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WO2017038968A1 - Procédé de purification de composés - Google Patents

Procédé de purification de composés Download PDF

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Publication number
WO2017038968A1
WO2017038968A1 PCT/JP2016/075774 JP2016075774W WO2017038968A1 WO 2017038968 A1 WO2017038968 A1 WO 2017038968A1 JP 2016075774 W JP2016075774 W JP 2016075774W WO 2017038968 A1 WO2017038968 A1 WO 2017038968A1
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WIPO (PCT)
Prior art keywords
group
integer
carbon atoms
purifying
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
PCT/JP2016/075774
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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
Original Assignee
Mitsubishi Gas Chemical Co Inc
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
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Priority to CN201680051083.4A priority Critical patent/CN108026011A/zh
Priority to JP2017538124A priority patent/JP7306790B2/ja
Publication of WO2017038968A1 publication Critical patent/WO2017038968A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
    • B01D63/02—Hollow fibre modules
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D63/00—Apparatus in general for separation processes using semi-permeable membranes
    • B01D63/14—Pleat-type membrane modules
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/26—Polyalkenes
    • B01D71/261—Polyethylene
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/30—Polyalkenyl halides
    • B01D71/32—Polyalkenyl halides containing fluorine atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/06—Organic material
    • B01D71/56—Polyamides, e.g. polyester-amides
    • 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
    • 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 purifying a compound (for example, a hydroxy-substituted aromatic compound).
  • 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, semiconductor underlayer film forming materials (for example, Patent Documents 1 to 4). 2). Moreover, a specific method is known as a purification method of hydroxy-substituted aromatic compounds such as dihydroxynaphthalene (see, for example, Patent Document 3).
  • the metal content is an important performance evaluation item for improving the yield.
  • a metal or a compound obtained using a hydroxy-substituted aromatic compound as a raw material contains a large amount of metal, the metal remains in the semiconductor and deteriorates the electrical characteristics of the semiconductor.
  • recrystallization was performed by adding ion-exchanged water or pure water to a mixture containing the compound or resin and an organic solvent.
  • the compound or resin is dissolved in an organic solvent which is not arbitrarily miscible with water, and the solution is brought into contact with an aqueous solution to perform extraction treatment, thereby transferring the metal component to the aqueous phase.
  • a method of reducing the metal content by separating the organic phase and the aqueous phase is conceivable.
  • the above method when a hydroxy-substituted aromatic compound having a high metal content is used as a raw material, there is a problem that the effect of removing specific metal species is not sufficient. Therefore, establishment of an industrially advantageous purification method for a high-purity hydroxy-substituted aromatic compound with a reduced metal content is desired.
  • An object of the present invention is to provide a method for industrially advantageously purifying hydroxy-substituted aromatic compounds.
  • the present invention is as follows.
  • a method for purifying a compound comprising a step of passing a solution containing a hydroxy-substituted aromatic compound represented by the following formula (A 0 ) and / or (B 0 ) and a solvent through a filter.
  • 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, where m 0 is 1.
  • each Ra independently represents a hydroxyl group, a halogen group, a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, An aryl group having 6 to 40 carbon atoms which may have a substituent, or a group selected from the group consisting of alkenyl groups having 2 to 40 carbon atoms and combinations thereof, the alkyl group, the aryl group or The alkenyl group may contain an ether bond, a ketone bond, or an ester bond, wherein n 1 is an integer of 0 to 9, and p 1 is an integer of 0 to 9 in the formula (B 0 ).
  • Rb are each independently a hydrogen atom, a hydroxyl group, a halogen group, From a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms which may have a substituent, or an alkenyl group having 2 to 40 carbon atoms and combinations thereof And the alkyl group, the aryl group or the alkenyl group may contain an ether bond, a ketone bond, or an ester bond.
  • n 0 is an integer from 0 to 9
  • m 0 is an integer from 0 to 2
  • p 0 is an integer from 0 to 9, where m 0 is 1.
  • the formula (A) indicates that it has a naphthalene skeleton or a biphenyl skeleton, and each R 0 independently has a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or a substituent.
  • the hydroxy-substituted aromatic compound is a compound represented by the following formula (A-1), a compound represented by the following formula (A-2), a compound represented by the following formula (A-3), The method for purifying a compound according to [1], which is at least one selected from the group consisting of a compound represented by A-4) and a compound represented by the following formula (B-1).
  • n 0 is an integer of 0 to 5
  • n 0 is an integer of 0 to 7
  • n 0 is an integer of 0 to 9
  • n 1 is an integer of 0 to 9.
  • [4] The method for purifying a compound according to [1], wherein the hydroxy-substituted aromatic compound is a compound represented by the following formula (1).
  • [5] The method for purifying a compound according to [1], wherein the hydroxy-substituted aromatic compound is at least one selected from the group consisting of 2,6-dihydroxynaphthalene and 2,7-dihydroxynaphthalene.
  • [6] The method for purifying a compound according to any one of [1] to [5], wherein the filter has a nominal pore size of less than 1.0 ⁇ m.
  • the filter is one or more selected from the group consisting of a hollow fiber membrane filter, a membrane filter, and a pleated membrane filter.
  • the filter medium of the filter is at least one selected from the group consisting of polyamide, polyolefin resin, and fluororesin.
  • a hydroxy-substituted aromatic compound can be purified industrially advantageously.
  • the method for purifying a compound according to this embodiment includes a step of passing a solution containing a hydroxy-substituted aromatic compound represented by the following formula (A 0 ) and / or (B 0 ) and a solvent through a filter. Since it is configured as described above, the hydroxy-substituted aromatic compound can be industrially advantageously purified by the compound purification method according to this embodiment. In particular, as shown in the examples described later, the content of chromium (Cr) contained in the dihydroxynaphthalene solution can be reduced to 50 ppb or less with respect to the mass of the dihydroxynaphthalene.
  • purification in the present embodiment means an operation for sufficiently reducing the metal component that can coexist with the hydroxy-substituted aromatic compound.
  • the amount of Na is 50 ppb or less and the amount of Fe is 60 ppb.
  • a hydroxy-substituted aromatic compound having a Cr amount of 70 ppb or less and a Sn amount of 50 ppb or less is obtained.
  • the amount of Na that can coexist with the hydroxy-substituted aromatic compound after purification is 50 ppb or less
  • the amount of Fe is 50 ppb or less
  • the amount of Cr is 50 ppb or less
  • the amount of Sn is 50 ppb or less.
  • liquid passage means that the solution passes from the outside of the filter to the inside of the filter and moves again to the outside of the filter. For example, the solution is simply passed through the surface of the filter. And a mode in which the solution is moved outside the ion exchange resin while being in contact with the surface (that is, a mode of simply contacting) are excluded.
  • 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, where m 0 is 1.
  • each Ra independently represents a hydroxyl group, a halogen group, a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, An aryl group having 6 to 40 carbon atoms which may have a substituent, or a group selected from the group consisting of alkenyl groups having 2 to 40 carbon atoms and combinations thereof, the alkyl group, the aryl group or The alkenyl group may contain an ether bond, a ketone bond, or an ester bond, wherein n 1 is an integer of 0 to 9, and p 1 is an integer of 0 to 9 in the formula (B 0 ).
  • Rb are each independently a hydrogen atom, a hydroxyl group, a halogen group, From a linear, branched or cyclic alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms which may have a substituent, or an alkenyl group having 2 to 40 carbon atoms and combinations thereof And the alkyl group, the aryl group or the alkenyl group may contain an ether bond, a ketone bond, or an ester bond.
  • the hydroxy-substituted aromatic compound is more preferably a compound represented by the following formula (A) and / or (B) from the viewpoint of raw material supply.
  • n 0 is an integer from 0 to 9
  • m 0 is an integer from 0 to 2
  • p 0 is an integer from 0 to 9, where m 0 is 1.
  • the formula (A) indicates that it has a naphthalene skeleton or a biphenyl skeleton, and each R 0 independently has a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or a substituent.
  • each R 1 is independently a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 15 carbon atoms which may have a substituent, or a carbon number 2 to 15 alkenyl groups.
  • the hydroxy-substituted aromatic compound is a compound represented by the following formula (A-1), represented by the following formula (A-2). 1 selected from the group consisting of a compound represented by the following formula (A-3), a compound represented by the following formula (A-4), and a compound represented by the following formula (B-1) More preferably, it is a seed or more.
  • n 0 is an integer of 0 to 5
  • n 0 is an integer of 0 to 7
  • n 0 is an integer of 0 to 9
  • n 1 is an integer of 0 to 9.
  • the hydroxy-substituted aromatic compound is particularly preferably a compound represented by the following formula (1) from the viewpoints of solubility in an organic solvent and purification pot efficiency.
  • 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 formula (1) is not particularly limited, but 2,6-dihydroxynaphthalene and a compound obtained from the compound represented by the formula (1) or a resin obtained from the viewpoint of heat resistance.
  • One or more selected from the group consisting of 2,7-dihydroxynaphthalene is more preferable.
  • the compound represented by the above formula (1) is not particularly limited, but 2,6-dihydroxynaphthalene is further selected from the viewpoint of further heat resistance of the compound or resin obtained using the compound represented by the formula (1) as a raw material. preferable.
  • the hydroxy-substituted aromatic compound used in this embodiment 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 present embodiment may be a single compound or a mixture 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 solvent used in this embodiment is not particularly limited, but an organic solvent that can be safely applied to a semiconductor manufacturing process is preferable.
  • the amount of the solvent to be used is preferably 1 to 100 times by mass with respect to the compound represented by the formula (1) to be used, from the viewpoint of improving the solubility and easy recovery of the solid after purification.
  • the amount is more preferably 5 to 50 times by mass, still more preferably 10 to 50 times by mass.
  • solvent used in the present embodiment include, but are not limited to, ethyl ether, isopropyl ether, n-butyl ether, hexyl ether, 2-ethylhexyl ether, ethylene oxide, 1,2-propylene oxide, dioxolane, 4 -Methyldioxolane, dioxane, dimethyldioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol diethyl ether, ethylene glycol monobutyl ether, ethylene glycol mono-n-hexyl ether, ethylene glycol monophenyl ether, ethylene glycol mono-2- Ethyl butyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol Noethyl ether, diethylene glycol diethyl ether, diethylene glycol monobutyl ether, diethylene glycol dibutyl
  • the above solvents can be used alone or in combination of two or more.
  • a filter that is usually used for liquid filtration can be used as the filter used for removing the metal content in the solution containing the hydroxy-substituted aromatic compound and the solvent.
  • the filtration accuracy of the filter is not particularly limited, but the nominal pore size of the filter is preferably less than 1.0 ⁇ m, more preferably 0.2 ⁇ m or less, and even more preferably 0.05 ⁇ m or less.
  • the lower limit value of the nominal pore diameter of the filter is not particularly limited, but is usually 0.005 ⁇ m.
  • the nominal pore diameter here is a nominal pore diameter indicating the separation performance of the filter, and is determined by a test method determined by the filter manufacturer, such as a bubble point test, a mercury intrusion test, a standard particle supplement test, etc.
  • the hole diameter When a commercial product is used, the value is described in the catalog data of the manufacturer.
  • the chromium (Cr) content tends to be preferably 50 ppb or less, more preferably 20 ppb or less, and even more preferably 5 ppb or less with respect to the mass of the hydroxy-substituted aromatic compound.
  • the liquid in order to further reduce the content of each metal component in the solution of the hydroxy-substituted aromatic compound, the liquid may be passed twice or more.
  • the form of the filter is not limited to the following.
  • a hollow fiber membrane filter, a membrane filter, a pleated membrane filter, and a filter filled with a filter medium such as nonwoven fabric, cellulose, and diatomaceous earth can be used.
  • the filter is preferably at least one selected from the group consisting of a hollow fiber membrane filter, a membrane filter, and a pleated membrane filter, particularly because of the high-definition filtration accuracy and the height of the filtration area compared with other forms. It is more preferable to use a thread membrane filter.
  • the material of the filter is not limited to the following, but, for example, a polyolefin resin such as polyethylene or polypropylene, a polyamide resin, a polar group-containing resin such as polyester or polyacrylonitrile, or a fluorine-containing resin such as fluorinated polyethylene (PTFE) Can be mentioned.
  • the filter medium is preferably at least one selected from the group consisting of polyamide resin, polyolefin resin, and fluororesin, more preferably. Made of polyamide resin.
  • polyamide-based filter examples include, but are not limited to, for example, Polyfix nylon series manufactured by KITZ Microfilter Co., Ltd., ULTIM PLEAT P-Nylon 66 manufactured by Nihon Pall Co., Ltd. Examples include Life Assure PSN series and Life Assure EF series manufactured by KK.
  • polyolefin filter examples include, but are not limited to, Ultiplez PE Clean manufactured by Nippon Pole Co., Ltd., Microguard Plus HC10 manufactured by Nihon Integris Co., Ltd., and Optimizer D.
  • fluororesin filter examples include, but are not limited to, Enflon HTPFR manufactured by Nippon Pole Co., Ltd., Lifesure FA series manufactured by 3M Co., Ltd., and the like. These filters may be used alone or in combination of two or more.
  • the filter may contain an ion exchanger such as a cation exchange resin, a cation charge control agent that generates a zeta potential in the organic solvent solution to be filtered, and the like.
  • an ion exchanger such as a cation exchange resin, a cation charge control agent that generates a zeta potential in the organic solvent solution to be filtered, and the like.
  • a filter containing a substance having a positive zeta potential such as a polyamide polyamine epichlorohydrin cation resin (hereinafter referred to as a trademark), but not limited to the following, for example, Zeta Plus 40QSH or Zeta Plus 020GN manufactured by 3M Corporation Or Life Assure EF series etc. are mentioned.
  • polyamide resin is preferable as a filter material for effectively reducing heavy metals such as chromium (Cr) and tin (Sn) is that it has excellent metal adsorption performance.
  • the metal adsorption performance of the filter material the contact angle between a sheet of the same material as the filter (hereinafter referred to as “base material”) and a solution in which the hydroxy-substituted compound is dissolved is measured, and the reduction behavior of the metal is measured. This can be confirmed by comparison. Specifically, the smaller the contact angle with the substrate, the higher the wettability between the solution and the filter surface, and even if the filtration accuracy of the filter is the same as compared with a substrate with a large contact angle, the metal Further reduction is possible.
  • the contact angle between the substrate containing the hydroxy-substituted aromatic compound and the solvent and the substrate is preferably in the range of 1 ° to 40 °, more preferably 1 ° to 30 °, and even more preferably 1 °. ⁇ 20 °.
  • the contact angle is in the range of 1 ° to 40 °, the wettability to the substrate is sufficient, and good adsorption performance tends to be obtained.
  • packing members such as filter connection joints and O-rings included in the housing is made of perfluoro rubber or perfluoro elastomer, and all of these constituent members are made of fluorine-containing resin, perfluoro rubber, perfluoro. It is preferably made of a material selected from elastomers. Furthermore, the packing member is particularly preferably made of a material selected from perfluoro rubber and perfluoro elastomer. Only with other members, the content of the metal compound in the hydroxy-substituted aromatic compound may not be reduced to the ppb level.
  • the temperature for preparing and passing the solution of the hydroxy-substituted aromatic compound is too high, hydrolysis tends to occur depending on the type of solvent, and volatile acids may be liberated. When too large, the solubility of the hydroxy-substituted aromatic compound tends to be small. Thus, from the viewpoint of preventing the release of volatile acids and from the viewpoint of efficiency, it is preferable to adjust the temperature, usually 0 to 40 ° C., preferably 5 to 30 ° C., More preferably, it is 10 to 25 ° C.
  • the water mixed in the solution containing the hydroxy-substituted aromatic compound and the solvent thus obtained can be easily removed by performing an operation such as vacuum distillation. Moreover, a solvent can be added as necessary to adjust the concentration of the hydroxy-substituted aromatic compound to an arbitrary concentration.
  • the method for obtaining only the hydroxy-substituted aromatic compound from the solution containing the hydroxy-substituted aromatic compound and the solvent is not particularly limited, and may be performed by a known method such as removal under reduced pressure, separation by reprecipitation, or a combination thereof. Can do. If necessary, known processes such as a concentration operation, a filtration operation, a centrifugal separation operation, and a drying operation can be performed.
  • Preparation of a solution containing a hydroxy-substituted aromatic compound and a solvent in this embodiment and liquid flow are preferably performed in an atmosphere having an oxygen concentration of less than 20%.
  • the oxygen concentration is more preferably less than 10%, further preferably less than 5%, and particularly preferably less than 1%.
  • the method for reducing the oxygen concentration can be carried out by a known method, and is not particularly limited.
  • the gas replacement is performed by flowing nitrogen into a column or kettle for purification or by introducing nitrogen after reducing the pressure. It can be carried out. It is convenient, reliable and preferable that the column or kettle for purification is decompressed and then nitrogen is introduced.
  • Confirmation of the oxygen concentration can be carried out 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 into a refining kettle. Can do.
  • An oxygen concentration meter can also be installed in the kettle for purification.
  • Example 1 In a Class 1000 clean booth, 2,6-dihydroxynaphthalene (hereinafter, also referred to as 2,6-DHN) with an organic purity of 99.3% was propylene in a 1000 mL four-necked flask (bottomed type). 500 g of a solution (concentration of 2.5% by mass) dissolved in glycol monomethyl ether (PGME) was added, and after the air inside the kettle was removed under reduced pressure, nitrogen gas was introduced and returned to atmospheric pressure. The inside oxygen concentration was adjusted to less than 1% under aeration at 100 mL / min, and then heated to 30 ° C. with stirring.
  • 2,6-DHN 2,6-dihydroxynaphthalene
  • PGME glycol monomethyl ether
  • the 2,6-DHN solution is withdrawn from the bottom valve, and the diaphragm pump is passed through a fluororesin pressure tube.
  • the solution was passed through a polyamide hollow fiber membrane filter (trade name: Polyfix nylon series, manufactured by KITZ Micro Filter Co., Ltd.) having a nominal pore size of 0.01 ⁇ m at a flow rate of 100 mL per minute.
  • the obtained 2,6-DHN solution was analyzed under the following conditions. The oxygen concentration was measured with an oxygen concentration meter “OM-25MF10” manufactured by AS ONE Co., Ltd. (the same applies hereinafter).
  • Example 2 Except for using a polyethylene hollow fiber membrane filter having a nominal pore size of 0.01 ⁇ m (product name: Polyfix, manufactured by KITZ Micro Filter Co., Ltd.), the obtained 2,6 was passed through in the same manner as in Example 1. -The DHN solution was analyzed under the following conditions.
  • Example 3 Except for using a polyamide hollow fiber membrane filter having a nominal pore size of 0.05 ⁇ m (trade name: Polyfix, manufactured by KITZ Micro Filter Co., Ltd.), obtained in the same manner as in Example 1, and obtained 2,6 -The DHN solution was analyzed under the following conditions.
  • Example 4 Except for using a polyethylene membrane filter having a nominal pore size of 0.05 ⁇ m (trade name: Ultipleat PE Clean, manufactured by Nippon Pole Co., Ltd.), the obtained 2,6- The DHN solution was analyzed under the following conditions.
  • Example 5 The resulting 2,6-DHN solution was passed through in the same manner as in Example 1 except that a PTFE membrane filter (trade name: Omnipore) manufactured by PTFE having a nominal pore size of 0.05 ⁇ m was used. Analysis was performed under conditions.
  • a PTFE membrane filter trade name: Omnipore
  • Example 6 Except for using a Zeta Plus filter 40QSH (manufactured by 3M Co., Ltd., with ion exchange capability) having a nominal pore size of 0.2 ⁇ m, the liquid was passed in the same manner as in Example 1 and the resulting 2,6-DHN solution was Analysis was performed under conditions.
  • a Zeta Plus filter 40QSH manufactured by 3M Co., Ltd., with ion exchange capability
  • Example 7 The obtained 2,6-DHN solution was passed through in the same manner as in Example 1 except that a zeta plus filter 020GN (manufactured by 3M Co., Ltd., with ion exchange capability) having a nominal pore size of 0.2 ⁇ m was used. Analysis was performed under conditions.
  • Example 8 No nitrogen gas replacement
  • 2,6-DHN having an organic purity of 99.3% was dissolved in PGME in a 1000 mL four-necked flask (bottomed type). 500 g of a solution (concentration: 2.5% by mass) was charged and heated to 30 ° C. with stirring. A 2,6-DHN solution is extracted from the bottom valve, and a hollow fiber membrane filter made of polyamide having a nominal pore diameter of 0.01 ⁇ m at a flow rate of 100 mL / min with a diaphragm pump via a pressure-resistant tube made of fluororesin (KITZ microfilter ( (Trade name: Polyfix nylon series). The obtained 2,6-DHN solution was analyzed under the following conditions.
  • Example 9 In a Class 1000 clean booth, a solution of 2,6-DHN with an organic purity of 99.3% in PGME (concentration 2.5% by mass) in a 1000 mL four-necked flask (bottomed) was added, and the air inside the kettle was removed under reduced pressure. Then, nitrogen gas was introduced to return to atmospheric pressure, and the nitrogen gas was aerated at 100 mL / min, and the internal oxygen concentration was adjusted to less than 1%, followed by stirring. While heating to 30 ° C.
  • PGME concentration 2.5% by mass
  • a 2,6-DHN solution is extracted from the bottom valve, and a polyethylene membrane filter having a nominal pore size of 1.0 ⁇ m at a flow rate of 100 mL / min with a diaphragm pump via a pressure-resistant tube made of fluororesin (manufactured by Nippon Pole Co., Ltd.) , Trade name: ULBLE BREATH PE CLEAN).
  • the obtained 2,6-DHN solution was analyzed under the following conditions.
  • Example 10 In a Class 1000 clean booth, a solution of 2,6-DHN with an organic purity of 99.3% in PGME (concentration 2.5% by mass) in a 1000 mL four-necked flask (bottomed) After the pressure inside the kettle was removed under reduced pressure, nitrogen gas was introduced and returned to atmospheric pressure, and the nitrogen gas was vented at 100 mL / min and the oxygen concentration inside was adjusted to 5.0%. The mixture was heated to 30 ° C. with stirring. After removing the vacuum from the bottom of the bottom valve to the end of the filter flow line with a vacuum pump, the 2,6-DHN solution is withdrawn from the bottom valve, and the diaphragm pump is passed through a fluororesin pressure tube.
  • PGME concentration 2.5% by mass
  • the solution was passed through a polyamide hollow fiber membrane filter (trade name: Polyfix nylon series, manufactured by KITZ Micro Filter Co., Ltd.) having a nominal pore size of 0.01 ⁇ m at a flow rate of 100 mL per minute.
  • the obtained 2,6-DHN solution was analyzed under the following conditions.
  • Example 11 In a Class 1000 clean booth, a solution of 2,6-DHN with an organic purity of 99.3% in PGME (concentration 2.5% by mass) in a 1000 mL four-necked flask (bottomed) After the air inside the kettle was removed under reduced pressure, nitrogen gas was introduced and the pressure was returned to atmospheric pressure. After nitrogen gas was vented at 100 mL / min and the internal oxygen concentration was adjusted to 10.0% The mixture was heated to 30 ° C. with stirring. After removing the vacuum from the bottom of the bottom valve to the end of the filter flow line with a vacuum pump, the 2,6-DHN solution is withdrawn from the bottom valve, and the diaphragm pump is passed through a fluororesin pressure tube.
  • PGME concentration 2.5% by mass
  • the solution was passed through a polyamide hollow fiber membrane filter (trade name: Polyfix nylon series, manufactured by KITZ Micro Filter Co., Ltd.) having a nominal pore size of 0.01 ⁇ m at a flow rate of 100 mL per minute.
  • the obtained 2,6-DHN solution was analyzed under the following conditions.
  • Example 12 The resulting purified solution was analyzed under the following conditions except that instead of 2,6-DHN, 4,4-biphenol having a purity of 99.2% was used, and the solution was passed in the same manner as in Example 1.
  • Example 13 The solution was passed in the same manner as in Example 1 except that resorcinol (1,3-benzenediol) having a purity of 99.1% was used instead of 2,6-DHN, and the resulting solution was analyzed under the following conditions. .
  • Example 14 instead of 2,6-DHN, 9,10-dihydroxyanthracene having a purity of 98.7% was used, and the solution was passed in the same manner as in Example 1, and the resulting solution was analyzed under the following conditions.
  • Example 15 The solution was passed in the same manner as in Example 1 except that 1-hydroxypyrene having a purity of 98.8% was used instead of 2,6-DHN, and the resulting solution was analyzed under the following conditions.
  • a 100 ⁇ m-thick sheet test piece (2 cm ⁇ 5 cm) made of the same material as the filter is prepared, and the contact angle between the sheet test piece and a PGME solution (concentration: 2.5 mass%) of various hydroxy-substituted compounds before purification. Measurements were made. The measurement results are shown in Table 2. In any of the examples, the time immediately before the prepared solution was passed through the filter was defined as “before purification”, and the solution at that time was subjected to the above measurement. Each measurement was performed with the following apparatus and measurement conditions.
  • a hydroxy-substituted aromatic compound can be industrially advantageously purified, and a hydroxy-substituted aromatic compound having a reduced metal content and a reduced metal content can be obtained.

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

Abstract

Un procédé de purification de composés selon la présente invention comprend : une étape qui consiste à amener une solution qui contient un solvant et un composé aromatique substitué par un groupe hydroxy représenté par la formule (A0) et/ou la formule (B0) à passer à travers un filtre. (Dans la formule (A0) : n0 représente un nombre entier de 0 à 9 ; m0 représente un nombre entier de 0 à 2 ; p0 représente un nombre entier de 0 à 9. Lorsque m0 représente 1, la formule (A0) indique que composé comprend un squelette naphtalène ou un squelette biphényle en son sein ; et chaque Ra représente indépendamment un groupe choisi dans le groupe constitué par un groupe hydroxyle, des groupes halogène, des groupes alkyle linéaires, ramifiés, ou cycliques ayant de 1 à 40 atomes de carbone, des groupes aryle ayant de 6 à 40 atomes de carbone et comprenant éventuellement un groupe substituant, ou des groupes alcényle ayant de 2 à 40 atomes de carbone, et des combinaisons de ceux-ci, ledit groupe alkyle, ledit groupe aryle, ou ledit groupe alcényle pouvant contenir une liaison éther, une liaison cétone, ou une liaison ester. Dans la formule (B0) : n1 représente un nombre entier de 0 à 9 ; p1 représente un nombre entier de 0 à 9 ; et chaque Rb représente indépendamment un groupe choisi dans le groupe constitué par un atome d'hydrogène, un groupe hydroxyle, des groupes halogène, des groupes alkyle linéaires, ramifiés ou cycliques ayant de 1 à 40 atomes de carbone, des groupes aryle ayant de 6 à 40 atomes de carbone et comprenant éventuellement un groupe substituant, ou des groupes alcényle ayant de 2 à 40 atomes de carbone, et des combinaisons de ceux-ci, ledit groupe alkyle, ledit groupe aryle, ou ledit groupe alcényle pouvant contenir une liaison éther, une liaison cétone, ou une liaison ester).
PCT/JP2016/075774 2015-09-04 2016-09-02 Procédé de purification de composés Ceased WO2017038968A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3505507A1 (fr) * 2017-12-26 2019-07-03 Shin-Etsu Chemical Co., Ltd. Procédé de purification de dihydroxynaphthalène

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116589343B (zh) * 2023-03-31 2025-05-06 北京袭明科技有限公司 一种电子化学品邻苯二酚的生产方法
CN116283508B (zh) * 2023-03-31 2025-05-06 北京袭明科技有限公司 一种电子化学品间苯二酚的生产方法
CN116283509B (zh) * 2023-03-31 2025-05-06 北京袭明科技有限公司 一种电子化学品对苯二酚的生产方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09208518A (ja) * 1996-02-05 1997-08-12 Mitsubishi Gas Chem Co Inc 高純度ナフタレンジカルボン酸の製造法
JPH11512713A (ja) * 1995-09-28 1999-11-02 クラリアント・インターナショナル・リミテッド 金属イオンを低濃度で含む４，４’−［１−［４−［１−（４−ヒドロキシフェニル）−１−メチルエチル］フェニル］エチリデン］ビスフェノール及びそれから得られるフォトレジスト組成物
JP2005023022A (ja) * 2003-07-03 2005-01-27 Honshu Chem Ind Co Ltd 高純度１，１−ビス（４−ヒドロキシフェニル）シクロヘキサン類の製造方法
JP2012190000A (ja) * 2011-02-25 2012-10-04 Shin Etsu Chem Co Ltd ポジ型レジスト材料及びこれを用いたパターン形成方法
JP2014006403A (ja) * 2012-06-25 2014-01-16 Shin Etsu Chem Co Ltd ポジ型レジスト材料及びパターン形成方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5643228A (en) * 1979-09-19 1981-04-21 Mitsui Toatsu Chem Inc Prevention of color development of aromatic compound having hydroxyl group
IL94554A (en) * 1990-05-29 1994-04-12 Bromine Compounds Ltd Process for the preparation of 4, (4) -dexyhydrophenyl clean by fractional refining of 4, 4 (- dibromobiphenyl after catalytic hydrolysis
JP3733192B2 (ja) * 1997-01-30 2006-01-11 本州化学工業株式会社 粗２，６‐ジアルキルフェノールの製造方法
JP2001114717A (ja) 1999-10-19 2001-04-24 Sumitomo Chem Co Ltd 金属含量の低減されたフェノール化合物の製造方法
JP2006018016A (ja) 2004-07-01 2006-01-19 Tokyo Ohka Kogyo Co Ltd ポジ型レジスト組成物およびレジストパターン形成方法
DE102005017126A1 (de) 2005-04-14 2006-10-19 Cognis Ip Management Gmbh Verfahren zur Herstellung von Cardanol (I)
FR2925489B1 (fr) 2007-12-19 2010-02-05 Rhodia Operations Procede de preparation de pyrocatechol purifie
EP2320467B1 (fr) * 2008-08-28 2014-08-13 Sumitomo Chemical Company, Limited Composition de résine, couche d'isolation de grille et transistor à couches minces organiques
JP5251433B2 (ja) 2008-10-31 2013-07-31 Ｊｓｒ株式会社 レジスト下層膜形成用組成物及びパターン形成方法
JP2011042583A (ja) * 2009-08-19 2011-03-03 Kawasaki Kasei Chem Ltd ナフトヒドロキノン化合物の水溶液の製造方法およびラジカル捕捉剤水溶液
JP5905207B2 (ja) 2011-04-21 2016-04-20 丸善石油化学株式会社 金属不純物量の少ない半導体リソグラフィー用共重合体の製造方法及び該共重合体を製造するための重合開始剤の精製方法
JP2014157169A (ja) 2011-06-24 2014-08-28 Nissan Chem Ind Ltd ポリヒドロキシベンゼンノボラック樹脂を含むレジスト下層膜形成組成物
US9244353B2 (en) 2012-08-10 2016-01-26 Nissan Chemical Industries, Ltd. Resist underlayer film forming composition
JP5835194B2 (ja) 2012-11-26 2015-12-24 信越化学工業株式会社 レジスト下層膜材料及びパターン形成方法
CN103145531B (zh) * 2013-03-04 2014-08-20 丹东深兰化工有限公司 1,5-二羟基萘提纯精制方法
WO2014199662A1 (fr) 2013-06-14 2014-12-18 Dic株式会社 Composé contenant un groupe hydroxyle phénolique, résine phénolique, composition durcissable, produit durci constitué de cette composition, matière de scellement semi-conductrice, et carte de circuit imprimé

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11512713A (ja) * 1995-09-28 1999-11-02 クラリアント・インターナショナル・リミテッド 金属イオンを低濃度で含む４，４’−［１−［４−［１−（４−ヒドロキシフェニル）−１−メチルエチル］フェニル］エチリデン］ビスフェノール及びそれから得られるフォトレジスト組成物
JPH09208518A (ja) * 1996-02-05 1997-08-12 Mitsubishi Gas Chem Co Inc 高純度ナフタレンジカルボン酸の製造法
JP2005023022A (ja) * 2003-07-03 2005-01-27 Honshu Chem Ind Co Ltd 高純度１，１−ビス（４−ヒドロキシフェニル）シクロヘキサン類の製造方法
JP2012190000A (ja) * 2011-02-25 2012-10-04 Shin Etsu Chem Co Ltd ポジ型レジスト材料及びこれを用いたパターン形成方法
JP2014006403A (ja) * 2012-06-25 2014-01-16 Shin Etsu Chem Co Ltd ポジ型レジスト材料及びパターン形成方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3505507A1 (fr) * 2017-12-26 2019-07-03 Shin-Etsu Chemical Co., Ltd. Procédé de purification de dihydroxynaphthalène

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