ES2662800T3 - Proceso para la fabricación de fluoroacrilato de alquilo - Google Patents

Proceso para la fabricación de fluoroacrilato de alquilo Download PDF

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Publication number
ES2662800T3
ES2662800T3 ES13730917.5T ES13730917T ES2662800T3 ES 2662800 T3 ES2662800 T3 ES 2662800T3 ES 13730917 T ES13730917 T ES 13730917T ES 2662800 T3 ES2662800 T3 ES 2662800T3
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ES
Spain
Prior art keywords
claisen
alkyl
alkane
manufacture
suitable solvent
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.)
Active
Application number
ES13730917.5T
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English (en)
Inventor
Peter Kapitan
Alexander Sajtos
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Patheon Austria GmbH and Co KG
Original Assignee
Patheon Austria GmbH and Co KG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/32—Decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Proceso para la fabricación de un fluoroacrilato de alquilo, que comprende las siguientes etapas: A. un fluoroacetato de alquilo con un éster de ácido oxálico se hace reaccionar en presencia de una base y un disolvente adecuado en una condensación de Claisen cruzada dando como resultado una sal de Claisen, B. la sal de Claisen obtenida en la etapa A se elimina por filtración opcionalmente y se lava con un disolvente adecuado, C. la sal de Claisen obtenida en la etapa A o B se hace reaccionar con paraformaldehído y D. el fluoroacrilato de alquilo obtenido en la etapa C se aísla usando un disolvente adecuado, en el que el disolvente en al menos la etapa C y opcionalmente en una de las etapas A, B o D comprende un alcano que es líquido en las condiciones de reacción de las etapas en las que se aplica el alcano, y en el que el alcano es pentano o hexano.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
30 % de NaOMe en metanol (48,9 g, 1,25 equiv.). La solución resultante se agita durante 24 h a 20-25 °C.
Etapa B
5 La suspensión se enfría a 0 °C, la sal de Claisen se elimina por filtración y se lava con pentano (3 x 40 ml).
Etapa C
La sal húmeda y el pentano (120 ml) se cargan en el reactor y la suspensión se enfría a 5-10 ºC. Se añade en 10 10 porciones paraformaldehído (4,0 g, 1,2 equiv.) y la suspensión se agita a 5-10 ºC durante 5 h más.
Etapa D
La mezcla de reacción se inactiva con agua (115 ml) y la fase acuosa se extrajo una vez con pentano (2 x 60 ml). 15 Las fases orgánicas se combinan y el producto se purifica mediante destilación al vacío.
Se espera que el rendimiento alcanzado antes de la destilación esté en línea con el rendimiento obtenido para los ejemplos de fluoroacrilato de metilo.
8

Claims (1)

  1. imagen1
ES13730917.5T 2012-06-25 2013-06-25 Proceso para la fabricación de fluoroacrilato de alquilo Active ES2662800T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12173485 2012-06-25
EP12173485 2012-06-25
PCT/EP2013/063324 WO2014001365A1 (en) 2012-06-25 2013-06-25 Process for the manufacture of alkylfluoroacrylate

Publications (1)

Publication Number Publication Date
ES2662800T3 true ES2662800T3 (es) 2018-04-09

Family

ID=48672654

Family Applications (1)

Application Number Title Priority Date Filing Date
ES13730917.5T Active ES2662800T3 (es) 2012-06-25 2013-06-25 Proceso para la fabricación de fluoroacrilato de alquilo

Country Status (8)

Country Link
US (2) US11420927B2 (es)
EP (1) EP2864286B1 (es)
JP (1) JP6146724B2 (es)
CN (2) CN109456187B (es)
CA (1) CA2877548C (es)
ES (1) ES2662800T3 (es)
IN (1) IN2015DN00531A (es)
WO (1) WO2014001365A1 (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2558147C1 (ru) * 2014-07-17 2015-07-27 Закрытое акционерное общество научно-производственное Объединение "ПиМ-Инвест" (ЗАО НПО "Пим-Инвест") Способ получения метил-2-фторакрилата
CN104478715B (zh) * 2014-11-21 2016-07-20 湖北华世通生物医药科技有限公司 化合物的制备方法
WO2017013683A1 (en) 2015-07-22 2017-01-26 Srf Limited Process for the preparation of fluoroacrylic acid esters
CN105646216B (zh) * 2016-02-23 2018-04-03 湖北工程学院 2‑氟‑3‑羟基丙酸甲酯合成方法
JP7104358B2 (ja) * 2020-08-19 2022-07-21 ダイキン工業株式会社 含ハロゲン（メタ）アクリル酸エステルの精製方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2454663A (en) 1945-04-09 1948-11-23 Ici Ltd Fluorodihalo esters
US3075002A (en) 1962-02-21 1963-01-22 American Cyanamid Co Process for preparing alpha-fluoroacrylates
US3262967A (en) * 1963-10-31 1966-07-26 American Cyanamid Co Process for the preparation of alpha-fluoroacrylates
US3262968A (en) * 1963-11-07 1966-07-26 American Cyanamid Co Process for the preparation of alpha-fluoroacrylates
US6509134B2 (en) * 2001-01-26 2003-01-21 International Business Machines Corporation Norbornene fluoroacrylate copolymers and process for the use thereof
DE102009030681A1 (de) 2009-06-26 2010-12-30 Saltigo Gmbh Herstellung von substituierten 2-Fluoracrylsäurederivaten
CN102211998A (zh) * 2011-04-08 2011-10-12 镇江蓝德特药业科技有限公司 α-氟代丙烯酸甲酯及其类似物的合成方法
CN102731304B (zh) 2011-04-11 2016-05-25 天津泰瑞倍药研科技有限公司 α-氟代丙烯酸酯的制备方法
CN102212000A (zh) 2011-05-25 2011-10-12 原平市同利化工有限责任公司 2-氟-3羟基丙酸烷基酯的合成方法
CN102757347A (zh) 2012-07-23 2012-10-31 太仓中化环保化工有限公司 一种2-卤代丙烯酸烷基酯的制备方法

Also Published As

Publication number Publication date
EP2864286B1 (en) 2018-02-14
US11420927B2 (en) 2022-08-23
IN2015DN00531A (es) 2015-06-26
CN109456187B (zh) 2022-08-30
US11492323B2 (en) 2022-11-08
CA2877548A1 (en) 2014-01-03
US20200369593A1 (en) 2020-11-26
JP6146724B2 (ja) 2017-06-14
EP2864286A1 (en) 2015-04-29
CA2877548C (en) 2020-09-01
WO2014001365A1 (en) 2014-01-03
JP2015523993A (ja) 2015-08-20
CN109456187A (zh) 2019-03-12
CN104520264A (zh) 2015-04-15
US20150368178A1 (en) 2015-12-24

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