JP5274349B2 - 9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法 - Google Patents
9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法 Download PDFInfo
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- JP5274349B2 JP5274349B2 JP2009097067A JP2009097067A JP5274349B2 JP 5274349 B2 JP5274349 B2 JP 5274349B2 JP 2009097067 A JP2009097067 A JP 2009097067A JP 2009097067 A JP2009097067 A JP 2009097067A JP 5274349 B2 JP5274349 B2 JP 5274349B2
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- Prior art keywords
- fluorene
- hydroxyethoxy
- bis
- phenyl
- reaction
- Prior art date
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- NQXNYVAALXGLQT-UHFFFAOYSA-N 2-[4-[9-[4-(2-hydroxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1(C=2C=CC(OCCO)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NQXNYVAALXGLQT-UHFFFAOYSA-N 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 16
- 239000013078 crystal Substances 0.000 claims description 42
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 27
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 3
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- -1 4- (2-hydroxyethoxy) phenyl Chemical group 0.000 claims 1
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- 239000010936 titanium Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
(1)ヘテロポリ酸存在下、フルオレノンとフェノキシエタノールを反応させ、9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンを製造する方法において、14×103Pa以下の減圧下、90〜150℃の温度範囲で反応させることを特徴とする9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法。
(2)ヘテロポリ酸存在下、フルオレノンとフェノキシエタノールを14×103Pa以下の減圧下、90〜150℃の温度範囲で反応させて得られた反応混合物を芳香族炭化水素溶媒、ケトン溶媒およびエステル溶媒からなる群から選ばれる少なくとも1つの溶媒に溶解させた後に50℃以上の温度で結晶種を添加して9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの析出を開始させることを特徴とする前記(1)項に記載製造法。
(3)6.7×103Pa以下の減圧下、反応させることを特徴とする前記(1)〜(2)項に記載の製造方法。
以下に本発明の実施例を示すが、本発明はこれらに限定されるものではない。
例中、純度および多量体成分量は逆相カラムを使用した液体クロマトグラフィー(島津製作所(株)製)を用い、254nmの波長で測定した面積百分率値であり、融点は示差走査熱量計(セイコー電子工業(株)製)を用い、下記条件で測定した示差走査熱量(DSC)の融解吸熱最大値である。
示差走査熱量(DSC)測定条件:
試薬 :酸化アルミニウム
昇温速度:10℃/min
測定範囲:40−260℃
雰囲気 :開放、窒素40ml/min
攪拌機、窒素吹込管、温度計および冷却管を付けた水分離器を備えたガラス製反応器に、フルオレノン86.4g(0.48モル)、2−フェノキシエタノール397.9g(2.88モル)、トルエン350gおよび触媒としてリンタングステン酸[(H3PW12O40)]4.3gを加え、常圧にてトルエン還流下、生成水を反応系外に除去しながら12時間反応した。反応終了後得られた反応混合物中の多量体成分量は9.1%であった。この反応液にトルエン300gを加え、水100gを用いて80℃で水洗をおこなった。得られた有機層を徐々に10℃まで冷却し、析出した結晶を濾過、乾燥することにより、9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの白色結晶146.2g(収率75.1%、純度99.0%)を得た。得られた9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの融点は109℃であった。得られた9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレン60.0gとトルエン300.0gの懸濁液を100℃に加熱し、同温度で1時間攪拌して均一な溶液とした。この溶液を徐々に冷却したところ、70℃で結晶が析出し始め、そのまま10℃まで冷却し、同温度で1時間保温攪拌した。析出した結晶を濾過、乾燥することにより、9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの白色結晶53.9g(収率89.9%(通算67.5%)、純度99.5%)を得た。得られた9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの融点は163℃であった。
攪拌機、窒素吹込管、温度計および冷却管を付けた水分離器を備えた反応器に、フルオレノン40.0kg(0.222kモル)、2−フェノキシエタノール307.0kg(2.22kモル)、トルエン160.1kgおよび触媒としてリンタングステン酸[(H3PW12O40)]0.92kgを加え、常圧にてトルエン還流下、生成水を反応系外に除去しながら27時間反応した。得られた反応混合物中の多量体成分量は12.1%であった。この反応液にトルエン150.0kgを加え、水49kgを用いて80℃で水洗をおこなった。得られた有機層を徐々に10℃まで冷却し析出した結晶を濾過、乾燥することにより、9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの白色結晶71.0kg(収率73.0%、LC純度97.9%)を得た。得られた9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの融点は109℃であった。この粗精製物59.0kgとトルエン300.0kgの懸濁液を100℃に加熱し、同温度で1時間攪拌して均一な溶液とした。この溶液を徐々に冷却したところ、65℃で結晶が析出し始め、そのまま10℃まで冷却し、同温度で1時間保温攪拌した。析出した結晶を濾過により取り出し、該結晶を減圧乾燥させることにより、9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの白色結晶51.3kg(収率87.0%(通算63.5%)、純度98.7%)を得た。得られた9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの融点は163℃であった。
攪拌機、窒素吹込管、温度計および冷却管を付けたガラス製反応器に、フルオレノン40.0g(0.222モル)、2−フェノキシエタノール306.7g(2.22モル)および触媒としてリンタングステン酸[(H3PW12O40)・nH2O]1.0gを加え、常圧にて温度170℃で2時間反応した。得られた反応混合物中の多量体成分量は14.0%であった。得られた反応混合物にトルエン400.0gを加え、水酸化ナトリウム水溶液で中和、水洗した後、有機層を分液した。得られた有機層から減圧濃縮によりトルエン及び過剰の2−フェノキシエタノールを除いた。得られた濃縮物にトルエン280.0gを加え80℃で1時間加熱攪拌した後、そのまま0℃まで冷却したが油状物となり結晶を得ることが出来なかった。
Claims (2)
- ヘテロポリ酸存在下、フルオレノンとフェノキシエタノールを反応させ、9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンを製造する方法において、6.7×10 3 Pa以下の減圧下、90〜150℃の温度範囲で反応させることを特徴とする9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法。
- ヘテロポリ酸存在下、フルオレノンとフェノキシエタノールを6.7×10 3 Pa以下の減圧下、90〜150℃の温度範囲で反応させて反応混合物を得、次いで、得られた反応混合物を芳香族炭化水素溶媒、ケトン溶媒およびエステル溶媒からなる群から選ばれる少なくとも1つの溶媒に溶解させた後に50℃以上の温度で結晶種を添加して9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの析出を開始させることを特徴とする9,9−ビス(4−(2−ヒドロキシエトキシ)フェニル)フルオレンの製造法。
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KR1020117023515A KR101624374B1 (ko) | 2009-04-13 | 2010-02-24 | 플루오렌 유도체의 제조방법 |
US13/263,029 US8841491B2 (en) | 2009-04-13 | 2010-02-24 | Method for producing fluorene derivative |
EP10764313.2A EP2420485B1 (en) | 2009-04-13 | 2010-02-24 | Method for producing fluorene derivative |
PCT/JP2010/052854 WO2010119727A1 (ja) | 2009-04-13 | 2010-02-24 | フルオレン誘導体の製造法 |
CN201080016054.7A CN102388012B (zh) | 2009-04-13 | 2010-02-24 | 芴衍生物的制造方法 |
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