RU2019141276A - Способ получения 1,4-бис(4-феноксибензоил)бензола при повышенной температуре - Google Patents

Способ получения 1,4-бис(4-феноксибензоил)бензола при повышенной температуре Download PDF

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RU2019141276A
RU2019141276A RU2019141276A RU2019141276A RU2019141276A RU 2019141276 A RU2019141276 A RU 2019141276A RU 2019141276 A RU2019141276 A RU 2019141276A RU 2019141276 A RU2019141276 A RU 2019141276A RU 2019141276 A RU2019141276 A RU 2019141276A
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reaction mixture
paragraphs
lewis acid
temperature
solvent
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RU2019141276A
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Жюльен ЖУАННО
Гийом ЛЕ
Жером АМШТУТЦ
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Аркема Франс
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/127—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
    • C08G65/4018—(I) or (II) containing halogens other than as leaving group (X)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
    • C08G2261/3442—Polyetherketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/45—Friedel-Crafts-type
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
    • C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/62—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the nature of monomer used

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyethers (AREA)

Claims (23)

1. Способ получения 1,4–бис(4–феноксибензоил)бензола, включающий:
– предоставление реакционной смеси, содержащей терефталоилхлорид и дифениловый эфир в растворителе;
– добавление кислоты Льюиса к реакционной смеси, для того, чтобы получить смешанный продукт;
где температура реакционной смеси составляет более чем 5°C во время по меньшей мере части стадии добавления кислоты Льюиса к реакционной смеси.
2. Способ по п. 1, где кислотой Льюиса является трихлорид алюминия.
3. Способ по п. 1 или 2, где температура реакционной смеси составляет по меньшей мере 15°C, предпочтительно по меньшей мере 25°C или по меньшей мере 35°C или по меньшей мере 45°C на по меньшей мере части стадии добавления кислоты Льюиса к реакционной смеси.
4. Способ по любому одному из пп. 1–3, где температура реакционной смеси составляет по меньшей мере 30°C, предпочтительно по меньшей мере 40°C и более предпочтительно по меньшей мере 45°C, после того, как 20% по массе кислоты Льюиса было добавлено к реакционной смеси, по отношению к общей массе кислоты Льюиса, добавленной к реакционной смеси.
5. Способ по любому одному из пп. 1–4, где температура реакционной смеси увеличивается во время стадии добавления кислоты Льюиса к реакционной смеси, от первоначальной температуры до конечной температуры.
6. Способ по п. 5, где первоначальная температура составляет от 0 до 80°C, предпочтительно от 30°C до 50°C.
7. Способ по п. 5 или 6, где конечная температура составляет по меньшей мере 30°C, предпочтительно по меньшей мере 40°C, более предпочтительно по меньшей мере 45°C и наиболее предпочтительно по меньшей мере 50°C.
8. Способ по любому одному из пп. 1–7, где температура реакционной смеси не превышает 100°C, предпочтительно 90°C, более предпочтительно 80°C, еще более предпочтительно 70°C, во время стадии добавления кислоты Льюиса.
9. Способ по любому одному из пп. 1–8, где растворителем является орто–дихлорбензол.
10. Способ по любому одному из пп. 1–9, где разность температуры между конечной температурой и первоначальной температурой составляет от 1 до 120°C, предпочтительно от 1 до 70°C, предпочтительно от 5 до 60°C, более предпочтительно от 10 до 50°C и в особенности от 20 до 40°C.
11. Способ по любому одному из пп. 1–10, где растворитель является отдельным растворителем из дифенилового эфира.
12. Способ по любому одному из пп. 1–11, где концентрация терефталоилхлорида (по отношению к сумме растворителя, терефталоилхлорида, дифенилового эфира и кислоты Льюиса) составляет от 2 до 25%, предпочтительно от 3 до 12%, предпочтительно от 5 до 10%.
13. Способ по любому одному из пп. 1–12, где концентрация дифенилового эфира (по отношению к сумме растворителя, терефталоилхлорида, дифенилового эфира и кислоты Льюиса) составляет от 2 до 42%, предпочтительно от 5 до 35%, предпочтительно от 12 до 25%.
14. Способ по любому одному из пп. 1–13, где массовое отношение терефталоилхлорида к дифениловому эфиру, введенных в реактор, составляет от 0,05 до 0,6, предпочтительно от 0,2 до 0,6, предпочтительно от 0,3 до 0,5.
15. Способ по любому одному из пп. 1–14, включающий следующие дополнительные стадии:
– смешивание смешанного продукта с протонным растворителем для того, чтобы предоставить продукт в виде суспензии;
– отделение 1,4–бис(4–феноксибензоил)бензола от продукта в виде суспензии, предпочтительно посредством фильтрации и необязательно промывания.
16. Способ получения полимера полиэфиркетонкетона, включающий:
– получение 1,4–бис(4–феноксибензоил)бензола способом по любому из пунктов 1–15;
– реакционное взаимодействие указанного 1,4–бис(4–феноксибензоил)бензола с по меньшей мере одним дифункциональным ароматическим ацилхлоридом.
RU2019141276A 2017-05-16 2018-05-16 Способ получения 1,4-бис(4-феноксибензоил)бензола при повышенной температуре RU2019141276A (ru)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP17305559.1 2017-05-16
EP17305559.1A EP3404008B1 (en) 2017-05-16 2017-05-16 Method for manufacturing 1,4-bis (4-phenoxybenzoyl)benzene at an elevated temperature
PCT/EP2018/062803 WO2018210963A1 (en) 2017-05-16 2018-05-16 Method for manufacturing 1,4-bis(4—phenoxybenzoylbenzene) at an elevated temperature

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US (2) US20200062683A1 (ru)
EP (2) EP3404008B1 (ru)
JP (1) JP2020520365A (ru)
KR (2) KR20200007874A (ru)
CN (1) CN110621648B (ru)
BR (1) BR112019023149A2 (ru)
CA (1) CA3061433A1 (ru)
ES (1) ES2829265T3 (ru)
MX (1) MX2019012998A (ru)
RU (1) RU2019141276A (ru)
WO (1) WO2018210963A1 (ru)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3404011B1 (en) * 2017-05-18 2020-08-26 Arkema France Dissociation of a 1,4-bis(4-phenoxybenzoyl)benzene-lewis acid-complex in an aqueous solution
EP3404012B1 (en) 2017-05-18 2020-09-09 Arkema France Ripening of 1,4-bis (4-phenoxybenzoyl)benzene
ES2829260T3 (es) 2017-05-16 2021-05-31 Arkema France Método para fabricar 1,4-bis(4-fenoxibenzoil)benceno usando cloruro de tereftaloílo sustancialmente no hidrolizado
US10793500B2 (en) * 2017-05-16 2020-10-06 Arkema France Dissociation of 1,4-bis (4-phenoxybenzoyl)benzene—Lewis acid complex in a protic solvent
EP3650433B1 (en) 2018-11-09 2024-04-24 Arkema France Method for manufacturing 1,4-bis (4-phenoxybenzoylbenzene) at an elevated temperature
KR20220028244A (ko) * 2020-08-28 2022-03-08 한화솔루션 주식회사 1,4-비스(4-페녹시벤조일)벤젠을 제조하는 방법 및 이에 의해 제조된 1,4-비스(4-페녹시벤조일)벤젠
WO2022258333A1 (en) * 2021-06-09 2022-12-15 Solvay Sa Cyclic oligo(arylene ether)s, processes for their preparation and their use
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EP3404012B1 (en) 2017-05-18 2020-09-09 Arkema France Ripening of 1,4-bis (4-phenoxybenzoyl)benzene
ES2829260T3 (es) 2017-05-16 2021-05-31 Arkema France Método para fabricar 1,4-bis(4-fenoxibenzoil)benceno usando cloruro de tereftaloílo sustancialmente no hidrolizado
US10793500B2 (en) 2017-05-16 2020-10-06 Arkema France Dissociation of 1,4-bis (4-phenoxybenzoyl)benzene—Lewis acid complex in a protic solvent
EP3404009B1 (en) 2017-05-16 2019-12-25 Arkema France Method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene in supersaturation conditions
EP3438085A1 (en) 2017-08-04 2019-02-06 Arkema France Process for producing polyether ketone ketone

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KR20220113844A (ko) 2022-08-16
JP2020520365A (ja) 2020-07-09
KR20200007874A (ko) 2020-01-22
US10618863B2 (en) 2020-04-14
EP3404008B1 (en) 2020-08-12
EP3625202A1 (en) 2020-03-25
WO2018210963A1 (en) 2018-11-22
MX2019012998A (es) 2020-01-20
US20180334418A1 (en) 2018-11-22
CN110621648A (zh) 2019-12-27
CN110621648B (zh) 2023-06-13
EP3404008A1 (en) 2018-11-21
US20200062683A1 (en) 2020-02-27
BR112019023149A2 (pt) 2020-06-02
CA3061433A1 (en) 2018-11-22

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