JPH03157342A - Purification of 4,4'-isopropylidenedicyclohexanol - Google Patents
Purification of 4,4'-isopropylidenedicyclohexanolInfo
- Publication number
- JPH03157342A JPH03157342A JP29626089A JP29626089A JPH03157342A JP H03157342 A JPH03157342 A JP H03157342A JP 29626089 A JP29626089 A JP 29626089A JP 29626089 A JP29626089 A JP 29626089A JP H03157342 A JPH03157342 A JP H03157342A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- catalyst
- liquid
- reaction
- product
- 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
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000746 purification Methods 0.000 title description 6
- 239000002904 solvent Substances 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 239000007810 chemical reaction solvent Substances 0.000 claims description 11
- OBTNQJQVKQVMSI-UHFFFAOYSA-N 1-[2-(1-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CCCCC1(O)C(C)(C)C1(O)CCCCC1 OBTNQJQVKQVMSI-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 abstract description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract description 5
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 6
- 239000012295 chemical reaction liquid Substances 0.000 abstract 3
- 239000000047 product Substances 0.000 description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 alicyclic hydrocarbons Chemical class 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- 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、不飽和ポリエステル樹脂、エポキシ樹脂等の
ポリマー原料などとして有用な４．４゜イソプロピリデ
ンジシクロヘキサノールを純度高く、しかも効率良く回
収することのできる４、４゛−イソプロピリデンジシク
ロヘキサノールの精製法に関する。[Detailed Description of the Invention] [Field of Industrial Application] The present invention is directed to the efficient recovery of 4.4° isopropylidene dicyclohexanol, which is useful as a raw material for polymers such as unsaturated polyester resins and epoxy resins, with high purity. The present invention relates to a method for purifying 4,4'-isopropylidene dicyclohexanol.
〔従来の技術および発明が解決しようとする課題〕従来
、４．４゛−イソプロピリデンジシクロヘキサノールを
精製する方法として、例えば■真空蒸留で溶媒を留出さ
せ、製品を回収する方法（特公昭４２−１４２３号公報
、特公昭６１−２６００３４号公報）、■再結晶法によ
り製品を回収する方法（特公昭４３−２６８５９号公報
、 Ｕ Ｓ Ｐ４，４８７．９７９号公報）などが知ら
れている。[Prior art and problems to be solved by the invention] Conventionally, as a method for purifying 4.4'-isopropylidene dicyclohexanol, for example (Japanese Patent Publication No. 42-1423, Japanese Patent Publication No. 61-260034), ■ A method of recovering the product by recrystallization method (Japanese Patent Publication No. 43-26859, US Pat. No. 4,487.979), etc. are known. .
上記■の方法によれば、製品である４、４“−イソプロ
ピリデンジシクロヘキサノールは、はイ完全に回収する
ことができるものの、かなり厳しい蒸・留条件が必要で
あり、製品の純度が上がるほど過度の高温に熱せられる
ため、製品が着色しやすくなるという欠点がある。また
、蒸留条件をマイルドにすると、溶媒が製品中に残存し
、低融点のものしか得られないおそれがある。According to method ① above, the product 4,4"-isopropylidene dicyclohexanol can be completely recovered, but it requires fairly severe distillation conditions, which increases the purity of the product. The drawback is that the product is likely to become discolored because it is heated to an excessively high temperature.Furthermore, if the distillation conditions are mild, the solvent may remain in the product and only a product with a low melting point can be obtained.
一方、上記■の方法によれば、水素添加反応時の分解副
生成物を除去することができ、その結果製品純度の向上
は期待できるものの、溶媒として良溶媒を用いているた
め、製品である４、４゛−イソプロピリデンジシクロヘ
キサノールの異性体分布が極端に変わったり、回収率が
著しく低ぐなるという欠点がある。すなわち、上記■の
方法では良溶媒を使用しているため、製品中の比較的溶
媒に溶けやすい成分（シス−シス体、シス−トランス体
）が溶媒中に一部移行し、この結果トランス−トランス
体の含有量が多くなり、異性体分布が変動するというお
それがある。On the other hand, according to method ① above, decomposition byproducts during the hydrogenation reaction can be removed, and as a result, an improvement in product purity can be expected, but since a good solvent is used as a solvent, the product There are disadvantages in that the isomer distribution of 4,4'-isopropylidene dicyclohexanol changes drastically and the recovery rate is extremely low. In other words, since a good solvent is used in method (1) above, some of the components in the product that are relatively easily soluble in solvents (cis-cis isomer, cis-trans isomer) migrate into the solvent, and as a result, trans- There is a risk that the content of trans isomer will increase and the isomer distribution will fluctuate.
本発明は、上記の如き従来の問題点を解決し、４．４°
−イソプロピリデンジシクロヘキサノールを純度高く、
しかも効率良く回収することのできる４、４′−イソプ
ロピリデンジシクロヘキサノールの精製法を提供するこ
とを目的とするものである。The present invention solves the conventional problems as described above, and achieves a 4.4°
- Isopropylidene dicyclohexanol with high purity,
Moreover, it is an object of the present invention to provide a method for purifying 4,4'-isopropylidene dicyclohexanol that can be efficiently recovered.
すなわち本発明は、４．４°−イソプロピリデンジフェ
ノールを、触媒を用いて、溶媒存在下に接触水素化して
得られる４、４°−イソプロピリデンジシクロヘキサノ
ールを精製するにあたり、反応溶媒を含む反応生成液か
ら触媒を除去し、次いで反応溶媒の一部を除去し、その
後４，４゛−イソプロピリデンジシクロヘキサノールに
対する貧溶媒で洗浄し、乾燥することを特徴とする４、
４“−イソプロピリデンジシクロヘキサノールの精製法
を提供するものである。That is, the present invention includes a reaction solvent when purifying 4,4°-isopropylidenedicyclohexanol obtained by catalytically hydrogenating 4.4°-isopropylidene diphenol using a catalyst in the presence of a solvent. 4, characterized in that the catalyst is removed from the reaction product liquid, then a part of the reaction solvent is removed, and then washed with a poor solvent for 4,4'-isopropylidene dicyclohexanol and dried;
A method for purifying 4"-isopropylidene dicyclohexanol is provided.
本発明において、精製の対象とする４、４“−イソプロ
ピリデンジシクロヘキサノールは、原料である４、４゛
−イソプロピリデンジフェノール（ビスフェノールＡ）
を、−船釣な核水添用の触媒を用いて、溶媒存在下に接
触水素化することにより、容易に得ることができる。In the present invention, 4,4"-isopropylidene dicyclohexanol to be purified is derived from the raw material 4,4"-isopropylidene diphenol (bisphenol A).
can be easily obtained by catalytic hydrogenation in the presence of a solvent using a commercially available nuclear hydrogenation catalyst.
この場合、触媒としては一般的な核水添用の触媒、例え
ばアルミナまたはカーボンを担体とするルテニウム触媒
、アルミナまたはカーボンを担体とするロジウム触媒、
ラネーニ・ンケル、アルミナ担持ニッケル触媒等を用い
ることができる。In this case, the catalyst used is a general nuclear hydrogenation catalyst, such as a ruthenium catalyst using alumina or carbon as a carrier, or a rhodium catalyst using alumina or carbon as a carrier.
Raneni catalysts, alumina-supported nickel catalysts, and the like can be used.
また、接触水素化の際に用いる反応溶媒としては、アル
コール系溶媒が好ましく、より具体的には脂肪族アルコ
ール、指環族アルコール等を用いることが好ましい。Further, as the reaction solvent used in the catalytic hydrogenation, an alcohol solvent is preferable, and more specifically, it is preferable to use an aliphatic alcohol, a ring group alcohol, or the like.
さらに、接触水素化の際の反応条件は、次の通りである
。まず、反応温度は、用いる触媒の種類により最適４度
があるが、通常５０〜２５０°Ｃの範囲である。Furthermore, the reaction conditions during catalytic hydrogenation are as follows. First, the reaction temperature is optimally 4 degrees Celsius depending on the type of catalyst used, but is usually in the range of 50 to 250 degrees Celsius.
また、反応圧力は反応速度および製品純度の面から高圧
はど望ましいが、通常は３０ｋｇ／ｃｆｆｌＧ〜７０ｋ
ｇ／ｄＧの範囲とされる。In addition, a high reaction pressure is desirable from the viewpoint of reaction rate and product purity, but it is usually 30 kg/cfflG to 70 kg.
g/dG range.
本発明の精製法においては、このように反応させて得ら
れる、反応溶媒を含む反応生成液（すなわち、触媒１反
応溶媒、５！品４，４°−イソプロピリデンジシクロヘ
キサノールを含む反応生成液）から、まず触媒を除去す
る。In the purification method of the present invention, the reaction product liquid containing the reaction solvent (i.e., the reaction product liquid containing the reaction solvent for the catalyst 1, the reaction product liquid containing the 5! product 4,4°-isopropylidene dicyclohexanol) obtained by the reaction as described above is used. ), first remove the catalyst.
触媒の除去は、通常、濾過により行なわれ、これにより
無色透明の液が得られる。The catalyst is usually removed by filtration, which yields a colorless and transparent liquid.
次に、上記の如く触媒の除去された反応生成液（無色透
明の液）から、反応溶媒の一部を除去する。Next, a portion of the reaction solvent is removed from the reaction product liquid (colorless and transparent liquid) from which the catalyst has been removed as described above.
反応溶媒の一部除去は、具体的には例えば、エバポレー
ターを用いて蒸発させることにより行なう。この蒸発に
より反応溶媒が濃縮される。Part of the reaction solvent is specifically removed by, for example, evaporating it using an evaporator. This evaporation concentrates the reaction solvent.
ここで溶媒除去量は、６０〜９５％とすることが好まし
い。溶媒の除去量が少ないと回収率が低下し、一方溶媒
の除去量が多いと固化し、洗浄効率が低下するため、い
ずれも好ましくない。Here, the amount of solvent removed is preferably 60 to 95%. If the amount of solvent removed is small, the recovery rate will decrease, while if the amount of solvent removed is large, it will solidify and the cleaning efficiency will decrease, so neither is preferable.
さらに本発明においては、このようにして得られる濃縮
液を４．４′−イソプロピリデンジシクロヘキサノール
に対する貧溶媒で洗浄し、乾燥する。Furthermore, in the present invention, the concentrate thus obtained is washed with a poor solvent for 4,4'-isopropylidene dicyclohexanol and dried.
すなわち、この濃縮液に、４，４”−イソプロピリデン
ジシクロヘキサノールに対する倉溶媒を加えて洗浄し、
その後乾燥により貧溶媒を蒸発除去することにより、目
的とする精ｌ！ｉ！物である４、４゛イソプロピリデン
ジシクロヘキサノールを得ることができる。That is, to this concentrated solution, a solvent for 4,4''-isopropylidene dicyclohexanol was added and washed,
After that, the poor solvent is removed by evaporation through drying to achieve the desired purity! i! 4,4' isopropylidene dicyclohexanol can be obtained.
ここで貧溶媒は、反応副生成物である分解生成物の軽質
分を選択的に溶解させる作用を果たし、これにより分解
生成物の軽質分が貧溶媒に移行する。一方、主生成物で
ある４、４°−イソプロピリデンジシクロヘキサノール
は貧溶媒にはほとんど溶解しない。したがって、高回収
率を維持しつつ、製品である４、４゛−イソプロピリデ
ンジシクロヘキサノールの純度を高めることが可能とな
る。Here, the poor solvent serves to selectively dissolve the light components of the decomposition products, which are reaction by-products, thereby transferring the light components of the decomposition products to the poor solvent. On the other hand, the main product, 4,4°-isopropylidene dicyclohexanol, hardly dissolves in poor solvents. Therefore, it is possible to increase the purity of the product, 4,4'-isopropylidene dicyclohexanol, while maintaining a high recovery rate.
なお、本発明で用いる貧溶媒としては、脂肪族炭化水素
おはびシクロペンクン、シクロヘキサンなどの脂環族炭
化水素が好ましい。本発明においては、製品純度の向上
および製品回収率の面から脂肪族炭化水素、とりわけ直
鎖状脂肪族炭化水素が好ましい。これら直鎖状脂肪族炭
化水素は、より選択的に反応副生成物である分解生成物
の軽質分を溶解するからである。このような直鎖状脂肪
族炭化水素としては、例えばｎ−ヘキサン、 ｎ −
ペンタン、ｎ−オクタン、ｎ−へブタン等を挙げること
ができる。In addition, as the poor solvent used in the present invention, aliphatic hydrocarbons and alicyclic hydrocarbons such as cyclopenkune and cyclohexane are preferable. In the present invention, aliphatic hydrocarbons, particularly linear aliphatic hydrocarbons, are preferred from the viewpoint of improving product purity and product recovery rate. This is because these linear aliphatic hydrocarbons more selectively dissolve light components of decomposition products that are reaction by-products. Examples of such linear aliphatic hydrocarbons include n-hexane, n-
Pentane, n-octane, n-hebutane, etc. can be mentioned.
また、貧溶媒の使用量は前記濃縮液の容量に対して、０
．５〜５倍量、特に１〜２倍量とすることが好ましい。In addition, the amount of poor solvent used is 0 relative to the volume of the concentrate.
．． The amount is preferably 5 to 5 times, particularly 1 to 2 times.
次に、本発明を実施例により詳しく説明する。 Next, the present invention will be explained in detail with reference to examples.
実施例１
（１）４４’−イソプロビリー゛ンジシクロヘキサ窒素
シールした２５０ｃｃの攪拌器付きオートクレーブに、
４．４°−イソプロピリデンジフェノール（ビスフェノ
ールＡ）２０ｇ、イソプロピルアルコール８０ｇおよび
カーボン担持ルテニウム触媒（ルテニウム担持１１５ｗ
ｔ％）０．２ｇを仕込み、まず、水素で５０ｋｇ／ｃｉ
Ｇに加圧し、２０分間かけて１６５ ’Ｃまで昇温した
。その後、さらに６０ｋｇ／ｃ＋ｊＧまで水素で加圧し
、攪拌しながら反応を行なった。反応中、レギュレータ
ーを通して水素をオートクレーブ内に張り込み、オート
クレーブ圧力を一定とした。Example 1 (1) 44'-isopropylene dicyclohexane was placed in a 250 cc autoclave equipped with a stirrer and sealed with nitrogen.
4.20 g of 4°-isopropylidene diphenol (bisphenol A), 80 g of isopropyl alcohol, and carbon-supported ruthenium catalyst (ruthenium-supported 115 w
t%) 0.2g, first, 50kg/ci with hydrogen.
The temperature was increased to 165'C over 20 minutes. Thereafter, the pressure was further increased to 60 kg/c+jG with hydrogen, and the reaction was carried out with stirring. During the reaction, hydrogen was introduced into the autoclave through a regulator to keep the autoclave pressure constant.
６０分後に水素吸収が無くなり反応が終了した。After 60 minutes, hydrogen absorption disappeared and the reaction was completed.
上記（１）の反応終了後、脱圧、冷却した。次いで、反
応生成液を取り出し、触媒を除去して、触媒の除去され
た反応生成液を得た。After the reaction in (1) above was completed, the pressure was removed and the mixture was cooled. Next, the reaction product liquid was taken out and the catalyst was removed to obtain a reaction product liquid from which the catalyst had been removed.
得られた反応生成液（４，４’−イソプロピリデンジシ
クロヘキサノール）の純度および異性体分布をガスクロ
マトグラフィー法により求めた結果、純度９５．０％、
シス−シス体７％、シス−トランス体４０％、トランス
−トランス体５３％であった。The purity and isomer distribution of the obtained reaction product liquid (4,4'-isopropylidene dicyclohexanol) were determined by gas chromatography, and the purity was 95.0%.
The cis-cis form was 7%, the cis-trans form was 40%, and the trans-trans form was 53%.
次に、上記反応生成液（溶媒イソプロピルアルコールを
８０重量％含む）２００ｃｃを、５０°Ｃ３２ＱＴｏｒ
ｒの条件でエバポレーターにより、溶媒のイソプロピル
アルコールを蒸発除去して濃縮し、粘稠な４，４゛−イ
ソプロピリデンジシクロヘキサノールを含む液６０ｃｃ
を得た。Next, 200 cc of the above reaction product solution (containing 80% by weight of solvent isopropyl alcohol) was heated at 50°C at 32Q Tor.
The solvent isopropyl alcohol is evaporated and concentrated using an evaporator under the conditions of
I got it.
これに、貧溶媒として、その２倍量のｎ−ヘキサン１２
０ｃｃを加え、洗浄後、結晶を濾別した。To this, double the amount of n-hexane 12 as a poor solvent.
After washing, the crystals were separated by filtration.
この結晶を１２０°Ｃで４時間乾燥し、溶媒を除去する
ことにより、目的とする４、４゛−イソプロピリデンジ
シクロヘキサノールの精製物く以下、製品という。）を
得た。The crystals were dried at 120°C for 4 hours and the solvent was removed to obtain a purified product of 4,4'-isopropylidene dicyclohexanol, hereinafter referred to as the product. ) was obtained.
この製品結晶の回収率、製品純度、異性体分布。Recovery rate, product purity, and isomer distribution of this product crystal.
結晶融点およびＯＨ価を第１表に示す。なお、製品純度
と異性体分布は、結晶をメタノールに溶解し、ガスクロ
マトグラフィー法により求めた。Crystal melting points and OH values are shown in Table 1. Note that the product purity and isomer distribution were determined by dissolving the crystals in methanol and using gas chromatography.
実施例２
実施例１において、貧溶媒としてのｎ−へキサンをｎ−
オクタンに代えたこと以外は、実施例１と同様に行なっ
た。結果を第１表に示す。Example 2 In Example 1, n-hexane as a poor solvent was replaced with n-
The same procedure as in Example 1 was carried out except that octane was used instead. The results are shown in Table 1.
比較例１
実施例１において、触媒の除去された反応生成液を、減
圧蒸留（２００″Ｃ，４Ｔｏｒｒ） シて、反応溶媒の
イソプロピルアルコールを除去した。Comparative Example 1 In Example 1, the reaction product liquid from which the catalyst had been removed was subjected to vacuum distillation (200″C, 4 Torr) to remove isopropyl alcohol as a reaction solvent.
得られた蒸留残渣製品をハツトに流し込み、無色透明の
固体を得た。結果を第１表に示す。The obtained distillation residue product was poured into a hat to obtain a colorless and transparent solid. The results are shown in Table 1.
比較例２
実施例１において、触媒の除去された反応生成液を濃縮
し、再結晶法により結晶を析出させた。Comparative Example 2 In Example 1, the reaction product liquid from which the catalyst had been removed was concentrated, and crystals were precipitated by a recrystallization method.
結果を第１表に示す。The results are shown in Table 1.
実施例３
実施例１において、貧溶媒としてのｎ−ヘキサンを３−
メチルペンタンに代えたこと以外は、実施例１と同様に
行なった。結果を第１表に示す。Example 3 In Example 1, n-hexane as a poor solvent was replaced with 3-
The same procedure as in Example 1 was carried out except that methylpentane was used. The results are shown in Table 1.
第１表
＊１：製品結晶の回収率（％）
＊２：製品純度（％）
乾燥後の結晶全重量
（発明の効果〕
本発明の精製法によれば、反応副生成物である分解生成
物の軽質骨を選択的に貧溶媒に溶解させ、選択的に貧溶
媒中に移行させることができる。−方、主生成物である
４、４°−イソプロピリデンジシクロヘキサノールは、
貧溶媒にはほとんど熔解しない。Table 1 *1: Recovery rate of product crystals (%) *2: Product purity (%) Total weight of crystals after drying (effects of the invention) According to the purification method of the present invention, decomposition products, which are reaction by-products, are produced. The light bones of objects can be selectively dissolved in a poor solvent and selectively transferred into a poor solvent.On the other hand, the main product, 4,4°-isopropylidene dicyclohexanol, is
It hardly dissolves in poor solvents.
したがって、本発明の精製法によれば、目的とする４、
４゛−イソプロピリデンジシクロヘキサノールの製品純
度を向上させることができる。Therefore, according to the purification method of the present invention, the objective 4,
The product purity of 4'-isopropylidene dicyclohexanol can be improved.
しかも、本発明の精製法によれば、製品の高回収率を充
分に維持しており、回収率を低下させるという問題もな
い。Moreover, according to the purification method of the present invention, a high recovery rate of the product is sufficiently maintained, and there is no problem of lowering the recovery rate.
さらに、本発明の精製法によれば、異性体分布を変える
ことなく、しかも高い融点を有する製品を得ることがで
きる。Furthermore, according to the purification method of the present invention, a product having a high melting point can be obtained without changing the isomer distribution.
Claims (1)
媒を用いて、溶媒存在下に接触水素化して得られる４，
４’−イソプロピリデンジシクロヘキサノールを精製す
るにあたり、反応溶媒を含む反応生成液から触媒を除去
し、次いで反応溶媒の一部を除去し、その後４，４’−
イソプロピリデンジシクロヘキサノールに対する貧溶媒
で洗浄し、乾燥することを特徴とする４，４’−イソプ
ロピリデンジシクロヘキサノールの精製法。(1) 4, obtained by catalytic hydrogenation of 4,4'-isopropylidene diphenol using a catalyst in the presence of a solvent.
In purifying 4'-isopropylidene dicyclohexanol, the catalyst is removed from the reaction product solution containing the reaction solvent, then a part of the reaction solvent is removed, and then 4,4'-
A method for purifying 4,4'-isopropylidene dicyclohexanol, which comprises washing with a poor solvent for isopropylidene dicyclohexanol and drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29626089A JP2684431B2 (en) | 1989-11-16 | 1989-11-16 | Method for purifying 4,4'-isopropylidenedicyclohexanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29626089A JP2684431B2 (en) | 1989-11-16 | 1989-11-16 | Method for purifying 4,4'-isopropylidenedicyclohexanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03157342A true JPH03157342A (en) | 1991-07-05 |
| JP2684431B2 JP2684431B2 (en) | 1997-12-03 |
Family
ID=17831268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29626089A Expired - Fee Related JP2684431B2 (en) | 1989-11-16 | 1989-11-16 | Method for purifying 4,4'-isopropylidenedicyclohexanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2684431B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9545617B2 (en) | 2014-12-09 | 2017-01-17 | Industrial Technology Research Institute | Catalyst and manufacturing method thereof and method for manufacturing hydrogenated bisphenol A or derivatives thereof using the same |
| WO2023042993A1 (en) * | 2021-09-15 | 2023-03-23 | 금호석유화학 주식회사 | Method for preparing hydrogenated bisphenol a |
-
1989
- 1989-11-16 JP JP29626089A patent/JP2684431B2/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9545617B2 (en) | 2014-12-09 | 2017-01-17 | Industrial Technology Research Institute | Catalyst and manufacturing method thereof and method for manufacturing hydrogenated bisphenol A or derivatives thereof using the same |
| US10005068B2 (en) | 2014-12-09 | 2018-06-26 | Industrial Technology Research Institute | Catalyst and manufacturing method thereof |
| WO2023042993A1 (en) * | 2021-09-15 | 2023-03-23 | 금호석유화학 주식회사 | Method for preparing hydrogenated bisphenol a |
| US11834395B2 (en) | 2021-09-15 | 2023-12-05 | Korea Kumho Petrochemical Co., Ltd. | Method for preparing hydrogenated bisphenol A |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2684431B2 (en) | 1997-12-03 |
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