JPH01160932A - Production of 3,3-bis(4-hydroxyphenyl)-cyclohexanol - Google Patents
Production of 3,3-bis(4-hydroxyphenyl)-cyclohexanolInfo
- Publication number
- JPH01160932A JPH01160932A JP62318704A JP31870487A JPH01160932A JP H01160932 A JPH01160932 A JP H01160932A JP 62318704 A JP62318704 A JP 62318704A JP 31870487 A JP31870487 A JP 31870487A JP H01160932 A JPH01160932 A JP H01160932A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyphenyl
- bis
- cyclohexanol
- reaction
- hydroxycyclohexanone
- 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
- LZLRPHXCSIKGQU-UHFFFAOYSA-N 4-[3-hydroxy-1-(4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(O)CCCC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 LZLRPHXCSIKGQU-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- TWEVQGUWCLBRMJ-UHFFFAOYSA-N 3-hydroxycyclohexanone Chemical compound OC1CCCC(=O)C1 TWEVQGUWCLBRMJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 7
- -1 alkyl mercaptan Chemical compound 0.000 abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 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 abstract description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- 239000003729 cation exchange resin Substances 0.000 abstract description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 abstract description 2
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007789 gas Substances 0.000 abstract description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract description 2
- 229960001755 resorcinol Drugs 0.000 abstract description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- BWBGEYQWIHXDKY-UHFFFAOYSA-N 3-(4-hydroxyphenyl)phenol Chemical group C1=CC(O)=CC=C1C1=CC=CC(O)=C1 BWBGEYQWIHXDKY-UHFFFAOYSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
- IPHDZYSMEITSBA-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-4-methylcyclohexyl]phenol Chemical compound C1CC(C)CCC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 IPHDZYSMEITSBA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- GTUIOIQPAWIFIZ-UHFFFAOYSA-N 2-(1-hydroxycyclohexyl)phenol Chemical compound OC1=CC=CC=C1C1(O)CCCCC1 GTUIOIQPAWIFIZ-UHFFFAOYSA-N 0.000 description 1
- NRXDVQQBDGLLCC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,5-dimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 NRXDVQQBDGLLCC-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012362 glacial acetic acid Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は３．３−ビス（４−ヒドロキシフェニル）−シ
クロヘキサノールの製造方法に関する。さらに詳細には
３−ヒドロキシフェニルシクロヘキサノンをフェノール
と縮合反応させることを特徴とする３、３−ビス（４−
ヒドロキシフェニル）−シクロヘキサノールの製造方法
に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing 3,3-bis(4-hydroxyphenyl)-cyclohexanol. More specifically, 3,3-bis(4-
The present invention relates to a method for producing (hydroxyphenyl)-cyclohexanol.
３．３−ビス（４−ヒドロキシフェニル）−シクロヘキ
サノール新規な化合物であり、３．４゛−ジヒドロキシ
ビフェニル等の前駆体として有用である。3.3-Bis(4-hydroxyphenyl)-cyclohexanol is a novel compound and is useful as a precursor for 3.4'-dihydroxybiphenyl and the like.
１．１−ビス（４−ヒドロキシフェニル）−シクロヘキ
サン、または４−メチル−１，１−ビス（４−ヒドロキ
シフェニル）−シクロヘキサン等のようなシクロヘキサ
ン環にアルキル基を持つ化合物は公知である。例えば、
１，１−ビス（４−ヒドロキシフェニル）−シクロヘキ
サンは融点１８４°Ｃを有する結晶であり、４−メチル
−１，１−ビス（４−ヒドロキシフェニル）−シクロヘ
キサンや３．５−ジメチル−１，１−ビス（４−ヒドロ
キシフェニル）−シクロヘキサンは、それぞれ融点１８
０°Ｃまたは１７４°Ｃを有する結晶である。〔メト−
デンプル オルガニイシェン ヒイミー（Ｍｅｔｈｏｄ
ｅｎ ｄｅｒ ｏｒｇａｎｉｓｈｅｎ Ｃｈｅｍｉｅ
、 Ｖｏｌ ６ 、 Ｎα２，１０２Ｂ） ）〔目的及
びこれを達成するための手段］３．３−ビス（４−ヒド
ロキシフェニル）−シクロヘキサノールについては、こ
れまで全く知られていなかったのであるが、本発明者等
は、その合成に成功し、本発明はこの新規な化合物の製
造方法を提供することにある。Compounds having an alkyl group on the cyclohexane ring, such as 1.1-bis(4-hydroxyphenyl)-cyclohexane or 4-methyl-1,1-bis(4-hydroxyphenyl)-cyclohexane, are known. for example,
1,1-bis(4-hydroxyphenyl)-cyclohexane is a crystal with a melting point of 184°C, and 4-methyl-1,1-bis(4-hydroxyphenyl)-cyclohexane and 3,5-dimethyl-1, 1-bis(4-hydroxyphenyl)-cyclohexane each has a melting point of 18
It is a crystal with a temperature of 0°C or 174°C. [metho-
Demple Organishen Hyimy (Method)
En der organischen Chemie
, Vol. 6, Nα2,102B) The inventors have succeeded in its synthesis, and the object of the present invention is to provide a method for producing this novel compound.
即ち、本発明は３−ヒドロキシシクロヘキサノンをフェ
ノールと縮合反応させることを特徴とする３、３−ビス
（４−ヒドロキシフェニル）−シクロヘキサノールの製
造方法である。That is, the present invention is a method for producing 3,3-bis(4-hydroxyphenyl)-cyclohexanol, which is characterized by subjecting 3-hydroxycyclohexanone to a condensation reaction with phenol.
本発明反応において原料として使用される３−ヒドロキ
シシクロヘキサノンはレゾルシンの還元、シクロヘキセ
ン−３−オンの水付加反応、あるいは１．３−シクロヘ
キサンジオールの酸化等の方法により得ることができる
。3-Hydroxycyclohexanone used as a raw material in the reaction of the present invention can be obtained by methods such as reduction of resorcin, water addition reaction of cyclohexen-3-one, or oxidation of 1,3-cyclohexanediol.
本発明反応は通常、触媒の存在下に行われる。The reaction of the present invention is usually carried out in the presence of a catalyst.
例えば塩酸、塩化水素ガスのほか、硫酸、リン酸、トル
エンスルホン酸、ＢＦｓ、ＺｎＣｌ 、、ＡＰ、Ｃ２１
，５ｎＣｊ２４及び移動酸性基を存する陽イオン交換樹
脂などが挙げられる。これらの触媒の使用量は３−ヒド
ロキシシクロへキサノン１００重量部あたり０．１〜３
０１ｉ１部の範囲である。また、助触媒の添加により反
応速度を高めることも可能であり、メチルメルカプタン
、エチルメルカプタン、ｎ−プロとルメルカブタン、イ
ソプロピルメルカプタン、ｎ−ブチルメルカプタン、イ
ソブチルメルカプタン、Ｌ−ブチルメルカプタンの如き
アルキルメルカプタン又は高分子量アルキルメルカプタ
ンなどが活性な助触媒である。For example, in addition to hydrochloric acid and hydrogen chloride gas, sulfuric acid, phosphoric acid, toluenesulfonic acid, BFs, ZnCl, AP, C21
, 5nCj24 and a cation exchange resin containing a mobile acidic group. The amount of these catalysts used is 0.1 to 3 per 100 parts by weight of 3-hydroxycyclohexanone.
01i1 part range. It is also possible to increase the reaction rate by adding co-catalysts, such as alkyl mercaptans or polymers such as methyl mercaptan, ethyl mercaptan, n-pro-lumercaptan, isopropyl mercaptan, n-butyl mercaptan, isobutyl mercaptan, L-butyl mercaptan. Active cocatalysts include molecular weight alkyl mercaptans.
また硫化水素、チオフェノール、チオアルコール、チオ
酸、重合体チオアセトン、ジアルキルスルフィドの如き
他のイオウ化合物やこれらと類似のセレン化合物もまた
用いることができる。Other sulfur compounds such as hydrogen sulfide, thiophenols, thioalcohols, thioacids, polymeric thioacetones, dialkyl sulfides, and similar selenium compounds can also be used.
本発明反応にいおては、芳香族炭化水素、塩素化脂肪族
炭化水素、氷酢酸などのような反応に悪影響を及ぼさな
い溶媒を用いて行うこともできる。The reaction of the present invention can also be carried out using solvents that do not adversely affect the reaction, such as aromatic hydrocarbons, chlorinated aliphatic hydrocarbons, glacial acetic acid, and the like.
しかしながら、生成物の収率を高め、かつ副反応を最少
にするには過剰量のフェノールを溶媒とするのが望まし
い。使用するフェノールの量は３−ヒドロキシシクロへ
キサノン１重量部あたり２重量部から１０重量部が適当
である。However, it is desirable to use an excess of phenol as the solvent to increase product yield and minimize side reactions. The amount of phenol used is suitably 2 to 10 parts by weight per 1 part by weight of 3-hydroxycyclohexanone.
また、本発明における反応温度は３０°Ｃから１００℃
の範囲で、好ましくは４０°Ｃから８０°Ｃの範囲であ
る。反応温度が高いと副生物が増え、収率が低下するの
で好ましくない。Furthermore, the reaction temperature in the present invention is from 30°C to 100°C.
, preferably in the range of 40°C to 80°C. If the reaction temperature is high, by-products will increase and the yield will decrease, which is not preferable.
本反応によって生成した３、３−ビス（４−ヒドロキシ
フェニル）−シクロヘキサノールは、例えばベンゼンな
どの本発明の化合物を溶解し難い溶媒に、反応マスを排
出し、冷却晶出させることにより、あるいは触媒は除去
したのち脱フエノールすること等によって取り出すこと
ができる。3,3-bis(4-hydroxyphenyl)-cyclohexanol produced by this reaction can be obtained by discharging the reaction mass into a solvent in which the compound of the present invention is difficult to dissolve, such as benzene, and cooling and crystallizing it, or After the catalyst is removed, it can be taken out by dephenolization or the like.
また過剰に使用したフェノールは、減圧下で蒸留するな
どの方法によって回収、再使用することができる。Moreover, the phenol used in excess can be recovered and reused by a method such as distillation under reduced pressure.
以下実施例により本発明を具体的に説明する。The present invention will be specifically explained below using Examples.
１００ ｄ反応フラスコに３−ヒドロキシシクロへキサ
ノン１１．４ｇ（０，１０モル）、フェノール４７．１
ｇ（０゜５０モル）、３６％塩酸３ｍｌ、ｎ−ブチルメ
ルカプタン０．５戚を仕込み４０°Ｃで６時間反応させ
た。反応終了後トルエン２００ ｍ、水５０ｍの混合液
中に排出し、−昼夜放置した。晶出した結晶を濾別洗浄
して乾燥し、白色結晶２１．６ｇを得た。液体クロマト
グラフィーによる３、３−ビス（４−ヒドロキシフェニ
ル）−シクロヘキサノールの純度８０％であった。収率
６１％。11.4 g (0.10 mol) of 3-hydroxycyclohexanone, 47.1 phenol in a 100 d reaction flask
(0.50 mol), 3 ml of 36% hydrochloric acid, and 0.5 mol of n-butyl mercaptan were charged and reacted at 40° C. for 6 hours. After the reaction was completed, the reactor was discharged into a mixture of 200 m of toluene and 50 m of water, and left to stand day and night. The precipitated crystals were filtered, washed, and dried to obtain 21.6 g of white crystals. The purity of 3,3-bis(4-hydroxyphenyl)-cyclohexanol was 80% as determined by liquid chromatography. Yield 61%.
Claims (1)
縮合反応させることを特徴とする３，３−ビス（４−ヒ
ドロキシフェニル）−シクロヘキサノールの製造方法。(1) A method for producing 3,3-bis(4-hydroxyphenyl)-cyclohexanol, which comprises subjecting 3-hydroxycyclohexanone to a condensation reaction with phenol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62318704A JP2515354B2 (en) | 1987-12-18 | 1987-12-18 | Process for producing 3,3-bis (4-hydroxyphenyl) -cyclohexanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62318704A JP2515354B2 (en) | 1987-12-18 | 1987-12-18 | Process for producing 3,3-bis (4-hydroxyphenyl) -cyclohexanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01160932A true JPH01160932A (en) | 1989-06-23 |
| JP2515354B2 JP2515354B2 (en) | 1996-07-10 |
Family
ID=18102064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62318704A Expired - Lifetime JP2515354B2 (en) | 1987-12-18 | 1987-12-18 | Process for producing 3,3-bis (4-hydroxyphenyl) -cyclohexanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2515354B2 (en) |
-
1987
- 1987-12-18 JP JP62318704A patent/JP2515354B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2515354B2 (en) | 1996-07-10 |
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