WO2009147524A1 - Method and apparatus for producing mono(lower alkyl)monoalkanolamine - Google Patents

Method and apparatus for producing mono(lower alkyl)monoalkanolamine Download PDF

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Publication number
WO2009147524A1
WO2009147524A1 PCT/IB2009/005943 IB2009005943W WO2009147524A1 WO 2009147524 A1 WO2009147524 A1 WO 2009147524A1 IB 2009005943 W IB2009005943 W IB 2009005943W WO 2009147524 A1 WO2009147524 A1 WO 2009147524A1
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reaction
mono
lower alkyl
distillation tower
producing
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PCT/IB2009/005943
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French (fr)
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Shinya Tachibana
Tatsuya Tsujiuchi
Tsuyoshi Oishi
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Mitsubishi Heavy Industries, Ltd.
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Publication of WO2009147524A1 publication Critical patent/WO2009147524A1/en

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    • 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
    • C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins

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  • the present invention relates to a method and apparatus for producing a mono (lower alkyl)monoalkanolamine, which is commercially high in demand, and obtained by a reaction of a mono (lower alkyl) amine and an alkylene oxide.
  • a mono (lower alkyl) monoalkanolamine is a useful compound, which is commercially high in demand, and examples thereof include an intermediate raw material in general organic synthesis including a cationic flocculating agent or an intermediate for medical and agricultural chemicals, an etching liquid for resins, a softening agent for synthetic fibers, a corrosion inhibitor, or a neutralizing agent for use in petroleum refining or petroleum process, and a dispersing agent.
  • the reaction of a mono (lower alkyl) amine and an alkylene oxide forms both a mono (lower alkyl) monoalkanolamine and a mono (lower alkyl) dialkanolamine at the same time.
  • this reaction for selectively obtaining a mono (lower alkyl) monoalkanolamine, it is necessary to use a great excess of the mono (lower alkyl) amine relative to the alkylene oxide. For this reason, a large amount of the mono (lower alkyl) amine remains unreacted in this reaction.
  • Fig. 8 is an example of a conventional apparatus for producing a mono (lower alkyl) monoalkanolamine using a zeolite catalyst.
  • reference numeral 1 denotes a liquid-liquid reaction tower which serves as a reactor, and that is filled with a zeolite catalyst, and a raw material I (mono (lower alkyl) amine) and a raw material II (alkylene oxide) are fed to the liquid-liquid reaction tower where the raw materials are reacted with each other in accordance with a zeolite catalyst method, obtaining a product 2 containing unreacted raw materials.
  • the product 2 containing the unreacted raw materials contains, as the unreacted raw materials, unreacted mono (lower alkyl) amine (unreacted raw material I) and unreacted alkylene oxide (unreacted raw material II), and therefore the unreacted raw materials are separated by distillation from a reaction product 3 by an unreacted-raw-material-recovery distillation tower 4, and the unreacted mono (lower alkyl) amine (raw material I) and unreacted alkylene oxide (raw material II), that have been separated and recovered, are fed as unreacted raw materials 5 back to the reactor 1.
  • non-aqueous distillation tower 6 water and light components 7 are removed by a distillation method from the reaction product 3 led from the unreacted-raw-material- recovery distillation tower 4, and a resultant reaction product 3a free of water and the light components 7 is fed to a purification distillation tower 8.
  • the "non-aqueous" state represents a state of the substance having a water concentration of 1000 ppm or less.
  • reaction product 3a free of water and the light components 7 is then fed to the purification distillation tower 8 where a mono (lower alkyl) monoalkanolamine and a mono (lower alkyl) dialkanolamine (dimer as residue), that are formed by the reaction, are separated from each other by a distillation method to recover the mono (lower alkyl) monoalkanolamine as a objective reaction product 9.
  • the "zeolite catalyst method" according to Japanese Patent Application Laid-open No. 2004-275933 has a problem in that the reaction rate or selectivity is lowered due to deterioration of the catalyst. In addition, there is a problem in that it is difficult to keep the temperature in the reactor 1 uniform, making it difficult to stably obtain a product. Furthermore, in the zeolite catalyst method, a cooling installation, such as a condenser, must be used for the distillation tower for separating the mono (lower alkyl) amine at a distillation step, disadvantageously increasing the energy consumption. In the zeolite catalyst method, solid (zeolite catalyst) and liquid (raw materials) are in contact to cause a reaction, and the reaction does not proceed at a position where solid and liquid are not in contact, resulting in a heterogeneous reaction.
  • the molar ratio of the mono (lower alkyl) amine to the alkylene oxide must be reduced.
  • the mono (lower alkyl) amine is recycled, and hence the reboiler load of the distillation tower is increased, causing a problem in that the energy consumption is increased.
  • a method for producing a mono (lower alkyl )monoalkanolamine by reacting a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) includes feeding a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) into a reaction tower to cause a reaction in a gas-liquid mixed phase state within the reaction tower; and separating a resultant reaction product in a liquid state from the reaction tower.
  • an apparatus for producing a mono (lower alkyl) monoalkanolamine by a reaction of a mono (lower alkyl) amine and an alkylene oxide includes a reaction distillation tower into which a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) are fed to cause a reaction in a gas-liquid mixed phase state within the reaction distillation tower, while separating a resultant reaction product in a liquid state from a bottom of the reaction distillation tower and recovering unreacted raw materials in a gaseous state; and a purification distillation tower that purifies the separated reaction product in a liquid state by distillation to obtain an objective product.
  • AA mono (lower alkyl) amine
  • AO alkylene oxide
  • Fig. 1 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 1 of the present invention.
  • Fig. 2 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 2 of the present invention.
  • Fig. 3 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 3 of the present invention.
  • Fig. 4 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 4 of the present invention.
  • Fig. 5 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 5 of the present invention.
  • Fig. 6 is a relationship diagram of mole fraction and the number of stages of a reaction tower.
  • Fig. 7 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to a test example of the present invention.
  • Fig. 8 depicts one example of a conventional apparatus for producing a mono (lower alkyl) monoalkanolamine using a zeolite catalyst.
  • the method according to the present invention is a method for producing a mono (lower alkyl) monoalkanolamine by reacting a mono (lower alkyl) amine (raw material I: AA) and an alkylene oxide (raw material II: AO), in which the method includes feeding a raw material I (AA) and a raw material II (AO) into a reaction tower to cause a reaction in a gas-liquid mixed phase state within the reaction tower, while separating the resultant reaction product (amine monomer) in a liquid state from the reaction tower.
  • the reaction tower within which a reaction is conducted in a gas-liquid mixed phase state is a reaction distillation tower or a gas- liquid mixed phase reaction tower.
  • a reaction is conducted in a gas-liquid mixed phase state within the reaction tower, and an objective product is obtained in a liquid state, and therefore the reaction yield is improved.
  • the ratio of the alkylene oxide raw material to the mono (lower alkyl) amine raw material is not reduced, and therefore the reboiler load upon recovering the unreacted raw materials can be lowered.
  • reaction tower is a reaction distillation tower or a gas-liquid mixed phase reaction tower
  • Fig. 1 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 1 of the present invention.
  • an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-1 includes a reaction distillation tower 12 into which a mixed raw material 11 containing a mono (lower alkyl) amine (AA: raw material I) and an alkylene oxide (AO: raw material II) is fed through a raw-material main-feed line Lo; and a purification distillation tower 19 that subjects a reaction product 13 separated in a liquid state to distillation to separate it into a objective reaction product 20 (monomer) and residue (dimer) 21.
  • Reference numeral 18 denotes a reboiler.
  • reaction distillation tower 12 In the reaction distillation tower 12, unreacted raw materials 16 are separated from a column top 12a through a line Li, and the reaction product 13 is separated from a tower bottom 12b through a line L 2 .
  • the unreacted raw materials 16 are cooled by a condenser 14 provided on the line Li and changed into liquid in a flash drum 15, and led through a line L 3 to a storage tank 17 where the resultant liquid is temporarily stored.
  • the liquid stored in the storage tank 17 includes mainly the raw material I, and therefore the liquid is fed through a line L 4 back to the feed line for the raw material I .
  • a recycled raw material 16a is fed to the reaction distillation tower 12 from the flash drum 15 through a line L 5 , and directly reused without feeding a part of the unreacted raw materials 16 back to the raw-material main-feed line L 0 .
  • the reaction distillation tower of the present example is of a multi-stage type, and the number of stages in the reaction distillation tower varies depending on the amount of the substance to be distilled, however, it is about 10 to 20, for example.
  • reaction temperature in the reaction distillation tower 12 is, for example, preferably 40 to 200°C.
  • the temperature at the top of the reaction distillation tower 12 is, for example, preferably 40 to 100 0 C, more preferably 70 to 80°C.
  • the temperature at the bottom of the reaction distillation tower 12 is, for example, preferably 120 to 200°C, more preferably 140 to 180°C.
  • the pressure in the reaction distillation tower 12 is, for example, preferably 0.45 to 1.3 megapascals, more preferably 0.6 to 1.0 megapascal.
  • reaction temperature or the like and pressure are specified as in the above range is that if they fall outside the above range, it is unlikely that the reaction efficiently proceeds.
  • Mono (lower alkyl) amine as the raw material I used in the present invention include, but not limited to, a linear or branched monoalkylamine having 1 to 6 carbon atoms, such as monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, mono-n-butylamine, monoisobutylamine, mono-sec-butylamine, mono-t-butylamine, mono-n-pentylamine, isopentylamine, or mono-n-hexylamine.
  • a linear or branched monoalkylamine having 1 to 6 carbon atoms such as monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, mono-n-butylamine, monoisobutylamine, mono-sec-butylamine, mono-t-butylamine, mono-n-pentylamine, isopentylamine, or mono-n-hexyl
  • monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, mono-n-butylamine, monoisobutylamine, or mono-t-butylamine can be preferably used, and monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, or mono-n-butylamine can be particularly preferably used.
  • Alkylene oxide as the raw material II used in the present invention suitably include, but not limited to, an alkylene oxide having 2 to 4 carbon atoms, such as ethylene oxide, propylene oxide, or butylene oxide. Particularly, an ethylene oxide or propylene oxide can be used preferably.
  • the raw materials to be fed to a reactor have a water concentration in the range of from 1 to 40% by weight.
  • the water concentration of the raw materials is more preferably in the range of from 5 to 30% by weight, particularly preferably in the range of from 5 to 20% by weight.
  • the reaction rate varies depending on the water concentration of the raw materials, and the higher the water concentration, the higher the reaction rate, and hence the water concentration is preferably higher.
  • the ratio for the fed raw materials is specified.
  • the molar ratio of the alkylene oxide raw material to the mono (lower alkyl) amine raw material ⁇ alkylene oxide (AO: raw material II) /mono (lower alkyl)amine (AA: raw material I) ⁇ is preferably in the range of from 0.05 to 0.5, more preferably in the range of from 0.1 to 0.3.
  • the reboiler load of the unreacted-raw-material-recovery distillation tower upon recovering the unreacted raw materials is lowered, however, the reaction disadvantageously requires a prolonged period of time.
  • the reaction time can be reduced, however, the reboiler load is disadvantageously increased remarkably.
  • the residue (dimer) 21 is removed using the purification distillation tower 19.
  • the residue (dimer) 21 can be mixed into the monomer as the objective reaction product 20, there can be provided only the reaction distillation tower 12.
  • the reaction in this method is exothermic, and therefore a cooling unit can be provided inside or outside of the reaction distillation tower 12 to cool the tower to a predetermined temperature.
  • the raw materials are reacted in a gas-liquid mixed phase state within the reaction distillation tower 12 as the reaction tower, while recovering the reaction product 13 in a liquid state and separating the unreacted raw materials in a gaseous state from the reaction tower. Therefore, there is no need for a further distillation tower, which has been required in a conventional apparatus, and a mono (lower alkyl) monoalkanolamine can be produced in high yield and in an energy-saving mode.
  • the monomer and the unreacted raw materials 16 are inhibited from reacting with each other, so that the formation of a dimer as the residue 21 is suppressed, improving the yield of the objective reaction product 20.
  • the ratio of the alkylene oxide raw material to the mono (lower alkyl) amine raw material can be increased, and therefore facilities can be made compact, so that the utility consumption can be reduced, making it possible to produce a mono (lower alkyl) monoalkanolamine at a low cost.
  • Fig. 2 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 2.
  • an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-2 according to Example 2 includes the reaction distillation tower 12 into which the mixed raw material 11 containing the raw material I and raw material II is fed through the raw-material main-feed line Lo; and the purification distillation tower 19 that subjects the separated reaction product 13 to distillation to separate it into the objective reaction product 20 (monomer) and residue (dimer) 21, where the raw material II (AO) to be fed is divided, in which a portion of the divided raw material II (AO) is fed into the reaction distillation tower through the raw-material main-feed line L 0 , and the rest of the raw material II (AO) is fed into the reaction distillation tower 12 through a secondary feed line L 6 positioned above the feeding point of the raw- material main-feed line Lo.
  • FIG. 3 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 3.
  • an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-3 according to Example 3 is substantially the same as the apparatus for producing a mono (lower alkyl) monoalkanolamine 10-1 according to Example 1, except that the apparatus further includes a non-aqueous distillation tower 22 that removes water from the reaction product 13, in which a reaction product 13a free of water 23 is fed to the purification distillation tower 19, obtaining the objective reaction product 20.
  • the objective reaction product 20 free of water can be thus obtained.
  • the nonaqueous distillation tower 22 is provided to remove water from the reaction product, and therefore a mono (lower alkyl) monoalkanolamine in a non-aqueous state can be produced in high yield and in an energy-saving mode.
  • Fig. 4 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 4.
  • an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-4 according to Example 4 is substantially the same as the apparatus for producing a mono (lower alkyl) monoalkanolamine 10-1 according to Example 1, except that the reaction distillation tower 12 includes catalyst packed tanks 30a and 30b, in which the catalyst filling the catalyst packed tanks 30a and 30b causes a catalytic reaction to form the reaction product 13
  • ZSM-5 that is conventionally known synthetic zeolite for use in a zeolite catalyst method.
  • ZSM is an abbreviation for "Zeolite Socony Mobil” derived from the name of company that has developed the zeolite.
  • ZSM-Il known as synthetic zeolite.
  • zeolite is preferably used, and ZSM-5 is particularly preferably used.
  • the catalyst is effective in a reaction of a nonaqueous system, and therefore, when the raw material I is in the form of an aqueous solution (for example, having a water content of 40%) , it is necessary to preliminarily remove water 23 from the raw material I using a non-aqueous distillation tower 31.
  • Fig. 5 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 5.
  • an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-5 according to Example 5 includes a gas-liquid mixed phase reaction tower 40 into which the mixed raw material 11 containing the raw material I and the raw material II is fed through the raw-material main-feed line Lo and the purification distillation tower 19 that subjects the reaction product 13 separated in a liquid state to distillation to separate it into the objective reaction product 20 (monomer) and the residue (dimer) 21.
  • the raw material I and the raw material II are reacted in a gaseous state, and the resultant reaction product 13 is collected at the bottom of the tower, and therefore the reaction product 13 is separated through the line L 2 .
  • the reaction temperature in the gas-liquid mixed phase reaction tower is preferably, for example, 80 to 200°C, and the pressure in the gas-liquid mixed phase reaction tower is preferably, for example, 0.2 to 0.8 megapascal.
  • the unreacted raw materials 16 are cooled by the condenser 14 provided on the line Li and changed into liquid in the flash drum 15, and led through the line L 3 to the storage tank 17 where the resultant liquid is temporarily stored.
  • the liquid stored in the storage tank 17 consists mainly of the raw material I, and therefore the liquid is fed through the line L 4 back to the feed line for the raw material I.
  • the mixed raw material 11 containing the raw material I and the raw material II is reacted in a gas-liquid mixed phase state within the gas-liquid mixed phase reaction tower 40.
  • Fig. 7 Conditions (temperature and pressure) for the operations of the reaction distillation tower 12, the non-aqueous distillation tower 22, and the purification distillation tower 19 are shown in Fig. 7 and below.
  • numbers each enclosed by a rectangle indicate temperature ( 0 C)
  • numbers each enclosed by an oval indicate pressure

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Abstract

An apparatus for producing a mono (lower alkyl) monoalkanolamine according to the present invention includes a reaction distillation tower (12) into which a mixed raw material (11) containing a mono (lower alkyl) amine (AA: raw material I) and an alkylene oxide (AO: raw material II) is fed through a raw-material main-feed line (L0); and a purification distillation tower (19) that subjects a reaction product (13) separated in a liquid state to distillation to separate it into a objective reaction product (monomer) (20) and residue (dimer) (21), where unreacted raw materials (16) are separated from a tower top (12a) through a line (L1) and the reaction product (13) is separated from a tower bottom (12b) through a line (L2).

Description

DESCRIPTION
METHOD AND APPARATUS FOR PRODUCING MONO(LOWER
ALKYL) MONOALKANOLAMINE
TECHNICAL FIELD
The present invention relates to a method and apparatus for producing a mono (lower alkyl)monoalkanolamine, which is commercially high in demand, and obtained by a reaction of a mono (lower alkyl) amine and an alkylene oxide.
BACKGROUND ART
A mono (lower alkyl) monoalkanolamine is a useful compound, which is commercially high in demand, and examples thereof include an intermediate raw material in general organic synthesis including a cationic flocculating agent or an intermediate for medical and agricultural chemicals, an etching liquid for resins, a softening agent for synthetic fibers, a corrosion inhibitor, or a neutralizing agent for use in petroleum refining or petroleum process, and a dispersing agent.
Production of a mono (lower alkyl) monoalkanolamine by a reaction of a mono (lower alkyl) amine and an alkylene oxide has been reported since many years ago in various literatures (for example, Ryohei ODA and Kazuhiro TERAMURA, "Surface Active Agent", Maki Shoten, 1965, p. 262 to 263) .
The reaction of a mono (lower alkyl) amine and an alkylene oxide forms both a mono (lower alkyl) monoalkanolamine and a mono (lower alkyl) dialkanolamine at the same time. In this reaction, for selectively obtaining a mono (lower alkyl) monoalkanolamine, it is necessary to use a great excess of the mono (lower alkyl) amine relative to the alkylene oxide. For this reason, a large amount of the mono (lower alkyl) amine remains unreacted in this reaction.
As a method for producing a mono (lower alkyl) monoalkanolamine by reacting a mono (lower alkyl) amine and an alkylene oxide, a zeolite catalyst method using zeolite as a catalyst has been proposed (Japanese Patent Application Laid-open No. 2004-275933) .
Fig. 8 is an example of a conventional apparatus for producing a mono (lower alkyl) monoalkanolamine using a zeolite catalyst. As shown in Fig. 8, reference numeral 1 denotes a liquid-liquid reaction tower which serves as a reactor, and that is filled with a zeolite catalyst, and a raw material I (mono (lower alkyl) amine) and a raw material II (alkylene oxide) are fed to the liquid-liquid reaction tower where the raw materials are reacted with each other in accordance with a zeolite catalyst method, obtaining a product 2 containing unreacted raw materials. The product 2 containing the unreacted raw materials contains, as the unreacted raw materials, unreacted mono (lower alkyl) amine (unreacted raw material I) and unreacted alkylene oxide (unreacted raw material II), and therefore the unreacted raw materials are separated by distillation from a reaction product 3 by an unreacted-raw-material-recovery distillation tower 4, and the unreacted mono (lower alkyl) amine (raw material I) and unreacted alkylene oxide (raw material II), that have been separated and recovered, are fed as unreacted raw materials 5 back to the reactor 1. In a non-aqueous distillation tower 6, water and light components 7 are removed by a distillation method from the reaction product 3 led from the unreacted-raw-material- recovery distillation tower 4, and a resultant reaction product 3a free of water and the light components 7 is fed to a purification distillation tower 8. The "non-aqueous" state represents a state of the substance having a water concentration of 1000 ppm or less.
The reaction product 3a free of water and the light components 7 is then fed to the purification distillation tower 8 where a mono (lower alkyl) monoalkanolamine and a mono (lower alkyl) dialkanolamine (dimer as residue), that are formed by the reaction, are separated from each other by a distillation method to recover the mono (lower alkyl) monoalkanolamine as a objective reaction product 9. On the other hand, as a method for producing a mono (lower alkyl) monoalkanolamine without using the zeolite catalyst, there has been proposed a method in which a mono (lower alkyl) monoalkanolamine is produced, for example, under supercritical conditions (such that the temperature is 100 to 200°C and the pressure is 17 to 24 megapascals) (Japanese Patent Application Laid-open No. S59-13751) .
As a method for producing a mono (lower alkyl) monoalkanolamine by a reaction of a mono (lower alkyl) amine and an alkylene oxide, a method in which the reaction is conducted in the presence of water (this method is referred to as "water catalyst method") has been widely known. However, this method has a problem in that large heat load is required to remove a great amount of water by distillation in the purification system. Further, a method for producing monomethylaminoethanol from monomethylamine and ethylene oxide has been disclosed (Japanese Patent Application Laid-open No. H8-333310) . In the method described in Japanese Patent Application Laid- open No. H8-333310, a crude product is mixed with alcohol in a distillation tower in an amine recovery system, or the crude product and alcohol are charged through separate lines to recover unreacted monomethylamine.
However, the "zeolite catalyst method" according to Japanese Patent Application Laid-open No. 2004-275933 has a problem in that the reaction rate or selectivity is lowered due to deterioration of the catalyst. In addition, there is a problem in that it is difficult to keep the temperature in the reactor 1 uniform, making it difficult to stably obtain a product. Furthermore, in the zeolite catalyst method, a cooling installation, such as a condenser, must be used for the distillation tower for separating the mono (lower alkyl) amine at a distillation step, disadvantageously increasing the energy consumption. In the zeolite catalyst method, solid (zeolite catalyst) and liquid (raw materials) are in contact to cause a reaction, and the reaction does not proceed at a position where solid and liquid are not in contact, resulting in a heterogeneous reaction.
In the "supercritical method" according to Japanese Patent Application Laid-open No. S59-13751, conditions such that the temperature is 100 to 200°C and the pressure is 17 to 24 megapascals are needed, leading to a problem in that the cost of power required for the operation is inevitably increased.
In the technique according to Japanese Patent Application Laid-open No. H8-333310, for recovering monomethylamine, it is necessary to mix the crude product with alcohol, and, for reusing the monomethylamine, a further distillation tower is needed, causing disadvantages in that the production process is cumbersome and the cost for the process is increased.
Therefore, it has been desired to provide a more efficient method and apparatus for the production.
With respect to the above water catalyst method, for improving the yield of mono (lower alkyl) monoalkanolamine, the molar ratio of the mono (lower alkyl) amine to the alkylene oxide must be reduced. In this case, the mono (lower alkyl) amine is recycled, and hence the reboiler load of the distillation tower is increased, causing a problem in that the energy consumption is increased.
DISCLOSURE OF INVENTION
It is an object of the present invention to at least partially solve the problems in the conventional technology. According to one aspect of the present invention, a method for producing a mono (lower alkyl )monoalkanolamine by reacting a mono (lower alkyl) amine (AA) and an alkylene oxide (AO), the method includes feeding a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) into a reaction tower to cause a reaction in a gas-liquid mixed phase state within the reaction tower; and separating a resultant reaction product in a liquid state from the reaction tower.
According to another aspect of the present invention, an apparatus for producing a mono (lower alkyl) monoalkanolamine by a reaction of a mono (lower alkyl) amine and an alkylene oxide, the apparatus includes a reaction distillation tower into which a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) are fed to cause a reaction in a gas-liquid mixed phase state within the reaction distillation tower, while separating a resultant reaction product in a liquid state from a bottom of the reaction distillation tower and recovering unreacted raw materials in a gaseous state; and a purification distillation tower that purifies the separated reaction product in a liquid state by distillation to obtain an objective product.
The above and other objects, features, advantages and technical and industrial significance of this invention will be better understood by reading the following detailed description of presently preferred embodiments of the invention, when considered in connection with the accompanying drawings .
BRIEF DESCRIPTION OF DRAWINGS
Fig. 1 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 1 of the present invention.
Fig. 2 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 2 of the present invention.
Fig. 3 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 3 of the present invention. Fig. 4 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 4 of the present invention.
Fig. 5 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 5 of the present invention.
Fig. 6 is a relationship diagram of mole fraction and the number of stages of a reaction tower.
Fig. 7 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to a test example of the present invention.
Fig. 8 depicts one example of a conventional apparatus for producing a mono (lower alkyl) monoalkanolamine using a zeolite catalyst.
BEST MODE(S) FOR CARRYING OUT THE INVENTION
The present invention will be explained below in detail with reference to the accompanying drawings. The present invention is not limited to the examples. In addition, components in the examples include those that can be easily assumed by those skilled in the art or that are substantially equivalent.
A method for producing a mono (lower alkyl) monoalkanolamine according to the present invention is described below. The method according to the present invention is a method for producing a mono (lower alkyl) monoalkanolamine by reacting a mono (lower alkyl) amine (raw material I: AA) and an alkylene oxide (raw material II: AO), in which the method includes feeding a raw material I (AA) and a raw material II (AO) into a reaction tower to cause a reaction in a gas-liquid mixed phase state within the reaction tower, while separating the resultant reaction product (amine monomer) in a liquid state from the reaction tower. It is preferred that the reaction tower within which a reaction is conducted in a gas-liquid mixed phase state is a reaction distillation tower or a gas- liquid mixed phase reaction tower.
In the present invention, a reaction is conducted in a gas-liquid mixed phase state within the reaction tower, and an objective product is obtained in a liquid state, and therefore the reaction yield is improved. In addition, the ratio of the alkylene oxide raw material to the mono (lower alkyl) amine raw material (alkylene oxide raw material/mono (lower alkyl) amine raw material) is not reduced, and therefore the reboiler load upon recovering the unreacted raw materials can be lowered.
Examples in which the reaction tower is a reaction distillation tower or a gas-liquid mixed phase reaction tower will be explained in detail. [Example 1]
An apparatus for producing a mono (lower alkyl) monoalkanolamine according to examples of the present invention is described below with reference to the accompanying drawings .
Fig. 1 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 1 of the present invention.
As shown in Fig. 1, an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-1 according to Example 1 includes a reaction distillation tower 12 into which a mixed raw material 11 containing a mono (lower alkyl) amine (AA: raw material I) and an alkylene oxide (AO: raw material II) is fed through a raw-material main-feed line Lo; and a purification distillation tower 19 that subjects a reaction product 13 separated in a liquid state to distillation to separate it into a objective reaction product 20 (monomer) and residue (dimer) 21. Reference numeral 18 denotes a reboiler.
In the reaction distillation tower 12, unreacted raw materials 16 are separated from a column top 12a through a line Li, and the reaction product 13 is separated from a tower bottom 12b through a line L2.
The unreacted raw materials 16 are cooled by a condenser 14 provided on the line Li and changed into liquid in a flash drum 15, and led through a line L3 to a storage tank 17 where the resultant liquid is temporarily stored. The liquid stored in the storage tank 17 includes mainly the raw material I, and therefore the liquid is fed through a line L4 back to the feed line for the raw material I .
In the present example, a recycled raw material 16a is fed to the reaction distillation tower 12 from the flash drum 15 through a line L5, and directly reused without feeding a part of the unreacted raw materials 16 back to the raw-material main-feed line L0. The reaction distillation tower of the present example is of a multi-stage type, and the number of stages in the reaction distillation tower varies depending on the amount of the substance to be distilled, however, it is about 10 to 20, for example.
In the present example, the reaction temperature in the reaction distillation tower 12 is, for example, preferably 40 to 200°C.
The temperature at the top of the reaction distillation tower 12 is, for example, preferably 40 to 1000C, more preferably 70 to 80°C.
The temperature at the bottom of the reaction distillation tower 12 is, for example, preferably 120 to 200°C, more preferably 140 to 180°C. The pressure in the reaction distillation tower 12 is, for example, preferably 0.45 to 1.3 megapascals, more preferably 0.6 to 1.0 megapascal.
The reason why the reaction temperature or the like and pressure are specified as in the above range is that if they fall outside the above range, it is unlikely that the reaction efficiently proceeds.
Mono (lower alkyl) amine as the raw material I used in the present invention include, but not limited to, a linear or branched monoalkylamine having 1 to 6 carbon atoms, such as monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, mono-n-butylamine, monoisobutylamine, mono-sec-butylamine, mono-t-butylamine, mono-n-pentylamine, isopentylamine, or mono-n-hexylamine. Of these, monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, mono-n-butylamine, monoisobutylamine, or mono-t-butylamine can be preferably used, and monomethylamine, monoethylamine, mono-n-propylamine, monoisopropylamine, or mono-n-butylamine can be particularly preferably used.
Alkylene oxide as the raw material II used in the present invention suitably include, but not limited to, an alkylene oxide having 2 to 4 carbon atoms, such as ethylene oxide, propylene oxide, or butylene oxide. Particularly, an ethylene oxide or propylene oxide can be used preferably.
In the water catalyst method of the present invention, it is preferred that the raw materials to be fed to a reactor have a water concentration in the range of from 1 to 40% by weight. The water concentration of the raw materials is more preferably in the range of from 5 to 30% by weight, particularly preferably in the range of from 5 to 20% by weight. In the production of a mono (lower alkyl)monoalkanolamine of the present invention by a water catalyst method, the reaction rate varies depending on the water concentration of the raw materials, and the higher the water concentration, the higher the reaction rate, and hence the water concentration is preferably higher.
In the present invention, the ratio for the fed raw materials is specified. Specifically, the molar ratio of the alkylene oxide raw material to the mono (lower alkyl) amine raw material {alkylene oxide (AO: raw material II) /mono (lower alkyl)amine (AA: raw material I) } is preferably in the range of from 0.05 to 0.5, more preferably in the range of from 0.1 to 0.3.
When the molar ratio is more than 0.5, the reboiler load of the unreacted-raw-material-recovery distillation tower upon recovering the unreacted raw materials is lowered, however, the reaction disadvantageously requires a prolonged period of time. On the other hand, when the molar ratio is less than 0.05, the reaction time can be reduced, however, the reboiler load is disadvantageously increased remarkably.
In the present example, the residue (dimer) 21 is removed using the purification distillation tower 19. However, when the residue (dimer) 21 can be mixed into the monomer as the objective reaction product 20, there can be provided only the reaction distillation tower 12.
The reaction in this method is exothermic, and therefore a cooling unit can be provided inside or outside of the reaction distillation tower 12 to cool the tower to a predetermined temperature.
As understood from the above, in the apparatus for producing a mono (lower alkyl) alkanolamine according to Example 1, the raw materials are reacted in a gas-liquid mixed phase state within the reaction distillation tower 12 as the reaction tower, while recovering the reaction product 13 in a liquid state and separating the unreacted raw materials in a gaseous state from the reaction tower. Therefore, there is no need for a further distillation tower, which has been required in a conventional apparatus, and a mono (lower alkyl) monoalkanolamine can be produced in high yield and in an energy-saving mode.
By positively separating the monomer (product) formed in the reaction distillation tower 12 from the reaction system, the monomer and the unreacted raw materials 16 are inhibited from reacting with each other, so that the formation of a dimer as the residue 21 is suppressed, improving the yield of the objective reaction product 20. The ratio of the alkylene oxide raw material to the mono (lower alkyl) amine raw material (alkylene oxide raw material/mono (lower alkyl) amine raw material) can be increased, and therefore facilities can be made compact, so that the utility consumption can be reduced, making it possible to produce a mono (lower alkyl) monoalkanolamine at a low cost. [Example 2]
The present example will be explained with reference to the accompanying drawings .
Fig. 2 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 2.
As shown in Fig. 2, an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-2 according to Example 2 includes the reaction distillation tower 12 into which the mixed raw material 11 containing the raw material I and raw material II is fed through the raw-material main-feed line Lo; and the purification distillation tower 19 that subjects the separated reaction product 13 to distillation to separate it into the objective reaction product 20 (monomer) and residue (dimer) 21, where the raw material II (AO) to be fed is divided, in which a portion of the divided raw material II (AO) is fed into the reaction distillation tower through the raw-material main-feed line L0, and the rest of the raw material II (AO) is fed into the reaction distillation tower 12 through a secondary feed line L6 positioned above the feeding point of the raw- material main-feed line Lo. As shown in Fig. 6, when the reaction distillation tower is of a multi-stage type (13 stages in Fig. 6) , the larger the height in the column, the higher the mole fraction of the raw material I (AA) . Therefore, the raw material II (AO) is divided and fed to the tower, improving the reaction efficiency.
In the apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 2, the raw materials are reacted in a gas-liquid mixed phase state within the reaction distillation tower 12 as the reaction tower, in which the raw material II is divided and fed into the reaction distillation tower 12. Therefore, the reaction efficiency is improved, so that a mono (lower alkyl) monoalkanolamine can be produced in high yield and in an energy-saving manner. [Example 3]
The present example will be explained with reference to the accompanying drawings. Fig. 3 is a schematic diagram of an apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 3.
As shown in Fig. 3, an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-3 according to Example 3 is substantially the same as the apparatus for producing a mono (lower alkyl) monoalkanolamine 10-1 according to Example 1, except that the apparatus further includes a non-aqueous distillation tower 22 that removes water from the reaction product 13, in which a reaction product 13a free of water 23 is fed to the purification distillation tower 19, obtaining the objective reaction product 20.
The objective reaction product 20 free of water can be thus obtained.
In the apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 3, the nonaqueous distillation tower 22 is provided to remove water from the reaction product, and therefore a mono (lower alkyl) monoalkanolamine in a non-aqueous state can be produced in high yield and in an energy-saving mode. [Example 4]
The present example will be explained with reference to the accompanying drawings.
Fig. 4 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 4.
As shown in Fig. 4, an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-4 according to Example 4 is substantially the same as the apparatus for producing a mono (lower alkyl) monoalkanolamine 10-1 according to Example 1, except that the reaction distillation tower 12 includes catalyst packed tanks 30a and 30b, in which the catalyst filling the catalyst packed tanks 30a and 30b causes a catalytic reaction to form the reaction product 13
As an example of the catalyst filling the catalyst packed tanks, there can be mentioned ZSM-5, that is conventionally known synthetic zeolite for use in a zeolite catalyst method. "ZSM" is an abbreviation for "Zeolite Socony Mobil" derived from the name of company that has developed the zeolite. As an example of zeolite having an MEL structure, there can be mentioned ZSM-Il known as synthetic zeolite. In the present invention, zeolite is preferably used, and ZSM-5 is particularly preferably used. The catalyst is effective in a reaction of a nonaqueous system, and therefore, when the raw material I is in the form of an aqueous solution (for example, having a water content of 40%) , it is necessary to preliminarily remove water 23 from the raw material I using a non-aqueous distillation tower 31.
In the apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 4, the raw materials are reacted in a gas-liquid mixed phase state by a zeolite method within the reaction distillation tower as the reaction tower, which is filled with a zeolite catalyst. Therefore, the reaction efficiency is improved, so that a mono (lower alkyl) monoalkanolamine can be produced in high yield and in an energy-saving mode. [Example 5]
The present example will be explained with reference to the accompanying drawings .
Fig. 5 is a schematic diagram of an apparatus for producing a mono (lower alkyl)monoalkanolamine according to Example 5.
As shown in Fig. 5, an apparatus for producing a mono (lower alkyl) monoalkanolamine 10-5 according to Example 5 includes a gas-liquid mixed phase reaction tower 40 into which the mixed raw material 11 containing the raw material I and the raw material II is fed through the raw-material main-feed line Lo and the purification distillation tower 19 that subjects the reaction product 13 separated in a liquid state to distillation to separate it into the objective reaction product 20 (monomer) and the residue (dimer) 21.
In the gas-liquid mixed phase reaction tower 40, the raw material I and the raw material II are reacted in a gaseous state, and the resultant reaction product 13 is collected at the bottom of the tower, and therefore the reaction product 13 is separated through the line L2.
The reaction temperature in the gas-liquid mixed phase reaction tower is preferably, for example, 80 to 200°C, and the pressure in the gas-liquid mixed phase reaction tower is preferably, for example, 0.2 to 0.8 megapascal.
The unreacted raw materials 16 are cooled by the condenser 14 provided on the line Li and changed into liquid in the flash drum 15, and led through the line L3 to the storage tank 17 where the resultant liquid is temporarily stored. The liquid stored in the storage tank 17 consists mainly of the raw material I, and therefore the liquid is fed through the line L4 back to the feed line for the raw material I. In the apparatus for producing a mono (lower alkyl) monoalkanolamine according to Example 5, using the gas-liquid mixed phase reaction tower 40, the mixed raw material 11 containing the raw material I and the raw material II is reacted in a gas-liquid mixed phase state within the gas-liquid mixed phase reaction tower 40.
Therefore, the reaction efficiency is improved, so that a mono (lower alkyl) monoalkanolamine can be produced in high yield and in an energy-saving mode. [Test Example]
The present invention will be explained in more detail with a test example; however, the present invention is not limited to thereto.
The apparatus for producing an amine 10-3 shown in Fig. 7 having the same construction as in Example 3 was used.
Conditions (temperature and pressure) for the operations of the reaction distillation tower 12, the non-aqueous distillation tower 22, and the purification distillation tower 19 are shown in Fig. 7 and below. In Fig. 7, numbers each enclosed by a rectangle indicate temperature (0C) , and numbers each enclosed by an oval indicate pressure
(megapascal) .
(Reaction distillation tower 12)
Inlet: Temperature 8O0C (pressure: 2.6 megapascals) Outlet at tower bottom: Temperature 163°C (pressure: 0.82 megapascal)
Outlet at tower top: Temperature 40°C (pressure: 0.80 megapascal)
(raw material I I /Raw material I) molar ratio at the inlet of the reaction distillation tower 12: 0.1
Water concentration at the inlet of the reaction distillation tower 12: 8% by weight When the molar ratio for the raw materials was 0.1, the reboiler load was reduced by about 20 per cent, as compared to that in a conventional apparatus, achieving reduction of the reboiler load. When a zeolite catalyst method is employed, the temperature of the outlet at the bottom of the reaction distillation tower 12 was 173°C (pressure: 1.02 megapascals) , and the temperature of the outlet at the tower top was 40°C (pressure: 1.0 megapascal) . According to the present invention with the configuration described above, a mono (lower alkyl)monoalkanolamine can be produced in high yield and in an energy-saving manner.
Although the invention has been described with respect to specific embodiments for a complete and clear disclosure, the appended claims are not to be thus limited but are to be construed as embodying all modifications and alternative constructions that may occur to one skilled in the art that fairly fall within the basic teaching herein set forth.

Claims

1. A method for producing a mono (lower alkyl) monoalkanolamine by reacting a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) , the method comprising: feeding a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) into a reaction tower to cause a reaction in a gas-liquid mixed phase state within the reaction tower; and separating a resultant reaction product in a liquid state from the reaction tower.
2. The method for producing a mono (lower alkyl) monoalkanolamine according to claim 1, wherein the reaction tower is a reaction distillation tower.
3. The method for producing a mono (lower alkyl) monoalkanolamine according to claim 2, wherein the reaction distillation tower is a multi-stage type reaction distillation tower.
4. The method for producing a mono (lower alkyl) monoalkanolamine according to claim 2, wherein a reaction temperature in the reaction distillation tower is 40 to 200°C, a temperature at a top of the reaction distillation tower is 40 to 100°C, a temperature at a bottom of the reaction distillation tower is 120 to 200°C, and a pressure in the reaction distillation tower is 0.45 to 1.3 megapascals.
5. The method for producing a mono (lower alkyl)monoalkanolamine according to claim 1, wherein the reaction tower is a gas-liquid mixed phase reaction tower.
6. The method for producing a mono (lower alkyl)monoalkanolamine according to claim 4, wherein the mono (lower alkyl) amine (AA) and alkylene oxide (AO) are reacted in a gaseous state at a reaction temperature of 80 to 200°C and a pressure of 0.2 to 0.8 megapascal, and the resultant reaction product is separated in a liquid state from a liquid phase.
7. The method for producing a mono (lower alkyl) monoalkanolamine according to claim 2 or 5, wherein the mono (lower alkyl) amine (AA) is separated and recovered from the top of the reaction distillation tower and reused.
8. The method for producing a mono (lower alkyl) monoalkanolamine according to claim 2 or 5, wherein the separated unreacted raw materials are fed back to a raw-material main-feed unit, or the separated unreacted raw materials are fed into the reaction distillation tower at a position above a feeding point of the raw-material main-feed unit.
9. The method for producing a mono (lower alkyl) monoalkanolamine according to claim 2 or 5, wherein the alkylene oxide (AO) to be fed is divided, a portion of the divided alkylene oxide (AO) is fed into the reaction distillation tower through a raw-material main-feed unit, and rest of the alkylene oxide (AO) is fed into the reaction distillation tower through a secondary feed unit positioned above the feeding point of the raw-material main-feed unit.
10. An apparatus for producing a mono (lower alkyl)monoalkanolamine by a reaction of a mono (lower alkyl) amine and an alkylene oxide, the apparatus comprising: a reaction distillation tower into which a mono (lower alkyl) amine (AA) and an alkylene oxide (AO) are fed to cause a reaction in a gas-liquid mixed phase state within the reaction distillation tower, while separating a resultant reaction product in a liquid state from a bottom of the reaction distillation tower and recovering unreacted raw materials in a gaseous state; and a purification distillation tower that purifies the separated reaction product in a liquid state by distillation to obtain an objective product.
11. The apparatus for producing a mono (lower alkyl) monoalkanolamine according to claim 10, wherein a reaction temperature in the reaction distillation tower is 40 to 200°C, a temperature at a top of the reaction distillation tower is 40 to 100°C, a temperature at a bottom of the reaction distillation tower is 120 to 200°C, and a pressure in the reaction distillation tower is 0.45 to 1.3 megapascals.
12. The apparatus for producing a mono (lower alkyl) monoalkanolamine according to claim 10 or 11, wherein a ratio of an alkylene oxide raw material to a mono (lower alkyl) amine raw material (alkylene oxide raw material/mono (lower alkyl) amine raw material) is 0.05 to
0 . 5 .
13. The apparatus for producing a mono (lower alkyl)monoalkanolamine according to any one of claims 10 to 12, wherein raw materials to be fed to the reaction distillation tower have a water content equal to or less than 20%.
14. The apparatus for producing a mono (lower alkyl)monoalkanolamine according to claim 10, wherein the reaction distillation tower is filled with a zeolite catalyst, and the raw materials are fed in a non-aqueous state to the reaction distillation tower.
PCT/IB2009/005943 2008-05-26 2009-06-15 Method and apparatus for producing mono(lower alkyl)monoalkanolamine WO2009147524A1 (en)

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