WO2015041471A1 - Procédé de préparation d'alcanol - Google Patents

Procédé de préparation d'alcanol Download PDF

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Publication number
WO2015041471A1
WO2015041471A1 PCT/KR2014/008666 KR2014008666W WO2015041471A1 WO 2015041471 A1 WO2015041471 A1 WO 2015041471A1 KR 2014008666 W KR2014008666 W KR 2014008666W WO 2015041471 A1 WO2015041471 A1 WO 2015041471A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
carbon atoms
group
butanol
Prior art date
Application number
PCT/KR2014/008666
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English (en)
Korean (ko)
Inventor
남현
김진수
최용진
최선혁
Original Assignee
주식회사 엘지화학
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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Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US14/917,167 priority Critical patent/US9624150B2/en
Priority to EP14845165.1A priority patent/EP3048090B1/fr
Priority to JP2016544289A priority patent/JP6301481B2/ja
Priority to CN201480050869.5A priority patent/CN105555746A/zh
Priority claimed from KR1020140123680A external-priority patent/KR101659163B1/ko
Publication of WO2015041471A1 publication Critical patent/WO2015041471A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group

Definitions

  • the present application relates to a method and apparatus for producing alkanol.
  • Alkanols such as n-butanol
  • n-butanol is used in a variety of applications as solvents and intermediates in the chemical industry.
  • n-butanol is used as a raw material for a solvent, butyl acetate, a medicine, a perfume, a plasticizer, and a stabilizer.
  • the present application aims to provide a method and apparatus for producing alkanol.
  • the present application relates to a method for preparing alkanol. According to the above-described production method of the present application, it is possible to produce alkanol economically and stably by a simple process compared to the conventional method using a high-pressure hydrogen gas.
  • the hydrogen production reaction and the production process of alkanol can be performed simultaneously.
  • secondary alcohols such as isopropyl alcohol and cyclohexanol are decomposed into acetone and hydrogen, cyclohexanone and hydrogen, respectively, under a Raney nickel catalyst to generate hydrogen, and the generated hydrogen is n.
  • n-butanol can be prepared by reducing the aldehyde group of -butylaldehyde, problems such as process risks caused by using a high-pressure hydrogen gas can be improved, and n-butanol can be economically produced.
  • the preparation method of alkanol of the present application includes a reaction step of reacting a compound of Formula 1 and a compound of Formula 2 below.
  • R 1 represents a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, or represents alkenyl having 1 to 12 carbon atoms.
  • R 1 represents an alkyl group having 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or carbon atoms.
  • Alkenyl of 1 to 4 and in one example, R 1 may be a methyl group, an ethyl group, a propyl group, a butyl group, or a vinyl group, but is not limited thereto.
  • R 2 , R 3, and R 4 are each independently hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 24 carbon atoms, and at least one of R 2 , R 3, and R 4 is hydrogen. to be.
  • R 3 and R 4 are each independently hydrogen, 1 to 12 carbon atoms, for example, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 carbon atoms It may be an alkyl group of 4 to 4 or an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms, 6 to 12 carbon atoms, when R 3 is hydrogen, R 2 and R 4 is hydrogen, 1 to 12, for example, an alkyl group having 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or an aryl having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms or 6 to 12 carbon atoms.
  • R 4 is hydrogen
  • R 2 and R 3 is hydrogen
  • an alkyl group having 1 to 12 carbon atoms for example, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms or It may be an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms and 6 to 12 carbon atoms.
  • the alkyl group may be a linear, branched or cyclic alkyl group, and is not particularly limited.
  • R 2 and R 3 each independently represent hydrogen, an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, in which case at least one of R 2 and R 3 is hydrogen, R 4 may be an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms.
  • R 3 is hydrogen, an alkyl group having 1 to 12 carbon atoms, for example, 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms, or It may be an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms, 6 to 12 carbon atoms, and when R 3 is hydrogen, R 2 is hydrogen, 1 to 12 carbon atoms, for example, 1 to 12 carbon atoms It may be an alkyl group having 10, 1 to 8 carbon atoms, 1 to 6 carbon atoms, 1 to 4 carbon atoms or an aryl group having 6 to 24 carbon atoms, for example, 6 to 18 carbon atoms, 6 to 12 carbon atoms.
  • the alkyl group having 1 to 12 carbon atoms may be, for example, a methyl group, an ethyl group, a propyl group, or a butyl group, and the aryl group having 6 to 24 carbon atoms may be, for example, a phenyl group, tolyl group, xylyl group, or naphthyl group.
  • the compound of Formula 2 may be methanol, primary alcohol or secondary alcohol, for example, primary alcohol or secondary alcohol, preferably secondary alcohol.
  • R 2 to R 4 are all alkyl groups, the compound of Formula 2 is a tertiary alcohol, and the tertiary alcohol may not generate hydrogen in the presence of a metal catalyst.
  • the reaction step can be carried out in the presence of a metal catalyst.
  • the metal catalyst is used in the preparation method of the present application in order to increase the reaction rate and reaction efficiency of the dehydrogenation reaction to decompose the compound of Formula 2 to generate hydrogen and the reduction reaction of aldehyde using the produced hydrogen.
  • the metal catalyst may be at least one selected from the group consisting of copper, cobalt, molybdenum, nickel, nickel-aluminum alloy, nickel-molybdenum alloy, Raney cobalt, Raney nickel, and zinc-chromium alloy, Preferably Raney nickel.
  • the Raney nickel catalyst is particularly excellent in substrate specificity or catalytic specificity for secondary alcohols.
  • substrate specificity or “catalyst specificity” means the effect of the catalytic activity with respect to a specific compound.
  • substrate specificity or “catalyst specificity” means the effect of the catalytic activity with respect to a specific compound.
  • R 1 may be an alkyl group having 2 to 6 carbon atoms or an alkenyl having 4 to 10 carbon atoms.
  • the compound of Formula 1 may be, for example, n-butylaldehyde or 2-ethyl-2-hexenal.
  • the compound of Formula 2 is not particularly limited as long as it satisfies Formula 2, and may be, for example, a primary alcohol or a secondary alcohol, preferably a secondary alcohol.
  • a primary alcohol or a secondary alcohol preferably a secondary alcohol.
  • the tertiary alcohol cannot produce hydrogen for reducing the compound of formula 1 to alkanol in the presence of a metal catalyst in molecular structure.
  • the primary alcohol although hydrogen may be generated in the presence of a catalyst, when the primary alcohol generates hydrogen, it is converted into an aldehyde compound such as Chemical Formula 1, and the aldehyde compound receives hydrogen again. Since it is reduced to a primary alcohol, it can be difficult to provide hydrogen to the compound of formula (1).
  • the secondary alcohol may be a compound of formula (3).
  • R 5 and R 6 each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, or R 5 and R 6 together form a cycloalkyl group having 3 to 16 carbon atoms can do.
  • each of R 5 and R 6 independently represents an alkyl group having 1 to 10 carbon atoms, 1 to 8 carbon atoms, 1 to 6 carbon atoms or 1 to 4 carbon atoms, or 6 to 24 carbon atoms or 6 to 18 carbon atoms.
  • an aryl group having 6 to 12 carbon atoms may be a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a tolyl group, a xylyl group, or a naphthyl group, but is not limited thereto.
  • R 5 and R 6 may together form a cycloalkyl group having 3 to 16 carbon atoms, for example, a cycloalkyl group having 4 to 12 carbon atoms or 5 to 8 carbon atoms, and may form a cyclohexyl group, for example. have.
  • the compound of Formula 3 is isopropyl alcohol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, glycerol, 3-methyl-2-butanol, ⁇ -phenylethanol, di 1 selected from the group consisting of phenylmethanol, 3-pentanol, 3,3-dimethyl-2-butanol, 4-phenyl-2-butanol, 1,2,3,4-tetrahydro-1-naphthol and cyclohexanol It may include more than one compound, preferably may include isopropyl alcohol, and / or cyclohexanol.
  • the reaction step may include a dehydrogenation step in which the compound of Formula 2 is dehydrogenated in the presence of a metal catalyst, in particular, Raney nickel catalyst, the dehydrogenation step,
  • a metal catalyst in particular, Raney nickel catalyst
  • the compound of Formula 2 may include being decomposed into a ketone compound and hydrogen in the presence of a Raney nickel catalyst.
  • dehydrogenation refers to a reaction in which a compound containing hydrogen is decomposed to generate hydrogen.
  • a secondary alcohol a compound of Formula 2
  • ketone in the presence of a metal catalyst. It may mean decomposed into a compound and hydrogen.
  • the ketone compound formed in the dehydrogenation step is acetone, cyclohexanone, butanone, 2-pentanone, 2-hexanone, 2-heptanone, dihydroxyacetone, methyl isopropyl ketone, It may include one or more compounds selected from the group consisting of acetophenone, benzophenone, 3-pentanone, 3,3-dimethyl-2-butanone, 4-phenyl-2-butanone and tetralone, When the compound of 2 is isopropyl alcohol and / or cyclohexanol, the ketone compound may be acetone and / or cyclohexanone.
  • the preparation method of the present application may further include a reduction step in which hydrogen decomposed from the compound of Formula 2 reduces the compound of Formula 1.
  • a reduction step hydrogen decomposed from the compound of Formula 2 in the dehydrogenation step of the reaction step to reduce the compound of Formula 1 by reducing the compound of Formula 1, according to the formula 1
  • the alkanol may be produced by reducing the compound of.
  • the reduction step may be performed after the above-described reaction step or at the same time as the reaction step, and may also be performed after the dehydrogenation step or simultaneously with the dehydrogenation step.
  • both the dehydrogenation step and the reduction step may be carried out under a metal catalyst, in particular a Raney nickel catalyst, in which case the metal catalyst decomposes the compound of formula 2 into a ketone compound and hydrogen in the dehydrogenation step.
  • a metal catalyst in particular a Raney nickel catalyst
  • the metal catalyst decomposes the compound of formula 2 into a ketone compound and hydrogen in the dehydrogenation step.
  • the hydrogen decomposed from the compound of Formula 2 may promote the reaction to reduce the compound of Formula 1.
  • the metal catalyst can be carried out at the same time the production reaction of hydrogen and the production process of alkanol, it is possible to improve the economics and stability of the process.
  • the metal catalyst may be present in an amount of 50 to 500 parts by weight, for example 100 to 450 parts by weight, 200 to 400 parts by weight or 250 to 350 parts by weight, based on 100 parts by weight of the compound of Formula 1.
  • the metal catalyst is present in the content in the above range, it is possible to produce alkanol with excellent efficiency.
  • the metal catalyst is present in less than 50 parts by weight based on 100 parts by weight of the compound of Formula 1, the degree of catalyst activity may be low to slow the reaction, or the conversion or selectivity may be low.
  • the metal catalyst when the metal catalyst is present in excess of 500 parts by weight based on 100 parts by weight of the compound of Formula 1, the catalyst content is increased, making the purification process difficult after the reaction and not having a high catalytic activity efficiency compared to the catalyst content. This can be.
  • the secondary alcohol used in the preparation method is 100 to 2000 parts by weight, for example 300 to 1800 parts by weight, 500 to 1600 parts by weight, 700 to 1400 parts by weight based on 100 parts by weight of the compound of Formula 1 900 to 1200 parts by weight or 1000 to 1100 parts by weight can be reacted.
  • the reaction amount of the secondary alcohol is less than 100 parts by weight, the yield of n-butanol produced may be reduced because hydrogen cannot be provided sufficiently, and when it exceeds 2000 parts by weight, the cost increases due to the excessive amount of use, Difficult problems can arise.
  • the method for preparing alkanol may be performed in a state in which the compound of Formula 1 and the compound of Formula 2 are dissolved in an organic solvent.
  • an organic solvent in the compound of Formula 1 and the compound of Formula 2 as described above it is possible to more easily mix the compound of Formula 1 and the compound of Formula 2 as a reactant, and maintain the concentration of the compound of Formula 2 optimally The reaction efficiency can be further improved.
  • the organic solvent may be an alcohol compound, an aromatic compound, a hydrocarbon compound, a heterocyclic compound, an ether compound.
  • the alcohol compound may be exemplified by a primary alcohol having 1 to 12 carbon atoms
  • the aromatic compound may be benzene, toluene or xylene
  • the heterocyclic compound may be tetrahydro.
  • Furan, 1,4-dioxane, and the like can be exemplified
  • the ether compound can be exemplified by diethyl ether, methyl-t-butyl ether, and the like.
  • the reaction step of reacting the compound of Formula 1 and the compound of Formula 2 is 50 to 150 °C, for example 60 to 120 °C, 65 to 100 °C, 70 to 90 °C or 75 to It may be carried out at a temperature of 85 °C. Accordingly, by adjusting the process temperature in the above range it is possible to obtain a high reaction efficiency in the reaction step of the compound of Formula 1 and the compound of Formula 2. For example, when the reaction step is performed at less than 50 ° C., the compound of Formula 1 and the compound of Formula 2 may not sufficiently react, thereby greatly reducing the effect of the reaction or reducing the amount of alkanol produced. In addition, when the reaction temperature exceeds 100 °C, there is a disadvantage that the unnecessary side reaction occurs excessively, the conversion or selectivity to alkanol is greatly reduced.
  • an aldehyde compound such as n-butylaldehyde by hydrogen dehydrogenated and decomposed to secondary alcohol, in particular isopropyl alcohol and / or cyclohexanol Since it can be reduced to alkanols, such as n-butanol, since the high-pressure hydrogen gas is not separately included as a reaction material as in the conventional method, the risk of the reaction process is low, and the production process equipment can be simplified. Moreover, according to the manufacturing method of this invention, since the economics of a process can be improved, mass production of n-butanol can be made possible.
  • the present application also relates to an apparatus for producing alkanol for use in the above production method.
  • Alkanol production apparatus of the present application may include a reactor and a reactant supply device.
  • the reactor is filled with a metal catalyst
  • the reactant supply device may be a device for supplying a compound of Formula 1 and a compound of Formula 2 to the reactor.
  • R 1 represents a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, or represents alkenyl having 1 to 12 carbon atoms
  • R 2 , R 3 and R 4 are each independently , Hydrogen, a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, at least one of R 2 , R 3 and R 4 is hydrogen.
  • Detailed description of the formula (1) and formula (2) is the same as described in the manufacturing method will be omitted.
  • the reactor is a device for reacting the compound of Formula 1 and the compound of Formula 2, the compound of Formula 1 and the compound of Formula 2 may be introduced into the reactor.
  • the inside of the reactor is filled with a metal catalyst, the compound of Formula 1 and the compound of Formula 2 may be maintained under appropriate conditions for causing a reaction.
  • the type of the reactor included in the production apparatus is not particularly limited as long as it is commonly used in compound synthesis, etc., and may be used by determining the size, form and type of the reactor in consideration of the reaction conditions, the amount of reactants and the product. For example, a three-necked flask equipped with a condenser and a stirrer may be used.
  • the compound of Formula 1 and the compound of Formula 2 are supplied to the reactor through the reactant supply device, the reactor may be filled with a metal catalyst.
  • the compound of Formula 1 and the compound of Formula 2 may react in the presence of the metal catalyst, the compound of Formula 2 may be dehydrogenated and decomposed into ketone compounds and hydrogen.
  • alkanol may be prepared by reducing hydrogen decomposed from the compound of Formula 2 with the compound of Formula 1.
  • the metal catalyst charged in the reactor may be Raney nickel, in this case, a high conversion rate due to the dehydrogenation and reduction reaction in the reaction step of the compound of Formula 1 and the compound of Formula 2 Alkanols can be prepared. Detailed description thereof is the same as described in the above-described method for preparing alkanol, and thus will be omitted.
  • the compound of Formula 1 is not particularly limited as long as it satisfies Formula 1.
  • R 1 may be an alkyl group having 2 to 6 carbon atoms or an alkenyl number of 4 to 10 carbon atoms. And preferably n-butylaldehyde or 2-ethyl-2-hexenal.
  • the compound of Formula 2 is not particularly limited as long as it satisfies Formula 2, and may be, for example, a secondary alcohol.
  • the secondary alcohol may be a compound of formula (3).
  • R 5 and R 6 each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 24 carbon atoms, or R 5 and R 6 together form a cycloalkyl group having 3 to 16 carbon atoms can do.
  • Detailed description of the formula (3) is the same as described in the manufacturing method will be omitted.
  • the compound of Formula 3 is isopropyl alcohol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, glycerol, 3-methyl-2-butanol, ⁇ -phenylethanol, di 1 selected from the group consisting of phenylmethanol, 3-pentanol, 3,3-dimethyl-2-butanol, 4-phenyl-2-butanol, 1,2,3,4-tetrahydro-1-naphthol and cyclohexanol It may comprise more than one compound, preferably may include isopropyl alcohol and / or cyclohexanol.
  • high-purity n-butanol can be produced at high conversion rate, and since high-pressure hydrogen gas is not used as a reaction material, economical efficiency and stability of the process can be improved.
  • n-butanol may be produced without using high pressure hydrogen gas as a reaction material at a reaction condition of about 70 to 100 ° C., in particular, Examples As shown in FIG. 1, when the temperature of the process and the content of the compound are properly adjusted, it can be seen that n-butanol can be prepared at a very high conversion rate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente application concerne un procédé et un appareil pour la préparation d'alcanol, le procédé et l'appareil, selon la présente application améliorent le procédé de préparation afin qu'il soit plus économique et plus stable, et permettent la production en masse d'alcanol.
PCT/KR2014/008666 2013-09-17 2014-09-17 Procédé de préparation d'alcanol WO2015041471A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US14/917,167 US9624150B2 (en) 2013-09-17 2014-09-17 Method of preparing alkanol
EP14845165.1A EP3048090B1 (fr) 2013-09-17 2014-09-17 Procédé de préparation d'alcanol
JP2016544289A JP6301481B2 (ja) 2013-09-17 2014-09-17 アルカノールの製造方法
CN201480050869.5A CN105555746A (zh) 2013-09-17 2014-09-17 制备烷醇的方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2013-0111558 2013-09-17
KR20130111558 2013-09-17
KR1020140123680A KR101659163B1 (ko) 2013-09-17 2014-09-17 알칸올의 제조방법
KR10-2014-0123680 2014-09-17

Publications (1)

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WO2015041471A1 true WO2015041471A1 (fr) 2015-03-26

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5922921A (en) * 1997-10-27 1999-07-13 Celanese International Corporation Process for the production of n-butanol
KR20050000528A (ko) * 2002-05-10 2005-01-05 옥세노 올레핀케미 게엠베하 Ｃ13-알콜 혼합물의 제조방법
JP2007223947A (ja) * 2006-02-23 2007-09-06 Daicel Chem Ind Ltd アルコールの製造法
US20070287868A1 (en) * 2006-06-07 2007-12-13 Arredondo Victor M Processes for converting glycerol to amino alcohols
JP2010159212A (ja) * 2008-12-11 2010-07-22 Daicel Chem Ind Ltd アルコールの分離方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5922921A (en) * 1997-10-27 1999-07-13 Celanese International Corporation Process for the production of n-butanol
KR20050000528A (ko) * 2002-05-10 2005-01-05 옥세노 올레핀케미 게엠베하 Ｃ13-알콜 혼합물의 제조방법
JP2007223947A (ja) * 2006-02-23 2007-09-06 Daicel Chem Ind Ltd アルコールの製造法
US20070287868A1 (en) * 2006-06-07 2007-12-13 Arredondo Victor M Processes for converting glycerol to amino alcohols
JP2010159212A (ja) * 2008-12-11 2010-07-22 Daicel Chem Ind Ltd アルコールの分離方法

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