WO2022168949A1 - イソブチルビニルエーテルの製造方法及びイソブチルビニルエーテルの精製方法 - Google Patents

イソブチルビニルエーテルの製造方法及びイソブチルビニルエーテルの精製方法 Download PDF

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WO2022168949A1
WO2022168949A1 PCT/JP2022/004489 JP2022004489W WO2022168949A1 WO 2022168949 A1 WO2022168949 A1 WO 2022168949A1 JP 2022004489 W JP2022004489 W JP 2022004489W WO 2022168949 A1 WO2022168949 A1 WO 2022168949A1
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vinyl ether
isobutyl
distillation
alcohol
isobutyl vinyl
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French (fr)
Japanese (ja)
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雄大 伊藤
雅弘 須戸
隆史 何木
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Maruzen Petrochemical Co Ltd
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Maruzen Petrochemical Co Ltd
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Priority to JP2022579620A priority Critical patent/JP7742370B2/ja
Priority to US18/262,651 priority patent/US20240076258A1/en
Priority to CN202280011782.1A priority patent/CN116724017A/zh
Priority to EP22749820.1A priority patent/EP4289809A4/en
Publication of WO2022168949A1 publication Critical patent/WO2022168949A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C07C41/08—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only to carbon-to-carbon triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C07C41/50—Preparation of compounds having groups by reactions producing groups
    • C07C41/54—Preparation of compounds having groups by reactions producing groups by addition of compounds to unsaturated carbon-to-carbon bonds

Definitions

  • the present invention relates to a method for producing isobutyl vinyl ether and a method for purifying isobutyl vinyl ether.
  • the addition reaction of alcohol to acetylene is widely known as a method for producing vinyl ether. becomes difficult to purify by distillation.
  • alcohols forming an azeotropic mixture and vinyl ethers corresponding to the alcohols for example, a combination of 2-ethylhexanol and 2-ethylhexyl vinyl ether and a combination of cyclohexanol and cyclohexyl vinyl ether are known.
  • 2-ethylhexyl vinyl ether or cyclohexyl vinyl ether produced by the above addition reaction is added to unreacted 2-ethylhexanol or cyclohexanol contained in the mixture obtained by the addition reaction of 2-ethylhexanol or cyclohexanol to acetylene as an acid catalyst.
  • a method has been proposed in which acetal is converted to acetal by reaction in its presence and then removed (Patent Document 1).
  • An object of the present invention is to provide a method for efficiently producing high-purity isobutyl vinyl ether from isobutyl alcohol and acetylene.
  • ⁇ 1> A method for producing isobutyl vinyl ether using isobutyl alcohol as a raw material alcohol, comprising the following steps A1, A2 and A3.
  • Step A1 A vinyl ether synthesis step of reacting isobutyl alcohol and acetylene to obtain a mixture containing unreacted isobutyl alcohol and isobutyl vinyl ether
  • Step A2 Converting unreacted isobutyl alcohol and isobutyl vinyl ether in the mixture to an acid Acetalization step of converting to acetaldehyde diisobutyl acetal by reacting in the presence of a catalyst
  • Step A3 Distillation step of removing acetaldehyde diisobutyl acetal by distillation from the acetal-containing mixture obtained in step A2 ⁇ 2>
  • Isobutyl alcohol and raw material alcohol A method for producing isobutyl vinyl ether, comprising the following steps A1, A2, A2-2 and A3.
  • Step A1 A vinyl ether synthesis step of reacting isobutyl alcohol and acetylene to obtain a mixture containing unreacted isobutyl alcohol and isobutyl vinyl ether
  • Step A2 Converting unreacted isobutyl alcohol and isobutyl vinyl ether in the mixture to an acid Acetalization step of converting to acetaldehyde diisobutyl acetal by reacting in the presence of a catalyst
  • Step A2-2 Step of performing a treatment selected from neutralization of the acid catalyst and removal of the acid catalyst
  • Step A3 Distillation step of removing acetaldehyde diisobutyl acetal by distillation from the acetal-containing mixture obtained in
  • step A2-2 is a step of neutralizing the acid catalyst using a basic compound.
  • step A1 is performed in the presence of an alkali metal alcoholate catalyst.
  • step A5> The production method according to any one of ⁇ 1> to ⁇ 4>, wherein the distillation pressure in step A3 is 40 kPaA to atmospheric pressure.
  • Step B1 Acetalization step of reacting isobutyl alcohol and isobutyl vinyl ether in the mixture in the presence of an acid catalyst to convert to acetaldehyde diisobutyl acetal
  • Step B2 Acetaldehyde by distillation from the acetal-containing mixture obtained in Step B1 Distillation process to remove diisobutyl acetal
  • isobutyl vinyl ether can be efficiently produced from isobutyl alcohol and acetylene. Further, according to the purification method of the present invention, isobutyl vinyl ether can be efficiently purified to a high purity from a mixture containing isobutyl alcohol and isobutyl vinyl ether.
  • FIG. 1 is a schematic diagram showing the configuration of an apparatus used in Examples.
  • the production method of the present invention is a method for producing isobutyl vinyl ether using isobutyl alcohol as a raw material alcohol, and includes the steps A1, A2 and A3. Specifically, after performing step A1 (vinyl ether synthesis step), a mixture containing unreacted raw material alcohol obtained in the step and isobutyl vinyl ether (when the vinyl ether synthesis was performed in the presence of a catalyst, a catalyst (a mixture containing the
  • Step A1 is a vinyl ether synthesis step of reacting isobutyl alcohol (boiling point: 108° C.) with acetylene to obtain a mixture containing unreacted starting alcohol and isobutyl vinyl ether (boiling point: 83° C.).
  • Isobutyl vinyl ether is a vinyl ether with a low boiling point, and according to the production method of the present invention, isobutyl vinyl ether, which is such a low boiling point vinyl ether, can be produced with high purity.
  • Step A1 is preferably carried out in the presence of a catalyst.
  • the catalyst is preferably an alkali metal alcoholate catalyst.
  • the alkali metal alcoholate catalyst is an alkali metal alcoholate of an alkali metal hydroxide and isobutyl alcohol, and is preferably soluble in isobutyl alcohol from the viewpoint of handling.
  • alkali metal hydroxides include sodium hydroxide, potassium hydroxide, rubidium hydroxide, and cesium hydroxide. One of these may be used alone, or two or more may be used in combination. may
  • an organic solvent may be used in step A1, and the organic solvent is preferably an aprotic polar solvent or the like that is miscible with isobutyl alcohol and dissolves the alkali metal alcoholate catalyst.
  • amide solvents such as dimethylacetamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone; sulfur-containing compound solvents such as sulfolane and dimethylsulfoxide; diethylene glycol dimethyl ether, diethylene glycol
  • glycol dialkyl ether solvents such as diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, tetraethylene glycol dimethyl ether, and tetraethylene glycol diethyl ether. One of these may be used alone, or two or more may be used in combination.
  • the reaction temperature in step A1 is usually in the range of 60 to 200°C, more preferably in the range of 80 to 150°C from the viewpoint of reaction rate and suppression of side reactions.
  • the higher the reaction pressure, the higher the reaction rate, the pressure is preferably 0.3 MPa or less in order to prevent decomposition explosion of acetylene.
  • the reaction time of step A1 is usually about 10 minutes to 48 hours.
  • Step A1-2 catalyst removal step In the production method of the present invention, when the vinyl ether synthesis is performed in the presence of a catalyst, the catalyst and the like may be removed from the reaction mixture obtained in step A1 prior to step A2.
  • the removal of catalysts and the like can be carried out by known methods such as solvent extraction, distillation, solid-liquid separation (in the case of solid catalysts or supported catalysts) such as filtration. Among these methods, distillation is preferred because the catalyst can be easily separated and the raw material alcohol can be reduced in advance.
  • the organic solvent can also be removed when the step A1 is performed using the organic solvent.
  • distillation may be further performed to reduce the raw material alcohol in the reaction mixture.
  • the distillation column used for removal of the catalyst or the like or distillation for concentration after removal of the catalyst (hereinafter also referred to as "preliminary distillation”) may be any of a packed column, a plate column, a bubble cap column, etc., and the number of stages of the distillation column is , for example, 1 to 100 theoretical plates, preferably 5 to 50 theoretical plates.
  • the preliminary distillation can be carried out under normal pressure, increased pressure or reduced pressure, preferably under normal pressure or reduced pressure. Specifically, it is usually 0.7 to 13.3 kPa, preferably 1.3 to 6.7 kPa.
  • the distillation method may be any of a batch method, a semi-batch method, and a continuous method.
  • Step A2 is an acetalization step in which the unreacted starting alcohol in the mixture obtained in step A1 or step A1-2 and isobutyl vinyl ether are reacted in the presence of an acid catalyst to convert to acetaldehyde diisobutyl acetal.
  • an acid catalyst to convert to acetaldehyde diisobutyl acetal.
  • Acid catalysts used in step A2 include, for example, inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid, and phosphoric acid; organic acids such as carboxylic acids and organic sulfonic acids; acid catalysts and the like. One of these may be used alone, or two or more may be used in combination. Among these, phosphoric acid, organic sulfonic acid, and sulfonic acid-type strongly acidic ion exchange resins (strongly acidic ion exchange resins having sulfonic acid groups in the molecule) are used from the viewpoint of suppressing side reactions (especially suppressing polymerization reactions of vinyl ether). Organic sulfonic acids are preferred, and organic sulfonic acids are more preferred.
  • Organic sulfonic acids include p-toluenesulfonic acid, o-toluenesulfonic acid, benzenesulfonic acid, p-xylene-2-sulfonic acid, dodecylbenzenesulfonic acid, 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, dinonyl aromatic sulfonic acids such as naphthalenesulfonic acid and dinonylnaphthalenedisulfonic acid; aliphatic sulfonic acids such as methanesulfonic acid, ethanesulfonic acid and trifluoromethanesulfonic acid; pyridinium p-toluenesulfonic acid, quinolinium p-toluenesulfonic acid aromatic sulfonates such as Examples of strongly acidic ion exchange resins include sulfonic acid-type strongly acidic ion-exchange
  • Amberlyst 15DRY is a commercially available mixture of a sulfonic acid type strongly acidic ion exchange resin and an amine type weakly basic ion exchange resin. and Amberlyst MSPS2-1 DRY manufactured by Organo Co., Ltd., respectively.
  • the amount of the acid catalyst used is usually 0.00001 to 5 parts by mass, preferably 0.0001 to 1 part by mass, more preferably 100 parts by mass of isobutyl vinyl ether. It is 0.001 to 0.1 parts by mass, more preferably 0.001 to 0.01 parts by mass.
  • the method of adding the acid catalyst to the mixture obtained in step A1 or step A1-2 may be appropriately selected according to the type of acid catalyst. For example, in the case of an inorganic acid or an organic acid, it may be added to the mixture obtained in step A1 or step A1-2 as it is or dissolved in an appropriate solvent (preferably isobutyl alcohol).
  • a solid acid catalyst it may be added as it is to the mixture obtained in step A1 or step A1-2, or the solid acid catalyst may be filled in a column vessel or the like and obtained in step A1 or step A1-2. The resulting mixture may be passed through.
  • the reaction temperature in step A2 is preferably in the range of 0 to 80°C, more preferably in the range of 10 to 60°C, from the viewpoint of reaction rate and side reaction suppression.
  • the reaction time of step A2 is usually about 10 minutes to 48 hours.
  • the acetal obtained in step A2 is acetaldehyde diisobutyl acetal (boiling point: 171°C).
  • step A2-2 neutralization of the acid catalyst and removal of the acid catalyst prior to step A3 after step A2.
  • Those that include the step of performing the selected treatment are preferred.
  • neutralization of the acid catalyst is preferable as the step A2-2.
  • Neutralization of the acid catalyst may be performed using a basic compound.
  • basic compounds include alkali metal compounds such as alkali metal hydroxides (eg, sodium hydroxide, potassium hydroxide, etc.), alkali metal carbonates, alkali metal hydrogen carbonates; basic ion exchange resins, and the like.
  • alkali metal compounds such as alkali metal hydroxides (eg, sodium hydroxide, potassium hydroxide, etc.), alkali metal carbonates, alkali metal hydrogen carbonates; basic ion exchange resins, and the like.
  • the amount of the basic compound used is generally 1 to 1000 molar equivalents, preferably 5 to 100 molar equivalents, more preferably 10 to 100 molar equivalents, relative to the acid catalyst used in step A2, from the viewpoint of isobutyl vinyl ether purity. , particularly preferably 20 to 100 molar equivalents. Isobutyl vinyl ether can be obtained particularly efficiently when the amount of the basic compound used is 20 molar equivalents or more.
  • an alkali metal compound is used as the basic compound, it may be added to the acetal-containing mixture obtained in step A2 as it is or dissolved in an appropriate solvent (preferably water).
  • a basic ion exchange resin when used, it may be added as it is to the acetal-containing mixture obtained in step A2. The mixture may be passed through.
  • solid-liquid separation may be performed by filtration, centrifugation, or the like, if necessary.
  • step A2-2 removal of the acid catalyst is preferable as step A2-2. Removal operations include solid-liquid separation operations such as filtration and centrifugation. In addition, when the solid acid catalyst is filled in a column container and used, the separation operation is not necessary.
  • Step A3 is a distillation step of removing acetaldehyde diisobutyl acetal by distillation from the acetal-containing mixture obtained in step A2 (step A2-2 if step A2-2 is performed).
  • the distillation apparatus and distillation method used in step A3 are not particularly limited, and a simple distillation or a number of distillation stages may be provided.
  • the method of distillation may be batch, semi-batch or continuous.
  • the distillation column may be a packed column, a plate column, a bubble cap column, or the like.
  • the number of stages of the distillation column is preferably 1 to 30 theoretical stages, more preferably 5 to 15 stages.
  • the reflux ratio is preferably in the range of 1-15.
  • the top temperature of the distillation column is preferably 40 to 100°C, more preferably 50 to 90°C, and the bottom temperature of the distillation column is preferably 40 to 180°C, more preferably 50 to 170°C. be.
  • the distillation pressure in step A3 is preferably 20 to 120 kPaA (A represents absolute pressure), more preferably 40 kPaA to atmospheric pressure, from the viewpoint of isobutyl vinyl ether purity.
  • A represents absolute pressure
  • 40 kPaA to atmospheric pressure from the viewpoint of isobutyl vinyl ether purity.
  • Step A4 acetal decomposition step As a method for converting acetaldehyde diisobutyl acetal into raw material alcohol and vinyl ether, a known method may be appropriately used. Specifically, a method of thermally decomposing in a gas phase in the presence of a silica/alumina catalyst supporting an alkali or alkaline earth metal (for example, Khim. Prom.
  • a silica/alumina catalyst supporting an alkali or alkaline earth metal for example, Khim. Prom.
  • the purification method of the present invention is a method for purifying isobutyl vinyl ether from a mixture containing isobutyl alcohol and isobutyl vinyl ether, and includes the following steps B1 and B2.
  • Step B1 Acetalization step of reacting isobutyl alcohol and isobutyl vinyl ether in the mixture in the presence of an acid catalyst to convert to acetaldehyde diisobutyl acetal
  • Step B2 Acetaldehyde by distillation from the acetal-containing mixture obtained in Step B1 Distillation process to remove diisobutyl acetal
  • Step B1 may be performed in the same manner as step A2 in the manufacturing method of the present invention, and step B2 may be performed in the same manner as step A3 in the manufacturing method of the present invention.
  • FIG. 1 shows a vapor-liquid equilibrium diagram of isobutyl vinyl ether and isobutyl alcohol at 80 kPaA.
  • IBVE in FIG. 1 means isobutyl vinyl ether.
  • Example 1 Production of isobutyl vinyl ether (IBVE) (1)] (Vinyl etherification step and catalyst removal step) A stainless steel autoclave with a capacity of 10 L as a reaction vessel, a stainless steel packed continuous distillation column with an inner diameter of 50 mm ⁇ , 12 theoretical plates (supply plate 7), and a pot capacity of 4 L as a continuous distillation column (filling: Sumitomo Heavy Industries, Sumitomo / Sulzer Lab Packing) were used, respectively.
  • FIG. 2 shows a schematic diagram showing the configuration of the apparatus used for the reaction. The autoclave was charged with 6.14 kg isobutyl alcohol (IBOH), 0.90 kg potassium hydroxide and 0.56 kg tetraglyme.
  • IBOH isobutyl alcohol
  • Autoclave conditions 100 ° C., 0.03 MPaG, maximum oil retention 5 L, continuous distillation tower conditions: tower top 65 to 68 ° C., bottom 100 to 120 ° C., 17 to 43 kPa, maximum oil retention 2 L, reflux ratio 8, autoclave and
  • the alcoholate catalyst (potassium-isobutyl alcoholate) was prepared for 15 hours with a circulation flow rate of 15 kg/hr between the distillation columns. The amount of distillate from the top of the continuous distillation column during this period was 2.04 kg, containing 0.28 kg of water.
  • the autoclave conditions were changed to 110° C. and 0.06 MPaG, and acetylene was continuously added at a rate of 105 g/hr and isobutyl alcohol at a rate of 265 g/hr. supplied to Then, the reaction liquid obtained by the above reaction was continuously supplied to the continuous distillation column at a rate of 15.0 kg/hr.
  • the composition of this reaction solution is isobutyl alcohol 38.4% by mass, isobutyl vinyl ether 8.5% by mass, potassium-isobutyl alcoholate 25.7% by mass, tetraglyme 27.1% by mass and heavy components 0.3%. % by mass.
  • the bottom product is extracted from the bottom of the continuous distillation column at 14.6 kg / hr. , fed into the autoclave.
  • the composition of this continuous distillation column bottoms is 39.1% by mass of isobutyl alcohol, 6.4% by mass of isobutyl vinyl ether, 26.4% by mass of potassium-isobutyl alcoholate, 27.8% by mass of tetraglyme and heavy The component was 0.3% by mass.
  • Crude vinyl ether was continuously synthesized in this way, and crude vinyl ether was obtained from the top of the continuous distillation column at a flow rate of 346 g/hr.
  • the composition of the crude vinyl ether was 95.3% by mass of isobutyl vinyl ether and 4.7% by mass of isobutyl alcohol.
  • IBOH in the solution after the reaction was 0.1% by mass or less, and IBVE and acetaldehyde diisobutyl acetal were contained in 89% by mass and 11% by mass, respectively.
  • 0.36 g of an aqueous potassium hydroxide solution (potassium hydroxide concentration: 42.1% by mass, potassium hydroxide 210 ppm relative to the reaction solution, 22 molar equivalents relative to p-toluenesulfonic acid) was added for neutralization.
  • distillation is performed using a packed column with 10 theoretical plates (internal pressure: 80 kPaA, bottom set temperature: 80 to 160 ° C., refrigerant set temperature: 5 ° C.), and high-purity IBVE 554 with a purity of 99% by mass or more. 8 g was obtained (recovery based on IBVE: 85.7% by weight).
  • Example 2 Production of IBVE (2) (Acetalization reaction step and distillation purification step) After obtaining crude IBVE by performing the vinyl etherification step and the catalyst removal step in the same manner as in Example 1, 791.4 g of the crude IBVE obtained was weighed into a 2000 mL three-necked flask equipped with a stirrer tip, and p - 1.2 g of an IBOH solution of toluenesulfonic acid (concentration of p-toluenesulfonic acid: 2% by mass, 30 ppm of p-toluenesulfonic acid relative to crude IBVE) was added and stirred for 60 minutes in a water bath set at 25°C.
  • IBOH in the solution after the reaction was 0.1% by mass or less, and IBVE and acetaldehyde diisobutyl acetal were contained in 89% by mass and 11% by mass, respectively.
  • 0.08 g of sodium hydroxide aqueous solution sodium hydroxide concentration: 34.3% by mass, sodium hydroxide 35 ppm relative to the reaction solution, 5 molar equivalents relative to p-toluenesulfonic acid
  • sodium hydroxide aqueous solution sodium hydroxide concentration: 34.3% by mass, sodium hydroxide 35 ppm relative to the reaction solution, 5 molar equivalents relative to p-toluenesulfonic acid
  • distillation is performed using a packed column with 10 theoretical plates (internal pressure: 80 kPaA, bottom set temperature: 80 to 160 ° C., refrigerant set temperature: 5 ° C.), and high-purity IBVE 557 with a purity of 99% by mass or more. 2 g was obtained (recovery based on IBVE: 73.7% by weight).

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PCT/JP2022/004489 2021-02-04 2022-02-04 イソブチルビニルエーテルの製造方法及びイソブチルビニルエーテルの精製方法 Ceased WO2022168949A1 (ja)

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JP2022579620A JP7742370B2 (ja) 2021-02-04 2022-02-04 イソブチルビニルエーテルの製造方法及びイソブチルビニルエーテルの精製方法
US18/262,651 US20240076258A1 (en) 2021-02-04 2022-02-04 Method for producing isobutyl vinyl ether and method for purifying isobutyl vinyl ether
CN202280011782.1A CN116724017A (zh) 2021-02-04 2022-02-04 异丁基乙烯基醚的制造方法和异丁基乙烯基醚的精制方法
EP22749820.1A EP4289809A4 (en) 2021-02-04 2022-02-04 PROCESS FOR PRODUCING ISOBUTYLVINYL ETHER AND PROCESS FOR PURIFYING ISOBUTYLVINYL ETHER

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1957680A1 (de) 1969-11-17 1971-05-19 Hoechst Ag Verfahren zur Herstellung von ungesaettigten AEthern
JPS4876803A (https=) 1972-01-18 1973-10-16
JPS4878109A (https=) 1972-01-25 1973-10-20
JPS6287247A (ja) 1985-10-02 1987-04-21 デグツサ・アクチエンゲゼルシヤフト ｇｅｍ−ジアルコキシ化合物の脱アルコキシル用触媒及びその製法
JPH08268945A (ja) 1995-03-28 1996-10-15 Kuraray Co Ltd ビニルエーテル類の製造方法
JPH08277237A (ja) 1995-04-04 1996-10-22 Kuraray Co Ltd ビニルエーテル類の製造法
CN101555198A (zh) * 2008-07-10 2009-10-14 杭州电化集团有限公司 一种异丁基乙烯基醚的合成方法及其装置
JP2010229049A (ja) * 2009-03-26 2010-10-14 Maruzen Petrochem Co Ltd 高純度ビニルエーテルの製造法
CN102976904A (zh) * 2012-12-24 2013-03-20 厦门大学 一种异丁基乙烯基醚制备装置及其制备方法
CN105837407A (zh) * 2016-04-27 2016-08-10 厦门大学 异丁基乙烯基醚的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS541683B1 (https=) * 1970-12-11 1979-01-27
DE10326403A1 (de) * 2003-06-12 2004-12-30 Basf Ag Verfahren zur destillativen Trennung eines Vinylether und Alkohol enthaltenden Gemischs
CN100567237C (zh) * 2007-02-09 2009-12-09 上海华谊丙烯酸有限公司 缩醛或缩酮气相分解制备烯基醚的方法
CN100590110C (zh) * 2007-09-19 2010-02-17 山西三维集团股份有限公司 乙烯基醚类的生产方法
EP3763352A1 (en) * 2019-07-09 2021-01-13 Basf Se 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives and their use as aroma chemicals

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1957680A1 (de) 1969-11-17 1971-05-19 Hoechst Ag Verfahren zur Herstellung von ungesaettigten AEthern
JPS4876803A (https=) 1972-01-18 1973-10-16
JPS4878109A (https=) 1972-01-25 1973-10-20
JPS6287247A (ja) 1985-10-02 1987-04-21 デグツサ・アクチエンゲゼルシヤフト ｇｅｍ−ジアルコキシ化合物の脱アルコキシル用触媒及びその製法
JPH08268945A (ja) 1995-03-28 1996-10-15 Kuraray Co Ltd ビニルエーテル類の製造方法
JPH08277237A (ja) 1995-04-04 1996-10-22 Kuraray Co Ltd ビニルエーテル類の製造法
CN101555198A (zh) * 2008-07-10 2009-10-14 杭州电化集团有限公司 一种异丁基乙烯基醚的合成方法及其装置
JP2010229049A (ja) * 2009-03-26 2010-10-14 Maruzen Petrochem Co Ltd 高純度ビニルエーテルの製造法
JP5312133B2 (ja) 2009-03-26 2013-10-09 丸善石油化学株式会社 高純度ビニルエーテルの製造法
CN102976904A (zh) * 2012-12-24 2013-03-20 厦门大学 一种异丁基乙烯基醚制备装置及其制备方法
CN105837407A (zh) * 2016-04-27 2016-08-10 厦门大学 异丁基乙烯基醚的制备方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BULL.CHEM.SOC.JPN., 1976, pages 3089
HELV.CHIM.ACTA, vol. 1158, 1967
J.ORG.CHEM., vol. 38, 1973, pages 2910
KHIM. PROM, vol. 48, no. 9, 1972, pages 657 - 660
See also references of EP4289809A4

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