WO2003037842A1 - Procédé de production d'un composé fluoré purifié - Google Patents

Procédé de production d'un composé fluoré purifié Download PDF

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Publication number
WO2003037842A1
WO2003037842A1 PCT/JP2002/011462 JP0211462W WO03037842A1 WO 2003037842 A1 WO2003037842 A1 WO 2003037842A1 JP 0211462 W JP0211462 W JP 0211462W WO 03037842 A1 WO03037842 A1 WO 03037842A1
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Prior art keywords
compound
formula
group
compound represented
product
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PCT/JP2002/011462
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English (en)
Japanese (ja)
Inventor
Masao Iwaya
Hidekazu Okamoto
Kazuya Oharu
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Asahi Glass Company, Limited
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Application filed by Asahi Glass Company, Limited filed Critical Asahi Glass Company, Limited
Priority to JP2003540125A priority Critical patent/JPWO2003037842A1/ja
Publication of WO2003037842A1 publication Critical patent/WO2003037842A1/fr

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    • 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
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides

Definitions

  • the present invention relates to a product obtained by reacting different reactive compounds with a reactive group of a compound having two reactive groups having the same reactivity, wherein a purified high-purity fluorine-containing compound is subjected to solvent extraction. And a method for obtaining the same.
  • the present invention also provides a method for obtaining a product in which a compound having two reactive groups having the same reactivity is reacted with only one of the reactive groups, wherein a purified high-purity fluorine-containing compound is obtained. How to get.
  • the present invention relates to a method for obtaining a product obtained by reacting a different compound with each of two reactive groups using a compound having two groups having the same reactivity at both ends as a raw material.
  • the present invention also relates to a method for obtaining a product having a high purity by reacting selectively with only one reactive group using the same raw material.
  • INDUSTRIAL APPLICABILITY The present invention is applicable to a compound having a high boiling point, a compound that is difficult to purify by distillation, a compound that is difficult to be distilled due to thermal instability, and a compound that is unstable to water. It is the following invention made for the purpose of providing the manufacturing method of.
  • a solvent extraction using a fluorinated organic solvent capable of phase separation and a non-fluorinated organic solvent to obtain a fluorine-containing compound represented by Formula 5 from the fluorinated organic solvent phase. 5.
  • R H Monovalent organic group without fluorine atom.
  • R F Monovalent organic group having a fluorine atom.
  • X, Y 1 Reactive groups that react with each other to form a divalent linking group (E 1 ).
  • Y 2 a reactive group that reacts with X to form a divalent linking group (E 2 ).
  • E 1 A divalent linking group formed by the reaction of X and Y 1 .
  • the difference in relative volatility of the compounds represented by the compound of formula 3 B of Formula 3 A is 1. 2 or less, or reduction if the formula 3 A 3.
  • the method according to 1 or 2 wherein the boiling point of the product and the boiling point of the compound represented by the formula 3B are at least 150 ° C at 200 Pa (absolute pressure).
  • the difference in relative volatility of the fluorine-containing compound and tables is the compound of formula 3 A of the formula 5 is 1. 2 or less, or, fluorine that you express by the formula 5
  • the ratio of the compound of formula 3 B to the total amount of the represented of compound with a compound of formula 3 B of Formula 3 A is from 30 to 99 wt% said 1 , 2, 3, or 4 manufacturing methods. 6.
  • X is a hydroxyl group, a halogen atom, a propyloxyl group, a halogenated acyl group, an amino group, or the like.
  • RH Monovalent organic group without fluorine atom.
  • E 1 A divalent linking group formed by the reaction of X and Y 1 .
  • Q is an alkylene group having a symmetrical structure, an alkyleneoxyalkylene group having a symmetrical structure, a group in which the alkylene group having a symmetrical structure is halogenated, and a group having a symmetrical structure, or an alkyleneoxy group having a symmetrical structure.
  • Q H Divalent organic group having a symmetric structure without a fluorine atom.
  • R H Monovalent organic group having no fluorine atom.
  • R F 1 and R F 2 each independently a fluorine atom or a perfluorinated monovalent organic group.
  • organic group refers to a group that essentially requires a carbon atom.
  • examples of the organic group include a hydrocarbon group and a hydrocarbon group in which a hetero atom or a hetero atom group is inserted between carbon and carbon atoms of the hydrocarbon group.
  • the hydrogen atom of these hydrocarbon groups may be substituted with a substituent such as a halo atom.
  • the substituent may be a functional group, but if it is a functional group, it is preferably selected from groups having low reactivity with the group (X) and the group (Y). No.
  • a reactive group is a divalent linking group in which two of the groups chemically react. Refers to a group that forms As an example of two reactive groups reacting to form a divalent linking group, a hydroxyl group reacts with one COZ 10 (Z 10 represents a halogen atom) to form a single OCO— bond. And the case where two hydroxyl groups react to form a —0 bond, and the reaction between a hydroxyl group and a halogen atom forms an —O— bond.
  • the two Xs in compound (1) are reactive groups that react with Y 1 in compound (2) to form a divalent linking group (E 1 ).
  • X is not particularly limited, and includes, for example, a hydroxyl group, a halogen atom, a propyloxyl group, a halogenated acyl group, and an amino group, and is not particularly limited.
  • Q is a divalent organic group having a symmetric structure. Examples of Q include an alkylene group having a symmetric structure, an alkyleneoxyalkylene group having a symmetric structure, a group in which these groups are halogenated, and a group having a symmetric structure.
  • Y 1 of compound (2) is a reactive group that reacts with X of compound ( 1 ) to form a divalent linking group (E 1 ), and can be appropriately changed depending on the combination with X. For example, when X is a hydroxyl group, examples of Y 1 include groups such as a carbonyl group, a halogenated acyl group, and a halogen atom.
  • R H of compound (2) is a monovalent organic group having no fluorine atom, and is an alkyl group, an alkenyl group, an etheric oxygen atom-containing alkyl group, an etheric oxygen atom-containing alkenyl group, or a group of these groups.
  • Examples include a group in which a hydrogen atom is substituted with a halogen atom other than a fluorine atom (for example, a chlorine atom or the like).
  • Examples of the reaction for obtaining a product P 1 include those exemplified below.
  • reaction Example 1 An example of reacting polymethylene diol such as 1,5-pentanediol as compound (1) with trichloroethylene as compound (2).
  • reaction Example 2 An example in which phosgene as the compound (1) is reacted with a hydrocarbon alcohol such as ethanol as the compound (2).
  • a hydrocarbon alcohol such as ethanol
  • reaction Example 3 An example in which a polymethylene diamine such as ethylenediamine as the compound (1) is reacted with a carbonyl chloride such as acetyl chloride as the compound (2).
  • a carbonyl chloride such as acetyl chloride
  • the product P 1 including the acetamide is produced.
  • reaction Example 4 An example in which terephthalic acid dichloride as the compound (1) is reacted with an alcohol such as ethanol as the compound (2).
  • the amount ratio of the compound (1) and the compound (2) is not particularly limited.
  • the proportion of the compound (3A) produced tends to decrease and the proportion of the target compound (3B) tends to increase.
  • the amount of the compound (2) is reduced, there is a problem that the volumetric efficiency is deteriorated.
  • the amount of the compound (2) increases, the volumetric efficiency of the reaction increases, but the undesired compound (3
  • the ratio of the compound (1) to the compound (2) is appropriately changed so as to be in an appropriate range in consideration of the volumetric efficiency and the amount of the compound (3A) produced.
  • the production ratio of the compound (3A) is too large, which is economically disadvantageous. Therefore, the product P 1, compound with the compound (3A) (3
  • the ratio of the compound (3B) to the total amount of (B) and (B) is preferably from 30 to 99 mol%, particularly preferably from 80 to 99 mol%.
  • the reaction between compound (1) and compound (2) may be performed in the presence of a solvent or in the absence of a solvent.
  • the reaction may be performed in the presence of a catalyst, or may be performed in the absence of a catalyst.
  • the method of the present invention is an advantageous method when the compound (3A) and the compound (3B) are difficult to separate by a distillation method or the like.
  • the compound (3A) and the compound (3B) are obtained by distillation.
  • This is an advantageous method for compounds that are difficult to separate. For example, if the difference in the relative volatility of both compounds is 1.2 or less, or if the boiling points of both are 150 ° C or more at 200 Pa (absolute pressure), or both compounds (especially the compounds (3 B)) is a compound that is easily decomposed under distillation conditions. This is an advantageous method when it is a product. Further, since the method of the present invention does not use water, it is also an advantageous method when both compounds are water-unstable compounds.
  • the product P 1 produced by the reaction is preferred to carry out post-treatment as required arbitrarily.
  • the reaction between compound (1) and compound (2) is performed in the presence of a reaction solvent or a catalyst, it is preferable to remove the reaction solvent or the catalyst.
  • the reaction solvent can be used in the next step, the reaction solvent need not be removed.
  • the compound (4) was allowed to act on the product P 1, a fluorine-containing compound with (5) to give the product P 11 containing the compound (3A).
  • compound (4) is to compound in the product P 1 (3 B) reacts with the generated fluorine-containing compound (5), does not react with the compound (3A). Therefore, the raw Narubutsu P 11 is included fluorinated compound (5) and the compound (3A) is.
  • the compound (3B) and the compound (4) fluorine-containing compound produced by reaction of the (5) reaction to yield only increases it can It is preferable to devise conditions.
  • the reaction between compound (3B) and compound (4) is an esterification reaction
  • the esterification reaction is an equilibrium reaction
  • a method for tilting the equilibrium is to remove HF, which is a by-product of the esterification reaction, continuously out of the system during esterification when one of X and Y 2 is --CO F and the other is OH.
  • Specific examples include a method of removing HF from the system by nitrogen bubbling, and a method of precipitating an amine such as triethylamine in the reaction system to precipitate hydrochloride of the amine.
  • X and Y 2 ′ are one COOH and the other is OH
  • a method of removing water by-produced by the reaction by a method such as azeotropic dehydration may be used.
  • the group (R F ) of the compound (4) is a monovalent organic group containing a fluorine atom, and is a group necessary for dissolving the fluorine-containing compound (5) in a fluorine-containing organic solvent.
  • This group (R F ) preferably has 5 or more carbon atoms, more preferably 5 to 10.
  • R F examples include a perfluoroalkyl group, a perfluoro (alkyl containing an oxygen atom with an etheric atom) group, a group in which all of the hydrogen atoms of an alkyl group partially containing a chlorine atom are fluorinated, A group in which all of the hydrogen atoms partially having an atom (etheric oxygen atom-containing alkyl group) are fluorinated, or a group having these groups as a partial structure is preferable.
  • Specific examples of the group (RF) include the following examples.
  • C m F 2 m + ⁇ (m is an integer of 5 or more, preferably 5 to 10), CF 3 CF 2 CF 2 OCF (CF 3 ), CF 3 CF 2 CF 2 OCF (CF 3 ) CF 2 OCF (CF 3 ) 1, CF 2 (C 1) CFC IO (CF 2 ) 4 , C m F 2 m + 1 CH 2 CH 2 — (m is an integer of 5 or more, 5 to 1 0 is preferred.) Etc.
  • fluorine-containing compound (5) examples include the following compounds.
  • CF 3 CF 2 CF 2 OCF (CF 3 ) COO (CH 2 ) 5 OC (CI) 2 CHC 1, CF 3 CF 2 CF 2 OCF (CF 3 ) CF 2 OCF (CF 3 ) COO (CH 2 ) 5 OC (CI) CHC 1, CF. CF 2 CF OC F (CF 3) CONHCH 2 CH 2 NHC ⁇ CH 2 CH 3 , CF 3 (CF 2 ) 7 CH 2 CH 2 C ⁇ OCH 2 CH 3 , CF 3 (CF 2 ) 7 CH 2 CH 2 C ⁇ C 6 H 5 C ⁇ CH 2 CH 3 etc.
  • the molar ratio of the fluorine-containing compound contained in the product P 11 (5) and the compound (3 A) is substantially corresponds to the molar ratio of the compound in the product P 1 (3 B) and the compound (3A).
  • the ratio of the fluorine-containing compound (5) to the total amount of the compound (3A) and the fluorine-containing compound (5) is preferably from 30 to 99 mol%, particularly preferably from 80 to 99 mol%.
  • the difference in the relative volatility between the fluorine-containing compound (5) and the compound (3A) is 1.2 or less. Or when both compounds have a boiling point of 150 ° C or more at 200 Pa (absolute pressure), or when both compounds are compounds that are easily decomposed under distillation conditions. Method. Further, since the method of the present invention does not use water, it is an advantageous method even when both compounds are water-unstable compounds.
  • the fluorinated organic solvent is not particularly limited, and is preferably selected from known fluorinated organic solvents.
  • the fluorinated organic solvent is preferably a solvent having a high fluorine content in order to more efficiently dissolve the fluorinated compound (5) containing a fluorine atom and to concentrate the fluorinated compound (5),
  • the fluorine content is preferably at least 60% by mass.
  • a perfluorinated organic solvent is used.
  • the fluorinated organic solvent include hexafluoropropylene oligomer, perfluorocarbon, perfluoroether and the like. Since most perfluorinated organic solvents can be phase-separated from non-fluorinated organic solvents, the use of perfluorinated organic solvents has the advantage of expanding the choice of non-fluorinated solvents.
  • the non-fluorinated solvent is selected from those which can be phase-separated from the fluorine-containing organic solvent.
  • the product P 1 1 comprises a catalyst
  • the product P 1 1 when containing a fluorine-containing organic solvent or a non-fluorine-based organic solvents may be used the solvent as the solvent during the solvent extraction. In this case, if the solvent amount is small, it is preferable to add the same solvent as the solvent contained in the product P 1 1.
  • the solvent amount is small, it is preferable to add the same solvent as the solvent contained in the product P 1 1.
  • the case of performing solvent extraction using different solvents and contains Murrell solvent in the product P 1 1 is to remove the solvent contained in the product P 1 1, and the newly fluorinated organic solvent It is preferable to add a non-fluorinated organic solvent.
  • the amount of the fluorinated organic solvent relative to the non-fluorinated organic solvent is 10 to 500 volumes %.
  • the total mass of the non-fluorinated organic solvent and the fluorinated organic solvent is preferably 2 to 50 times the mass of the compound (3A) and the fluorinated and hydrogenated compound (5).
  • the fluorine-containing compound contained in the product P 11 (5) was dissolved in a fluorine-containing organic solvents, by dissolving the compound (3A) to the non-fluorine-containing organic solvent, a fluorine-containing organic solvent phase A fluorine-containing compound (5) is obtained.
  • Concentration is possible in principle if the partition coefficient of the fluorinated compound (5) with respect to the fluorinated organic solvent is equal to or higher than the partition coefficient of the compound (3A) with respect to the fluorinated organic solvent.
  • the yield may be reduced due to the necessity of multi-stage extraction.
  • the partition coefficient of the fluorine-containing compound (5) with respect to the fluorine-containing organic solvent is preferably 1 or more, and particularly preferably 2 or more. Further, the partition coefficient of the compound (3A) with respect to the fluorine-containing organic solvent is preferably 0.1 or less, particularly preferably 0.01 or less.
  • the desired fluorinated compound (5) is obtained from the fluorinated organic solvent phase separated from the non-fluorinated organic solvent phase, if necessary, by performing post-treatment (eg, drying, filtration, etc.). Further, the fluorinated organic solvent and the fluorinated compound (5) may be used for intended purposes without separation.
  • the fluorine-containing compound (5) can be used for any purpose. Further, in the present invention, as a product in which RH is introduced into only one X portion of the compound (1) by a reaction of cleaving only the group (E 2 ) of the fluorine-containing compound (5), The following compound (6) can be obtained.
  • R H , E 1 , and Q H in the following formula have the same meanings as described above, and E 3 indicates a residue generated by cleavage of E 2 .
  • the compound (1-1) is reacted with the compound (2-1) to obtain a product (P 1 —:! Containing the compound (3A-1) and the compound (3B-1).
  • the product (Pi-l) to be reacted with compound (4 one 1), compound (5-1) with compound (3A-1) and the product containing the (P 11 - 1) to give, following the product - in (P 11 1), by performing solvent extraction using a fluorine-containing organic solvents and non-fluorine-containing organic solvents which can be separated into two phases from each other, compound a fluorine-containing organic solvent phase (5-1)
  • a process for producing a compound (5-1) which comprises obtaining
  • Q H a symmetric divalent organic group having no fluorine atom.
  • R H Monovalent organic group having no fluorine atom.
  • R F 1 , R F 2 each is independently a fluorine atom or perfluorinated Monovalent organic groups.
  • Y 10 a reactive group that reacts with a hydroxyl group to form a divalent linking group (E 1 Q).
  • ⁇ 20 A reactive group that reacts with a hydroxyl group to form an ester bond.
  • the compound (3A) obtained from the non-fluorinated organic solvent phase may be used for other purposes, and the compound (1) may be obtained by cleaving the group (E 1 ) of the compound (3A).
  • the divalent linking group (E 1 ) in the compound (3A) is an ester bond. This bond can be easily cleaved by a known method, and the compound (1) in which X is a hydroxyl group can be recovered. By recycling the recovered compound (1) in the method of the present invention, the desired fluorine-containing compound (5) and compound (3B) can be obtained with high production efficiency.
  • HC (C 1) C (C 1) 0 in a two-phase solvent to which a mixture of methylene chloride (2.0 g) and C 6 F t 4 (trade name: FC 62, 2.0 g) was added.
  • (CH 2 ) 5 OC (CI) CF 3 CF 2 CF 2 OC F containing 8% by mass of CHC 1
  • a compound having a reactive group at both ends is used as a raw material,
  • a method is provided for obtaining a highly pure target compound by removing the compound reacted at both ends irrespective of the chemical properties of the compound.
  • the method of the present invention is useful for a product having a high boiling point, a small difference in non-volatility, a compound which is difficult to separate by distillation such as a thermally unstable compound, and a compound which is easily decomposed by water. It is a way.

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

Abstract

La présente invention concerne un procédé de production d'un composé de pureté élevée (formule 5), obtenu à partir d'un composé (formule 1) présentant deux groupes réactifs possédant la même réactivité, par mise en réaction des deux groupes réactifs respectivement avec des composés différents. Ledit procédé consiste à : faire réagir un composé (formule 1) tel que du 1,5-pentanediol avec un composé (formule 2) tel que du trichloroéthylène (TE) pour obtenir un produit réactionnel (PI) comprenant un composé (formule 3A) présentant du TE qui s'est ajouté à chaque extrémité et un composé (formule 3B) présentent du TE qui s'est ajouté à une extrémité ; amener un composé fluoré (formule 4) réactif avec le composé (3B) à agir sur le produit réactionnel (PI) pour obtenir un produit réactionnel (PII) comprenant un composé (formule 5) et le composé (formule 3A) ; et soumettre ensuite le produit réactionnel (PII) à l'extraction par solvant à l'aide d'un solvant organique fluoré et d'un solvant organique non fluoré qui peuvent être séparés en deux phases pour ainsi obtenir le composé (formule 5) à partir de la phase du solvant organique fluoré.
PCT/JP2002/011462 2001-11-02 2002-11-01 Procédé de production d'un composé fluoré purifié WO2003037842A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009029741A (ja) * 2007-07-26 2009-02-12 Tokai Univ 層間移動式光学分割法
US20200283351A1 (en) * 2017-09-27 2020-09-10 Arkema Inc. Halogenated heteroalkenyl- and heteroalkyl-functionalized organic compounds and methods for preparing such compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06128189A (ja) * 1991-04-26 1994-05-10 Hoechst Ag ペルフルオロエーテルカルボン酸の製造方法
JPH07267897A (ja) * 1994-03-30 1995-10-17 Mitsubishi Rayon Co Ltd ヒドロキシアルキルモノ（メタ）アクリレートの精製方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06128189A (ja) * 1991-04-26 1994-05-10 Hoechst Ag ペルフルオロエーテルカルボン酸の製造方法
JPH07267897A (ja) * 1994-03-30 1995-10-17 Mitsubishi Rayon Co Ltd ヒドロキシアルキルモノ（メタ）アクリレートの精製方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009029741A (ja) * 2007-07-26 2009-02-12 Tokai Univ 層間移動式光学分割法
US20200283351A1 (en) * 2017-09-27 2020-09-10 Arkema Inc. Halogenated heteroalkenyl- and heteroalkyl-functionalized organic compounds and methods for preparing such compounds

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