Source: http://www.google.com/patents/US8197646?ie=ISO-8859-1&dq=5537618
Timestamp: 2014-07-29 01:02:48
Document Index: 367448245

Matched Legal Cases: ['art.\n33', 'art 5', 'arts 3', 'Application No. 06121427', 'art 5', 'arts 3']

Patent US8197646 - Processes for continuous fractional distillation of mixtures comprising ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign in<nobr>Advanced Patent Search</nobr>PatentsProcess for the continuous fractional distillation of mixtures including morpholine (MO), monoaminodiglycol (ADG), ammonia and water obtained by reaction of diethylene glycol (DEG) with ammonia, which includes separating off ammonia at the top of a first distillation column K10, feeding the bottoms from...http://www.google.com/patents/US8197646?utm_source=gb-gplus-sharePatent US8197646 - Processes for continuous fractional distillation of mixtures comprising morpholine, monoaminodiglycol, ammonia and waterAdvanced Patent SearchPublication numberUS8197646 B2Publication typeGrantApplication numberUS 12/443,573PCT numberPCT/EP2007/059556Publication dateJun 12, 2012Filing dateSep 12, 2007Priority dateSep 28, 2006Also published asCN101522650A, CN101522650B, DE502007003425D1, EP2079718A1, EP2079718B1, US20100084258, WO2008037589A1Publication number12443573, 443573, PCT/2007/59556, PCT/EP/2007/059556, PCT/EP/2007/59556, PCT/EP/7/059556, PCT/EP/7/59556, PCT/EP2007/059556, PCT/EP2007/59556, PCT/EP2007059556, PCT/EP200759556, PCT/EP7/059556, PCT/EP7/59556, PCT/EP7059556, PCT/EP759556, US 8197646 B2, US 8197646B2, US-B2-8197646, US8197646 B2, US8197646B2InventorsHelmut Schmidtke, Oliver Buβmann, Ralph Versch, Udo Rheude, Uwe Leyk, Manfred Julius, Martin Rudloff, Erhard HenkesOriginal AssigneeBasf SeExport CitationBiBTeX, EndNote, RefManPatent Citations (27), Non-Patent Citations (1), Referenced by (2), Classifications (18), Legal Events (2) External Links: USPTO, USPTO Assignment, EspacenetProcesses for continuous fractional distillation of mixtures comprising morpholine, monoaminodiglycol, ammonia and waterUS 8197646 B2Abstract Process for the continuous fractional distillation of mixtures including morpholine (MO), monoaminodiglycol (ADG), ammonia and water obtained by reaction of diethylene glycol (DEG) with ammonia, which includes separating off ammonia at the top of a first distillation column K10, feeding the bottoms from K10 to a second distillation column K20 in which water and organic products are separated off at the top at a temperature at the top in the range from 45 to 198� C. and a pressure in the range from 0.1 to 15 bar, feeding the bottoms from K20 to a third distillation column K30 in which MO and organic products having a boiling point of <140� C. (1.013 bar) are separated off at the top or at a side offtake and ADG and organic products having a boiling point of >190� C. (1.013 bar) are separated off at the bottom, feeding the MO including stream which is separated off at the top or at a side offtake of the column K30 to a fourth column K40 in which organic products having a boiling point of ≦128� C. (1.013 bar) are separated off at the top and MO and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom and the bottoms from K40 are fed to a fifth distillation column K55 in which MO is separated off at the top and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom.
feeding a bottom fraction from K10 to a second distillation column K20 in which water and organic products are separated off at the top at a temperature at the top in the range from 45 to 198� C. and a pressure in the range from 0.1 to 15 bar;
feeding a bottom fraction from K20 to a third distillation column K30 in which MO and organic products having a boiling point of <140� C. (1.013 bar) are separated off at the top or at a side offtake and ADG and organic products having a boiling point of >190� C. (1.013 bar) are separated off at the bottom,
feeding the MO-comprising stream which is separated off at the top or at a side offtake of the column K30 to a fourth column K40 in which organic products having a boiling point of ≦128� C. (1.013 bar) are separated off at the top and MO and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom and the bottoms from K40 are fed to a fifth distillation column K55 in which MO is separated off at the top and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom.
19. The process according to claim 1, wherein the bottoms from K30 are fed to a distillation column K60 in which organic products having a boiling point of 224.8� C. (1.013 bar) are separated off at the top and ADG and organic products having a boiling point of ≧224.8� C. (1.013 bar) are separated off at the bottom.
24. The process according to claim 19, wherein the ADG-comprising stream separated off at the bottom offtake of the column K60 is fed to a column K70 in which ADG is separated off at the top and DEG and organic products having a boiling point of ≧255� C. (1.013 bar) are separated off at the bottom.
27. The process according to claim 24, wherein the DEG-comprising stream separated off at the bottom offtake of the column K70 is fed to a column K80 in which DEG is separated off at the top and organic products having a boiling point of ≧255� C. (1.013 bar) are separated off at the bottom.
31. The process according to claim 1, wherein the bottoms from K30 are fed to a distillation column K60 which is a dividing wall column (DWC) which has a dividing wall (DW) in the longitudinal direction of the column to form an upper combined column region, a lower combined column region, an inflow part having an enrichment section and a stripping section, and also an offtake part having an enrichment section and a stripping section, with the bottoms from K30 being fed in in the upper or middle third of the inflow part, based on the number of theoretical plates of the inflow part, organic products having a boiling point of >255� C. (1.013 bar) being discharged at the bottom, organic products having a boiling point of ≦224.8� C. (1.013 bar) being discharged at the top, ADG being discharged from the column region 1 and optionally gaseous organic products having a boiling point of ≧224.8� C. (1.013 bar), e.g. DEG, being discharged from the upper or middle third of the offtake part, based on the number of theoretical plates of the offtake part.
33. The process according to claim 1, wherein the bottoms from K30 are fed to a distillation column K60 which is a dividing wall column (DWC) which has a dividing wall (DW) in the longitudinal direction of the column to form an upper combined column region, an inflow part having an enrichment section and a stripping section, and also a part, with the dividing wall DW extending to the bottom of the column and the bottoms from K30 being fed in in the upper or middle third of the inflow part, based on the number of theoretical plates of the inflow part, DEG and organic products having a boiling point of ≧224.8� C. (1.013 bar) being discharged at the bottom below the part 5, organic products having a boiling point of >255� C. (1.013 bar) being discharged at the bottom below the parts 3 and 4, organic products having a boiling point of ≦224.8� C. (1.013 bar) being discharged at the top and ADG being discharged from the middle part of the upper combined column region.
39. The process according to claim 1, wherein the mixture comprises morpholine, monoaminodiglycol, ammonia, water, N-ethylmorpholine, 1,2-ethylenediamine and an organic product having a boiling point of >224.8� C. (1.013 bar).
CROSS-REFERENCE TO RELATED APPLICATIONS This application is a national stage application, under 35 U.S.C. �371, of PCT/EP2007/059556, filed Sep. 12, 2007, which claims benefit of European Patent Application No. 06121427.6, filed Sep. 28, 2006.
BACKGROUND OF THE INVENTION Aminodiglycol (ADG) [=2-(2-aminoethoxy)ethanol=2,2′-aminoethoxyethanol, formula
Ullmann's Encyclopedia of Industrial Chemistry, 6th Edition, 2000 electronic release, Wiley-VCH Verlag, Rubrik �cyclic amines� in the chapter �aliphatic amines�, describes the synthesis of ADG and MO by amination of DEG under hydrogen pressure and in the presence of a cobalt or nickel catalyst (citations: EP-A-696 572 (BASF AG), DE-A-1 049 864) or other catalysts (citations: DE-A-3 002 342, DE-A-3 125 662 (BASF AG), U.S. Pat. No. 3,155,657).
BRIEF SUMMARY OF THE INVENTION The present invention relates to a process for the continuous fractional distillation of mixtures comprising morpholine (MO), monoaminodiglycol (ADG), ammonia and water obtained by reaction of diethylene glycol (DEG) of the formula
It was an object of the present invention to overcome a disadvantage or a number of disadvantages of the prior art and discover an improved economical process for the fractionation of mixtures comprising morpholine (MO), monoaminodiglycol (ADG), ammonia and water and possibly N-ethylmorpholine (E-MO) and possibly 1,2-ethylenediamine (EDA) and possibly organic products having a boiling point of >224.8� C. (1.013 bar). The individual organic components (amines), in particular MO and ADG and possibly E-MO, should be obtained in high purity and quality (e.g. color quality).
feeding the bottoms from K10 to a second distillation column K20 in which water and organic products are separated off at the top at a temperature at the top in the range from 45 to 198� C. and a pressure in the range from 0.1 to 15 bar,
feeding the bottoms from K20 to a third distillation column K30 in which MO and organic products having a boiling point of <140� C. (1.013 bar) are separated off at the top or at a side offtake and ADG and organic products having a boiling point of >190� C. (1.013 bar) are separated off at the bottom,
feeding the MO-comprising stream which is separated off at the top or at a side offtake of the column K30 to a fourth column K40 in which organic products having a boiling point of ≦128� C. (1.013 bar), preferably <128� C. (1.013 bar), are separated off at the top and MO and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom and feeding the bottoms of from K40 to a fifth distillation column K55 in which MO is separated off at the top and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom.
DETAILED DESCRIPTION OF THE INVENTION The products separated off at the bottom of column K55 are recirculated in their entirety or in part, preferably in their entirety, to the feed to the column K30.
The feed point of column K40 is preferably located in the middle or lower third, particularly preferably the middle third, based on the number of theoretical plates. In the column K40, organic products having a boiling point of ≦128� C. (1.013 bar) (low boilers=LB), e.g. EDA, are separated off at the top and MO and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom.
In the column K55, MO is separated off at the top and organic products having a boiling point of ≧128� C. (1.013 bar) are separated off at the bottom.
To isolate pure E-MO, the aqueous N-ethylmorpholine solution is firstly dewatered. As dewatering agent, preference is given to using sodium hydroxide, e.g. as a 40-60% strength by weight aqueous solution, particularly preferably a 50% strength by weight aqueous solution. The dewatering using the sodium hydroxide is preferably carried out continuously in an extraction column. The extraction temperature is preferably 25-60� C., particularly preferably 30-55� C. The sodium hydroxide solution is diluted to 15-35% by weight, particularly preferably 20-30% by weight, during the extraction.
In a preferred embodiment, the bottoms from K30 are fed to a distillation column K60 in which organic products having a boiling point of ≦224.8� C. (1.013 bar) are separated off at the top and ADG and organic products having a boiling point of ≧224.8� C. (1.013 bar) are separated off at the bottom.
The ADG-comprising stream separated off at the bottom offtake of the column K60 is preferably fed to a column K70 in which ADG is separated off at the top and DEG and organic products having a boiling point of ≧255� C. (1.013 bar).
The DEG-comprising stream which is separated off at the bottom offtake of the column K70 is preferably fed to a column K80 in which DEG is separated off at the top and organic products having a boiling point of ≧255� C. (1.013 bar) (high boilers=HB) are separated off at the bottom.
The dividing wall column (DWC) preferably has a dividing wall (DW) in the longitudinal direction of the column to form an upper combined column region (1), a lower combined column region (6), an inflow part (2, 4) having an enrichment section (2) and a stripping section (4), and also an offtake part (3, 5) having an enrichment section (3) and a stripping section (5), with the bottoms from K30 being fed in in the upper or middle third, particularly preferably the upper third, of the inflow part (2, 4), based on the number of theoretical plates of the inflow part, organic products having a boiling point of >255� C. (1.013 bar) being discharged at the bottom, organic products having a boiling point of ≦224.8� C. (1.013 bar) being discharged at the top, ADG being discharged from the column region 1 and optionally, in a particular embodiment preferably, gaseous organic products having a boiling point of ≧224.8� C. (1.013 bar), particularly preferably >235� C. (1.013 bar), e.g. DEG, being discharged from the upper or middle third, particularly preferably the upper third, of the offtake part (3, 5) (side offtake), based on the number of theoretical plates of the offtake part.
In a further advantageous embodiment, the dividing wall column (DWC) has a dividing wall (DW) in the longitudinal direction of the column to form an upper combined column region (1) and (2), an inflow part (3, 4) having an enrichment section (3) and a stripping section (4), and also a part (5), with the dividing wall DW extending to the bottom of the column and the bottoms from K30 being fed in in the upper or middle third, particularly preferably the upper third, of the inflow part (3, 4), based on the number of theoretical plates of the inflow part, DEG and organic products having a boiling point of ≧224.8� C. (1.013 bar), preferably >235� C. (1.013 bar), being discharged at the bottom below the part 5, organic products having a boiling point of >255� C. (1.013 bar) (high boilers=HB) being discharged at the bottom below the parts 3 and 4, organic products having a boiling point of ≦224.8� C. (1.013 bar) being discharged at the top and ADG being discharged from the middle part of the upper combined column region (1) and (2) (side offtake).
The mixture comprising morpholine (MO), monoaminodiglycol (ADG), ammonia and water, and possibly E-MO and possibly EDA and possibly organic products having a boiling point of >224.8� C. (1.013 bar) which is used in the process of the invention has, in an embodiment (A), preferably been obtained by reaction of diethylene glycol (DEG) with ammonia in the presence of a catalyst comprising Cu, Ni and Co on zirconium dioxide as support.
The temperature in the reactor which is preferred for the reaction of diethylene glycol (DEG) with ammonia is in the range from 170 to 220� C. Preference is given to isothermal operation of the reactor. The pressure preferred for the reaction of diethylene glycol (DEG) with ammonia is in the range from 100 to 200 bar.
In another embodiment (B), the mixture comprising morpholine (MO), monoaminodiglycol (ADG), ammonia and water, and possibly E-MO and possibly EDA and possibly organic products having a boiling point of >224.8� C. (1.013 bar), which is used in the process of the invention has preferably been obtained by reaction of diethylene glycol (DEG) with ammonia in the presence of a catalyst comprising Cu and Ni on aluminum oxide as support, as described, in particular, in EP-A-70 397 (BASF AG).
The temperature in the reactor which is preferred for the reaction of diethylene glycol (DEG) with ammonia is in this case in the range 190-235� C. Preference is given to isothermal operation of the reactor. The pressure preferred for the reaction of diethylene glycol (DEG) with ammonia is in the range from 20 to 30 bar.
In the desired product morpholine, the content of morpholine, 1,2-ethylenediamine, N-ethylmorpholine, 2-methoxyethanol is determined by means of GC (GC conditions: 30 m DB-1; temperature program with 60� C. initial temperature, 4� C./min heating rate, 190� C. final temperature).
In the desired product ADG, the content of ADG and DEG is determined by means of GC (GC conditions: 30 m DB1, temperature program with 100� C. initial temperature, 8� C./min heating rate, 250� C. final temperature).
EXAMPLES Example 1 See FIGS. 5 and 6 Diglycol (DEG) is mixed with the top product from the column K80 (main components: diglycol and morpholyl-ADG) and fed continuously to the heat exchanger W 1.
Both streams are mixed with the recycle gas consisting predominantly of hydrogen upstream of the heat exchanger W 1. The recycle gas is brought from the high-pressure separator B 1 located at the outlet from the synthesis by means of the compressor V 1. After the heat exchanger W 1, the mixture which has a temperature of 145� C. is heated to 195� C. by means of a heater W 2 and conveyed to the reactor C 1.
The reaction of the diglycol to form aminodiglycol and morpholine takes place over the fixed-bed catalyst there at a pressure of 200 bar and temperatures up to 215� C. The reactor is operated isothermally. The heat of reaction is removed by evaporative cooling on the reactor. For this purpose, water is vaporized at 14 barabs.. The steam is used as heating steam on K20. The output from the reactor is then cooled to 45� C. in the heat exchangers W 1, W 3 and the air cooler W 4. In the high-pressure separator B 1, separation into a gas phase and a liquid phase occurs. The gas phase is, as described above, conveyed as recycle gas to the heat exchanger W 1.
In the column K10, the ammonia is distilled off at a purity of >99.9% from the feed at a pressure at the top of 16 barabs. and recirculated to the reactor inlet. The offgas is connected to an absorber. The ammonia-free bottoms having a temperature of 220� C. are depressurized into the column K20 for the removal of water. K10 has 17 theoretical plates and the feed point is at plate 14.
In the column K20, the water of reaction is separated off at atmospheric pressure. The distillate, which comprises 98% by weight of water and 2% by weight of low boilers (predominantly ethylmorpholine), is fed to the column K50. In addition, the overhead product of the LB removal in K40 (main components: 1,2-ethylenediamine, morpholine and water) is fed to the column K20. The largely water-free bottoms from K20 are depressurized at a temperature of 158� C. (main components: morpholine, aminodiglycol, diglycol and high-boiling residue) into the column K30. K20 has 56 theoretical plates and the feed point is at plate 25. K20 is partly operated using heating steam from the evaporative cooling of the reactor. The additional heat requirement is covered by heating steam from the steam supply network.
In the column K30, the feed comprising the bottoms from the column K20 and the recirculated bottoms from the pure distillation K55 is separated at a pressure at the top of 120 mbar into a low-boiling fraction (main component: morpholine) and a high-boiling fraction having a bottoms temperature of 164� C. (main components: aminodiglycol, diglycol and high-boiling residue). The bottoms are fed to the column K60. The condensate comprising 95% by weight of morpholine, 4.5% by weight of 1,2-ethylenediamine and 2-methoxyethanol and water is fed to the column K40. K30 has 14 theoretical plates and the feed point is at plate 11.
In the column K40, low boilers (LB) are separated off at the top at a pressure at the top of 3.4 barabs.. The distillate (main components: 1,2-ethylenediamine, morpholine and water) is recirculated to K20 or, after concentration of ethylenediamine, discharged discontinuously via a container. The bottoms from the column K40 (morpholine together with higher-boiling secondary components), which have a temperature of 174� C., go to K55.
In the column K55, morpholine having a purity of >99.6% by weight and a 1,2-ethylenediamine (EDA) content of <0.10% by weight is separated off at the top at a pressure at the top of 4.25 barabs.. The bottoms from the column, which have a temperature of 184� C., are recirculated to the feed to the column K30. K55 has 8 theoretical plates and the feed point is at plate 5. The heat from the vapor from K55 is integrated into the bottom of K30.
In the column K50, N-ethylmorpholine is separated off from the feed as an azeotrope with water at atmospheric pressure. The bottoms from the column, which have a temperature of 103� C., are discharged. K50 has 21 theoretical plates and the feed point is at plate 11.
In the column K60, low boilers are separated off from the feed at a pressure at the top of 160 mbar. The distillate from the column (main components: aminoethoxyethylamine, aminoethylmorpholine, methoxyethylmorpholine and small amounts of aminodiglycol) is recirculated to the reaction of DEG with ammonia. The bottoms from the column, whose main components are aminodiglycol, diethylene glycol and which have a bottoms temperature of 181� C., are fed to the downstream column K70. K60 has 18 theoretical plates and the feed point is at plate 10.
In the column K70, aminodiglycol having a purity of >98.5% by weight and a DEG content of <0.10% by weight is obtained as distillate from the feed at a pressure at the top of 475 mbar. The bottoms from the column (64% by weight of DEG, 22% by weight of morpholyl-ADG, 5% by weight of morpholinodiglycol and 9% by weight of high boilers), which have a bottoms temperature of 225� C., are fed to K80. K70 has 33 theoretical plates and the feed point is at plate 22. The heat from the vapor from K70 is integrated into the bottom of K40.
In the column K80, diethylene glycol having a purity of �80% is obtained at the top at a pressure at the top of 350 mbar. The distillate, which comprises morpholylaminodiglycol in addition to diethylene glycol, is recirculated to the inlet of the reactor. The high boilers (HB) which accumulate at the bottom at a bottoms temperature of about 240� C. are discharged from the process. The column has 28 theoretical plates and the feed point is at plate 15. The heat from the vapor from K80 is integrated into the bottom of K55.
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