WO2016190044A1 - Procédé de production d'un composé aromatique substitué par un groupe hydroxy - Google Patents

Procédé de production d'un composé aromatique substitué par un groupe hydroxy Download PDF

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Publication number
WO2016190044A1
WO2016190044A1 PCT/JP2016/063204 JP2016063204W WO2016190044A1 WO 2016190044 A1 WO2016190044 A1 WO 2016190044A1 JP 2016063204 W JP2016063204 W JP 2016063204W WO 2016190044 A1 WO2016190044 A1 WO 2016190044A1
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Prior art keywords
hydroxy
substituted aromatic
group
aromatic compound
compound represented
Prior art date
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PCT/JP2016/063204
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English (en)
Japanese (ja)
Inventor
直哉 内山
淳矢 堀内
牧野嶋　高史
越後　雅敏
篤 大越
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Mitsubishi Gas Chemical Co Inc
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Mitsubishi Gas Chemical Co Inc
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Priority to JP2017520582A priority Critical patent/JP7233164B2/ja
Priority to CN201680030656.5A priority patent/CN107614473A/zh
Publication of WO2016190044A1 publication Critical patent/WO2016190044A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with at least one hydroxy group on a condensed ring system containing two rings

Definitions

  • the present invention relates to a method for producing a hydroxy-substituted aromatic compound (for example, dihydroxynaphthalene).
  • a hydroxy-substituted aromatic compound for example, dihydroxynaphthalene
  • Hydroxy-substituted aromatic compounds such as dihydroxynaphthalene are useful as raw materials for compounds or resins used as semiconductor sealing materials, coating agents, resist materials, and semiconductor underlayer film forming materials (for example, Patent Document 1).
  • Patent Document 1 a specific method is known as a purification method of a hydroxy-substituted aromatic compound, for example, dihydroxynaphthalene (see, for example, Patent Document 3).
  • the methods for purifying hydroxy-substituted aromatic compounds disclosed herein, such as dihydroxynaphthalene have a problem in that there is a limit to improvement in purity or variations in purity and yield.
  • the metal content is an important performance evaluation item particularly for improving the yield. That is, when a large amount of metal is contained in a hydroxy-substituted aromatic compound, for example, a compound or resin obtained from dihydroxynaphthalene as a raw material, the metal remains in the semiconductor and the electrical characteristics of the semiconductor are deteriorated. It is demanded to reduce the content of the metal.
  • a method for purifying a compound or resin obtained from a hydroxy-substituted aromatic compound for example, dihydroxynaphthalene
  • a mixture containing the compound or resin and an organic solvent is brought into contact with an ion exchange resin.
  • the method, the method of filtering with a filter, etc. can be considered.
  • a hydroxy-substituted aromatic compound having a high metal content for example, dihydroxynaphthalene is used as a raw material
  • the above method has a problem that the burden on metal removal is large and the cost is high.
  • An object of the present invention is to provide an industrially advantageous method for producing a hydroxy-substituted aromatic compound such as dihydroxynaphthalene.
  • the present inventors have purified hydroxy-substituted aromatic compounds (for example, dihydroxynaphthalene) under specific conditions, thereby achieving high purity and high yield and stably.
  • the inventors have found that a hydroxy-substituted aromatic compound (for example, dihydroxynaphthalene) can be produced, and have reached the present invention.
  • the present inventors contacted a solution containing a hydroxy-substituted aromatic compound (for example, dihydroxynaphthalene) and a specific organic solvent with an acidic aqueous solution for extraction treatment.
  • a hydroxy-substituted aromatic compound for example, dihydroxynaphthalene
  • the present invention is as follows.
  • a method for producing a hydroxy-substituted aromatic compound comprising a step of contacting a hydroxy-substituted aromatic compound with an organic solvent and / or water in an atmosphere having an oxygen concentration of less than 20% by volume (contact step).
  • contact step a step of contacting a hydroxy-substituted aromatic compound with an organic solvent and / or water in an atmosphere having an oxygen concentration of less than 20% by volume.
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • each Ra is independently hydrogen.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • R b is each independently a hydrogen atom, a hydroxyl group, a halogen group, a carbon number of 1 to A group consisting of 40 linear, branched or cyclic alkyl groups, optionally substituted aryl groups having 6 to 40 carbon atoms, or alkenyl groups having 2 to 40 carbon atoms and combinations thereof.
  • the alkyl group, aryl group or alkenyl group may contain an ether bond, a ketone bond or an ester bond.
  • the hydroxy-substituted aromatic compound represented by the formula (A 0 ) is a compound represented by the following formula (A), and the hydroxy-substituted aromatic compound represented by the formula (B 0 ) is represented by the following formula (B)
  • the production method according to [2] which is a compound represented by the formula: (In the above formula (A), n 0 is an integer of 0 to 9, m 0 is an integer of 0 to 2, p 0 is an integer of 0 to 9, and R 0 is each independently carbon.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • each R 1 is independently a linear, branched or branched group having 1 to 30 carbon atoms.
  • the hydroxy-substituted aromatic compound represented by the formula (A) is a compound represented by the following formula (A-1), a compound represented by the following formula (A-2), or a formula (A-3) And at least one selected from the group consisting of a compound represented by the following formula (A-4):
  • n 0 is an integer from 0 to 9
  • n 1 is an integer from 0 to 9.
  • the organic solvent is made of methanol, ethanol, isopropanol, acetone, N-methylpyrrolidone, propylene glycol monomethyl ether, toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, and ethyl acetate.
  • a hydroxy-substituted aromatic compound comprising a step of bringing a solution ( ⁇ ) containing an organic solvent that is not miscible with water and a hydroxy-substituted aromatic compound into contact with an acidic aqueous solution and extracting a metal component in the hydroxy-substituted aromatic compound Manufacturing method.
  • the hydroxy-substituted aromatic compound is a hydroxy-substituted aromatic compound represented by the following formula (A 0 ) and / or (B 0 ).
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • each Ra is independently hydrogen.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • R b is each independently a hydrogen atom, a hydroxyl group, a halogen group, a carbon number of 1 to A group consisting of 40 linear, branched or cyclic alkyl groups, optionally substituted aryl groups having 6 to 40 carbon atoms, or alkenyl groups having 2 to 40 carbon atoms and combinations thereof.
  • the alkyl group, aryl group or alkenyl group may contain an ether bond, a ketone bond or an ester bond.
  • the hydroxy-substituted aromatic compound represented by the formula (A 0 ) is a compound represented by the following formula (A), and the hydroxy-substituted aromatic compound represented by the formula (B 0 ) is represented by the following formula (B ]
  • the manufacturing method as described in [11] which is a compound represented by.
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • R 0 is each independently carbon.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • each R 1 is independently a linear, branched or branched group having 1 to 30 carbon atoms.
  • the hydroxy-substituted aromatic compound represented by the formula (A) is a compound represented by the following formula (A-1), a compound represented by the following formula (A-2), or a formula (A-3) And at least one selected from the group consisting of a compound represented by the following formula (A-4):
  • n 0 is an integer from 0 to 9
  • n 1 is an integer from 0 to 9.
  • the organic solvent that is not miscible with water is at least one selected from the group consisting of toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, and ethyl acetate.
  • the acidic aqueous solution is one or more mineral acid aqueous solutions selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, or acetic acid, propionic acid, succinic acid, malonic acid, succinic acid, fumaric acid, maleic acid Any one of [10] to [17], which is one or more organic acid aqueous solutions selected from the group consisting of tartaric acid, citric acid, methanesulfonic acid, phenolsulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid.
  • the manufacturing method as described.
  • a method for producing a hydroxy-substituted aromatic compound for example, dihydroxynaphthalene
  • a high-purity hydroxy-substituted aromatic compound for example, dihydroxynaphthalene
  • a method for producing a hydroxy-substituted aromatic compound (for example, dihydroxynaphthalene) that can reduce the content of various metals can be advantageously provided industrially.
  • the first method for producing a hydroxy-substituted aromatic compound according to this embodiment is a step of bringing the hydroxy-substituted aromatic compound into contact with an organic solvent and / or water in an atmosphere having an oxygen concentration of less than 20% by volume (contact step). including.
  • the hydroxy-substituted aromatic compound is not particularly limited as long as it is an aromatic compound having at least one phenolic hydroxy group.
  • the following formula (A 0 ) and / or A hydroxy-substituted aromatic compound represented by (B 0 ) is preferable.
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • each Ra is independently hydrogen.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • R b is each independently a hydrogen atom, a hydroxyl group, a halogen group, a carbon number of 1 to A group consisting of 40 linear, branched or cyclic alkyl groups, optionally substituted aryl groups having 6 to 40 carbon atoms, or alkenyl groups having 2 to 40 carbon atoms and combinations thereof.
  • the alkyl group, aryl group or alkenyl group may contain an ether bond, a ketone bond or an ester bond.
  • the hydroxy-substituted aromatic compound represented by the formula (A 0 ) is preferably a compound represented by the following formula (A).
  • the hydroxy-substituted aromatic compound represented by the formula (B 0 ) is preferably a compound represented by the following formula (B).
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • R 0 is each independently carbon.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • each R 1 is independently a linear, branched or branched group having 1 to 30 carbon atoms.
  • the hydroxy-substituted aromatic compound represented by the formula (A) is represented by the following formula (A-1), the following formula (A-2): And at least one selected from the group consisting of a compound represented by the following formula (A-3) and a compound represented by the following formula (A-4).
  • the hydroxy-substituted aromatic compound represented by the formula (B) is preferably a compound represented by the following formula (B-1).
  • n 0 is an integer from 0 to 9
  • n 1 is an integer from 0 to 9.
  • the hydroxy-substituted aromatic compound is brought into contact with an organic solvent and / or water in an atmosphere having an oxygen concentration of less than 20% by volume, for example, impurities in the hydroxy-substituted aromatic compound. Is dissolved in an organic solvent and / or water and separated, whereby the hydroxy-substituted aromatic compound can be stably purified with a high yield.
  • hydroxy-substituted aromatic compounds such as dihydroxynaphthalene have a problem that dimers are particularly easily formed.
  • hydroxy-substituted aromatics are obtained. Generation of by-products such as dimers due to oxidation of aromatic compounds such as dihydroxynaphthalene, and stable production of hydroxy-substituted aromatic compounds such as dihydroxynaphthalene with high purity and high yield become.
  • the oxygen concentration in the contact step is preferably less than 10% by volume, more preferably less than 5% by volume, and even more preferably less than 1% by volume.
  • the lower the oxygen concentration in the contacting step the greater the effect of suppressing the alteration of the hydroxy-substituted aromatic compound, for example, dihydroxynaphthalene.
  • the minimum of the oxygen concentration of a drying process is not specifically limited, For example, it is 0.01 volume%.
  • a known method can be applied to reduce the oxygen concentration, and is not particularly limited.
  • the gas replacement can be performed by flowing nitrogen gas into a kettle for purification or reducing the pressure and then introducing nitrogen gas.
  • the method of performing can be mentioned.
  • a method in which the pressure is reduced and the reaction is performed in a vacuum can be used.
  • a method in which the kettle for purification is decompressed and nitrogen gas is introduced thereafter is simple, reliable and preferable.
  • the oxygen concentration can be confirmed by a known method and is not particularly limited.
  • the oxygen concentration of the gas discharged from the vent is measured with an oximeter by flowing nitrogen gas into a refining kettle. Can be mentioned. A method of installing an oximeter in the kettle for purification can also be mentioned.
  • the contact temperature is not particularly limited as long as it can suppress alteration of the hydroxy-substituted aromatic compound, for example, dihydroxynaphthalene, but is preferably in the range of 0 to 150 ° C., more preferably in the range of 5 to 100 ° C. A range of ° C is more preferred.
  • the contact temperature is within the above range, the purity and yield are good, and temperature adjustment tends to be easy.
  • the contact time is not particularly limited as long as it can suppress alteration of a hydroxy-substituted aromatic compound, for example, dihydroxynaphthalene, but is preferably in the range of 1 minute to 120 minutes, more preferably in the range of 1 minute to 60 minutes. More preferably, the range is from 30 minutes to 30 minutes.
  • the pressure in the contact step can be any of reduced pressure, normal pressure and increased pressure.
  • the hydroxy-substituted aromatic compound represented by the formula (A) used in the first production method of the present embodiment is particularly preferably a compound represented by the following formula (1).
  • the compound represented by the above formula (1) is not particularly limited, but 1,2-dihydroxynaphthalene, 1,3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, , 5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene One or more selected from the above are preferred.
  • the compound represented by the above formula (1) is not particularly limited, but from the viewpoint of heat resistance of a compound or resin obtained using the compound as a raw material, 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene are preferred.
  • 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene are preferred.
  • the compound represented by the formula (1) is not particularly limited, but 2,6-dihydroxynaphthalene is more preferable from the viewpoint of further heat resistance of a compound or resin obtained using the compound as a raw material.
  • the compound represented by the above formula (1) can be easily obtained by known means such as a manufacturer and a reagent manufacturer. Moreover, it can synthesize
  • the hydroxy-substituted aromatic compound used in the first production method of the present embodiment may be used alone or in combination of two or more. Further, the hydroxy-substituted aromatic compound may contain various surfactants, various crosslinking agents, various acid generators, various stabilizers and the like.
  • the organic solvent and / or water used in the first production method of the present embodiment is not particularly limited, but for example, an organic solvent and / or water that can be safely applied to a semiconductor production process is preferable.
  • the amount of the organic solvent and / or water to be used is preferably about 0.1 to 1000 times by mass with respect to the hydroxy-substituted aromatic compound to be used, and more preferably 0.5 to 500 from the viewpoint of economy.
  • the mass is more preferably 1 to 100 mass times.
  • organic solvent used in the first production method of the present embodiment include, but are not limited to, ethers such as tetrahydrofuran and 1,3-dioxolane, alcohols such as methanol, ethanol, and isopropanol.
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 2-pentanone, N-methylpyrrolidone, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl Ether (PGME), glycol ethers such as propylene glycol monoethyl ether, ethers such as diethyl ether and diisopropyl ether, ethyl acetate, n-butyl acetate , Esters such as isoamyl acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), glycol ether acetates such as propylene glycol monomethyl
  • methanol, ethanol, isopropanol, acetone, N-methylpyrrolidone, propylene glycol monomethyl ether, toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate and ethyl acetate One or more selected are preferable, and one or more selected from the group consisting of methanol, ethanol, isopropanol, acetone, N-methylpyrrolidone, propylene glycol monomethyl ether, cyclohexanone and propylene glycol monomethyl ether acetate are more preferable.
  • water used in the first production method of the present embodiment are not limited to the following, but examples include tap water, industrial water, ion-exchanged water, and ultrapure water.
  • An acidic aqueous solution may also be used.
  • the acidic aqueous solution is not particularly limited and is appropriately selected from aqueous solutions in which generally known organic and inorganic compounds are dissolved in water.
  • aqueous solution in which an organic acid such as acid, phenolsulfonic acid, p-toluenesulfonic acid or trifluoroacetic acid is dissolved in water may be mentioned.
  • the pH of the acidic aqueous solution is not particularly limited, but it is preferable to adjust the acidity of the aqueous solution in consideration of adverse effects on the hydroxy-substituted aromatic compound.
  • the pH range of the acidic aqueous solution is preferably about 0 to 5, more preferably about pH 0 to 4, and still more preferably about pH 0 to 3.
  • ion-exchanged water, ultrapure water, and the like are preferable in order to suppress metal and chlorine content contamination.
  • These organic solvents and water can be used alone or in combination of two or more.
  • a method for reducing dissolved oxygen is not particularly limited, and a known method can be applied. However, an inert gas such as nitrogen gas is passed through an organic solvent and / or water under normal pressure or reduced pressure, or ultrasonic waves are used. The method of adding is effective.
  • the first production method of the present embodiment preferably includes a step of dissolving the hydroxy-substituted aromatic compound in an organic solvent.
  • the hydroxy-substituted aromatic compound is dissolved in an organic solvent, and then the activated carbon is brought into contact with the solution of the hydroxy-substituted aromatic compound. It is preferable to include a process.
  • the activated carbon contact step is more preferably performed in an atmosphere having an oxygen concentration of less than 20% by volume.
  • the method for reducing the oxygen remaining in the activated carbon is not particularly limited, and a known method can be applied, but by adding activated carbon to the refining kettle and flowing nitrogen gas or reducing the pressure and then introducing nitrogen. The method of performing can be mentioned.
  • the contact step of activated carbon is performed in an atmosphere having an oxygen concentration of less than 20% by volume, the deterioration of the hydroxy-substituted aromatic compound, for example, dihydroxynaphthalene is suppressed, and the purity of the hydroxy-substituted aromatic compound tends to be further improved. Some or more variability in purity and yield is suppressed, resulting in a more industrially advantageous process.
  • the first production method of this embodiment preferably includes a step of crystallizing the hydroxy-substituted aromatic compound after dissolving the hydroxy-substituted aromatic compound in an organic solvent.
  • a method for isolating the hydroxy-substituted aromatic compound known methods such as removal under reduced pressure, separation by reprecipitation, and combinations thereof can be applied. If necessary, known processes such as a concentration operation, a filtration operation, a centrifugal separation operation, and a drying operation can be performed. When performing these operations, it is preferable to carry out in an atmosphere having an oxygen concentration of less than 20% by volume in order to improve purity or suppress variations in purity and yield.
  • a solution ( ⁇ ) containing an organic solvent that is not miscible with water and a hydroxy-substituted aromatic compound is brought into contact with an acidic aqueous solution to make a hydroxy-substituted aromatic compound.
  • a step of extracting a metal content in the compound is provided.
  • the hydroxy-substituted aromatic compound is not particularly limited as long as it is an aromatic compound having at least one phenolic hydroxy group.
  • the following formula (A 0 ) and / or A hydroxy-substituted aromatic compound represented by (B 0 ) is preferable.
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • each Ra is independently hydrogen.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • R b is each independently a hydrogen atom, a hydroxyl group, a halogen group, a carbon number of 1 to A group consisting of 40 linear, branched or cyclic alkyl groups, optionally substituted aryl groups having 6 to 40 carbon atoms, or alkenyl groups having 2 to 40 carbon atoms and combinations thereof.
  • the alkyl group, aryl group or alkenyl group may contain an ether bond, a ketone bond or an ester bond.
  • the hydroxy-substituted aromatic compound represented by the formula (A 0 ) is preferably a compound represented by the following formula (A).
  • the hydroxy-substituted aromatic compound represented by the formula (B 0 ) is preferably a compound represented by the following formula (B).
  • n 0 is an integer of 0 to 9
  • m 0 is an integer of 0 to 2
  • p 0 is an integer of 0 to 9
  • R 0 is each independently carbon.
  • n 1 is an integer of 0 to 9
  • p 1 is an integer of 0 to 9
  • each R 1 is independently a linear, branched or branched group having 1 to 30 carbon atoms.
  • the hydroxy-substituted aromatic compound represented by the formula (A) is represented by the following formula (A-1), the following formula (A-2): And at least one selected from the group consisting of a compound represented by the following formula (A-3) and a compound represented by the following formula (A-4).
  • the hydroxy-substituted aromatic compound represented by the formula (B) is preferably a compound represented by the following formula (B-1).
  • n 0 is an integer from 0 to 9
  • n 1 is an integer from 0 to 9.
  • the hydroxy-substituted aromatic compound is dissolved in an organic solvent that is not arbitrarily miscible with water, and the solution is contacted with an acidic aqueous solution to perform an extraction treatment, whereby a hydroxy-substituted aromatic compound is obtained.
  • a metal component contained in a solution ( ⁇ ) containing a compound and an organic solvent is transferred to an aqueous phase, and then the organic phase and the aqueous phase are separated to obtain a hydroxy-substituted aromatic compound having a reduced metal content.
  • the hydroxy-substituted aromatic compound represented by the formula (A) used in the second production method of the present embodiment is particularly preferably a compound represented by the following formula (1).
  • the compound represented by the above formula (1) is not particularly limited, but 1,2-dihydroxynaphthalene, 1,3-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, , 5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene One or more selected from the above are preferred.
  • the compound represented by the above formula (1) is more preferably at least one selected from the group consisting of 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene from the viewpoint of the heat resistance of the resulting compound or resin. preferable.
  • the compound represented by the above formula (1) is more preferably 2,6-dihydroxynaphthalene from the viewpoint of further heat resistance of the resulting compound or resin.
  • the compound represented by the above formula (1) can be easily obtained by known means such as a manufacturer and a reagent manufacturer. Moreover, it can also synthesize
  • the hydroxy-substituted aromatic compound used in the second production method of the present embodiment may be used alone or in combination of two or more. Further, the hydroxy-substituted aromatic compound may contain various surfactants, various crosslinking agents, various acid generators, various stabilizers and the like.
  • the organic solvent that is arbitrarily miscible with water used in the second manufacturing method of the present embodiment is not particularly limited, but an organic solvent that can be safely applied to a semiconductor manufacturing process is preferable.
  • the organic solvent that is not arbitrarily miscible with water means an organic solvent having a solubility in water at room temperature of less than 30%, more preferably less than 20%, and particularly preferably less than 10%.
  • Specific examples of the organic solvent used in the second production method of the present embodiment include, but are not limited to, ethers such as diethyl ether and diisopropyl ether, ethyl acetate, n-butyl acetate, isoamyl acetate, and the like.
  • Esters methyl ethyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, 2-pentanone and other ketones, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate (PGMEA), glycol ether acetates such as propylene glycol monoethyl ether acetate, aliphatic hydrocarbons such as n-hexane and n-heptane, toluene, Aromatic hydrocarbons such as alkylene, methylene chloride, halogenated hydrocarbons such as chloroform and the like.
  • At least one selected from the group consisting of toluene, 2-heptanone, cyclohexanone, cyclopentanone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate and ethyl acetate is preferable.
  • Cyclohexanone, propylene glycol monomethyl ether acetate and ethyl acetate One or more selected from the group consisting of These organic solvents can be used alone or in combination of two or more.
  • the amount of the organic solvent to be used is usually preferably about 0.1 to 1000 times by mass with respect to the hydroxy-substituted aromatic compound to be used, and more preferably 0.5 to 500 times by mass from the viewpoint of economy.
  • the amount is preferably 1 to 100 times by mass.
  • the solution ( ⁇ ) further contains an organic solvent arbitrarily mixed with water.
  • an organic solvent arbitrarily mixed with water By containing an organic solvent arbitrarily mixed with water, the amount of the hydroxy-substituted aromatic compound can be increased, the liquid separation property is improved, and the production can be performed with high pot efficiency.
  • the method for adding an organic solvent arbitrarily mixed with water is not particularly limited. For example, a method of adding to a solution containing an organic solvent in advance, a method of adding to a water or acidic aqueous solution in advance, and a method of adding after bringing a solution containing an organic solvent into contact with water or an acidic aqueous solution are possible.
  • a method of adding to a solution containing an organic solvent is preferable in terms of workability of operation and ease of management of the charged amount.
  • the organic solvent arbitrarily mixed with water used in the second manufacturing method of the present embodiment is not particularly limited, but an organic solvent that can be safely applied to a semiconductor manufacturing process is preferable.
  • the organic solvent arbitrarily mixed with water refers to an organic solvent having a solubility in water at room temperature of 70% or more, more preferably 80% or more, and particularly preferably 90% or more.
  • organic solvent arbitrarily mixed with water examples include, but are not limited to, ethers such as tetrahydrofuran and 1,3-dioxolane, alcohols such as methanol, ethanol, and isopropanol, acetone, and N-methylpyrrolidone. And the like, and glycol ethers such as ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether (PGME), and propylene glycol monoethyl ether.
  • ethers such as tetrahydrofuran and 1,3-dioxolane
  • alcohols such as methanol, ethanol, and isopropanol
  • acetone acetone
  • N-methylpyrrolidone N-methylpyrrolidone
  • glycol ethers such as ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether (PGME), and prop
  • N-methylpyrrolidone, propylene glycol monomethyl ether and the like are preferable, and one or more selected from the group consisting of N-methylpyrrolidone and propylene glycol monomethyl ether are more preferable.
  • Each of the organic solvents can be used alone or in combination of two or more.
  • the amount of the organic solvent arbitrarily mixed with water is not particularly limited as long as the solution phase and the aqueous phase are separated, but usually 0.1 to 1000 mass based on the hydroxy-substituted aromatic compound to be used. From the viewpoint of economy, it is more preferably 0.5 to 500 times by mass, and still more preferably 1 to 100 times by mass.
  • the acidic aqueous solution used in the second production method of the present embodiment is not limited to the following, and is appropriately selected from aqueous solutions in which generally known organic and inorganic compounds are dissolved in water.
  • aqueous solutions in which generally known organic and inorganic compounds are dissolved in water.
  • mineral acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid is dissolved in water, or acetic acid, propionic acid, succinic acid, malonic acid, succinic acid, fumaric acid, maleic acid, tartaric acid, citric acid, methanesulfone
  • An aqueous solution in which an organic acid such as acid, phenolsulfonic acid, p-toluenesulfonic acid or trifluoroacetic acid is dissolved in water may be mentioned.
  • These acidic aqueous solutions can be used alone or in combination of two or more.
  • one or more mineral acid aqueous solutions selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, or acetic acid, propionic acid, succinic acid, malonic acid, succinic acid, fumaric acid, maleic acid
  • Aqueous solutions of carboxylic acids such as succinic acid, tartaric acid and citric acid are more preferred, aqueous solutions of sulfuric acid, succinic acid, tartaric acid and citric acid are more preferred, and aqueous solutions of succinic acid are particularly preferred.
  • the water used here is preferably water having a low metal content, such as ion-exchanged water, in accordance with the purpose of this embodiment.
  • the pH of the acidic aqueous solution used in the present embodiment is not particularly limited, but it is preferable to adjust the acidity of the aqueous solution in consideration of adverse effects on the hydroxy-substituted aromatic compound.
  • the pH range of the acidic aqueous solution is preferably about 0 to 5, more preferably about pH 0 to 4, and still more preferably about 0 to 3.
  • the amount of the acidic aqueous solution used in the second production method of the present embodiment is not particularly limited, but the viewpoint of reducing the number of extractions for metal removal and the viewpoint of ensuring operability in consideration of the total liquid amount. It is preferable to adjust the amount of use. From such a viewpoint, the amount of the acidic aqueous solution used is preferably 0.01 to 200% by mass with respect to the solution ( ⁇ ) containing an organic solvent which is not arbitrarily miscible with water and the hydroxy-substituted aromatic compound. More preferably, it is 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass.
  • an acidic aqueous solution as described above is contacted with a solution ( ⁇ ) containing a hydroxy-substituted aromatic compound and an organic solvent that is arbitrarily immiscible with water, to thereby perform hydroxy substitution.
  • the metal content in the aromatic compound can be extracted.
  • the temperature during the extraction treatment is usually preferably from 0 to 90 ° C, more preferably from 10 to 85 ° C, and even more preferably from 20 to 80 ° C.
  • extraction operation is not specifically limited, For example, after mixing well by stirring etc., it is performed by leaving still. Thereby, the metal content contained in the solution containing the hydroxy-substituted aromatic compound and the organic solvent is transferred to the aqueous phase. Moreover, the acidity of a solution falls by this operation, and the quality change of a hydroxy substituted aromatic compound can be suppressed.
  • the solution phase containing the hydroxy-substituted aromatic compound and the organic solvent is separated into the aqueous phase, and the solution containing the hydroxy-substituted aromatic compound and the organic solvent is recovered by decantation or the like.
  • the standing time is not particularly limited, but it is preferable to adjust the standing time from the viewpoint of improving the separation between the solution phase containing the organic solvent and the aqueous phase.
  • the standing time is preferably 1 minute or longer, more preferably 10 minutes or longer, and further preferably 30 minutes or longer.
  • the extraction process may be performed only once, but it is also effective to repeat the operations of mixing, standing, and separation a plurality of times.
  • the second production method of the present embodiment after performing the extraction treatment by the step of bringing the solution ( ⁇ ) into contact with the acidic aqueous solution, further performing the extraction treatment of the metal content in the hydroxy-substituted aromatic compound with water. It is preferable to contain. That is, after performing an extraction process using an acidic aqueous solution, it is preferable to subject the recovered solution containing the hydroxy-substituted aromatic compound and the organic solvent to an extraction process with water.
  • the extraction treatment with water is not particularly limited, but can be performed by, for example, stirring well and then allowing to stand after mixing.
  • the solution phase containing the hydroxy-substituted aromatic compound and the organic solvent can be recovered by decantation or the like. it can.
  • the water used here is water with a small metal content, for example, ion-exchanged water or ultrapure water, in accordance with the purpose of the present embodiment.
  • the extraction process with water may be performed only once, but it is also effective to repeat the operations of mixing, standing, and separation a plurality of times.
  • the use ratio of both in the extraction process with water, conditions such as temperature and time are not particularly limited, but may be the same as in the case of the contact process with the acidic aqueous solution.
  • the water that can be mixed in the solution containing the hydroxy-substituted aromatic compound and the organic solvent thus obtained can be easily removed by performing an operation such as vacuum distillation. Further, if necessary, an organic solvent can be added to adjust the concentration of the hydroxy-substituted aromatic compound to an arbitrary concentration.
  • the method for isolating the hydroxy-substituted aromatic compound from the resulting solution containing the hydroxy-substituted aromatic compound and the organic solvent is not particularly limited, and known methods such as removal under reduced pressure, separation by reprecipitation, and combinations thereof are known. It can be done by the method. Moreover, well-known processes, such as concentration operation, filtration operation, centrifugation operation, and drying operation, can be performed as needed.
  • the second production method of the present embodiment is preferably performed in an atmosphere having an oxygen concentration of less than 20% by volume.
  • an atmosphere having an oxygen concentration of less than 20% by volume alteration of the hydroxy-substituted aromatic compound can be suppressed, and a high-purity hydroxy-substituted aromatic compound can be obtained.
  • the oxygen concentration is more preferably less than 10% by volume, further preferably less than 5% by volume, and particularly preferably less than 1% by volume.
  • the lower the oxygen concentration the more the alteration of the second manufacturing method of this embodiment can be suppressed.
  • the minimum of the oxygen concentration in the 2nd manufacturing method of this embodiment is not specifically limited, For example, it is 0.01 volume%.
  • a known method can be applied as a method for reducing the oxygen concentration, and is not particularly limited.
  • gas replacement is performed by flowing nitrogen gas into a kettle for purification or reducing the pressure and then introducing nitrogen gas.
  • a method can be mentioned.
  • a method in which the pressure is reduced and the reaction is performed in a vacuum can be used.
  • a method in which the kettle for purification is decompressed and nitrogen gas is introduced thereafter is simple, reliable and preferable.
  • the oxygen concentration of the gas discharged from the vent is measured with an oximeter by flowing nitrogen gas into a kettle for purification. Can be mentioned. Moreover, the method of installing an oxygen concentration meter in the kettle which refine
  • Example 1 In a 3000L capacity glass-lined purification kettle, 100kg of crude 90% pure 2,6-dihydroxynaphthalene (hereinafter also referred to as "2,6-DHN”) was charged into 220kg of acetone and 280g of ion-exchanged water. The internal air was removed under reduced pressure, nitrogen gas was introduced, and the mixture was heated and dissolved to 50 ° C. with stirring to obtain a solution. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 10 kg of activated carbon that had been previously deoxygenated was added to the resulting solution, cooled to room temperature, stirred for 1 hour, and then the activated carbon was filtered off.
  • 2,6-DHN crude 90% pure 2,6-dihydroxynaphthalene
  • Example 2 A 500-mL glass-lined purification kettle was charged with 500 g of 90-% pure 2,6-dihydroxynaphthalene (2,6-DHN) in 1000 g of isopropanol-modified ethanol, and then the air inside the kettle was removed under reduced pressure. Nitrogen gas was introduced and dissolved by heating to 60 ° C. with stirring to obtain a solution. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 1250 g of ion-exchanged water was charged into the refining kettle to precipitate crystals, and 1250 g of ion-exchanged water was further charged to cool to 10 ° C. or lower and stirred for 2 hours. Thereafter, after filtration by centrifugation, rinsing with 500 g of ion-exchanged water and vacuum drying were performed, and 450 g (yield 90%) of 2,6-DHN having a purity of 99% was obtained.
  • Example 3 In a 3000L capacity glass-lined purification kettle, 100kg of 98% pure 4,4'-biphenol crude material was charged in 150kg of acetone and 200kg of ion-exchanged water, and then nitrogen gas was introduced by removing the pressure inside the kettle under reduced pressure. The solution was obtained by heating to 50 ° C. with stirring. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 10 kg of activated carbon that had been previously deoxygenated was added to the resulting solution, cooled to room temperature, stirred for 1 hour, and then the activated carbon was filtered off. Subsequently, the filtrate was rinsed with 100 kg of acetone / ion exchange water (1/1). Thereafter, acetone was removed from the filtrate under reduced pressure and filtered by centrifugation, followed by vacuum drying to obtain 95 kg (yield 95%) of 4,4′-biphenol having a purity of 99%.
  • Example 4 In a 5000 mL capacity glass-lined purification kettle, 300 g of 98% pure 4,4′-biphenol crude product was charged in 1000 g of isopropanol-modified ethanol, and then the air inside the kettle was removed under reduced pressure to introduce nitrogen gas. The solution was obtained by heating and dissolving to 60 ° C. with stirring. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 1200 g of ion-exchanged water was charged into the refining kettle to precipitate crystals, and 1200 g of ion-exchanged water was further charged to cool to 10 ° C. or lower and stirred for 2 hours. Thereafter, after filtration by centrifugation, rinsing with 500 g of ion exchange water and vacuum drying were performed to obtain 280 g (yield 95%) of 4,4′-biphenol having a purity of 99%.
  • Example 5 In a 3000L capacity glass-lined purification kettle, 100kg of a 90% pure resorcinol (1,3-dihydroxybenzene) crude product was charged in 150kg of acetone and 200kg of ion-exchanged water, and then the air inside the kettle was removed under reduced pressure. A gas was introduced and heated to 50 ° C. with stirring to obtain a solution. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 10 kg of activated carbon that had been previously deoxygenated was added to the resulting solution, cooled to room temperature, stirred for 1 hour, and then the activated carbon was filtered off.
  • Example 6 In a 5000 mL capacity glass-lined purification kettle, 300 g of 90% pure resorcinol crude product was charged in 1000 g of isopropanol-modified ethanol, and then the air inside the kettle was removed under reduced pressure, nitrogen gas was introduced, and the mixture was stirred at 60 ° C. The solution was obtained by heating until dissolution. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 1000 g of ion-exchanged water was charged into the refining kettle to precipitate crystals, and 1500 g of ion-exchanged water was further charged to 10 ° C. or lower and stirred for 2 hours. Thereafter, after filtration by centrifugation, rinsing with 500 g of ion exchange water and vacuum drying were performed to obtain 270 g of resorcinol having a purity of 98% (yield 90%).
  • Example 7 In a 5000 mL glass-lined purification vessel, 300 g of 98% pure 9,10-dihydroxyanthracene crude product was charged into 1000 g of methyl ethyl ketone, and then the air inside the vessel was removed under reduced pressure to introduce nitrogen gas and stirring. While heating to 60 ° C., a solution was obtained. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 1000 g of ion-exchanged water was charged into the refining kettle to precipitate crystals, and 1500 g of ion-exchanged water was further charged to 10 ° C. or lower and stirred for 2 hours.
  • Example 8 In a 5000 mL glass-lined purification kettle, 300 g of 98% pure 1-hydroxypyrene crude product was charged into 1000 g of isopropanol-modified ethanol, and then the air inside the kettle was removed under reduced pressure and nitrogen gas was introduced and stirred. While heating to 80 ° C., a solution was obtained. In this process, the oxygen concentration in the refining kettle was less than 1% by volume. Next, 1000 g of ion-exchanged water was charged into the refining kettle to precipitate crystals, and 1500 g of ion-exchanged water was further charged to 10 ° C. or lower and stirred for 2 hours.
  • Example 1 The same procedure as in Example 1 was performed, except that the air inside the kettle was removed under reduced pressure and nitrogen gas was not introduced. In this process, the oxygen concentration in the refining kettle was 20.8% by volume. As a result, 90 kg (yield 90%) of 2,6-DHN having a purity of 95% was obtained. Since the purity of 2,6-DHN was insufficient, the same operation as this comparative example was performed again with the aim of further increasing the purity. As a result, 80 kg (yield of 98% purity of 2,6-DHN was obtained. 89%). From 100 kg of crude product to 80 kg of purified product, the total yield was as low as 80%. This process is considered to be industrially disadvantageous.
  • Example 2 The same procedure as in Example 2 was performed except that the air inside the kettle was removed under reduced pressure and nitrogen gas was not introduced. In this process, the oxygen concentration in the refining kettle was 20.8% by volume. As a result, 450 g (yield 90%) of 2,6-DHN having a purity of 95% was obtained. Since the purity of 2,6-DHN was insufficient, the same operation as in this comparative example was performed again with the aim of further increasing the purity. As a result, 400 g of 98% pure 2,6-DHN (yield) 89%). From 500 g of crude product to 400 g of purified product, the total yield was as low as 80%. This process is considered to be industrially disadvantageous.
  • Example 1-1 Production of Ethyl Acetate Solution of Compound Represented by Formula (1) with Reduced Metal Content
  • a 1000 mL four-necked flask bottomed type
  • 2,6-dihydroxynaphthalene ( Hereinafter, 150 g of a solution (2.5% by mass) in which “2,6-DHN” is dissolved in ethyl acetate is charged, and then the air inside the flask is removed under reduced pressure to introduce nitrogen gas and stirring. While heating to 25 ° C., a solution was obtained. In this step, the oxygen concentration in the flask was less than 1% by volume.
  • Example 2-1 Except that the air inside the kettle was removed under reduced pressure and the introduction of nitrogen gas was omitted, the same treatment as in Example 1-1 was performed to obtain an ethyl acetate solution of 2,6-DHN. In this step, the oxygen concentration in the flask was 20.8% by volume.
  • Example 3-1 Into a 1000 mL four-necked flask (bottomed type) was charged 300 g of a solution (5.0% by mass) of a crude 4,4′-biphenol dissolved in ethyl acetate. Subsequently, the air inside the flask was removed under reduced pressure, nitrogen gas was introduced, and the mixture was heated to 40 ° C. with stirring to obtain a solution. In this step, the oxygen concentration in the flask was less than 1% by volume. Next, 75 g of an oxalic acid aqueous solution (pH 1.3) was added to the obtained solution, and the mixture was stirred for 5 minutes and then allowed to stand for 30 minutes.
  • an oxalic acid aqueous solution pH 1.3
  • Example 5-1 A 1000 mL four-necked flask (bottomed type) was charged with 300 g of a solution (5.0% by mass) of a resorcinol crude substance dissolved in ethyl acetate, and then the air inside the flask was removed under reduced pressure to remove nitrogen gas. And heated to 40 ° C. with stirring to obtain a solution. In this step, the oxygen concentration in the flask was less than 1% by volume. Next, 75 g of an oxalic acid aqueous solution (pH 1.3) was added to the obtained solution, and the mixture was stirred for 5 minutes and then allowed to stand for 30 minutes. Since it separated into the oil phase and the water phase by this, the water phase was removed.
  • a solution 5.0% by mass
  • a resorcinol crude substance dissolved in ethyl acetate
  • Example 7-1 A 1000 mL four-necked flask (bottomed) was charged with 300 g of a crude solution of 9,10-dihydroxyanthracene dissolved in ethyl acetate (2.5% by mass), and the air inside the flask was then evacuated. After removing, nitrogen gas was introduced and heated to 40 ° C. with stirring to obtain a solution. In this step, the oxygen concentration in the flask was less than 1% by volume. Next, 75 g of an oxalic acid aqueous solution (pH 1.3) was added to the obtained solution, and the mixture was stirred for 5 minutes and then allowed to stand for 30 minutes. Since it separated into the oil phase and the water phase by this, the water phase was removed.
  • an oxalic acid aqueous solution pH 1.3
  • Example 8-1 A 1000 mL four-necked flask (bottomed type) was charged with 300 g of a solution (2.0% by mass) of a crude 1-hydroxypyrene dissolved in ethyl acetate, and then the air inside the flask was removed under reduced pressure. Nitrogen gas was introduced and heated to 40 ° C. with stirring to obtain a solution. In this step, the oxygen concentration in the flask was less than 1% by volume. Next, 75 g of an oxalic acid aqueous solution (pH 1.3) was added to the obtained solution, and the mixture was stirred for 5 minutes and then allowed to stand for 30 minutes. Since it separated into the oil phase and the water phase by this, the water phase was removed.
  • a solution (2.0% by mass) of a crude 1-hydroxypyrene dissolved in ethyl acetate was removed under reduced pressure. Nitrogen gas was introduced and heated to 40 ° C. with stirring to obtain a solution. In this step, the oxygen concentration in the flask
  • Example 2-1 was the same as Example 1-1 except that the air inside the kettle was removed under reduced pressure and the introduction of nitrogen gas was omitted, and the effect of carrying out in a nitrogen gas atmosphere was shown. .
  • a hydroxy-substituted aromatic compound for example, a compound represented by the formula (1) can be produced industrially advantageously.
  • the hydroxy substituted aromatic compound with which metal content was reduced for example, the compound represented by Formula (1), can be manufactured industrially advantageously.

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Abstract

La présente invention concerne un premier procédé de production d'un composé aromatique substitué par un groupe hydroxy qui implique une étape (étape de contact) de mise en contact d'un composé aromatique substitué par un groupe hydroxy avec un solvant organique et/ou de l'eau sous une atmosphère dans laquelle la concentration en oxygène est inférieure à 20 % en vol. Un second procédé de production d'un composé aromatique substitué par un groupe hydroxy selon l'invention implique une étape de mise en contact, avec une solution aqueuse acide, d'une solution (α) incluant un composé aromatique substitué par un groupe hydroxy et un solvant organique qui ne se mélange pas librement avec l'eau, pour extraire les contenus métalliques dans le composé aromatique substitué par un groupe hydroxy.
PCT/JP2016/063204 2015-05-27 2016-04-27 Procédé de production d'un composé aromatique substitué par un groupe hydroxy Ceased WO2016190044A1 (fr)

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