CN115197047A - Coupling reaction method for preparing ethanol from dimethyl ether - Google Patents
Coupling reaction method for preparing ethanol from dimethyl ether Download PDFInfo
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- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
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- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
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Abstract
The invention discloses a coupling reaction method for preparing ethanol from dimethyl ether. The method comprises the following steps: carbon monoxide, dimethyl ether and hydrogen enter a dimethyl ether carbonylation reactor according to a proportion, fresh supplementary hydrogen is mixed with outlet gas of the carbonylation reactor, and the mixed gas enters a hydrogenation reactor after being preheated by a preheater; the outlet gas enters a gas-liquid separation tank after heat exchange through a heat exchanger, and the upper gas phase is mixed with fresh gases of carbon monoxide and dimethyl ether after being pressurized by a circulating gas compressor; the liquid phase at the lower part enters a dimethyl ether recovery tower, the dimethyl ether extracted from the tower top is mixed with the circulating gas, the tower bottom liquid enters an acetate recovery tower, the acetate extracted from the tower top is circulated back to a hydrogenation reactor to continue hydrogenation reaction, and the crude ethanol product extracted from the tower bottom enters an ethanol refining unit. The method effectively couples the carbonylation reaction and the hydrogenation reaction, reduces heat loss and equipment investment, is simple and easy to operate, and has good industrial application prospect.
Description
Technical Field
The invention belongs to the field of ethanol products, and particularly relates to a coupling reaction method for preparing ethanol from dimethyl ether.
Background
With the increasing energy demand and the increasing contradiction of the shortage of petroleum supply and the increasing of the global environmental pressure, the fuel ethanol is generally concerned by countries in the world due to the cleanness and environmental protection of the fuel ethanol, the ethanol is used as an important clean energy source and is mixed with gasoline in a proportion of 10 percent, and the fuel ethanol gasoline can reduce the emission of carbon monoxide and hydrocarbon in automobile exhaust, thereby having important significance for solving the problem of atmospheric pollution in China and realizing sustainable development. After the global fuel ethanol yield is increased rapidly in 2006-2010, the global fuel ethanol yield is influenced by grain consumption disputes, and the global fuel ethanol yield is increased slowly in 2011-2013 and is maintained at the level of 830-857 hundred million liters per year. In 2014, the fuel ethanol market has been recovered to a certain extent, and the fuel ethanol market is increased by 5 percent on a par. The worldwide demand for fuel ethanol will reach 17753 million tons in 2025 as predicted by the united states energy information center.
At present, fuel ethanol is mainly divided into grain ethanol, non-grain ethanol and cellulosic ethanol. The grain ethanol is prepared from grains such as corn and wheat, occupies more cultivated land due to the production of the grain ethanol and non-grain ethanol, has the problem of food competition with people and livestock, and is gradually limited or prohibited by relevant policies of governments of various countries. China is a country rich in coal and less in oil, so that ethanol prepared by coal chemical industry conforms to the basic national conditions of China. In recent years, researchers at home and abroad explore an economic, environment-friendly and green process route of 'synthesis gas → methanol → dimethyl ether → methyl acetate → ethanol'. At present, the total yield of the domestic dimethyl ether device can reach about 1400 million tons, but the operating rate is only 38 percent, and the problem of serious surplus of dimethyl ether production capacity and the like is solved by the route.
At present, a technical route of 'dimethyl ether → methyl acetate → ethanol' is developed domestically, dimethyl ether and carbon monoxide are subjected to carbonylation reaction to generate methyl acetate, and methyl acetate and hydrogen are subjected to hydrogenation reaction to generate ethanol, wherein the technology for preparing ethanol by hydrogenating methyl acetate is mature, and industrial application is realized.
Disclosure of Invention
The invention provides a coupling reaction method for preparing ethanol from dimethyl ether, aiming at saving energy and reducing consumption in the whole process flow. The method reduces the steam consumption of the preheating hydrogenation raw material and reduces the equipment investment such as a hydrogen circulation supercharger and the like by coupling the processes of preparing the methyl acetate from the dimethyl ether and hydrogenating the methyl acetate.
In order to realize the purpose, the invention adopts the technical scheme that:
a coupling reaction method for preparing ethanol from dimethyl ether comprises the following steps:
carbon monoxide, dimethyl ether and hydrogen enter a dimethyl ether carbonylation reactor in proportion to carry out carbonylation reaction, fresh supplementary hydrogen is mixed with outlet gas of the carbonylation reactor, and the mixed gas is preheated by a preheater and then enters a hydrogenation reactor to carry out hydrogenation reaction; the outlet gas of the hydrogenation reactor enters a gas-liquid separation tank after heat exchange through a heat exchanger, and the upper gas phase of the gas-liquid separation tank is pressurized through a circulating gas compressor and then mixed with fresh gases of carbon monoxide and dimethyl ether; the liquid phase at the lower part enters a dimethyl ether recovery tower, dimethyl ether extracted from the top of the dimethyl ether recovery tower is mixed with circulating gas, tower bottom liquid enters an acetate recovery tower, acetate extracted from the top of the acetate recovery tower is circulated back to a hydrogenation reactor to continue hydrogenation reaction, and a crude ethanol product extracted from the tower bottom enters an ethanol refining unit.
As a preferred embodiment of the present application, the reactor type is a fixed bed reactor or a fluidized bed reactor.
As a preferred embodiment of the present application, the catalyst type filled in the carbonylation reactor is modified catalyst which contains eight-membered ring or ten-membered ring channel molecular sieve such as MOR, FER or ZSM-35 or metal such as Cu, zn, fe loaded on the molecular sieve.
In a preferred embodiment of the present application, the catalyst species in the hydrogenation reaction is silica or alumina as a carrier to support one or more of Cu, zn, pt, sn, pd metals.
As a preferred embodiment of the present application, the carbonylation reaction temperature is 140-250 deg.C, and the reaction pressure is 1.0-10.0 MPa. The reaction temperature of the hydrogenation reaction is 230-300 ℃, and the reaction pressure is 1.0-10.0 Mpa.
Wherein the hydrogenation reaction pressure is less than the carbonylation reaction pressure, and the hydrogenation reaction temperature is more than the carbonylation reaction temperature.
As a preferred embodiment of the present application, CO, DME and H are present in the carbonylation feed gas 2 The volume ratio of (3-30): (0.5-5): 0.5-5; the space velocity is 1000-10000 h -1 。
In a preferred embodiment of the present application, the ratio of fresh make-up hydrogen to carbonylation off-gas is in the range of 0 to 0.5.
As a preferred embodiment of the present application, the ratio of hydrogen to ester in the hydrogenation reactor inlet gas is (4-15): 1.
As a preferred embodiment of the application, the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is more than or equal to 99.0wt.%.
Compared with the prior art, the positive effects of the invention are as follows:
the invention couples carbonylation reaction and hydrogenation reaction, the outlet gas after dimethyl ether carbonylation reaction is supplemented by fresh hydrogen and directly sent to hydrogenation reaction, the product is subjected to gas-liquid separation, dimethyl ether recovery and acetic ester recovery, and the obtained crude ethanol is rectified to obtain an ethanol product. The unreacted dimethyl ether is returned to the carbonylation reaction, and the recovered acetic ester is returned to the hydrogenation reaction. Various devices of methyl acetate rectification process devices are reduced, the flow is shortened, and the cost investment is reduced.
And (II) the steam consumption of raw materials such as preheated hydrogen, methyl acetate and the like in the hydrogenation process is reduced, and the equipment investment such as a hydrogen circulation supercharger and the like in the hydrogenation reaction is reduced.
Drawings
FIG. 1 is a schematic process flow diagram of a coupled reaction method for preparing ethanol from dimethyl ether according to an embodiment of the present invention.
Description of reference numerals: 101: a carbonylation reactor; 102: heat exchanger I, 103: a hydrogenation reactor; 104: a heat exchanger II; 105, a gas-liquid separator; 106, a dimethyl ether recovery tower; 107: an acetate recovery tower; 108 ethanol rectification unit; 109, a circulating gas compressor; fresh CO and fresh DME 201; 202 fresh H 2 (ii) a 203, circulating gas; 204, a dimethyl ether recovery tower; 205 acetic ester recovery tower; 206, dimethyl ether recovery tower bottom liquid; 207, exhausting gas.
Detailed Description
A coupling reaction method for preparing ethanol from dimethyl ether comprises the following steps:
carbon monoxide, dimethyl ether and hydrogen enter a dimethyl ether carbonylation reactor according to a proportion to carry out carbonylation reaction, fresh supplementary hydrogen is mixed with outlet gas of the carbonylation reactor, the mixed gas is heated to the temperature required by a hydrogenation reactor through a heat exchanger I, and is decompressed to the required hydrogenation pressure, and then enters the hydrogenation reactor to carry out hydrogenation reaction. The outlet gas of the hydrogenation reactor enters a gas-liquid separation tank after heat exchange through a heat exchanger II, and the gas phase at the upper part of the gas-liquid separation tank is pressurized through a circulating gas compressor and then mixed with fresh gases of carbon monoxide and dimethyl ether; the liquid phase at the lower part enters a dimethyl ether recovery tower, dimethyl ether extracted from the top of the dimethyl ether recovery tower is mixed with circulating gas, tower bottom liquid enters an acetate recovery tower, acetate extracted from the top of the acetate recovery tower is circulated back to a hydrogenation reactor to continue hydrogenation reaction, and a crude ethanol product extracted from the tower bottom enters an ethanol refining unit.
Preferably, the reactor type is a fixed bed reactor or a fluidized bed reactor.
Preferably, the catalyst type filled in the carbonylation reactor is modified catalyst such as MOR, FER or ZSM-35 containing eight-membered ring or ten-membered ring channel molecular sieve or molecular sieve loading metal such as Cu, zn, fe and the like. The method specifically comprises the following steps: MOR, FER or ZSM-35; or MOR molecular sieve loaded with metal Cu, or MOR molecular sieve loaded with metal Zn, or MOR molecular sieve loaded with metal Fe; or FER molecular sieve loaded with metal Cu, or FER molecular sieve loaded with metal Zn, or FER molecular sieve loaded with metal Fe; or ZSM-35 molecular sieve carries Cu, or ZSM-35 molecular sieve carries Zn, or ZSM-35 molecular sieve carries Fe, etc.
Preferably, the catalyst type in the hydrogenation reaction is one or a combination of more of metals of Cu, zn, pt, sn and Pd supported by silica or alumina. Specifically, the method can load Cu by taking silicon oxide as a carrier; or taking silicon oxide as a carrier to load Zn; or taking silicon oxide as a carrier to load Pt; or taking silicon oxide as a carrier to load Sn; or taking silicon oxide as a carrier to load Pd; or taking alumina as a carrier to load Cu; or taking alumina as a carrier to load Zn; or taking alumina as a carrier to load Pt; or taking alumina as a carrier to load Sn; or taking alumina as a carrier to load Pd; or taking silicon oxide as a carrier to load two or more than two of Cu, zn, pt, sn and Pd metals; or taking alumina as a carrier to load two or more of Cu, zn, pt, sn and Pd metals.
Preferably, the carbonylation reaction temperature is 140-250 deg.C, the hydrogenation reaction temperature is 230-300 deg.C, and the reaction pressure is 1.0-10.0 MPa.
Wherein the hydrogenation reaction pressure is less than the carbonylation reaction pressure, and the hydrogenation reaction temperature is more than the carbonylation reaction temperature.
Preferably, the carbonylation reaction feed gas comprises CO, DME and H 2 The volume ratio of (3-30), (0.5-5) and (0.5-5); the space velocity is 1000-10000 h -1 。
Preferably, the ratio of fresh make-up hydrogen to carbonylation reaction off-gas is in the range 0 to 0.5.
Preferably, the ratio of hydrogen to ester in the carbonylation reactor inlet gas is (4-15): 1.
Preferably, the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is more than or equal to 99.0wt.%.
Any feature disclosed in this specification may be replaced by alternative features serving equivalent or similar purposes, unless expressly stated otherwise. That is, unless expressly stated otherwise, each feature is only an example of a generic series of equivalent or similar features.
In the present invention, some conventional operation devices, apparatuses and components are omitted or simply described.
Example 1:
the embodiment provides a coupling reaction method for preparing ethanol from dimethyl ether, the process flow is shown in figure 1, and the specific process steps are the same as those in the specific embodiment:
in this particular example, the carbonylation reactor was charged with MOR molecular sieve and the hydrogenation reactor was charged with a Cu, zn metal catalyst on alumina. The carbonylation reaction temperature is 180 ℃, and the pressure is 5.0Mpa. Carbonylation reactor inlet CO, DME and H 2 Has a volume ratio of 6 -1 . The volume ratio of the fresh hydrogen to the outlet gas of the carbonylation reaction is 0.09, the hydrogenation reaction temperature is 230 ℃, the pressure is 4.0MPa, and the gas space velocity is 2350h -1 The molar ratio of hydrogen to ester in the inlet gas was 10.1.
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.5wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
Example 2:
the present embodiment provides a method for coupling reaction of dimethyl ether to ethanol, which is the same as embodiment 1 except that: the hydrogenation reaction temperature is adjusted to 260 ℃, the hydrogenation pressure is adjusted to 4.5Mpa, and the gas space velocity is adjusted to 2200h -1 。
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.7wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
Example 3:
the embodiment provides a coupling reaction method for preparing ethanol from dimethyl ether, and the process flow is shown in figure 1, and the specific process steps are the same as those in the specific embodiment.
In this example, the carbonylation reactor was loaded with metallic Cu loaded MOR molecular sieve and the hydrogenation reactor was loaded with Pt, sn metallic catalyst on silica. The carbonylation reaction temperature is 190 ℃ and the pressure is 4.5Mpa. Carbonylation reactor inlet CO, DME and H 2 Is 6 -1 . The volume ratio of fresh hydrogen to outlet gas of the carbonylation reaction is 0.09, the hydrogenation reaction temperature is 260 ℃, the pressure is 4.3Mpa, and the gas space velocity is 2300h -1 The molar ratio of hydrogen to ester in the inlet gas was 10.3.
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.5wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
Example 4:
the embodiment provides a coupling reaction method for preparing ethanol from dimethyl ether, and the process flow is shown in figure 1, and the specific process steps are the same as those in the specific embodiment.
In this example, MOR molecular sieve supported by Cu metal is used in the carbonylation reactor, and Pt and Sn metal catalyst supported on silica is used in the hydrogenation reactor. The carbonylation reaction temperature is 210 ℃, and the pressure is 4.5Mpa. Carbonylation reactor inlet CO, DME and H 2 Is 6, and the gas space velocity is 2200h -1 . The volume ratio of fresh hydrogen to outlet gas of the carbonylation reaction is 0.05.
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.5wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
Comparative example 1
The embodiment provides a method for coupling reaction of preparing ethanol from dimethyl ether, which is consistent with embodiment 1, and the following needs to be adjusted: the carbonylation reaction and the hydrogenation reaction both have the temperature of 240 ℃.
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.0wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
Comparative example 2
The embodiment provides a method for coupling reaction of preparing ethanol from dimethyl ether, which is consistent with embodiment 1, and the following needs to be adjusted: the carbonylation reaction and the hydrogenation reaction both have the temperature of 190 ℃.
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.0wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
Comparative example 3:
this example provides a method for coupling reaction of dimethyl ether to ethanol, which is consistent with example 2, and requires adjustment: carbonylation reactor inlet CO, DME and H 2 Has a volume ratio of 6 -1 . The volume ratio of fresh hydrogen to carbonylation reaction off-gas was 0:1.
Through determination: the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is 99.2wt.%. The analysis results of the composition and the content of the dimethyl ether recovery tower bottom liquid are shown in the table 1, and the analysis results of the alkane content in the circulating gas are shown in the table 2.
TABLE 1
TABLE 2
The activity test results in table 1 show that in the coupling reaction of dimethyl ether carbonylation-hydrogenation to prepare methyl acetate, the carbonylation reaction and the hydrogenation reaction are coupled to synthesize the ethanol by adopting the method of the invention. As the carbonylation and hydrogenation reaction temperature are difficult to match, the coupling temperature is too high (comparative example 1), so that the carbonylation side reaction acetone is increased, more isopropanol which is difficult to rectify and separate appears in crude ethanol, and more alkane is produced by the side reaction. The coupling temperature is too low (comparative example 2), so that the conversion rate of methyl acetate in the hydrogenation reaction is reduced, the purity of ethanol in a crude ethanol product is low, and the energy consumption of subsequent separation is increased. In addition, fresh supplementary hydrogen is directly mixed with dimethyl ether carbonylation feed gas (comparative example 3), so that the conversion rate of dimethyl ether in carbonylation reaction is obviously reduced, and the product yield is influenced.
Although the present invention has been described in detail with respect to specific embodiments thereof, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the scope of the invention encompassed by the appended claims.
Claims (10)
1. A coupling reaction method for preparing ethanol from dimethyl ether is characterized by comprising the following steps: carbon monoxide, dimethyl ether and hydrogen enter a dimethyl ether carbonylation reactor in proportion to carry out carbonylation reaction, fresh supplementary hydrogen is mixed with outlet gas of the carbonylation reactor, and the mixed gas is preheated by a preheater and then enters a hydrogenation reactor to carry out hydrogenation reaction; the outlet gas of the hydrogenation reactor enters a gas-liquid separation tank after heat exchange through a heat exchanger, and the upper gas phase of the gas-liquid separation tank is pressurized through a circulating gas compressor and then mixed with fresh gases of carbon monoxide and dimethyl ether; the liquid phase at the lower part enters a dimethyl ether recovery tower, dimethyl ether extracted from the top of the dimethyl ether recovery tower is mixed with circulating gas, tower bottom liquid enters an acetate recovery tower, acetate extracted from the top of the acetate recovery tower is circulated back to a hydrogenation reactor to continue hydrogenation reaction, and a crude ethanol product extracted from the tower bottom enters an ethanol refining unit.
2. The method of claim 1, wherein the dimethyl ether carbonylation reactor and the hydrogenation reactor are both fixed bed reactors or fluidized bed reactors.
3. The process of claim 1, wherein the catalyst used in the dimethyl ether carbonylation reactor is MOR, FER or ZSM-35 molecular sieve containing eight-or ten-membered ring channels and Cu, zn or Fe modified catalyst.
4. The coupled reaction method for preparing ethanol from dimethyl ether according to claim 1, wherein the catalyst loaded in the hydrogenation reactor is any one or more of Cu, zn, pt, sn and Pd metals loaded on silica or alumina as a carrier.
5. The method of claim 1, wherein the reaction temperature of the carbonylation reaction is 140-250 ℃, the reaction pressure is 1.0-10.0 Mpa; the reaction temperature of the hydrogenation reaction is 230-300 ℃, and the reaction pressure is 1.0-10.0 Mpa.
6. The method of claim 5, wherein the hydrogenation pressure is lower than the carbonylation pressure, and the hydrogenation temperature is higher than the carbonylation temperature.
7. The method of claim 1, wherein the coupling reaction of dimethyl ether to ethanol comprises reacting CO, DME and H in the carbonylation feed gas 2 The volume ratio of (A) is 3-30 -1 。
8. The method of claim 1, wherein the volume ratio of fresh make-up hydrogen to carbonylation reaction outlet gas is 0-0.5.
9. The method for coupling reaction of dimethyl ether to ethanol as claimed in claim 1, wherein the ratio of hydrogen to ester in the gas at the inlet of the hydrogenation reactor is 4-15.
10. The method of claim 1, wherein the purity of the dimethyl ether extracted from the top of the dimethyl ether recovery tower is not less than 99.0wt%.
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