (R represents a C5-C2G alkyl group).
本発明の触媒物質として用いる一般式ＲＳ Ｈ（ここに
ＲはＣ５〜Ｃ２０のアルキル基を示す）で表わされる。It is represented by the general formula RSH (where R represents a C5-C20 alkyl group) used as the catalyst material of the present invention.
アルキルメルカプタンの具体例としてｌｉ、ｎ−アミル
メルカプタン、５ｅｃ−アミルメルカプタン、ｎ−へキ
シルメルカプタン、５ｅｃ−へキシルメルカプタン、ｎ
−オクチルメルカプタン。Specific examples of alkyl mercaptan include li, n-amyl mercaptan, 5 ec-amyl mercaptan, n-hexyl mercaptan, 5 ec-hexyl mercaptan, n
-Octyl mercaptan.
５ｅｃ−オクチルメルカプタン、ｎ−ドデシルメルカプ
タン、ｎ−セチルメルカプタン、ｎ−エイコシルメルカ
プタン等が使用でき、特にｎ−オクチルメルカプタン、
５ｅｃ−オクチルメルカプクン、ｎ−へキシルメルカプ
タン等は好結果を与える０これらのアルキルメルカプタ
ンは、いずれも１００℃以上の沸点を有する化合物であ
るため、取り扱いが容易であり、かつ常圧下での反応が
可能である。5ec-octylmercaptan, n-dodecylmercaptan, n-cetylmercaptan, n-eicosylmercaptan, etc. can be used, especially n-octylmercaptan,
5ec-octylmercaptan, n-hexylmercaptan, etc. give good results. These alkylmercaptans are all compounds with a boiling point of 100°C or higher, so they are easy to handle and can be reacted under normal pressure. is possible.
本発明においては、フェノールとレプリン酸は化学量論
的比が好ましく、アルキルメルカプタンの使用量として
は、レプリン酸に対し、０．１〜１０モル％の範囲で用
いるのが好ましい。０．１モルにより少ないと反応速度
が遅く、収率が低下し、１０モル％以上を用いても顕著
な効果は認められないので不経済である。In the present invention, phenol and leplic acid are preferably used in a stoichiometric ratio, and the amount of alkylmercaptan used is preferably 0.1 to 10 mol% based on leplic acid. When the amount is less than 0.1 mol, the reaction rate is slow and the yield is reduced, and even if 10 mol % or more is used, no significant effect is observed, which is uneconomical.
また、縮合剤および反応溶剤として用いられる鉱酸とし
ては、塩酸、硫酸等が使用できるが、特に塩酸は好結果
を与える。用いられる塩酸の濃度は３４〜５０％の範囲
で使用でき、特に３７〜４２％の範囲で行なうと好結果
が得られる。Further, as the mineral acid used as the condensing agent and the reaction solvent, hydrochloric acid, sulfuric acid, etc. can be used, and particularly hydrochloric acid gives good results. The concentration of hydrochloric acid used can be in the range of 34 to 50%, and particularly good results are obtained when the concentration is in the range of 37 to 42%.
縮合の際の反応温度は２５〜８０℃、望ましくは４０〜
６０℃の範囲で行なうと好結果が得られるＯ
温度が低すぎると反応速度が遅く、逆に温度が高すぎる
と副生物が生成する九め収率が低下する。The reaction temperature during condensation is 25-80°C, preferably 40-80°C.
Good results are obtained when carried out within the range of 60°C. If the temperature is too low, the reaction rate is slow, and on the other hand, if the temperature is too high, by-products are produced and the yield is reduced.
縮合の際の反応時間は通常１５〜２０時間で完了する。The reaction time for condensation is usually 15 to 20 hours.
（作 用）
反応機構は詳らかでないが、従来知られていなかっ友高
級メルカプタンを用いると、収率よ＜４゜４−ビス（４
−ヒドロキシフェニル）ペンタン酸が製造できるのは意
外ともいうべく本発明の効果である。(Function) Although the reaction mechanism is not clear, if a previously unknown high-grade mercaptan is used, the yield will be <4°4-bis(4
-Hydroxyphenyl)pentanoic acid can be produced, which is a surprising effect of the present invention.
（実施例） 以下、実施例により詳細に説明する。(Example) Hereinafter, it will be explained in detail using examples.
実施例ル
プリン酸５８ＰＣ０，５モル）、フェノール９４ＰＣ１
，０モル）、４２％塩酸１６２Ｐ、ｎ−オクチルメルカ
プタン３．６５ＰＣ０，０２５モル）を仕込み５５℃に
て、２０時間攪拌した。反応後、水２００ｗＩ！、を加
え、冷却後析出した結晶をｒ別水洗した。得られた湿ケ
ーキに水６００−および無水重亜硫酸ソーダ（Ｎａ２５
ｚＯｓ ） １．２Ｆを加え還流下で溶解させ、付着し
たｎ−オクチルメルカプタンを水との共沸蒸留で取り除
いたのち、冷却し析出した結晶をＰ別、水洗、乾燥して
、淡黄色の４，４−ビス（４−ヒドロキシフェニル）ペ
ンタン酸１２６．６ｙ（融点１７３．５−１７５℃）ｔ
−得た。Example Lupuric acid 58PC0.5 mol), Phenol 94PC1
, 0 mol), 42% hydrochloric acid (162 P, n-octyl mercaptan 3.65 P, 0,025 mol) and stirred at 55° C. for 20 hours. After reaction, 200wI of water! , and after cooling, the precipitated crystals were washed with water separately. The resulting wet cake was mixed with water and anhydrous sodium bisulfite (Na25).
zOs ) 1.2F was added and dissolved under reflux, and the adhering n-octyl mercaptan was removed by azeotropic distillation with water. After cooling, the precipitated crystals were separated from P, washed with water, and dried to give pale yellow 4 , 4-bis(4-hydroxyphenyl)pentanoic acid 126.6y (melting point 173.5-175°C)t
-I got it.
収率は、８８．５％であった。The yield was 88.5%.
実施例２〜７
アルキルメルカプタンとその使用ｔｔ表−１のとおりと
した以外は、実施例１と同様に操作を行ない表−１の結
果を得た。Examples 2 to 7 Alkyl mercaptan and its use ttThe same procedure as in Example 1 was carried out except that the procedure was as shown in Table 1, and the results shown in Table 1 were obtained.
（発明の効果）
本発明の方法で４．４−ビス（４−ヒドロキシフェニル
）ペンタン酸を製造すれば桑常圧で〉容易に高収率で目
的物を取得することができる。(Effects of the Invention) If 4,4-bis(4-hydroxyphenyl)pentanoic acid is produced by the method of the present invention, the desired product can be easily obtained in high yield under normal pressure.
出願人 製鉄化学工業株式会社 代表者 佐々木 浩Applicant: Steel Chemical Industry Co., Ltd. Representative Hiroshi Sasaki
Claims (4)
せしめる際、触媒物質として一般式ＲＳＨ（ここにＲは
Ｃ＿５〜Ｃ＿２＿０のアルキル基を示す）で表わされる
アルキルメルカプタンを使用することを特徴とする４，
４−ビス（４−ヒドロキシフェニル）ペンタン酸の製造
法。(1) When condensing phenol and leplic acid in the presence of a mineral acid, an alkyl mercaptan represented by the general formula RSH (where R represents an alkyl group of C_5 to C_2_0) is used as a catalyst substance. 4,
A method for producing 4-bis(4-hydroxyphenyl)pentanoic acid.
ンである特許請求の範囲（１）記載の方法。(2) The method according to claim (1), wherein the alkyl mercaptan is n-octyl mercaptan.
範囲（１）記載の方法。(3) The method according to claim (1), wherein the mineral acid is hydrochloric acid with a concentration of 34 to 50%.
し、０．１〜１０モルにである特許請求の範囲（１）記
載の方法。(4) The method according to claim (1), wherein the amount of alkyl mercaptan used is 0.1 to 10 mol based on leplic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60027244A JPH0643366B2 (en) | 1985-02-13 | 1985-02-13 | Process for producing 4,4-bis (4-hydroxyphenyl) pentanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60027244A JPH0643366B2 (en) | 1985-02-13 | 1985-02-13 | Process for producing 4,4-bis (4-hydroxyphenyl) pentanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61186346A true JPS61186346A (en) | 1986-08-20 |
| JPH0643366B2 JPH0643366B2 (en) | 1994-06-08 |
Family
ID=12215664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60027244A Expired - Lifetime JPH0643366B2 (en) | 1985-02-13 | 1985-02-13 | Process for producing 4,4-bis (4-hydroxyphenyl) pentanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0643366B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5969180A (en) * | 1998-01-30 | 1999-10-19 | General Electric Company | Method for making bis-xylenols containing acid moieties |
-
1985
- 1985-02-13 JP JP60027244A patent/JPH0643366B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5969180A (en) * | 1998-01-30 | 1999-10-19 | General Electric Company | Method for making bis-xylenols containing acid moieties |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0643366B2 (en) | 1994-06-08 |
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