Method for producing acrylonitrile and preparing hydrogen cyanide and acetonitrile as co-products (variants)

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to methods (variants) for producing acrylonitrile and preparing hydrogen cyanide and acetonitrile as co-products. Methods involve addition of hydrocarbon that is taken among propylene or propane, ammonia and oxygen-containing gas to the reaction zone containing a catalyst for oxidative ammonolysis and reaction is carried out at increased temperature to form acrylonitrile, hydrogen cyanide and acetonitrile, and isolation of acrylonitrile, hydrogen cyanide and acetonitrile from reactor also. According to the first variant reaction is carried out in the presence of alcohols mixture containing methanol and a second alcohol among ethanol, propanol or their mixtures wherein the weight ratio of methanol to the second alcohol in alcohols mixture is maintained depending on necessary amounts of hydrogen cyanide and acetonitrile. According to the second variant reaction is carried out in the presence of alcohols mixture containing methanol and ethanol taken in the weight ratio from about 99:1 to 1::99. According to the third variant reaction is carried out in the presence of one or more alcohols taken among crude methanol, crude ethanol or crude propanol. According to the fourth variant reaction is carried out in the presence of one or more crude (C1-C4)-alcohol. Proposed method provides enhancing yield of one or both co-products, i. e. HCN and acetonitrile, formed in producing acrylonitrile.

EFFECT: improved producing method.

21 cl, 2 tbl, 8 ex

 

Background of invention

The present invention relates to a new method of oxidative ammonolysis of a mixture of alcohols to a mixture of NITRILES. In particular, the present invention aims to increase the output of and preferably the ratio of coproduction - hydrogen cyanide and acetonitrile produced during the oxidative ammonolysis of propylene to Acrylonitrile.

There are several patents that offer to obtain hydrogen cyanide or acetonitrile to inject methanol or ethanol in the fluidized bed reactor. In addition, in these patents contain information about the introduction of methanol or ethanol in the fluidized bed reactor can increase the yield of hydrogen cyanide or acetonitrile in the production of Acrylonitrile. For example, U.S. Patent No. 3911089; 4485079 and 5288473 dedicated oxidative ammonolysis of methanol and obtain hydrogen cyanide by injection of methanol in a fluidized bed reactor containing a catalyst suitable for the production of Acrylonitrile. In each of the references States that methanol can inject simultaneously with the receipt of Acrylonitrile. In addition, Japanese application patent No. 74-87474; 79-08655 and 78-35232 are close to methods of increasing the yield of hydrogen cyanide in the production of Acrylonitrile. Application 2[1990]-38,333 dedicated to increasing the yield of acetonitrile by means of V.N.Karazin the AI acetone and/or ethanol in the reactor oxidative ammonolysis, containing an appropriate catalyst. The method proposed in this application, involves the simultaneous injection of acetone and/or ethanol in the reactor for oxidative ammonolysis in the production of Acrylonitrile. In all these application notes additional receiving either hydrogen cyanide or acetonitrile.

The present invention relates to a method, which allows to increase the output of one or both coproducts (i.e. HCN and acetonitrile) in the production of Acrylonitrile at (1) the preservation of raw material costs by increasing output coproducts and (2) achieve the same or better conversion and selectivity for the target coproducts (carbon-based) compared to the values obtained when using pure alcohols, such as methanol/ethanol. The method in accordance with this invention allows to control the number of generated hydrogen cyanide and acetonitrile.

The authors unexpectedly found that the use of a mixture of crude alcohols leads to the desired increase in the yield of acetonitrile and hydrogen cyanide upon receipt of Acrylonitrile.

The invention

The present invention is to develop a method allowing to significantly increase the output of one or more soproducts - hydrogen cyanide and acetonitrile in the course of obtaining acrylonitril the and of propylene or propane.

Another objective of this invention is to develop a way of turning crude mixture of alcohols containing methanol, ethanol, other alcohols and water, hydrogen cyanide and acetonitrile in the process of obtaining Acrylonitrile without noticeable effect on the yield of Acrylonitrile.

The next task of the invention is to develop a method of converting ethanol to acetonitrile in the presence or in the absence of methanol. Methanol can be added to the ethanol in amounts necessary to maintain the ratio of received soproducts - hydrogen cyanide and acetonitrile. So, if there is increasing demand for hydrogen cyanide to the original mixture of ethanol can be added methanol to obtain increased amounts of hydrogen cyanide. Or when you want to receive the additional amount of acetonitrile compared to hydrogen cyanide, you can increase the amount of ethanol in the mixture.

To achieve these goals in accordance with the main objective of the present invention, the essence of this invention is the introduction into the reactor (e.g., fluidized bed reactor) hydrocarbon, which is chosen from propylene or propane, crude alcohol, which is a mixture of alcohols C1-C4, ammonia and oxygen-containing gas, the reaction in the presence of a catalyst (e.g. catalyst method in CI is present layer) and receiving the output of Acrylonitrile, hydrogen cyanide and acetonitrile by passing the stream exiting the reactor and containing Acrylonitrile, hydrogen cyanide and acetonitrile, through the column for cooling and separation of Acrylonitrile, acetonitrile and hydrogen cyanide.

The preferred implementation of the present invention involves feeding a mixture of crude alcohols consisting of crude ethanol, crude propanol and/or crude methanol. For the purposes of this invention the crude ethanol may be a mixture of ethanol, propanol, butanol and water. Typical industrial crude ethanol contains at 86.34% ethanol, 1.025% propanol-1, 1.266% n-butanol and 11.37% water. Almost any mixture of the crude ethanol, propanol and/or methanol without limiting composition suitable for the present invention. Preferably, the crude alcohol contained water in an amount of not less than 3 wt.%, more preferably about 5 wt.%, that reduces the costs for the method proposed in this invention. One of the unexpected advantages of this invention is the fact that the results obtained for the selectivity of formation of coproducts and conversion when using raw alcohol was of the same order and even better (carbon balance)than the results obtained when using pure alcohol.

The practice of the present invention shows that any katal is the blockage of oxidative ammonolysis can be used in order to increase the output of coproduction - acetonitrile and hydrogen cyanide. Typical catalysts of oxidative ammonolysis can be described by the following two formulas:

AaBbCcDdMo12Oxwhere

A=Li, Na, K, Cs, Tl, and combinations thereof, the preferred Cs and K;

In=Ni, Co, Mn, Mg, Ca, and combinations thereof, the preferred Ni, Co and Mg;

C=Fe, Cr, CE, Cu, V, Sb, W, Sn, Ga, Ge, In, P, and combinations thereof, preferably Fe, Cr and CE;

D=Bi and/or preferably Bi;

a=0.1-4.0, preferably from 0.1 to 0.5, particularly preferably from 0.1 to 0.2;

b=0.1-10.0, preferably from 5 to 9, especially predpochtitelno from 6 to 8, and

C, d=0.1-10.0, preferably from 0.5 to 4, especially preferably from 0.5 to 3;

and AaBbSb12Oxwhere

A=Fe, Cr, CE, V, U, Sn, Ti, Nb and combinations thereof, preferably Fe, V, Sn and Ti;

In=Mo, W, Co, Cu, Te, Bi, Zn, In, Ni, Ca, TA, and combinations thereof, preferably Mo and Cu;

a=0.1 to 16, preferably from 2 to 12, particularly preferably from 4 to 10;

b=0.0 to 12, preferably from 1 to 10, particularly preferably from 2 to 6, and the value of x depends on the oxidation state of the elements.

The catalyst can be used in nenalezena the form or media: the oxides of silicon, aluminum, titanium, zirconium and the like; a preferred carrier is silica. Typical catalysts suitable for the practical implementation of the present invention are disclosed in U.S. Patents 3642930, 4485079, 3911089, 483215, 5134105 and 5093299.

Below will be considered in detail the preferred implementations of the invention.

Detailed description of the invention

The present invention is directed to the utilization of crude alcohols containing a mixture of alcohols C1-C4as starting substances for the production of valuable coproducts in the production of NITRILES (hydrogen cyanide and acetonitrile), formed during the production of Acrylonitrile. In addition, in the framework of the present invention can be disposed of crude alcohols containing significant amounts of diluents, such as water, which reduces the cost of raw materials for production of valuable coproducts.

In one aspect of the present invention includes a method for increasing the output of one or both coproducts, HCN and acetonitrile, in the production of Acrylonitrile, which consists in the introduction of a hydrocarbon chosen from propylene or propane, crude alcohol, a mixture of methanol, ethanol or propanol, ammonia and air in the zone of the reactor, the reaction of the hydrocarbon, alcohol, ammonia and oxygen on the specified catalyst at elevated temperature to produce Acrylonitrile, hydrogen cyanide and acetonitrile, and the selection of Acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.

This crude ethanol preferably is a mixture, not necessarily containing water and with whom containing a series of from about 5 to 95 weight percent ethanol, preferably from about 5 to 94 weight percent of ethanol, more preferably from about 50 to about 90 weight percent ethanol. Additionally, the mixture may contain other components, for example water, methanol, alcohols With3-C4and other organic compounds. However, it is preferable to select other components of water and one or more alcohols, especially alcohols mentioned above. And raw propanol means a mixture, not necessarily containing water and containing from about 5 to about 99 weight percent of one or more propanolol, preferably from about 50 to about 95 weight percent of one or more propanolol. Usually propanol, in particular crude propanol, is a mixture of propanolol consisting of isopropanol to about 50 weight percent, more preferably at least 75 weight percent. Moreover, the crude methanol preferably means a mixture consisting of methanol to about 98 weight percent, preferably about 97 weight percent and more preferably about 95 weight percent. Water, if it is present in the alcohols should be from about 0.1 to about 10 weight percent, preferably from 3 to about 10 weight percent based on the amount of alcohol and water present.

As indicated above, in one of the variations is tov the invention the relative amounts of hydrogen cyanide and acetonitrile, obtained by the method according to this invention, can be maintained by maintaining a constant relationship of the amounts of methanol and ethanol, are added to the reaction zone in the process of producing Acrylonitrile. So, if you want to get increased amounts of hydrogen cyanide, it is necessary to increase the ratio of methanol to ethanol. On the contrary, if you want to get less hydrogen cyanide, this ratio can be reduced. Therefore, the invention provides a method of maintaining the relative amounts of hydrogen cyanide and acetonitrile produced during the manufacture of Acrylonitrile by adding a mixture of methanol, ethanol or propanol and regulatory relationships of methanol to ethanol or propanol, preferably ethanol, is added to the reaction zone receiving Acrylonitrile. Although in this embodiment, it is possible to use methanol, ethanol or propanol any degree of cleaning, it is advantageous to use the crude methanol, ethanol or propanol, preferably crude methanol, ethanol and crude propanol, as described above. Therefore, this invention also provides a method of maintaining the relative amounts of hydrogen cyanide and acetonitrile produced during the manufacture of Acrylonitrile comprising introducing a hydrocarbon chosen from propylene or propane, ammonia, air, and mixtures of alcohols containing methanol and a second alcohol of the number e is anola, propanol or mixtures thereof in a reaction zone containing a catalyst of oxidative ammonolysis described above, the reaction of hydrocarbons, alcohols, ammonia and oxygen on the specified catalyst at elevated temperature to produce Acrylonitrile, hydrogen cyanide and acetonitrile, as well as the allocation of Acrylonitrile, hydrogen cyanide and acetonitrile from the reaction products in which the weight ratio of methanol to the second alcohol in the mixture of alcohols is from about 99:1 to 1:99, preferably from about 98:2 to 2:98, and more preferably from 95:5 to 5:95. For example, if you want to get a relatively large amount of hydrogen cyanide compared to acetonitrile, you should use the original mixture containing 90 weight percent ethanol and 10 percent by weight of methanol. If you want to increase the number of hydrogen cyanide, the ratio of the alcohols in the mixture fed to the reactor, may be 10 weight percent ethanol and 90 percent by weight of methanol. It is clear that the alcohol mixture introduced into the reactor obtain Acrylonitrile may be prepared to feed to the reactor or various alcohols can be submitted separately and mix already in the reactor. In the most preferred embodiment of the present invention to achieve the desired relationship soproduktov - hydrogen cyanide and acetonitrile as a source of ethanol used in isoamsa crude ethanol and methanol is added to the crude ethanol.

In a preferred embodiment of the present invention to obtain a high yield of acetonitrile and hydrogen cyanide by utilizing the crude mixture of alcohols is necessary to maintain certain conditions in the reactor. The practice of implementation of the present invention dictates the following parameters of the reaction of oxidative ammonolysis: feed rate of raw alcohol is from 1 to 50% of propylene and / or propane in the total carbon content. The reaction temperature should be between 410 and 460°C, preferably from 430 to 460°C. Typically, the pressure support between 1 and 5 atmospheres, preferably from 1 to 3 atmospheres.

In a more preferred embodiment of this invention, the crude mixture of alcohols is a mixture of ethanol, isopropanol, butanol and water.

In an even more preferred variant of the present invention the method is carried out in the fluidized bed reactor.

For illustration purposes of this invention the following examples are not exhaustive of all possible applications. The catalyst used in all examples was a promoted BiFeMoOxknown as an active catalyst for the oxidative ammonolysis of propylene to Acrylonitrile. In the original mixture of 5, 10 and 15% propylene was replaced by a crude ethanol (total carbon content), and the results are shown in table 1. In every the example, the reactor temperature was 440° With the pressure of 9.5 psig (˜0.6 ATM) and the ratio of propylene + alcohol/ammonia/air was 1/1.2/9 .3. The performance of the reactor was 0.07 (gram hydrocarbon/g of catalyst·h).

Table 1
No. approx.% EtOHOutput'AN,%Output ACET., %O. HCN, %
on Society.
1078.81.56.5
2575.33.96.9
31071.55.07.4
41567.56.58.0

To illustrate the value of using the mixture of alcohols mixed crude ethanol with 30% by weight of methanol and the mixture was filed in the same reactor for oxidative ammonolysis. The results are shown in table 2 and indicate a change in the selectivity towards HCN. If you want to obtain a high yield of HCN, this mixture should be used in industrial settings.

Output'AN,%
Table 2
No. approx.% mixtureOutput ACET.,%O. HCN,%
on Society.
5078.81.56.5
6575.32.97.8
71071.54.69.0
81567.26.210.0

In General, all alcohols can undergo oxidative ammonolysis with formation of a mixture of NITRILES. Preferred are alcohols C1-C4. You can also use alcohols with multiple IT groups, for example ethylene glycol or propylene glycol.

Although the examples illustrate the possibilities of this invention, they do not limit its scope and in light of the above, other variations and modifications of the method.

1. Method for the production of Acrylonitrile with getting as coproduct hydrogen cyanide and acetonitrile, involving the introduction of a hydrocarbon chosen from propylene or propane, ammonia, oxygen-containing gas and a mixture of alcohols containing methanol and a second alcohol from among ethanol, propanol or mixtures thereof in a reaction zone containing rolled the ATOR oxidative ammonolysis, reactions of hydrocarbons, alcohols, ammonia and oxygen on the specified catalyst at elevated temperature to produce Acrylonitrile, hydrogen cyanide and acetonitrile, and the selection of Acrylonitrile, hydrogen cyanide and acetonitrile from the reaction products, and the weight ratio of methanol to the second alcohol in the mixture of alcohols is supported depending on the required quantities of hydrogen cyanide and acetonitrile.

2. The method according to claim 1, wherein the second alcohol is an ethanol.

3. The method according to claim 2, in which the weight ratio of methanol to ethanol is about 99:1 ÷ 1:99.

4. The method according to claim 3, in which the weight ratio of methanol to ethanol is about 98:2 ÷ 2:98.

5. Method for the production of Acrylonitrile with getting as coproduct hydrogen cyanide and acetonitrile, involving the introduction of a hydrocarbon chosen from propylene or propane, mixtures of alcohols containing methanol and ethanol in a weight ratio of about 99:1 ÷ 1:99, ammonia and oxygen-containing gas into the reaction zone containing the catalyst of oxidative ammonolysis reaction of a hydrocarbon, a mixture of alcohols, ammonia and oxygen on the specified catalyst at elevated temperature to produce Acrylonitrile, hydrogen cyanide and acetonitrile, as well as the allocation of Acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.

p> 6. The method according to claim 5, in which the weight ratio of methanol to ethanol is about 98:2 ÷ 2:98.

7. Method for the production of Acrylonitrile with getting as coproduct hydrogen cyanide and acetonitrile, involving the introduction of a hydrocarbon chosen from propylene or propane, one or more alcohols selected from the crude methanol, the crude ethanol or crude propanol, ammonia and oxygen-containing gas into the reaction zone containing the catalyst of oxidative ammonolysis reaction of a hydrocarbon, a mixture of alcohols, ammonia and oxygen on the specified catalyst at elevated temperature to produce Acrylonitrile, hydrogen cyanide and acetonitrile, as well as the allocation of Acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.

8. The method according to claim 7, in which the ratio of hydrocarbon : alcohol in the mixture ranges from 1:0.01 to 1:0.5 in the calculation of the full carbon.

9. The method according to claim 8, in which the temperature change from 410° 460°C.

10. The method according to claim 9, in which the temperature change from 430° up to 450°C.

11. The method according to claim 8, in which the pressure change from 1 to 5 atmospheres.

12. The method according to claim 10, in which the pressure change from 1 to 5 atmospheres.

13. The method according to claim 7, in which the crude alcohol is a crude ethanol.

14. The method according to claim 7, in which the catalyst of oxidative ammonolysis corresponds to the formula:

< num="61"> AaBbCcDdMo12Oxwhere

A=Li, Na, K, Cs, T1, and combinations thereof;

In=Ni, Co, Mn, Mg, Ca, and combinations thereof;

C=Fe, Cr, CE, Cu, V, Sb, W, Sn, Ga, Ge, In, P, and combinations thereof;

D=Bi and/or preferably Bi;

a=0,1-4,0;

b=0,1-10,0 and

C, d=0,1-10,0.

15. The method according to claim 7, in which the catalyst corresponds to the formula:

AaBbSb12Oxwhere

A=Fe, Cr, CE, V, U, Sn, Ti, Nb, and combinations thereof;

In=Mo, W, Co, Cu, Te, Bi, Zn, In, Ni, Ca, TA, and combinations thereof;

a=0,1-16;

b=0.0 to 12 and

the value of x depends on the oxidation state of the elements used.

16. The method according to item 13, in which the crude ethanol contains about 5 ÷ 94 wt.% of ethanol.

17. The method according to claim 7, in which the crude alcohol is a crude methanol.

18. The method according to 17, in which the crude methanol contains about 98 wt.% of methanol.

19. The method according to claim 7, in which the crude alcohol is a raw propanol.

20. The method according to claim 19, in which raw propanol contains about 50 to 95 wt.% propanol.

21. Method for the production of Acrylonitrile with getting as coproduct hydrogen cyanide and acetonitrile, involving the introduction of a hydrocarbon chosen from propylene or propane, one or more raw alcohol C1-C4, ammonia and oxygen-containing gas into the reaction zone containing the catalyst will oxidize the high of ammonolysis, the reaction of hydrocarbon, alcohol, ammonia and oxygen on the specified catalyst at elevated temperature to produce Acrylonitrile, hydrogen cyanide and acetonitrile, as well as the allocation of Acrylonitrile, hydrogen cyanide and acetonitrile from the reactor.



 

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