JP5289783B2 - Method for producing 2- (isopropylamino) ethanol - Google Patents
Method for producing 2- (isopropylamino) ethanol Download PDFInfo
- Publication number
- JP5289783B2 JP5289783B2 JP2008011017A JP2008011017A JP5289783B2 JP 5289783 B2 JP5289783 B2 JP 5289783B2 JP 2008011017 A JP2008011017 A JP 2008011017A JP 2008011017 A JP2008011017 A JP 2008011017A JP 5289783 B2 JP5289783 B2 JP 5289783B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ethanol
- isopropylamino
- aminoethanol
- acetone
- 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.)
- Active
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 title claims description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- LZAMLBFWTLFDKM-UHFFFAOYSA-N 1-(propan-2-ylamino)ethanol Chemical compound CC(C)NC(C)O LZAMLBFWTLFDKM-UHFFFAOYSA-N 0.000 claims description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical group C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 238000010667 large scale reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- -1 isopropylamino Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本発明は、２−（イソプロピルアミノ）エタノールの製造方法に関する。 The present invention relates to a method for producing 2- (isopropylamino) ethanol.
２−（イソプロピルアミノ）エタノールの製造方法としては、貴金属触媒の存在下、アセトンを２−アミノエタノール及び水素と反応させて定量的に製造する方法が知られている（例えば、非特許文献１参照）。
本発明者は、非特許文献１の方法について、製造プラントでの大スケール反応を検討するにあたり、かかる大スケール反応ではオートクレーブへの原料仕込みにかなりの時間を要するので、この影響を調べるために、原料仕込み時間を１時間と想定して実験室規模での反応、すなわち貴金属触媒、アセトン及び２−アミノエタノールをオートクレーブに仕込み、仕込み終了後１時間放置した後に水素を導入、昇温して反応を行った。その結果、触媒濾過後の反応終了液は、２−（イソプロピルアミノ）エタノール５２．９％、２−アミノエタノール６．５％及びメチルイソブチルケトン１７．０％を含有しており、メチルイソブチルケトンが大量に副生し、非特許文献１の実験例（収率９４〜９５％）に比べ、２−（イソプロピルアミノ）エタノールの収率が大きく低下していることがわかった（後述の比較例１）。
In order to investigate this influence, since this inventor takes considerable time for the raw material preparation to an autoclave in such large-scale reaction in examining the large-scale reaction in a manufacturing plant about the method of a nonpatent literature 1, Assuming a raw material charging time of 1 hour, a reaction on a laboratory scale, that is, charging a noble metal catalyst, acetone and 2-aminoethanol into an autoclave, letting it stand for 1 hour after completion of the charging, introducing hydrogen, raising the temperature and reacting went. As a result, the reaction completion liquid after catalyst filtration contains 5 (2.9%) 2- (isopropylamino) ethanol, 6.5% 2-aminoethanol, and 17.0% methyl isobutyl ketone. By-produced in large quantities, it was found that the yield of 2- (isopropylamino) ethanol was significantly reduced compared to the experimental example (yield 94 to 95%) of Non-Patent Document 1 (Comparative Example 1 described later). ).
本発明は、メチルイソブチルケトンの副生を抑制し、大スケール反応でも収率よく２−（イソプロピルアミノ）エタノールを製造する方法を提供することを課題とする。 An object of the present invention is to provide a method for producing 2- (isopropylamino) ethanol with high yield even in a large-scale reaction by suppressing the by-production of methyl isobutyl ketone.
本発明者は、上述の大スケール反応を想定した実験におけるメチルイソブチルケトンの大量副生の原因について検討を行った。その結果、想定実験では、アセトン及び２−アミノエタノールをオートクレーブに仕込んだ１時間後に水素を導入、昇温し反応を行ったため、その１時間の間にオートクレーブに仕込まれたアセトン同士の２分子縮合が生じることによって、メチルイソブチルケトンが大量に副生したものと推察した。かかる推察に基づいて、上記の課題を解決すべく本発明者が鋭意検討した結果、アセトンを反応系内に供給しながら反応を実施することによって、アセトン同士の２分子縮合によるメチルイソブチルケトンの副生が抑制できるため、２−（イソプロピルアミノ）エタノールを大スケール反応でも収率よく製造できる方法を見出し、本発明を完成するに至った。 The present inventor examined the cause of a large amount of methyl isobutyl ketone as a by-product in the experiment assuming the above-described large-scale reaction. As a result, in the assumed experiment, hydrogen was introduced and heated for 1 hour after acetone and 2-aminoethanol were charged into the autoclave, so that the bimolecular condensation of acetone charged in the autoclave during that 1 hour was performed. It was speculated that a large amount of methyl isobutyl ketone was produced as a by-product. As a result of intensive studies by the present inventor to solve the above problems based on such inference, by carrying out the reaction while supplying acetone into the reaction system, a secondary of methyl isobutyl ketone by bimolecular condensation between acetones is obtained. Since the raw material can be suppressed, a method for producing 2- (isopropylamino) ethanol with a high yield even in a large scale reaction has been found, and the present invention has been completed.
即ち本発明は、水素化触媒の存在下に、アセトンを２−アミノエタノール及び水素と反応させて２−（イソプロピルアミノ）エタノールを製造するにあたり、アセトンを反応系内に供給しながら反応させることを特徴とする２−（イソプロピルアミノ）エタノールの製造方法に関する。 That is, in the present invention, in the production of 2- (isopropylamino) ethanol by reacting acetone with 2-aminoethanol and hydrogen in the presence of a hydrogenation catalyst, the reaction is performed while supplying acetone into the reaction system. The present invention relates to a method for producing 2- (isopropylamino) ethanol, which is characterized.
本発明の製造方法によれば、原料の仕込みに時間のかかる大スケール反応においてもメチルイソブチルケトンの副生を抑制できるため、本発明は、２−（イソプロピルアミノ）エタノールを大スケールで収率よく製造することができる方法である。よって、当該製造方法は工業的に有益なものである。 According to the production method of the present invention, since the by-production of methyl isobutyl ketone can be suppressed even in a large-scale reaction that takes time to charge raw materials, the present invention can produce 2- (isopropylamino) ethanol on a large scale with a high yield. It is a method that can be manufactured. Therefore, the manufacturing method is industrially useful.
本発明の製造方法は、水素化触媒の存在下にアセトンを２−アミノエタノール及び水素と反応させるものであり、反応系内にアセトンを供給しながら反応を行う。このようにすれば、メチルイソブチルケトンの副生が抑制できるため、２−（イソプロピルアミノ）エタノールを大スケールで収率よく製造することができる。 In the production method of the present invention, acetone is reacted with 2-aminoethanol and hydrogen in the presence of a hydrogenation catalyst, and the reaction is carried out while supplying acetone into the reaction system. In this way, since the by-product of methyl isobutyl ketone can be suppressed, 2- (isopropylamino) ethanol can be produced on a large scale with good yield.
本発明の反応は、通常、オートクレーブに予め水素化触媒、２−アミノエタノール及び必要に応じて溶媒を仕込み、水素を導入して所定の水素圧にした後、所定の反応温度に昇温し、アセトンをオートクレーブに所定の速度で連続的又は断続的に供給しながら行う。水素は反応の進行とともに消費されるので適宜供給しながら反応を実施する。 In the reaction of the present invention, usually, a hydrogenation catalyst, 2-aminoethanol and, if necessary, a solvent are charged in an autoclave in advance, hydrogen is introduced to a predetermined hydrogen pressure, and then the temperature is increased to a predetermined reaction temperature. Acetone is supplied continuously or intermittently to the autoclave at a predetermined rate. Since hydrogen is consumed with the progress of the reaction, the reaction is carried out while appropriately supplying it.
アセトンの使用量は、２−アミノエタノール１モルに対して、通常１．０モル以上、好ましくは１．０〜２．０モルである。アセトンの供給速度は、反応スケール等により適宜決定すればよいが、水素化触媒１ｇ及び１時間当たりの供給速度として、通常２０．０ｇ／（ｈｒ・ｇ−ｃａｔ）以下、好ましくは２．０〜１０．０ｇ／（ｈｒ・ｇ−ｃａｔ）である。 The usage-amount of acetone is 1.0 mol or more normally with respect to 1 mol of 2-aminoethanol, Preferably it is 1.0-2.0 mol. The supply rate of acetone may be appropriately determined depending on the reaction scale and the like, but the supply rate per 1 g of hydrogenation catalyst and 1 hour is usually 20.0 g / (hr · g-cat) or less, preferably 2.0 to 10.0 g / (hr · g-cat).
２−アミノエタノールは、そのまま用いても良いし、水溶液或いは有機溶媒溶液として用いることもできる。水溶液或いは有機溶媒溶液として用いる場合、その濃度は特に制限されず、反応スケールにより適宜決定すればよい。 2-aminoethanol may be used as it is, or as an aqueous solution or an organic solvent solution. When used as an aqueous solution or an organic solvent solution, the concentration is not particularly limited, and may be appropriately determined depending on the reaction scale.
水素化触媒としては、公知の水素化触媒を用いることができ、例えば、白金触媒（例えば、白金−アルミナ触媒、白金−カーボン触媒）、パラジウム触媒（例えば、パラジウム−カーボン触媒）等の貴金属触媒、還元ニッケル、これを安定化処理したもの（いわゆる、安定化ニッケル）、ラネーニッケル等のニッケル触媒、還元コバルト、ラネーコバルト等のコバルト触媒等が挙げられる。水素化触媒の使用量は、２−アミノエタノール１重量部に対して、通常０．００１〜０．２重量部、好ましくは０．０１〜０．１重量部である。 As the hydrogenation catalyst, a known hydrogenation catalyst can be used. For example, a noble metal catalyst such as a platinum catalyst (for example, a platinum-alumina catalyst, a platinum-carbon catalyst), a palladium catalyst (for example, a palladium-carbon catalyst), Examples thereof include reduced nickel, stabilized nickel (so-called stabilized nickel), nickel catalyst such as Raney nickel, cobalt catalyst such as reduced cobalt and Raney cobalt, and the like. The usage-amount of a hydrogenation catalyst is 0.001-0.2 weight part normally with respect to 1 weight part of 2-aminoethanol, Preferably it is 0.01-0.1 weight part.
本発明の製造方法では、必要に応じて溶媒を用いることもできる。溶媒としては、ケトン或いはアミンに対し不活性な溶媒であれば特に制限されず、例えばメタノール、エタノール等のアルコール系溶媒、ジエチルエーテル、テトラヒドロフラン、ジオキサン、ジメトキシエタン等のエーテル系溶媒、トルエン、キシレン等の芳香族炭化水素系溶媒、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素系溶媒、水、或いはこれらの混合溶媒が挙げられる。溶媒の使用量は特に制限されないが、２−アミノエタノール１重量部に対して、通常２．０重量部以下、好ましくは０．２〜１．０重量部である。- In the production method of the present invention, a solvent can be used as necessary. The solvent is not particularly limited as long as it is inert to ketones or amines. For example, alcohol solvents such as methanol and ethanol, ether solvents such as diethyl ether, tetrahydrofuran, dioxane and dimethoxyethane, toluene, xylene and the like And aromatic hydrocarbon solvents such as hexane, heptane, and octane, water, or a mixed solvent thereof. Although the usage-amount of a solvent is not restrict | limited in particular, It is 2.0 weight part or less normally with respect to 1 weight part of 2-aminoethanol, Preferably it is 0.2-1.0 weight part. -
反応温度は、通常５０〜２００℃、好ましくは１１０〜１５０℃である。また、反応における水素圧は、通常１．０〜１０．０ＭＰaであり、好ましくは３．０〜６．０ＭＰａである。反応による水素の消費に応じて水素を導入しながら上記水素圧に保ち、上記反応温度にて反応を行う。 The reaction temperature is usually 50 to 200 ° C, preferably 110 to 150 ° C. Further, the hydrogen pressure in the reaction is usually 1.0 to 10.0 MPa, preferably 3.0 to 6.0 MPa. The reaction is carried out at the reaction temperature while maintaining the hydrogen pressure while introducing hydrogen according to the consumption of hydrogen by the reaction.
反応終了後、得られた反応混合物を濾過して触媒を濾別した後、蒸留等の所望の分離操作により１−（イソプロピルアミノ）エタノールを得ることができる。 After completion of the reaction, the resulting reaction mixture is filtered to remove the catalyst, and then 1- (isopropylamino) ethanol can be obtained by a desired separation operation such as distillation.
以下、実施例により本発明をさらに具体的に説明するが、本発明はそれらの実施例に限定されるものではない。なお、下記の実施例におけるガスクロマトグラフィー（以下、ＧＣという。）分析の条件は次の通りであり、各化合物の含有量は面積百分率法により算出し、その含有量をもとに２−（イソプロピルアミノ）エタノールの収率を算出した。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. The conditions of gas chromatography (hereinafter referred to as GC) analysis in the following examples are as follows, and the content of each compound is calculated by the area percentage method, and 2- ( The yield of isopropylamino) ethanol was calculated.
［ＧＣ分析条件］
カラム；Ｊ＆Ｗ社製ＤＢ−５、長さ３０ｍ、内径０．２５ｍｍ、膜厚さ０．２５μｍ
キャリアガス；ヘリウム
カラム温度；４０℃から２８０℃に５℃／ｍｉｎで昇温
検出器；ＦＩＤ
検出器温度；３００℃
注入口温度；２５０℃
分析時間；３０分
スプリット比；５０／１
[GC analysis conditions]
Column: DB-5 manufactured by J & W, length 30 m, inner diameter 0.25 mm, film thickness 0.25 μm
Carrier gas; helium Column temperature; temperature rise from 40 ° C to 280 ° C at 5 ° C / min Detector; FID
Detector temperature: 300 ° C
Inlet temperature: 250 ° C
Analysis time: 30 minutes Split ratio: 50/1
実施例１
オートクレーブに、２−アミノエタノール２３３ｇ（３．８１モル）、５０重量％含水５重量％パラジウム−カーボン１１．７ｇ（２−アミノエタノールに対して５重量％）及びメタノール１１５ｇを仕込み、水素圧を４．５ＭＰａとして、１３０℃に昇温した。同温度、同水素圧下でオートクレーブへの水素の導入及び攪拌をしながら、且つ高圧定量ポンプによりアセトン２６３ｇ（４．５２モル）を４時間かけてオートクレーブに供給しながら反応を行った。このときのアセトンの供給速度は５．９ｇ／（ｈｒ・ｇ−ｃａｔ）であった。その後、同温度、同水素圧下でオートクレーブへの水素の導入しながら３時間撹拌し、反応液の冷却後、触媒を濾過し、濾液を得た。得られた濾液をＧＣ分析した結果、１−（イソプロピルアミノ）エタノール７９．２％、２−アミノエタノール不検出、アセトン０．９％及びメチルイソブチルケトン２．８％を含有しており、１−（イソプロピルアミノ）エタノールの収率は８７％（２−アミノエタノール基準）であった。
Example 1
An autoclave was charged with 233 g (3.81 mol) of 2-aminoethanol, 11.7 g of 50 wt% water-containing 5 wt% palladium-carbon (5 wt% based on 2-aminoethanol) and 115 g of methanol, and the hydrogen pressure was adjusted to 4 The temperature was raised to 130 ° C. at 5 MPa. The reaction was carried out while introducing and stirring hydrogen into the autoclave at the same temperature and under the same hydrogen pressure, and supplying 263 g (4.52 mol) of acetone to the autoclave with a high-pressure metering pump over 4 hours. The supply rate of acetone at this time was 5.9 g / (hr · g-cat). Thereafter, the mixture was stirred for 3 hours while introducing hydrogen into the autoclave at the same temperature and under the same hydrogen pressure, and after cooling the reaction solution, the catalyst was filtered to obtain a filtrate. As a result of GC analysis of the resulting filtrate, it contained 79.2% 1- (isopropylamino) ethanol, no 2-aminoethanol detected, 0.9% acetone and 2.8% methyl isobutyl ketone, The yield of (isopropylamino) ethanol was 87% (based on 2-aminoethanol).
比較例１
オートクレーブに、２−アミノエタノール２３３ｇ（３．８１モル）、５０重量％含水５重量％パラジウム−カーボン１１．７ｇ（２−アミノエタノールに対して５重量％）、メタノール１１５ｇ及びアセトン２６３ｇ（４．５２モル）を仕込み、１時間放置後に水素圧を４．５ＭＰａとして、１３０℃に昇温した。同温度、同水素圧下でオートクレーブへの水素の導入及び攪拌をしながら反応を行った。反応液の冷却後、触媒を濾過し、濾液を得た。得られた濾液をＧＣ分析した結果、１−（イソプロピルアミノ）エタノール５２．９％、２−アミノエタノール６．５％、アセトン不検出及びメチルイソブチルケトン１７．０％を含有しており、１−（イソプロピルアミノ）エタノールの収率は５３％（２−アミノエタノール基準）であった。
Comparative Example 1
In an autoclave, 233 g (3.81 mol) of 2-aminoethanol, 11.7 g of 50 wt% water-containing 5 wt% palladium-carbon (5 wt% based on 2-aminoethanol), 115 g of methanol and 263 g of acetone (4.52 The hydrogen pressure was 4.5 MPa and the temperature was raised to 130 ° C. The reaction was carried out while introducing and stirring hydrogen into the autoclave under the same temperature and hydrogen pressure. After cooling the reaction solution, the catalyst was filtered to obtain a filtrate. As a result of GC analysis of the obtained filtrate, 1- (isopropylamino) ethanol 52.9%, 2-aminoethanol 6.5%, acetone not detected and methyl isobutyl ketone 17.0% were contained. The yield of (isopropylamino) ethanol was 53% (based on 2-aminoethanol).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008011017A JP5289783B2 (en) | 2008-01-22 | 2008-01-22 | Method for producing 2- (isopropylamino) ethanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008011017A JP5289783B2 (en) | 2008-01-22 | 2008-01-22 | Method for producing 2- (isopropylamino) ethanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009173553A JP2009173553A (en) | 2009-08-06 |
| JP5289783B2 true JP5289783B2 (en) | 2013-09-11 |
Family
ID=41029065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008011017A Active JP5289783B2 (en) | 2008-01-22 | 2008-01-22 | Method for producing 2- (isopropylamino) ethanol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP5289783B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2947265B1 (en) | 2009-06-25 | 2011-08-05 | Arkema France | PROCESS FOR THE PREPARATION OF ALKYLALCANOLAMINES |
| US9102587B2 (en) | 2012-07-20 | 2015-08-11 | Koei Chemical Company, Limited | Method for producing 2-(isopropylamino)ethanol |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55100343A (en) * | 1979-01-22 | 1980-07-31 | Uop Inc | Manufacture of n*n**dialkylphenylenediamine |
| JPS58194843A (en) * | 1982-05-10 | 1983-11-12 | Sumitomo Chem Co Ltd | Preparation of n-alkyl-n'-phenyl-p-phenylenediamine |
| EP0309980A1 (en) * | 1987-10-02 | 1989-04-05 | The B.F. Goodrich Company | Alkylated polyalkylene polyamines and process for selective alkylation |
| JPH0761989B2 (en) * | 1989-11-10 | 1995-07-05 | 住友化学工業株式会社 | Method for producing N-alkylaminophenols |
| US6232494B1 (en) * | 1998-02-12 | 2001-05-15 | Monsanto Company | Process for the preparation of N-(phosphonomethyl)glycine by oxidizing N-substituted N-(phosphonomethyl)glycine |
| JP2000344699A (en) * | 1999-06-01 | 2000-12-12 | Mitsui Chemicals Inc | Production of bisphenol a |
| US20040015016A1 (en) * | 2002-07-22 | 2004-01-22 | Huntsman Petrochemical Corporation | Preparation of secondary amines |
-
2008
- 2008-01-22 JP JP2008011017A patent/JP5289783B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009173553A (en) | 2009-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2925046A1 (en) | PROCESS FOR OBTAINING ALCOHOL FROM ALDEHYDE | |
| EP3763696A1 (en) | Production method for gamma, delta-unsaturated alcohols | |
| EP2017248A1 (en) | Method for production of 3-methyl-1,5-pentanediol | |
| WO2019240009A1 (en) | Method for producing 1,3-butylene glycol | |
| US9475786B2 (en) | Method for synthesising 2,5-di(hydroxymethyl)furan and 2,5-di(hydroxymethyl)tetrahydrofuran by selective hydrogenation of furan-2,5-dialdehyde | |
| JP5289783B2 (en) | Method for producing 2- (isopropylamino) ethanol | |
| EP3696172B1 (en) | Method for producing 2,5-bis (aminomethyl) tetrahydrofuran | |
| JP2008063335A (en) | Method for producing 1,2-diol from carbonyl compound | |
| EP2699538B1 (en) | Process for the preparation of alkyldiamines | |
| EP3696173B1 (en) | Method for producing 2,5-bis(aminomethyl) tetrahydrofuran | |
| JP4743960B2 (en) | Method for producing 3-amino-1-propanol | |
| FR2480743A1 (en) | PROCESS FOR THE PREPARATION OF OXYGEN COMPOUNDS | |
| JP5028730B2 (en) | Process for producing 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol | |
| JP2009040750A (en) | Method for producing tertiary amine | |
| JP4200704B2 (en) | Method for producing fluorinated benzonitrile | |
| US9029576B2 (en) | 5-sec-butyl-2-(2-4-dimethyl-cyclohex-3-enyl)-5-methyl-[1,3]dioxane and process for making the same | |
| JPH08109170A (en) | Method for producing hexahydropyridazine | |
| JP2004131439A (en) | A method for producing a 2,5-disubstituted cyclopentanone compound and a 2,5-disubstituted cyclopentanol compound. | |
| JP2015227293A (en) | Production method of 2,3-dihalogenoaniline | |
| JP5512202B2 (en) | Process for producing β, β-dimethyl-ε-caprolactam | |
| RU2201417C2 (en) | Method of preparing n,n-dimethyl(3,5-di-tert-butyl-4-hydroxybenzyl)amine | |
| JP4386977B2 (en) | Method for producing ketones methylated at α-position | |
| Alvares et al. | Amino compounds and benzimidazoles derived from trifluralin and flumetralin | |
| JP2001302650A (en) | Production method of epoxycyclododecane | |
| EP3339300A1 (en) | Method for preparing thienyl alanine having optical activity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110120 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20120712 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120731 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130604 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130605 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5289783 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |