Method of recovering molybdenum form catalytic olefin epoxidation products

FIELD: industrial organic synthesis.

SUBSTANCE: molybdenum is recovered from catalytic olefin epoxidation products using organic hydroperoxides. Method comprises treating heavy epoxidate fraction with alkali solution, treating resultant spent alkali stream with extractant, and subsequent precipitation of molybdenum trisulfide using sulfur-alkali effluents formed in production of olefins by pyrolysis of hydrocarbon feedstock.

EFFECT: increased molybdenum recovery degree and simplified operation.

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The invention relates to the field of chemistry, particularly to a process of separating the molybdenum-containing catalyst from the products of the catalytic epoxidation of olefins with organic hydroperoxides.

A known method of extraction of molybdenum from the reaction mixture after epoxydecane olefins organic peroxides by treating them with aqueous solutions of alkaline agents (U.S. Patent No. 3523956, IPC 01 J 23/92, publ. 1970).

The method has such disadvantages as large losses of target products, soluble in water, and pollution of their water phase containing molybdenum, which in turn hampers the regeneration of the catalyst.

A known way of separating molybdenum catalyst from products of catalytic epoxidation of water-insoluble tertiary amine (U.S. Patent No. 5439657, IPC 01 D 11/00, publ. 08.08.95). Removing molybdenum catalyst from the reaction mixture epoxidation is carried out by treatment with an aqueous solution of caustic soda. The spent alkaline stream is processed by an acid (hydrochloric, sulfuric, phosphoric, formic, etc.,) to pH 2 and below. After phase separation the organic layer is sent for recycling, and the acid aqueous layer containing dissolved molybdenum and sodium, washed with an organic solvent and is directed to the extraction of the tertiary AMI is Ohm (5%solution in benzene). The quantity of molybdenum after extraction decreases from the initial content of more than 1000 ppm to 20 ppm and below. Next, the extract is sent to the step of Stripping the alkaline compound (aqueous solutions of alkali, sodium hydroxide, ammonium hydroxide and the like). The extractant is regenerated with a 15%aqueous solution of sodium hydroxide and returns to repeat the cycle for reuse. The degree of extraction of molybdenum is 97-99 wt.%.

The disadvantage of this method is the use of toxic, scarce, expensive imported extractant, and a multi-stage process.

There is a method of acid treatment of spent alkaline stream process of obtaining propylene oxide and styrene in order to remove sodium salts from the organic phase for further use as fuel (U.S. Patent No. 5276235, IPC C 07 C 1/20, publ. 04.01.94). The acid is used in such a molar concentration which allows the formation of a sodium salt in the solution above their limit of solubility. Thus, the saline products form a suspension with a large difference in density between the phases, which facilitates the separation of the phases and improves the quality of the organic phase. The amount of water introduced with the acid should be sufficient for complete dissolution of the formed sodium salts. Sodium salt of USAID who are as insoluble crystals in the bottom water layer. For acid treatment preference is given to sulfuric acid, and the number should be such that it can communicate with the sodium of spent alkaline stream, i.e. 0.5 mol of sulfuric acid per 1 mol of contained sodium. For the formation of sodium bisulfate is recommended to take the sulfuric acid in the amount of 1 mol per 1 mol of sodium. Usually used in industry 93-96%sulfuric acid, but to reduce the cost of the process can be used 25%. When using other acids are also equivalent to the number.

In this patent, all attention is paid to the removal of sodium salts from spent alkaline stream to further its use is not considered that the presence of ions of the catalyst in the epoxidation process of the fuel is also unacceptable. This task should be solved in the complex: 1) to receive an additional amount of quality fuel that can be used in the process; 2) suppress the metals from the organic part of the alkaline stream; 3) to regenerate the catalyst in the epoxidation process.

The method for extracting molybdenum-containing catalyst for the epoxidation of olefins with organic hydroperoxides by processing the cubic product with a water-alcohol mixture containing alcohol in an amount of 0.01-50 wt.% (A.S. CCC IS NO 485754, IPC 01 J 11/02, publ. 30.09.75). CBM product obtained by separation of the products of the epoxidation β-isoamylene hydropredict tertiary amyl contained in the oxidized isopentane, contains 0.4 wt.% molybdenum. Determination of molybdenum carried out by the colorimetric method. As alcohol use one - or polyhydric alcohols or mixtures thereof. The degree of extraction of molybdenum in water-alcohol mixture is 90-95%. The obtained water-alcohol layer evaporated. The rest is painted a dark brown viscous liquid, soluble in organic solvents and containing from 3.85 to 5.9 wt.% molybdenum. The extraction time is from 4 minutes to 1 hour and the temperature of the process varies from 0 to 80°C. All of these factors complicate the technology.

There is also known a method of extraction of molybdenum catalyst contained in the distillation residues after epoxidation of olefins with organic hydroperoxides by extraction with an aqueous solution of organic acids: acetic, formic, propionic, butyric, with a concentration of 0.01 to 2 wt.% (A.S. USSR №491398, IPC 01 J 11/02, publ. 15.11.75). The epoxidation catalyst contains a metal of variable valence and can be extracted from the distillation of products of various organic hydroperoxides containing from 3 to 100 wt.% osnovnosti. The volumetric ratio of the cubic residue containing molybdenum product, the extractant is from 10:1 to 1:20. The extraction process is carried out at 10-80°during the time interval from 1 min to 1 h the resulting aqueous extract is evaporated, the resulting residue is painted a dark brown viscous liquid, soluble in organic solvents and containing 5.5 wt.% molybdenum. The content of molybdenum determine colorimetrically. Dedicated molybdenum-containing product can be used as a recycle catalyst or can be allocated metallsoderjasimi connection.

However, not all of the above conditions, the extraction is fairly complete extraction of molybdenum-containing product, it can be only 93%. In addition, the high volume ratio of VAT residue to the extractant, the need to regulate the temperature, the duration of the extraction process complicate the technology of extraction of the catalyst.

Closest to the present invention is a method of separation of molybdenum catalyst from products of catalytic epoxidation after removal of epoxide target epoxysilane and poroshkoobraznogo alcohol (corresponding to the gidroperekisi), produce molybdenum in the form of a solid molybdenum-containing sludge (Patent is SHA No. 4317801, IPC C 01 G 39/06, publ. 1982). CBM product containing molybdenum and high-molecular organic compounds, is subjected to solvent extraction with water. The spent catalyst and water-soluble organic compounds pass into the aqueous layer. After separation of the phases in the aqueous phase when heat is added to the hydrogen sulfide or water-soluble salt sulfide (sulphide of sodium, magnesium, potassium, calcium or ammonium). Preference is given to sodium sulfide, which can be added in solid form or dissolved in water, hydrogen sulfide may be added directly to the mixture. The deposition of molybdenum is achieved when the molar ratio of H2S or Na2S to Mo, equal to 10:1, at a temperature of from 50 to 125°C, deposition time up to 3 hours. Solid molybdenum precipitate is separated by filtration, centrifugation or decantation of the liquid. The degree of deposition of molybdenum when heated to 50°C for 1 hour under atmospheric pressure is 31,72%, when heated to 100°C for 1 hour under vacuum is 72,07%, at 25°C for 16 hours under vacuum is 52,76%.

The disadvantage of this method is the long time of deposition of molybdenum with a low degree of extraction.

The objective of the invention is to increase the degree of extraction of molybdenum and simplification of the method in General.

The problem is solved SPO is obom extraction of molybdenum products from the catalytic epoxidation of olefins with organic hydroperoxides, includes treatment of the heavy fraction of epoxide alkali solution, treatment of the resulting waste alkaline extractant stream with subsequent deposition trisulde molybdenum, as a precipitator trisulde molybdenum use of sulfur-alkaline wastewater production of olefins by the pyrolysis of hydrocarbons.

The reaction products of the epoxidation of olefins with organic hydroperoxides separated by rectification method on a light fraction and a heavy fraction containing molybdenum and unreacted hydroperoxide and products of side reactions. After washing the heavy fraction of epoxide solution of caustic soda from the side and oxidation products from waste molybdenum catalyst is formed the spent alkaline stream (waste) (SL). Formed THAT is the solution dark brown color with a pungent smell, density of 1.11-1.18 g/cm3that is a complex mixture of sodium salts of organic acids, reaction, tar and other substances (up 35%). Molybdenum in an amount of 0.1-0.3 wt.% presented in the form of organic complexes of unknown composition, recycling molybdenum catalyst impossible due to the variability of the composition of the ions on molybdenum and sodium. Next, WE processed the extractant, which is used as an aqueous solution of mineral acid is (sulfuric, hydrochloric, nitric, phosphoric and other) with a concentration of 2-2,5 N. the Treatment is carried out at a temperature of 50-100°s at a volume ratio THAT the extractant from 1:1.5 to 1:2, followed by the deposition of the molybdenum from the aqueous phase. In the aqueous phase, in addition to molybdenum ions, extracted with sodium ions, which do not prevent the deposition of molybdenum. The organic phase was purified from metals, can be subjected to further processing in order to obtain a number of useful components.

As a precipitator trisulde molybdenum use of sulfur-alkaline wastewater production of olefins by the pyrolysis of hydrocarbons (BOILING), for example, ethylene complex, which is a full substitute for pure sodium sulphide. Sulfur-alkaline wastewater fed to the deposition at a volume ratio to the aqueous phase, equal to 0.19-1:1 depending on the content of Na2S.

The content of molybdenum determine photocolorimetric method based on the formation of colored compounds of molybdenum (V) thiocyanate-ion.

The implementation of the method of extraction of molybdenum products from the catalytic epoxidation of olefins with organic hydroperoxides are illustrated in the following examples.

Example 1

In thermostatic funnel at a temperature of 70°poured With 100 ml of alkaline waste resulting from epoxidase the project propylene with ethylbenzene hydroperoxide, containing of 0.21 wt.% molybdenum and having a density of d420=1,1530, add 150 ml of 2.5 N solution of sulfuric acid (123 g/l), stirred for 5 minutes. The time separation of phases is less than 1 minute. The aqueous phase drained from the bottom, the degree of extraction of molybdenum is 90,52 wt.%, the content of molybdenum - 967 mg/l, pH of 1.0.

For deposition trisulde molybdenum take a 20%excess of sodium sulphide in the sulphur-alkaline effluents production of olefins by the pyrolysis of hydrocarbons. To 100 ml of the aqueous phase is poured to 18.3 ml BOILING until the pH value of the solution is equal 1,95. The content of total concentration of compounds of sodium BOILING is 63,25 g/l, the content of sodium sulfide - 20,66 g/l, the content of sodium hydroxide - 45,75 g/l Volumetric ratio of aqueous phase: - BOILING (Vin:Vboiling) =1: 0,19. The solution is boiled for 1-2 minutes for the best coagulation sludge, brown flocculent precipitate trisulde molybdenum filter. The molybdenum content in the filtrate is 48 mg/l, the degree of deposition of molybdenum - 95,22 wt.%.

Example 2

100 ml of the aqueous phase obtained after extraction of the alkaline waste solution of sulfuric acid, as in example 1, add to 34.5 ml of sulfur-alkaline waste water production of olefins by the pyrolysis of hydrocarbons to the value of pH of the solution is equal 1,95. The content of total concentration of compounds of sodium BOILING is 39,52 g/l, the contents of sodium sulfide - 10,85 g/l, the content of sodium hydroxide - 28,68 g/l Volumetric ratio of Vin:Vboiling=1:0,35. An excess of sodium sulfide with respect to the desired reaction number is 20%.

The solution is boiled for 1-2 minutes for the best coagulation sludge, brown flocculent precipitate trisulde molybdenum filter. The molybdenum content in the filtrate is 46 mg/l, the degree of deposition of molybdenum - 94,56 wt.%.

Example 3

The method is carried out as described in example 1. For deposition trisulde molybdenum to 100 ml of the aqueous phase add to 42.5 ml of sulfur-alkaline waste water (analogous to example 2) to a pH value of 2.5. The volumetric ratio of Vin:Vboiling=1:0,43. An excess of sodium sulfide with respect to the desired reaction number is 50%.

The solution boil for 1-2 min, the precipitate trisulde molybdenum filter. The molybdenum content in the filtrate is 16 mg/l, the degree of deposition of molybdenum - 97,88 wt.%.

Example 4

The method is carried out as described in example 1. For deposition trisulde molybdenum to 100 ml of the aqueous phase add a 21.5 ml of sulfur-alkaline waste water (same as example 1) to a pH value of 2.4. The volumetric ratio of Vin:Vboiling=1:0,22. An excess of sodium sulfide with respect to the desired reaction number is 40%.

The solution boil for 1-2 min, the precipitate trisulde is olindina filtered. The molybdenum content in the filtrate is 27 mg/l, the degree of deposition of molybdenum - 97,06 wt.%.

Example 5

The method is carried out as described in example 1. For deposition trisulde molybdenum to 100 ml of the aqueous phase add 65 ml of sulfur-alkaline waste water (analogous to example 2) until a pH equal to 7. The volumetric ratio of Vin:Vboiling=1:0,65. An excess of sodium sulfide with respect to the desired reaction number is 130%. Then acidified to a pH equal to 2.2 by adding 1 ml of sulfuric acid.

The solution boil for 1-2 min, the precipitate trisulde molybdenum filter. The molybdenum content in the filtrate is 7 mg/l, the degree of deposition of molybdenum - 99,06 wt.%.

Example 6

The method is carried out as described in example 1. For deposition trisulde molybdenum to 100 ml of the aqueous phase add 40 ml of sulfur-alkaline waste water (same as example 1) to a pH value of 7.2. The volumetric ratio of Vin:Vboiling=1:0.4 to. An excess of sodium sulfide with respect to the desired reaction number is 160%. Then acidified to a pH equal to 2.2 by adding 1.25 ml of sulphuric acid.

The solution boil for 1-2 min, the precipitate trisulde molybdenum filter. The molybdenum content in the filtrate is 8 mg/l, the degree of deposition of molybdenum - 98,97 wt.%.

Example 7

The method is carried out as described in the example . For deposition trisulde molybdenum to 100 ml of the aqueous phase add 76.5 ml of sulfur-alkaline waste water (analogous to example 2) to a pH value of 9.0. The volumetric ratio of Vin:Vboiling=1:0,77. An excess of sodium sulfide with respect to the desired reaction number is 170%. Then add 1.7 ml of sulfuric acid to a pH of 2.2.

Molybdenum in the filtrate is missing, the deposition of molybdenum full.

Example 8

The method is carried out as described in example 1. For deposition trisulde molybdenum to 100 ml of the aqueous phase add to 45.5 ml of sulfur-alkaline waste water (same as example 1) to a pH value of 9.0. The volumetric ratio of Vin:Vboiling=1:0,46. An excess of sodium sulfide with respect to the desired reaction quantity is 200%. Then add 1.5 ml of sulfuric acid to a pH of 2.2.

Molybdenum in the filtrate is missing, the deposition of molybdenum full.

Example 9

In thermostatic funnel at a temperature of 70°load 100 ml of alkaline waste resulting from washing with a solution of caustic soda heavy fractions of the process of epoxidation of cyclohexene with tert-butyl hydroperoxide. The content of molybdenum in alkaline waste amounts to 0.24 wt.%. Poured 150 ml of 2.5 N solution of sulfuric acid (123 g/l) and stirred for 5 minutes. The time separation of phases is less than 1 minute. The aqueous phase from the bottom scarfing, the degree of extraction of molybdenum is 91,46 wt.%, the content of molybdenum in the aqueous phase is 984 g/l

For deposition trisulde molybdenum to 100 ml of the aqueous phase add 48 ml of sulfur-alkaline waste water (same as example 1) to a pH value of 9.2. The volumetric ratio of Vin:Vboiling=1:0,48. An excess of sodium sulfide with respect to the desired reaction number is 190%. Next, add 1.6 ml of sulfuric acid to a pH of 2.2.

Molybdenum in the filtrate is missing, the deposition of molybdenum full.

Example 10

The method is carried out as described in example 9. For deposition trisulde molybdenum to 100 ml of the aqueous phase add 80 ml of sulfur-alkaline waste water (analogous to example 2) to a pH value of 9.0. The volumetric ratio of Vin:Vboiling=1:0,8. An excess of sodium sulfide with respect to the desired reaction number is 180%. Next, add 1.9 ml of sulfuric acid to a pH of 2.2.

Molybdenum in the filtrate is missing, the deposition of molybdenum full.

Example 11

From the obtained trisulde molybdenum synthesize the catalyst for the epoxidation of olefins: 0,44 g trisulde molybdenum dissolved in 12.5 ml of 25%ethyl benzene hydroperoxide. The mixture is heated to 50°and add 12.5 ml of ethanol. The oxidation of lead for four hours at a temperature of 70°With the content of the plants is Oronogo molybdenum in the catalyst is prepared and 0.61 wt.%. Simultaneously prepare the catalyst for the epoxidation based metal of molybdenum-dissolved molybdenum and 0.6 wt.%. The obtained solutions of the catalysts of the face during the epoxidation of 1-octene. Conversion of hydroperoxide using a catalyst derived from a metal of molybdenum, is a 94.6 wt.%, using the catalyst obtained from trisulde molybdenum, 97,2 wt.%. The selectivity of the formation of the oxide, octene - 92,8 and 93.8 wt.% respectively.

As seen from the above examples, the proposed method can achieve a high degree of extraction of molybdenum products from the catalytic epoxidation of olefins with organic hydroperoxides.

The method of extraction of molybdenum products from the catalytic epoxidation of olefins with organic hydroperoxides, including the processing of heavy fractions of epoxide alkali solution, treatment of the resulting waste alkaline extractant stream with subsequent deposition trisulde molybdenum, characterized in that as a precipitator trisulde molybdenum use of sulfur-alkaline wastewater production of olefins by the pyrolysis of hydrocarbons.



 

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