WO2004080987A1 - Procede pour produire un compose d'oxetan en utilisant un polyalkyl-ether - Google Patents

Procede pour produire un compose d'oxetan en utilisant un polyalkyl-ether Download PDF

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Publication number
WO2004080987A1
WO2004080987A1 PCT/JP2003/002904 JP0302904W WO2004080987A1 WO 2004080987 A1 WO2004080987 A1 WO 2004080987A1 JP 0302904 W JP0302904 W JP 0302904W WO 2004080987 A1 WO2004080987 A1 WO 2004080987A1
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Prior art keywords
group
formula
ether
oxetane compound
reaction
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PCT/JP2003/002904
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English (en)
Japanese (ja)
Inventor
Nobuaki Koike
Naokazu Ito
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Toagosei Co., Ltd.
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.)
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Application filed by Toagosei Co., Ltd. filed Critical Toagosei Co., Ltd.
Priority to CN03826135.9A priority Critical patent/CN1759107A/zh
Priority to AU2003220824A priority patent/AU2003220824A1/en
Priority to JP2003067267A priority patent/JP2003335764A/ja
Priority to PCT/JP2003/002904 priority patent/WO2004080987A1/fr
Publication of WO2004080987A1 publication Critical patent/WO2004080987A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms

Definitions

  • the present invention relates to a method for synthesizing an oxetane compound by dehydrohalogenating and cyclizing 3-halo 1-propanols, wherein a photocurable or thermosetting resin derived from the obtained oxetane compound has curability, It has excellent flame retardancy and mechanical properties, and is used for paints, coatings, adhesives and lenses.
  • a method for obtaining a ether compound from an alcohol and a halogen compound a method using a polyalkylene glycol or a polyalkylene glycol ether as a phase transfer catalyst is known (for example, see JP-A-57-5866). No. 37). However, there is no mention of cyclization.
  • a method for dechlorination and hydrogenation of 3-chloro-1-propanols a method using a quaternary ammonium salt compound as a phase transfer catalyst in an aqueous solution or suspension of an alkali is also known ( For example, Japanese Patent Application Laid-Open
  • the present invention provides a dehalogenation / hydrocyclization reaction of 3-halo-1-propanol represented by the following formula (1) in a high yield, and a 3-chloro mouth which is one of the compounds represented by the formula (1).
  • — 1 It is possible to carry out the dehydrochlorination cyclization of monopropanols (formula (2) below) in good yield, and it is also possible to carry out the reaction without using a two-layer system with water and an organic solvent.
  • An object of the present invention is to provide a method for producing an oxetane compound that is advantageous for production.
  • R 1 and R 2 in the formula (1) each represent a hydrogen atom which may be different from each other, an aliphatic hydrocarbon group which may have a substituent and has 1 to 8 carbon atoms and may have a branch, or R 1 and
  • R 2 represents one and represents a divalent aliphatic hydrocarbon group having 2 to 8 carbon atoms which may have a branch, and X represents a chlorine atom, a bromine atom or an iodine atom.
  • R 1 and R 2 in the formula (2) each represent a hydrogen atom which may be different from each other, an aliphatic hydrocarbon group which may have a substituent and has 1 to 8 carbon atoms and may have a branch, or R 1 and R 2 are combined to form a divalent aliphatic hydrocarbon group which may have 2 to 8 carbon atoms.
  • the present inventors have conducted various studies to solve the above-mentioned problems, and as a result, have found that in the presence of an alkali and a polyalkyl ether, a 3-halo-l-propanol (the above-mentioned dehalogenated hydrogen ring of the formula (1)) It has been found that the chemical reaction can be carried out with good yield, and the present invention has been completed.
  • the present invention provides a method for dehydrohalogenating a 3-halo-1-propanol represented by the above formula (1), which comprises reacting polyalkyl ethers in an aqueous solution or an organic solvent in the presence of an alkali. And a method for producing an oxetane compound. ⁇ Best mode for carrying out the invention>
  • the halogen (X) of the 3-halo 1-propanol represented by the above formula (1) is a chlorine atom, a bromine atom or an iodine atom, and is preferably a chlorine atom.
  • 3-halo 1-propanols is 3-chloro-1-propanols represented by the above formula (2), which is disclosed in Japanese Patent Application Laid-Open No. H10-139700. It can be easily synthesized by the chlorination method for 1,3-propanediols described. For example, in the presence of a small amount of an aliphatic carboxylic acid having 2 to 5 carbon atoms, trimethylolpropane is reacted with hydrogen chloride gas to produce 1-mono (chloromethyl) 1-1,1-hydroxymethylpropane. can do.
  • the aliphatic hydrocarbon group which may have a substituent represented by R 1 and R 2 and may have a branched chain having 1 to 8 carbon atoms includes a methyl group, And alkyl groups such as ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, amyl group, isoamyl group, hexyl group and octyl group.
  • the aliphatic hydrocarbon group has 3 or more carbon atoms, it may have a branch.
  • Examples of the divalent aliphatic hydrocarbon group having 2 to 8 carbon atoms in which R 1 and R 2 in Formula (1) and Formula (2) are united include, for example, trimethylene group, tetramethylene group, Examples include a xamethylene group.
  • the substituent which may be possessed by the aliphatic hydrocarbon group of R 1 and R 2 in the formulas (1) and (2) may be any substituent which does not adversely affect the dehydrochlorination cyclization reaction.
  • a cycloalkyl group having 3 to 8 carbon atoms such as a cyclohexyl group; more preferably a halogen atom such as a hydroxyl group, a chlorine atom, a bromine atom or an iodine atom; a carbon atom such as a methoxy group or an ethoxy group; Examples thereof include an alkoxy group which may have up to 8 branches, and
  • Charcoal such as ethoxy and ethoxy groups
  • Examples thereof include an alkoxy group having a prime number of 1 to 8, which may be branched, and a cycloalkyl group having 3 to 8 carbon atoms such as a cyclopentyl group and a cyclohexyl group.
  • 3-chloro-1-propanols represented by the formula (2) include, for example, 3-chloro-1-propanol, 3-chloro-2-methyl-1-propanol, 3-chloro-2,2-dimethyl- 1-propanol, 3-chloro-1- 2—methyl 2-cyclomethyl-1 monopropanol, 3-chloro-2-ethyl 2-hydroxymethyl-1 propanol, 3-chloro-1,2,2-bis (Hydroxymethyl) 1-propanol, 3-chloro-1,2-chloromethyl-12-ethyl-1 propanol, 3-chloro-1,2,2-bis (chloromethyl) -1-propanol, cycloto Examples thereof include xan-l-chloromethyl-1-methanol and 1-chloromethyl-2-methyl-cyclohexane-l-methylethanol.
  • carboxylic acid esters of 3-chloro-1-propanols for example, esters with acetic acid, propionic acid, butyric acid, and benzoic acid can also be used. Among them, availability and industrial handling are also available. Esters of acetic acid and propionic acid are preferred for their ease.
  • the alkali used in the dehydrohalogenation cyclization of the formula (1) or the formula (2) includes an alkali metal hydroxide, an alkaline earth metal hydroxide, and an alkali metal carbonate.
  • Alkaline earth metal carbonates, alkali metal bicarbonates, alkaline earth metal bicarbonates, alkali metal hydrides, alkaline earth metal hydrides, etc., and a plurality of these may be mixed.
  • These alkalis can be used in an aqueous solution, aqueous suspension, a mixed solvent of water and an organic solvent or an organic solvent.
  • the alkali used in the present invention include sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, sodium carbonate and sodium hydrogen carbonate.
  • sodium hydroxide and potassium hydroxide are preferred because a sufficient conversion can be obtained in a short time.
  • the amount of the above-mentioned alcohol is preferably 1 mol or more, more preferably 1 mol or more and 5 mol or less with respect to 1 mol of the raw material. More preferably, it is more than 1 mol and not more than 2 mol.
  • a carboxylic acid ester of 3-chloro-1-propanol When a carboxylic acid ester of 3-chloro-1-propanol is used as a raw material, it is preferably at least 2 mol, more preferably 2 mol, per mol of the raw material. And more preferably 6 mol or less, particularly preferably more than 2 mol and 3 mol or less.
  • the concentration of the alkali in an aqueous solution or suspension of the alkali is preferably 1 to 96% by mass, more preferably 20 to 96% by mass.
  • polyalkyl ethers such as polyalkylene glycols and polyalkylene glycol ethers used in the present invention are those represented by the following formulas (3), (4) and (5). is there.
  • R 3 and R 4 each represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group which may be different from each other, and m represents an integer of 1 or more.
  • R 3 and R 4 each represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group which may be different, and m represents an integer of 1 or more.
  • R 3 and R 4 each represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group which may be different, and m and n each represent an integer of 1 or more which may be the same or different. Represent.
  • the alkyl group represented by R 3 and R 4 has 1 to 20 carbon atoms, for example, a methyl group , Ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, amyl, isoamyl, hexyl, octyl, nonyl, decyl, lau
  • the alkenyl group include a ruyl group, a cetyl group, and a stearyl group.
  • the alkenyl group has 2 to 20 carbon atoms, and examples thereof include an oleyl group.
  • the aryl group includes, for example, a phenyl group, an octylphenyl group, a noerphenyl group, a naphthyl group and the like, and the aralkyl group includes, for example, a benzyl group, a 2-phenylethyl group, a 3-phenylpropyl group.
  • m is preferably:! To 200, more preferably 2 to 100, and particularly preferably 3 to 50.
  • m and n are preferably from 1 to 100, more preferably from 1 to 50, and particularly preferably from 1 to 25.
  • the values of m and n in commercially available polyalkyl ethers include a plurality of values due to the synthesis method.
  • Specific examples of the polyalkyl ethers represented by the formulas (3), (4) and (5) used in the present invention include, for example, diethylene glycol, triethylene glycol, tetraethylene glycol and polyethylene glycol 20.
  • these mono or dimethyl ethers mono or getyl ether, mono or dipropyl ether, mono or dibutyl ether, mono or dipentyl ether, mono or dihexyl ether, mono or diheptyl ether, mono or dioctyl .Ether, mono or dinonyl ether, mono or didecyl ether, monolauryl ether, monocet Monoether, monostearyl ether, monooleyl ether, monooctylphenyl ether, monononylphenyl ether, monophenyl ether, mononaphthyl ether, monobenzyl ether, monophenylethyl ether, lauryl methyl ether, lauryl ethyl Ether, lauryl propyl ether, lauryl butyl ether, cetyl methyl ether, cetyl ethyl ether, cetyl propyl ether, cetyl butyl ether,
  • Polyalkyl ethers can be used not only as a catalyst but also as a solvent, and their usage is not particularly limited. Polyalkyl ethers can also be recovered from the reaction mixture by resentment means. For example, after the completion of the reaction, the reaction solution is distilled to separate and purify water and the desired oxetane compound, to separate the precipitated salt from the distillation residue, and to reuse the filtrate. ⁇ Solvent
  • any compound that is inert to the raw materials and the reaction products can be used as the solvent used for the reaction.
  • a solvent azeotropic with water produced in the reaction system is desirable, and suitable reaction solvents include benzene, toluene, xylene, ethylbenzene, chlorobenzene, 1,2-dichloroethane and tetrachloroethylene.
  • the water generated in the reaction system is distilled off together with the solvent and separated and removed in a water separation tank, which can be expected to shorten the reaction time for obtaining the oxen compound.
  • the amount of the solvent is preferably from 0.1 to 100 parts by mass, more preferably from 0.5 to 20 parts by mass, based on 1 part by mass of the raw materials and the reaction product in the reactor. . If the amount exceeds 100 parts by mass, the yield per unit volume is reduced, and it is not economical in terms of an increase in energy required for recovering the reaction solvent.
  • the compounds represented by the formulas (3), (4) and (5) can be used as a solvent, in which case the above-mentioned solvent may or may not be used. ⁇ Reaction conditions
  • the reaction in the present invention can be performed not only under normal pressure but also under reduced pressure or increased pressure.
  • the reaction temperature is in the range of room temperature to 200 ° C., preferably 40 to 180 ° C., more preferably 60 to 160 ° C., and particularly preferably 80 to 1 ° C. 50 ° C. If the reaction temperature is higher than 200, by-products may increase and the yield may decrease.On the other hand, if the reaction temperature is lower than room temperature, the reaction rate may decrease and the conversion of raw materials may decrease. is there.
  • the polyalkyl ether is represented by the formula (1) 0.1 to 200 mol%, preferably 1 to 150 mol%, more preferably 4 to 150 mol% of 3-halo 1-propanols can be used.
  • a 3-halo 1-propanol of formula (1), an aqueous alkali solution, an aqueous suspension or organic solvent solution, polyalkyl ethers, and if necessary, a solvent are charged into a reactor, and a predetermined reaction temperature is set. By stirring for 1 to 48 hours, an oxetane compound can be obtained.
  • the reaction time can be shortened by performing this reaction while removing water in the reaction system. That is, hexane, toluene, xylene, etc., which azeotropes with water, are used as the reaction solvent, water is distilled off together with the solvent under normal pressure or reduced pressure, and the distillate is condensed and then separated into a solvent and water. It may be returned to the reactor, and the reaction may be performed while extracting water out of the reaction system. After completion of the reaction, water is added to dissolve the salt formed, the organic layer and the aqueous layer are separated, and the obtained organic solvent is separated and purified by rectifying or another method to obtain the desired oxetane compound. Can be.
  • the reaction When the reaction is carried out while distilling water, the salts formed from the reaction solution are removed by a method such as filtration, and the obtained organic solvent is subjected to a method such as rectification and separation.
  • the oxetane compound can be separated and purified.
  • the polyalkyl ethers may be substituted with the 3- (3) 0.1 to 100 parts by mass, preferably 0.15 to 50 parts by mass, more preferably 0.5 to 20 parts by mass, per 1 part by mass of halo 1-propanol. It is possible.
  • a polyalkyl ether and, if necessary, another organic solvent are charged into a reactor, and an aqueous alkali solution, water suspension, or organic solvent liquid is added with stirring, heated to a predetermined temperature, and then stirred. Add 3-chloro-1-propanol to the mixture and heat and stir for 1-48 hours.
  • the solvent is distilled off, and the desired oxetane compound can be separated and purified by a method such as rectification separation.
  • salts can be removed from the residual liquid obtained by distilling the oxetane compound by a method such as filtration, and the filtrate containing polyalkyl ethers can be reused as a solvent.
  • This method is preferably applied to oxetane compounds having a relatively low boiling point, such as oxetane, 3-methyloxetane, and 3,3-dimethyloxetane.
  • An oxetane compound obtained by using the synthesis method of the present invention from 3-octyl-1-propanols includes a compound represented by the following general formula (6).
  • R 1 and R 2 in the formula (6) are the same as those in the formula (1) or the formula (2), and may be different hydrogen atoms or carbon atoms which may have a substituent.
  • oxetane compound obtained by the synthesis method of the present invention include 3,3-dimethyloxyxetane, 3-methyl-3-hydroxymethyloxetane, and 3-ethyl-3-hydroxymethyloxetane.
  • a method for producing an oxetane compound which comprises using a polyalkyl ether and an alkali in a method for dehydrohalogenating a 3-halo-1-propanol of the formula (1).
  • Oxetane carried out while removing water from the 3-halo-1-propanol dehydrohalogenation cyclization system of formula (1) using a solvent that forms an azeotrope with water in the presence of polyalkyl ethers A method for producing a compound.
  • a process for producing an oxetane compound wherein water is removed from the dehydrochlorination cyclization reaction system of the formula (2) using a solvent that forms an azeotrope with water in the presence of a polyalkyl ether and an alkali.
  • OXA selectivity (%) product ⁇ XA ⁇ (prepared MCP—unreacted MCP)
  • X I 00 yield (%) MCP conversion
  • Carrier gas helium
  • Example 3> 76.3 g of MCP (0.5 mol), 25.lg of PEG 1000 (0.025 mol), 76.5 g of toluene and 41.7 g of a 48% by weight aqueous sodium hydroxide solution (0.5 mol) ) And the same operation as in Example 1 was performed, and the precipitated salt was washed with 43 g of toluene to obtain 20.1 g of a reaction solution. The obtained reaction solution was analyzed in the same manner as in Example 1 to determine the MCP conversion, OXA selectivity, and yield. The results are shown in Table 1.
  • Example 3> 76.3 g of MCP (0.5 mol), 25.lg of PEG 1000 (0.025 mol), 76.5 g of toluene and 41.7 g of a 48% by weight aqueous sodium hydroxide solution (0.5 mol) )
  • the precipitated salt was washed with 43 g of toluene to obtain 20.1 g of a reaction solution.
  • the obtained reaction solution
  • Example 2 Performed without PEG 600 using 152.6 g of MCP (1.0 mol), 152.6 g of toluene and 83.3 g of 48% by weight aqueous sodium hydroxide solution (1.0 mol) The same operation as in Example 1 was performed to obtain 242.45 g of a reaction solution. The obtained reaction solution was analyzed in the same manner as in Example 1, and the MCP conversion, OXA selectivity, and yield were determined. The results are shown in Table 1. Comparative Example 2>
  • the reaction solution was distilled to obtain 124.4 g of DMOX containing water. 405 g of water was added to the distillation residue to obtain 2.2 g of an organic layer and 661.7 g of an aqueous layer.
  • the contents of CNP and DMOX were quantified by GC analysis (substantially the same as the analysis conditions in Example 1), and the CNP conversion, DMOX selectivity and yield were determined. . The results are shown in Table 2.
  • NPG 2,2-dimethyl-1,3-propanediol
  • XYL 165.5 gm-xylene
  • a dehalogenation cyclization reaction of 3-halo-1-propanols and a dehydrochlorination cyclization reaction of 3-chloro-1-propanols can be performed in a short time and with high yield.
  • the present invention provides an economically advantageous method for producing an oxenone compound. From this, this manufacturing method can be used industrially, and its value is high.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Cette invention propose un procédé industriellement avantageux pour produire un composé d'oxétan par lequel un 3-halo-1-propanol représenté par la formule générale (1) peut être cyclisé par élimination d'un halogénure d'hydrogène avec un rendement élevé et du 3-chloro-1-propanol également représenté par la formule générale (1) peut être cyclisé par élimination du chlorure d'hydrogène avec un rendement élevé, sans qu'il soit nécessaire de recourir à un système à deux couches comprenant de l'eau et un solvant organique. Dans cette formule (1) R1 et R2, qui peuvent être différents, représentent chacun hydrogène ou un hydrocarbyle C1-8 aliphatique éventuellement substitué et éventuellement ramifié, ou R1 et R2 peuvent former ensemble un hydrocarbyle C2-8 divalent aliphatique éventuellement ramifié ; et X représente chlore, brome ou iode. Plus précisément, un tel procédé pour produire une composé d'oxétan se caractérise en ce que, dans la réaction de cyclisation d'un 3-halo-1-propanol représenté par la formule générale (1) par élimination d'un halogénure d'hydrogène, un polyalkyle-éther est utilisé en présence d'un alcali.
PCT/JP2003/002904 2002-03-12 2003-03-12 Procede pour produire un compose d'oxetan en utilisant un polyalkyl-ether WO2004080987A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN03826135.9A CN1759107A (zh) 2003-03-12 2003-03-12 使用聚烷基醚类的氧杂环丁烷化合物的制造方法
AU2003220824A AU2003220824A1 (en) 2003-03-12 2003-03-12 Process for producing oxetane compound using polyalkyl ether
JP2003067267A JP2003335764A (ja) 2002-03-12 2003-03-12 ポリアルキルエーテル類を用いるオキセタン化合物の製造方法
PCT/JP2003/002904 WO2004080987A1 (fr) 2002-03-12 2003-03-12 Procede pour produire un compose d'oxetan en utilisant un polyalkyl-ether

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2002067611 2002-03-12
JP2003067267A JP2003335764A (ja) 2002-03-12 2003-03-12 ポリアルキルエーテル類を用いるオキセタン化合物の製造方法
PCT/JP2003/002904 WO2004080987A1 (fr) 2002-03-12 2003-03-12 Procede pour produire un compose d'oxetan en utilisant un polyalkyl-ether

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5758637A (en) * 1980-09-24 1982-04-08 Nippon Tokushu Kagaku Kogyo Kk Preparation of ether
JPH10212282A (ja) * 1997-01-31 1998-08-11 Toagosei Co Ltd ３−クロロメチル−３−アルキルオキセタンの製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5758637A (en) * 1980-09-24 1982-04-08 Nippon Tokushu Kagaku Kogyo Kk Preparation of ether
JPH10212282A (ja) * 1997-01-31 1998-08-11 Toagosei Co Ltd ３−クロロメチル−３−アルキルオキセタンの製造方法

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