WO2016163551A1 - Composition contenant un dérivé d'acide acrylique, et procédé de stabilisation du dérivé d'acide acrylique - Google Patents

Composition contenant un dérivé d'acide acrylique, et procédé de stabilisation du dérivé d'acide acrylique Download PDF

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Publication number
WO2016163551A1
WO2016163551A1 PCT/JP2016/061624 JP2016061624W WO2016163551A1 WO 2016163551 A1 WO2016163551 A1 WO 2016163551A1 JP 2016061624 W JP2016061624 W JP 2016061624W WO 2016163551 A1 WO2016163551 A1 WO 2016163551A1
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Prior art keywords
acrylic acid
acid derivative
group
carbon atoms
amide
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PCT/JP2016/061624
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English (en)
Japanese (ja)
Inventor
誠 松浦
麻子 吉山
洋介 岸川
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ダイキン工業株式会社
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP2015090688A external-priority patent/JP6160651B2/ja
Application filed by ダイキン工業株式会社 filed Critical ダイキン工業株式会社
Priority to RU2017135347A priority Critical patent/RU2748836C2/ru
Priority to CN201680019804.3A priority patent/CN107428661A/zh
Priority to US15/564,267 priority patent/US10577302B2/en
Priority to EP16776717.7A priority patent/EP3281932B1/fr
Publication of WO2016163551A1 publication Critical patent/WO2016163551A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/64—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
    • 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
    • C07C67/62—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters

Definitions

  • the present invention relates to an acrylic acid derivative-containing composition, a method for stabilizing an acrylic acid derivative, and the like.
  • Acrylic acid derivatives are (1) raw materials for water-absorbing polymers, (2) as substitutes for inorganic glass, windows for buildings or vehicles, covers for lighting fixtures, lantern signs, road signs, daily necessities, office supplies, crafts It is widely used as a raw material for acrylic resins used for windshields of wristwatches and (3) acrylic resin paints.
  • fluorine-containing acrylic acid derivatives are synthetic intermediates for pharmaceuticals (for example, antibiotics), synthetic intermediates for optical fiber sheath materials, synthetic intermediates for coating materials, and semiconductor resist materials. It is useful as an intermediate and a monomer of a functional polymer.
  • a method for producing an acrylic acid derivative a method of producing an acrylic acid derivative by oxidizing isobutylene or propylene, or a method of producing an acrylic acid derivative using a transition metal catalyst using ethylene, propyne or the like as a raw material is known.
  • Patent Document 1 discloses a method in which 2-fluoropropionic acid ester is reacted with a brominating agent having a nitrogen-bromine bond in the presence of a radical initiator.
  • 2-fluoropropionic acid ester is reacted with a brominating agent having a nitrogen-bromine bond in the presence of a radical initiator.
  • 3-halo-2-fluoropropionic acid derivatives are substituted with 2-fluoroacrylic acid substituted in the presence of at least one base and in the presence of at least one polymerization inhibitor. Methods for converting to derivatives are disclosed.
  • Acrylic acid derivatives structurally contain active unsaturated bonds, so they are unstable to external stimuli such as heat, light, and oxygen, and easily converted into oligomers or polymers by polymerization reactions. Have the potential to
  • the present invention aims to provide a method for stabilizing an acrylic acid derivative and a composition containing the acrylic acid derivative, in which the acrylic acid derivative is stabilized.
  • R 1 and R 2 are the same or different and each represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, a halogen atom, or a hydrogen atom;
  • R c is a group: —OR 3 (wherein R 3 represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, or a hydrogen atom), or a halogen atom
  • X represents a fluoroalkyl group, an alkyl group, a hydrogen atom, or a halogen atom.
  • R 1 and R 2 are the same or different and each represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, a halogen atom, or a hydrogen atom;
  • R c is a group: —OR 3 (wherein R 3 represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, or a hydrogen atom), or a halogen atom
  • X represents a fluoroalkyl group, an alkyl group, a hydrogen atom, or a halogen atom.
  • a composition containing an acrylic acid derivative represented by: and (B) an amide The composition whose content of acrylic acid derivative (A) is 30% (w / w) or more.
  • Item 2. The composition according to Item 1, wherein the amide (B) is an amide having 1 to 6 carbon atoms.
  • Item 3. The composition according to Item 3, wherein the amide (B) is N, N-dimethylformamide or N, N-dimethylacetamide.
  • Item 4. Item 4. The composition according to any one of Items 1 to 3, wherein R 1 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a fluoroalkyl group having 1 to 20 carbon atoms.
  • Item 5. Item 5.
  • R 1 and R 2 are the same or different and each represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, a halogen atom, or a hydrogen atom;
  • R c is a group: —OR 3 (wherein R 3 represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, or a hydrogen atom), or a halogen atom
  • X represents a fluoroalkyl group, an alkyl group, a hydrogen atom, or a halogen atom.
  • a method for stabilizing an acrylic acid derivative represented by A stabilization method comprising coexisting an acrylic acid derivative represented by the formula (I) with an amide.
  • composition of the present invention contains an acrylic acid derivative, and the acrylic acid derivative is stabilized.
  • the acrylic acid derivative is stabilized.
  • an “alkyl group” (the term “alkyl group” includes a part of “alkyl group” in “fluoroalkyl group” and the like) is cyclic, linear or branched. It can be an alkyl group.
  • alkyl group specifically includes, for example, cyclic alkyl groups having 3 to 6 carbon atoms (cycloalkyl groups) such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • fluoroalkyl group is an alkyl group in which at least one hydrogen atom is substituted with a fluorine atom.
  • the number of fluorine atoms of the “fluoroalkyl group” is 1 or more (eg, 1 to 3, 1 to 6, 1 to 12, or the maximum number that can be substituted from one). be able to.
  • Fluoroalkyl group includes perfluoroalkyl group.
  • a “perfluoroalkyl group” is an alkyl group in which all hydrogen atoms are substituted with fluorine atoms.
  • examples of the “aryl group” include a phenyl group and a naphthyl group.
  • alkoxy group is an alkyl-O— group.
  • acyl group examples include an alkanoyl group (that is, an alkyl-CO— group) and the like.
  • ester group examples include an alkylcarbonyloxy group (that is, an alkyl-CO—O— group), an alkoxycarbonyl group (that is, an alkyl-O—CO— group), and the like.
  • R 1 and R 2 are the same or different and each represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, a halogen atom, or a hydrogen atom;
  • R c is a group: —OR 3 (wherein R 3 represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, or a hydrogen atom), or a halogen atom
  • X represents a fluoroalkyl group, an alkyl group, a hydrogen atom, or a halogen atom.
  • substituent in the “aryl group optionally having one or more substituents” represented by R 1 , R 2 and R 3 are fluorine atom, alkyl group, alkoxy group, acyl Groups, ester groups, cyano groups, nitro groups, and fluoroalkyl groups, and more preferred examples include fluorine atoms.
  • the number of the “substituents” is preferably 0 (that is, unsubstituted), 1, 2, or 3.
  • R 1 is preferably a hydrogen atom, 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, still more preferably 1 to 3 carbon atoms). And particularly preferably an alkyl group having 1 or 2 carbon atoms, or a fluoroalkyl group having 1 to 20 carbon atoms, and more preferably a hydrogen atom.
  • R 2 is preferably a hydrogen atom, 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, still more preferably 1 to 3 carbon atoms).
  • the halogen atom represented by R c is preferably a fluorine atom or a chlorine atom, and more preferably a fluorine atom.
  • R c is preferably of the formula: —OR 3
  • R 3 is preferably a linear alkyl group having 1 to 20 carbon atoms (preferably having 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, still more preferably carbon atoms). 1 to 3, particularly preferably 1 or 2).
  • X has 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, still more preferably 1 to 4 carbon atoms, still more preferably 1 to 3 carbon atoms, and particularly preferably carbon number). 1 or 2) a fluoroalkyl group, a fluorine atom, or a chlorine atom, and more preferably a fluorine atom.
  • R 1 is a hydrogen atom
  • R 2 is a hydrogen atom
  • R c is a group: —OR 3
  • R 3 is a methyl group or an ethyl group (more preferably a methyl group)
  • X is a fluorine atom or a chlorine atom (more preferably a fluorine atom) It is.
  • composition of the present invention can contain one or more acrylic acid derivatives (A), but the composition of the present invention preferably contains only one acrylic acid derivative (A).
  • the acrylic acid derivative (A) used in the present invention can be produced by a known production method or a method analogous thereto, or is commercially available.
  • R c in the formula (I) is a group: —OR 3 , for example, International Publication No. 2014/034906, JP 2014-24755, and US Patent It can be produced by a production method described in known literature such as No. 3262968 or a method analogous thereto.
  • R c in the formula (I) is a halogen atom
  • R c in the formula (I) is a halogen atom
  • publicly known ones such as JP-A-60-078940 and JP-A-61-085345 It can be produced by a production method described in the literature or a method analogous thereto.
  • the content of the acrylic acid derivative (A) in the composition of the present invention is 30% (w / w) or more.
  • the concentration of the acrylic acid derivative (A) is high, an undesirable polymerization reaction or the like is likely to occur.
  • the acrylic acid derivative (A) can be stable.
  • the content of the acrylic acid derivative (A) in the composition of the present invention is preferably 40% (w / w) or more, 50% (w / w) or more, 60% (w / w) or more, 70%. (W / w) or more, 80% (w / w) or more, or 90% (w / w) or more.
  • the upper limit of the content of the acrylic acid derivative (A) in the composition of the present invention is not particularly limited. For example, 98% (w / w), 95% (w / w), or 90% (w / w) Can be. However, as will be understood by those skilled in the art, the upper limit of the content of the acrylic acid derivative (A) in the composition of the present invention is limited by the amount of the amide (B) contained in the composition of the present invention. There is.
  • Amide (B) Specific examples of the amide (B) contained in the composition of the present invention include N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMAC), N-methylpyrrolidone, 1,3-dimethyl-2- Including imidazolidinone, N, N-dimethylacrylamide, N, N-dimethylacetoacetamide, N, N-diethylformamide, and N, N-diethylacetamide.
  • DMF N-dimethylformamide
  • DMAC N-dimethylacetamide
  • N-methylpyrrolidone 1,3-dimethyl-2- Including imidazolidinone, N, N-dimethylacrylamide, N, N-dimethylacetoacetamide, N, N-diethylformamide, and N, N-diethylacetamide.
  • the amide (B) contained in the composition of the present invention preferably has the formula: R 10 R 11 —N—CO—R 12 (wherein R 10 and R 11 are alkyl groups having 1 to 3 carbon atoms) And R 12 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.)
  • the amide (B) contained in the composition of the present invention is preferably an amide having 3 to 8 carbon atoms.
  • the amide (B) contained in the composition of the present invention is particularly preferably N, N-dimethylformamide or N, N-dimethylacetamide.
  • the amide (B) can be used alone or in combination of two or more.
  • the lower limit of the amide (B) content in the composition of the present invention is preferably 0.01% (w / w), 0.05% (w / w), 0.1% (w / w), 0 0.5% (w / w), 1.0% (w / w), more preferably 3.0% (w / w), and still more preferably 5.0% (w / w).
  • the upper limit of the content of the amide (B) in the composition of the present invention is not particularly limited, but there is an effect of stabilizing the desired acrylic acid derivative (A).
  • the use of amide (B) in excess of the amount achieved is disadvantageous in cost. Therefore, the upper limit of the content of the amide (B) in the composition of the present invention is usually 50% (w / w), 40% (w / w), 30% (w / w), 20% ( w / w), or 10% (w / w).
  • the content of the amide (B) in the composition of the present invention is preferably within the range of 0.01 to 50% (w / w), more preferably within the range of 1.0 to 40% (w / w), More preferably, it is in the range of 5.0 to 30% (w / w), still more preferably 1 to 3% (w / w).
  • the lower limit of the amount ratio [amide (B) / acrylic acid derivative (A)] of amide (B) to acrylic acid derivative (A) is preferably 0.01% (w / w), 0.05% (w / w), more preferably 0.1% (w / w), still more preferably 0.5% (w / w), still more preferably 1.0% (w / w), Especially preferably, it is 3.0%, More preferably, it is 5.0% (w / w).
  • the upper limit of the amount ratio of the amide (B) to the acrylic acid derivative (A) [amide (B) / acrylic acid derivative (A)] is not particularly limited. It is disadvantageous in cost to use the amide (B) in an amount exceeding the amount that achieves the stabilization effect of the desired acrylic acid derivative (A). Therefore, the upper limit of the ratio of the amide (B) to the acrylic acid derivative (A) [amide (B) / acrylic acid derivative (A)] is usually 200% (w / w), 190% (w / w), for example.
  • the amount ratio of the amide (B) to the acrylic acid derivative (A) is preferably in the range of 0.01 to 200% (w / w), more preferably 0.1 to 190% ( w / w), more preferably in the range 1 to 170% (w / w), even more preferably 3 to 50% (w / w), and particularly preferably in the range 5 to 50% (w / w). Is within.
  • composition of the present invention may contain an optional component in addition to the acrylic acid derivative (A) and the amide (B).
  • the optional component may be an impurity present in the acrylic acid derivative (A) or amide (B) prepared for the production of the composition of the present invention.
  • Such optional components include water and organic solvents.
  • composition of the present invention since the acrylic acid derivative (A) is stabilized by the amide (B), it is less meaningful to contain a polymerization inhibitor for the purpose of stabilizing the acrylic acid derivative (A).
  • the composition of the present invention may contain a polymerization inhibitor as an optional component.
  • the acrylic acid derivative (A) is stabilized. That is, in the composition of the present invention, the acrylic acid derivative (A) contained therein has high stability.
  • the acrylic acid derivative (A) suppresses the change of the acrylic acid derivative (A) to a polymer or the like as compared with the case where the amide (B) does not coexist. ing.
  • the change of the acrylic acid derivative (A) to another substance can be analyzed by a method such as NMR analysis. Further, for example, the change of the acrylic acid derivative into the polymer can be easily detected by observing that the colorless and transparent solution of the acrylic acid derivative is changed into a solid.
  • the acrylic acid derivative (A) is stabilized by the coexistence of the acrylic acid derivative (A) with the amide (B).
  • the acrylic acid derivative (A) can be exposed to various conditions during storage or use, it is often difficult to coexist with the acrylic acid derivative. In this case, the polymerization inhibitor cannot sufficiently perform its function.
  • the acrylic acid derivative (A) in the composition of the present invention is stabilized under various conditions.
  • the composition of the present invention can be produced, for example, by mixing the acrylic acid derivative (A), the amide (B), and optional components added as desired, by a conventional method such as stirring. Part or all of the amide (B) may be contained as an impurity or additive in the acrylic acid derivative (A) prepared for the production of the composition of the present invention.
  • the method for stabilizing the acrylic acid derivative represented by the formula (I) comprises the acrylic acid derivative (A), Including coexistence with an amide (the amide (B)).
  • the method for allowing the acrylic acid derivative (A) to coexist with the amide (B) is not particularly limited, and examples thereof include: [1] mixing an acrylic acid derivative (A) and an amide (B); [2] generating an amide (B) in a system containing the acrylic acid derivative (A), [3] Acrylic acid derivative (A) is produced in a system containing amide (B), and [4] Acrylic acid derivative (A) and amide (B) in a single system, respectively. Generation.
  • the acrylic acid derivative (A) in the method for stabilizing the acrylic acid derivative (A) of the present invention is as described for the composition of the present invention.
  • the amide (B) in the method for stabilizing the acrylic acid derivative (A) of the present invention is as described for the composition of the present invention.
  • amide (B) is preferably used in a predetermined quantitative ratio with respect to acrylic acid derivative (A).
  • the amount ratio is as described for the composition of the present invention.
  • Example 1 Distilled and purified 2-fluoroacryloyl fluoride was prepared.
  • the sample composition or 2-fluoroacryloyl fluoride as a control was placed in a sample bottle, covered, and allowed to stand at room temperature for 1 day, and then the properties of both were observed. As a result, solids were observed in the control, but the sample composition containing N, N-dimethylacetamide and 2-fluoroacryloyl fluoride was a transparent liquid, and no change was observed in its properties.
  • Example 2 Each sample was prepared by adding the amount of N, N-dimethylformamide shown in Table 1 to 100% by mass of 2-fluoroacrylic acid methyl ester.
  • N, N-dimethylacetamide can stabilize 2-fluoroacrylic acid methyl ester.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention vise à fournir un procédé de stabilisation d'un dérivé d'acide acrylique et une composition qui contient un dérivé d'acide acrylique qui a été stabilisé. La composition comprend (A) un dérivé d'acide acrylique représenté par la formule (I) et (B) un amide, et a une teneur en dérivé d'acide acrylique (A) de 30 % (poids/poids) ou plus. [Dans la formule, R1 et R2 sont identiques ou différents et représentent chacun un groupe alkyle, un groupe fluoroalkyle, un groupe aryle qui peut avoir un ou plusieurs substituants, un atome d'halogène ou un atome d'hydrogène, RC représente un groupe -OR3 (où R3 représente un groupe alkyle, un groupe fluoroalkyle, un groupe aryle qui peut avoir un ou plusieurs substituants ou un atome d'hydrogène) ou un atome d'halogène, et X représente un groupe fluoroalkyle, un groupe alkyle, un atome d'hydrogène ou un atome d'halogène.]
PCT/JP2016/061624 2015-04-09 2016-04-08 Composition contenant un dérivé d'acide acrylique, et procédé de stabilisation du dérivé d'acide acrylique WO2016163551A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
RU2017135347A RU2748836C2 (ru) 2015-04-09 2016-04-08 Композиция, содержащая производное акриловой кислоты, и способы стабилизации производного акриловой кислоты
CN201680019804.3A CN107428661A (zh) 2015-04-09 2016-04-08 含有丙烯酸衍生物的组合物和丙烯酸衍生物的稳定化方法
US15/564,267 US10577302B2 (en) 2015-04-09 2016-04-08 Composition containing acrylic acid derivative, and method for stabilizing acrylic acid derivative
EP16776717.7A EP3281932B1 (fr) 2015-04-09 2016-04-08 Composition contenant un dérivé d'acide acrylique, et procédé de stabilisation du dérivé d'acide acrylique

Applications Claiming Priority (4)

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JP2015-080382 2015-04-09
JP2015080382 2015-04-09
JP2015-090688 2015-04-27
JP2015090688A JP6160651B2 (ja) 2015-04-09 2015-04-27 アクリル酸誘導体含有組成物、及びアクリル酸誘導体の安定化方法

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4993315A (fr) * 1972-11-21 1974-09-05
DE2350119A1 (de) * 1973-10-05 1975-04-10 Bayer Ag Verfahren zur herstellung von 2-chloracrylsaeurechlorid
JPS5785337A (en) * 1981-09-25 1982-05-28 Mitsui Petrochem Ind Ltd Production of beta-acryloxypropionic acid
JPS60158136A (ja) * 1984-01-30 1985-08-19 Daikin Ind Ltd 含フツ素アクリル酸またはその誘導体の重合防止方法
JPS62106049A (ja) * 1985-10-31 1987-05-16 Mitsui Toatsu Chem Inc カルボン酸エステルの製法
JPH02500026A (ja) * 1986-09-26 1990-01-11 イーストマン・コダック・カンパニー イソ酪酸とメタクリル酸の分離方法
JPH11255703A (ja) * 1998-03-12 1999-09-21 Nippon Shokubai Co Ltd 酸クロライドの製造方法
JP2003277319A (ja) * 2002-03-19 2003-10-02 Hodogaya Chem Co Ltd アクリル酸クロライドまたはメタクリル酸クロライドの製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4993315A (fr) * 1972-11-21 1974-09-05
DE2350119A1 (de) * 1973-10-05 1975-04-10 Bayer Ag Verfahren zur herstellung von 2-chloracrylsaeurechlorid
JPS5785337A (en) * 1981-09-25 1982-05-28 Mitsui Petrochem Ind Ltd Production of beta-acryloxypropionic acid
JPS60158136A (ja) * 1984-01-30 1985-08-19 Daikin Ind Ltd 含フツ素アクリル酸またはその誘導体の重合防止方法
JPS62106049A (ja) * 1985-10-31 1987-05-16 Mitsui Toatsu Chem Inc カルボン酸エステルの製法
JPH02500026A (ja) * 1986-09-26 1990-01-11 イーストマン・コダック・カンパニー イソ酪酸とメタクリル酸の分離方法
JPH11255703A (ja) * 1998-03-12 1999-09-21 Nippon Shokubai Co Ltd 酸クロライドの製造方法
JP2003277319A (ja) * 2002-03-19 2003-10-02 Hodogaya Chem Co Ltd アクリル酸クロライドまたはメタクリル酸クロライドの製造方法

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