EP1937625A1 - Verfahren zur herstellung von aminodiglykol (adg) und morpholin - Google Patents
Verfahren zur herstellung von aminodiglykol (adg) und morpholinInfo
- Publication number
- EP1937625A1 EP1937625A1 EP06793775A EP06793775A EP1937625A1 EP 1937625 A1 EP1937625 A1 EP 1937625A1 EP 06793775 A EP06793775 A EP 06793775A EP 06793775 A EP06793775 A EP 06793775A EP 1937625 A1 EP1937625 A1 EP 1937625A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- catalyst
- reaction
- morpholine
- adg
- reactor
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Definitions
- the present invention relates to a process for the preparation of aminodiglycol (ADG) and morpholine by reaction of diethylene glycol (DEG) of the formula
- Aminodiglycol (ADG) and morpholine find inter alia. Use as solvents, stabilizers, for the synthesis of chelating agents, synthetic resins, pharmaceuticals, inhibitors and surfactants.
- ADG aminodiglycol
- morpholine For the preparation of aminodiglycol (ADG) and morpholine numerous methods are described in the literature.
- EP-A-36331 and US-A-4,647,663 describe a process for the preparation of morpholine and morpholine derivatives by reacting a dialkylene glycol with ammonia in the presence of H2 and a hydrogenation catalyst in a trickle bed reactor.
- Khim. Prom-st. (Moscow) (1 1), 653-5 (1982) (Chem. Abstr. 98: 91383q) describes the preparation of morpholine by gas-phase cycloamination of diethylene glycol with ammonia in the presence of H2 and a Cu, Co or Ni. Cr2 ⁇ 3 catalyst.
- a parallel German patent application with the same filing date (BASF AG) relates to a process for the preparation of ethylene amines by reacting ethylenediamine (EDA) in the presence of specific heterogeneous catalyst molding.
- a parallel German patent application with the same filing date (BASF AG) relates to a process for the preparation of ethylene amines by reacting monoethanolamine (MEOA) with ammonia in the presence of specific heterogeneous catalyst shaped bodies.
- MEOA monoethanolamine
- ADG aminodiglycol
- the method is intended in particular the non-cyclic amine ADG of the formula
- the proportion of ADG to morpholine in the product mix should be increased compared to the prior art, especially at a high DEG conversion, in particular at a DEG conversion of greater than 85%.
- ADG aminodiglycol
- DEG diethylene glycol
- the volume can also be calculated using the following method, where:
- the surface can also be calculated theoretically by the following method, in which one defines an envelope of the molding, the curve radii max. 5 ⁇ m (in order not to take the inner pore surface into the pores by "penetrating" the envelope) and which touches the mold body as intimately as possible (no cut surface with the support) and then creates a vacuum from the inside, so that the film lays as close as possible to the molding.
- the diethylene glycol (DEG) required as starting material can be prepared by known processes, for example by reacting ethylene oxide (EO) with H 2 O or EO with monoethylene glycol.
- EO ethylene oxide
- the reaction according to the invention is generally carried out at an absolute pressure in the range of 1-260 bar, preferably 100-250 bar, in particular at 150-240 bar, especially at 175-225 bar, and generally at elevated temperature, e.g. in the temperature range of 100-300 ° C, in particular 130-240 ° C, preferably at 175-225 ° C.
- the ratio of morpholine: ADG is determined in the process according to the invention in particular by the DEG conversion and the molar ratio NH 3: DEG.
- the catalysts are preferably used in the form of catalysts which either consist only of catalytically active material and optionally a molding assistant (such as graphite or stearic acid), or the catalytically active components on a substantially inactive Su- material.
- a molding assistant such as graphite or stearic acid
- the catalytically active composition can be introduced into the reaction vessel as a powder or as a grit or, after milling, mixing with molding aids, shaping and heat treatment, as a shaped catalyst body - for example as tablets, spheres, rings, extrudates (eg strands, tubes) - in be introduced into the reactor.
- the concentration data (in% by weight) of the components of the catalyst are in each case - unless stated otherwise - on the catalytically active composition of the catalyst prepared before treatment with hydrogen.
- the catalytically active mass of the catalyst is defined as the sum of the masses of the catalytically active constituents and contains, prior to treatment with hydrogen, preferably substantially the catalytically active constituents oxygen-containing compounds of aluminum and / or zirconium, copper, nickel and cobalt.
- the sum of the o.g. catalytically active constituents, calculated as Al 2 O 3, ZrO 2, CuO, NiO and CoO, in the catalytically active composition prior to treatment with hydrogen is for example 70 to 100 wt .-%, preferably 80 to 100 wt .-%, particularly preferably 90 to 100 wt .-%, in particular 95 to 100 wt .-%, most preferably> 99 to 100 wt .-%.
- Preferred heterogeneous catalysts in the process according to the invention contain in their catalytically active composition prior to treatment with hydrogen
- oxygen-containing compounds of nickel calculated as NiO, wherein preferably the molar ratio of nickel to copper greater than 1, in particular greater than 1, 2, very particularly 1, 8 to 8.5, and
- the oxygen-containing compounds of copper, nickel and cobalt, each calculated as CuO, NiO and CoO, of the preferred catalysts are generally generally in amounts of 15 to 80 wt .-%, preferably 35 to 80 wt .-%, particularly preferred 60 to 78 wt .-%, in the catalytically active composition (before treatment with Hydrogen), wherein particularly preferably the molar ratio of nickel to copper is greater than 1.
- catalysts comprising cobalt, nickel and copper and alumina having a metal content of 5 to 80 wt .-%, in particular 10 to 30 wt .-%, based on the total catalyst, wherein the catalysts, calculated on the metal content, contain from 70 to 95% by weight of a mixture of cobalt and nickel and from 5 to 30% by weight of copper, and wherein the weight ratio of cobalt to nickel is 4: 1 to 1: 4, in particular 2: 1 to 1: 2, is, for example, the catalyst used in the examples there with the composition 10 wt .-% CoO, 10 wt .-% NiO and 4 wt .-% CuO to Al 2 O 3 ,
- EP-A-382 049 disclosed or correspondingly preparable catalysts whose catalytically active composition prior to treatment with hydrogen 20 to 85 wt .-%, preferably 70 to 80 wt .-%, ZrO 2 and / or AI 2 O 3 , 1 to 30 wt .-%, preferably 1 to 10 wt .-%, CuO, and in each case 1 to 40 wt .-%, preferably 5 to 20 wt .-%, CoO and NiO contains, for example, those in loc. cit. 76 wt% Zr calculated as ZrO 2 , 4 wt% Cu, calculated as CuO, 10 wt% Co, calculated as CoO, and 10 wt% Ni, on page 6 calculated as NiO,
- EP-A-963 975 and EP-A-1 106 600 both BASF AG, whose catalytically active composition before treatment with hydrogen contains from 22 to 40% by weight ZrO 2 ,
- Particularly preferred catalysts in the process according to the invention contain no chromium (Cr).
- the catalyst is preferably at a temperature in the range of 100 to 500 ° C, especially 150 to 400 ° C, especially 180 to 300 ° C, over a period of at least 25 min., Particularly at least 60 min., A hydrogen - exposed to a living atmosphere or a hydrogen atmosphere.
- the period of activation of the catalyst may be up to 1 h, especially up to 12 h, in particular up to 24 h.
- At least a portion of the oxygen-containing metal compounds present in the catalysts is reduced to the corresponding metals, so that they are present together with the various oxygen compounds in the active form of the catalyst.
- the catalyst used preferably has a bulk density in the range of 0.6 to 1.2 kg / l.
- ADG selectivities are obtained when the catalyst is used in the form of small shaped articles.
- a small shaped body are meant those whose diameter in spherical shape in each case below 3 mm, in particular below 2.5 mm, e.g. in the range of 1 to 2 mm.
- a small shaped body those are also meant whose diameter in strand form (strand length >> strand diameter) or their height in the case of tablet form (tablet diameter >> tablet height) is in each case below 3 mm, in particular below 2.5 mm, e.g. in the range of 1 to 2 mm.
- the catalyst is preferably present as a fixed bed in a reactor.
- the reactor is preferably a tube reactor or tube bundle reactor.
- the reaction of DEG in the reactor preferably takes place in a straight pass.
- the catalyst bed is preferably surrounded by an inert material both at the inlet and at the outlet of the reactor.
- an inert material e.g. Pall rings
- balls of an inert material e.g., ceramic, steatite, aluminum
- an inert material e.g., ceramic, steatite, aluminum
- the reactor can be operated in both bottom and trickle mode.
- a liquid distributor for the reactor feed is preferably used at the inlet of the reactor.
- catalyst activity are preferably 0.01 to 1, 00 wt .-%, especially 0.20 to 0.60 wt .-%, hydrogen (based on the reactor feed DEG + NH3) in the reactor.
- WHSV weight hourly space velocity
- S selectivities
- ADG and morpholine will be in a weight ratio ADG: morpholine greater than 0.20, especially greater than 0.24, especially greater than 0.27, e.g. in the range of 0.28 to 0.36.
- the workup of the product streams obtained in the process according to the invention which contain, in particular, the particularly desired ADG but also morpholine, morpholine derivatives, higher polyalkylamines and unreacted DEG, can be carried out by distillation processes known to the person skilled in the art.
- the distillation columns required for the pure distillation of the individual products, above all the particularly desired ADGs and also morpholines, can be designed by methods familiar to the person skilled in the art (eg number of separation stages, reflux ratio, etc.).
- the separation of the reaction product resulting from the reaction takes place in particular by multi-stage distillation.
- the separation of the reaction effluent resulting from the reaction into two separation sequences is carried out by multistage distillation, wherein in the first separation sequence ammonia and optionally present hydrogen are separated off and in the second separation sequence a separation into unreacted DEG and ADG, morpholine, Morpholine derivatives and higher polyalkylamines takes place.
- an aqueous solution of nickel nitrate, copper nitrate, cobalt nitrate and zirconium acetate was added simultaneously with a 20% aqueous solution of sodium carbonate into a stirring vessel at a temperature of 70 ° C. in a constant flow so that the pH was within a range of 5.5 - 6.0 was maintained.
- the metal salt solution and the sodium carbonate solution was stirred for a further hour at 70 ° C and then the pH was increased by the addition of some sodium carbonate solution to a value of 7.4.
- the suspension obtained was filtered and the filter cake was washed with demineralized water. Thereafter, the filter cake was dried at a temperature of 200 ° C in a drying oven or a spray dryer. The hydroxide carbonate mixture obtained in this way was then tempered at a temperature of 400 ° C over a period of 2 hours.
- the catalyst powder thus obtained had the composition:
- the catalyst powder of A1 was mixed with 2% by weight of graphite and shaped into 5 ⁇ 3 mm tablets. After tabletting, the tablets were post-calcined for 2 h at 350 ° C in a muffle furnace. Before installation in the test reactor, it was reduced and then passivated. For the reduction, the catalyst was heated in a hydrogen / nitrogen stream to temperatures between 100 and 200 ° C. This temperature was maintained until no more water has formed. It was then heated to a final temperature of 280 ° C and held this temperature for 90-120 hours. The catalyst was cooled to room temperature under a nitrogen stream and then passivated with a dilute oxygen stream. During passivation, care was taken that the temperature in the reactor did not rise above 50 ° C at any point.
- the catalyst powder of A1 was mixed with 2% by weight of graphite and shaped into 1.5 ⁇ 2 mm tablets.
- the post-calcination, reduction and passivation was carried out as described in A2.
- Example 1 small shaped article (catalyst B), according to the invention
- ADG 31, 4% by weight of morpholine: 32.1% by weight
- ADG 28.7% by weight of morpholine: 43.7% by weight
- ADG 20.6% by weight of morpholine: 60.2% by weight
- Morpholine 46.9% by weight
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06793775A EP1937625A1 (de) | 2005-09-30 | 2006-09-25 | Verfahren zur herstellung von aminodiglykol (adg) und morpholin |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005047458A DE102005047458A1 (de) | 2005-09-30 | 2005-09-30 | Verfahren zur Herstellung von Aminodiglykol (ADG) und Morpholin |
EP06101339 | 2006-02-06 | ||
EP06793775A EP1937625A1 (de) | 2005-09-30 | 2006-09-25 | Verfahren zur herstellung von aminodiglykol (adg) und morpholin |
PCT/EP2006/066665 WO2007036496A1 (de) | 2005-09-30 | 2006-09-25 | Verfahren zur herstellung von aminodiglykol (adg) und morpholin |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1937625A1 true EP1937625A1 (de) | 2008-07-02 |
Family
ID=37648393
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06793775A Withdrawn EP1937625A1 (de) | 2005-09-30 | 2006-09-25 | Verfahren zur herstellung von aminodiglykol (adg) und morpholin |
Country Status (5)
Country | Link |
---|---|
US (1) | US20080255351A1 (ja) |
EP (1) | EP1937625A1 (ja) |
JP (1) | JP2009510018A (ja) |
DE (1) | DE102005047458A1 (ja) |
WO (1) | WO2007036496A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023135035A1 (en) | 2022-01-14 | 2023-07-20 | Basf Se | Method for the manufacture or conversion of alkanolamines |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101273007B (zh) | 2005-09-30 | 2012-02-01 | 巴斯夫欧洲公司 | 制备亚乙基胺化合物的方法 |
US7696384B2 (en) | 2005-09-30 | 2010-04-13 | Basf Se | Process for producing ethyleneamines |
JP5124486B2 (ja) * | 2006-02-14 | 2013-01-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 触媒の存在でモノエチレングリコール及びアンモニアの水素化アミノ化によるエチレンアミン及びエタノールアミンの製造方法 |
JP4938802B2 (ja) * | 2006-02-14 | 2012-05-23 | ビーエーエスエフ ソシエタス・ヨーロピア | モノエチレングリコール(meg)からのエチレンアミン及びエタノールアミンの製造方法 |
EP2061747B1 (de) | 2006-07-14 | 2013-04-17 | Basf Se | Verfahren zur herstellung eines amins |
WO2008006754A1 (de) | 2006-07-14 | 2008-01-17 | Basf Se | Verfahren zur herstellung eines amins |
US7754922B2 (en) | 2006-07-14 | 2010-07-13 | Basf Se | Process for preparing amines and zirconium dioxide- and nickel-containing catalysts for use therein |
JP5637684B2 (ja) * | 2006-07-14 | 2014-12-10 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | アミンの製造方法 |
EP2043779A1 (de) * | 2006-07-14 | 2009-04-08 | Basf Se | Verfahren zur herstellung eines amins |
CN101484105B (zh) * | 2006-07-20 | 2012-04-18 | Sca卫生产品股份公司 | 用于形成气流成网吸收芯体的设备和方法 |
WO2008037589A1 (de) | 2006-09-28 | 2008-04-03 | Basf Se | Verfahren zur kontinuierlichen destillativen auftrennung von gemischen enthaltend morpholin (mo), monoaminodiglykol (adg), ammoniak und wasser |
DE502007003040D1 (de) | 2006-09-28 | 2010-04-15 | Basf Se | Verfahren zur kontinuierlichen destillativen auftrennung von gemischen enthaltend morpholin (mo), monoaminodiglykol (adg), ammoniak und wasser |
CN101516830B (zh) | 2006-09-28 | 2013-11-27 | 巴斯夫欧洲公司 | 通过蒸馏连续分离含有吗啉(mo)、单氨基二甘醇(adg)、氨和水的混合物的方法 |
CN101528665B (zh) * | 2006-09-28 | 2012-09-19 | 巴斯夫欧洲公司 | 制备电子级2-(2-氨基乙氧基)乙醇的方法 |
JP5528349B2 (ja) * | 2007-12-21 | 2014-06-25 | ビーエーエスエフ ソシエタス・ヨーロピア | アミンの製造方法 |
WO2009080510A1 (de) * | 2007-12-21 | 2009-07-02 | Basf Se | Verfahren zur herstellung eines amins |
EP2225027B1 (de) * | 2007-12-21 | 2012-05-23 | Basf Se | Verfahren zur herstellung eines amins |
ATE553844T1 (de) * | 2007-12-21 | 2012-05-15 | Basf Se | Verfahren zur herstellung eines amins |
RU2481887C2 (ru) * | 2008-01-25 | 2013-05-20 | Басф Се | Реактор для осуществления реакций под высоким давлением, способ пуска реактора и способ осуществления реакции |
EP2346602B1 (de) * | 2008-09-19 | 2014-03-19 | Basf Se | Verfahren zur kontinuierlichen herstellung eines amins unter verwendung eines aluminium-kupfer-katalysators |
WO2011042916A1 (en) | 2009-10-06 | 2011-04-14 | Alkyl Amines Chemicals Ltd | A process for the preparation of 2-(2-aminoethoxy) ethanol (2aee) and morpholine with 2aee: morpholine >3 |
CN102639231B (zh) * | 2009-12-03 | 2014-12-10 | 巴斯夫欧洲公司 | 制备胺的催化剂和方法 |
CN102781571B (zh) * | 2009-12-03 | 2015-06-17 | 巴斯夫欧洲公司 | 用于制备胺的催化剂和方法 |
CN102933549B (zh) | 2010-06-15 | 2015-08-12 | 巴斯夫欧洲公司 | 制备环状叔甲基胺的方法 |
US8637668B2 (en) | 2010-06-15 | 2014-01-28 | Basf Se | Process for preparing a cyclic tertiary methylamine |
WO2012049101A1 (de) | 2010-10-14 | 2012-04-19 | Basf Se | Verfahren zur herstellung eines zyklischen tertiären amins |
US8933223B2 (en) | 2010-10-14 | 2015-01-13 | Basf Se | Process for preparing a cyclic tertiary amine |
US8884015B2 (en) | 2012-06-01 | 2014-11-11 | Basf Se | Process for the preparation of a mono-N-alkypiperazine |
CN104364243B (zh) | 2012-06-01 | 2017-03-08 | 巴斯夫欧洲公司 | 生产单‑n‑烷基哌嗪的方法 |
US8981093B2 (en) | 2012-06-06 | 2015-03-17 | Basf Se | Process for preparing piperazine |
EP3755692B1 (de) | 2018-02-22 | 2022-04-06 | Basf Se | Verfahren zur abreicherung von 2-methoxyethanol (moe) |
WO2019162121A1 (de) | 2018-02-22 | 2019-08-29 | Basf Se | Verfahren zur kontinuierlichen destillativen auftrennung von gemischen enthaltend morpholin (mo), monoaminodiglykol (adg), ammoniak, wasser und methoxyethanol (moe) |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4014933A (en) * | 1969-10-23 | 1977-03-29 | Basf Aktiengesellschaft | Production of amines from alcohols |
US4647663A (en) * | 1982-05-25 | 1987-03-03 | Air Products And Chemicals, Inc. | Synthesis of morpholine |
JPS59115746A (ja) * | 1982-12-23 | 1984-07-04 | Nippon Shokubai Kagaku Kogyo Co Ltd | モルホリン製造用触媒およびその製造法 |
US4568746A (en) * | 1982-12-29 | 1986-02-04 | Union Carbide Corporation | Catalytic preparation of diethylenetriamine |
SE461095B (sv) * | 1983-09-09 | 1990-01-08 | Berol Kemi Ab | Amineringsfoerfarande med anvaendning av en ruteniumdopad nickel och/eller kovoltkatalysator |
DE3903367A1 (de) * | 1989-02-04 | 1990-08-16 | Basf Ag | Katalysator und verfahren zur hydrierenden aminierung von alkoholen |
US5410086A (en) * | 1989-06-27 | 1995-04-25 | Burgess; Lloyd M. | Selective preparation of diethylenetriamine |
DE19645047A1 (de) * | 1996-10-31 | 1998-05-07 | Basf Ag | Katalysatoren für die Aminierung von Alkylenoxiden, Alkoholen, Aldehyden und Ketonen |
DE19826396A1 (de) | 1998-06-12 | 1999-12-16 | Basf Ag | Verfahren zur Herstellung von Aminen |
DE19859776B4 (de) * | 1998-12-23 | 2008-06-19 | Basf Se | Verfahren zur Herstellung von Aminen |
EP1106600B1 (de) * | 1999-12-06 | 2004-08-04 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Aminen |
DE10211101A1 (de) * | 2002-03-14 | 2003-09-25 | Basf Ag | Katalysatoren und Verfahren zur Herstellung von Aminen |
DE10335991A1 (de) * | 2003-08-01 | 2005-02-24 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
JP2007533603A (ja) * | 2003-08-01 | 2007-11-22 | ビーエーエスエフ アクチェンゲゼルシャフト | エチレンアミンの製造方法 |
DE10349059A1 (de) * | 2003-10-17 | 2005-05-19 | Basf Ag | Verfahren zur destillativen Auftrennung von Gemischen enthaltend Ethylenamine |
US7696384B2 (en) * | 2005-09-30 | 2010-04-13 | Basf Se | Process for producing ethyleneamines |
CN101273007B (zh) * | 2005-09-30 | 2012-02-01 | 巴斯夫欧洲公司 | 制备亚乙基胺化合物的方法 |
JP5124486B2 (ja) * | 2006-02-14 | 2013-01-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 触媒の存在でモノエチレングリコール及びアンモニアの水素化アミノ化によるエチレンアミン及びエタノールアミンの製造方法 |
-
2005
- 2005-09-30 DE DE102005047458A patent/DE102005047458A1/de not_active Withdrawn
-
2006
- 2006-09-25 JP JP2008532747A patent/JP2009510018A/ja not_active Withdrawn
- 2006-09-25 EP EP06793775A patent/EP1937625A1/de not_active Withdrawn
- 2006-09-25 US US12/088,718 patent/US20080255351A1/en not_active Abandoned
- 2006-09-25 WO PCT/EP2006/066665 patent/WO2007036496A1/de active Application Filing
Non-Patent Citations (1)
Title |
---|
See references of WO2007036496A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023135035A1 (en) | 2022-01-14 | 2023-07-20 | Basf Se | Method for the manufacture or conversion of alkanolamines |
Also Published As
Publication number | Publication date |
---|---|
JP2009510018A (ja) | 2009-03-12 |
WO2007036496A1 (de) | 2007-04-05 |
DE102005047458A1 (de) | 2007-04-12 |
US20080255351A1 (en) | 2008-10-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1937625A1 (de) | Verfahren zur herstellung von aminodiglykol (adg) und morpholin | |
EP2029520B1 (de) | Verfahren zur herstellung von ethylenaminen und ethanolaminen aus monoethylenglykol (meg) | |
EP1934165B1 (de) | Verfahren zur herstellung von ethylenaminen | |
EP1106600B1 (de) | Verfahren zur Herstellung von Aminen | |
EP1986990B1 (de) | Verfahren zur herstellung von ethylenaminen und ethanolaminen durch hydrierende aminierung von monoethylenglykol und ammoniak in gegenwart eines katalysators | |
EP2513037B1 (de) | Verfahren zur herstellung von höheren ethanolaminen | |
EP2513036B1 (de) | Umsetzung von glykolaldehyd mit einem aminierungsmittel | |
EP2465844B1 (de) | Verfahren zur Herstellung und Aufreinigung von 3-Aminopropanol | |
EP1934166B1 (de) | Verfahren zur herstellung von ethylenaminen | |
EP1035106A1 (de) | Verfahren zur Herstellung von Aminen | |
DE10261195A1 (de) | Verfahren zur Herstellung eines symmetrischen sekundären Amins | |
EP2855443B1 (de) | Verfahren zur herstellung eines mono-n-alkyl-piperazins | |
EP2632909B1 (de) | Verfahren zur herstellung von 1,4-bishydroxyethyl-piperazin | |
WO2005012223A1 (de) | Verfahren zur herstellung von ethylenaminen | |
DE102005047464A1 (de) | Verfahren zur Herstellung von Ethylenaminen | |
EP1106601B1 (de) | Verfahren zur Herstellung von Monoisopropylamin | |
WO2000047545A1 (de) | Verfahren zur racemisierung von optisch aktiven aminen | |
EP3717448B1 (de) | Verfahren zur kontinuierlichen herstellung von 1,2-propylendiamin (1,2-pda) und dimethyldiethylentriamin (dmdeta) | |
WO2010012672A2 (de) | Verfahren zur herstellung von diaminen aus lactamen | |
WO2014184048A1 (de) | Verfahren zur herstellung von n-alkyl-piperazinen | |
EP2858978A1 (de) | Verfahren zur herstellung von piperazin | |
WO2013178534A1 (de) | Verfahren zur herstellung eines mono-n-alkyl-piperazins | |
WO2014009292A1 (de) | Verfahren zur herstellung von pyrrolidin | |
DE102005052376A1 (de) | Verfahren zur Herstellung von Ethylenaminen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20080502 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR |
|
17Q | First examination report despatched |
Effective date: 20090909 |
|
18D | Application deemed to be withdrawn |
Effective date: 20110405 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
R18D | Application deemed to be withdrawn (corrected) |
Effective date: 20110302 |