Method of recycling wastes from catalytic epoxidation of olefins

FIELD: chemistry.

SUBSTANCE: invention relates to a method of recycling wastes from catalytic epoxidation of olefins using organic hydroperoxides, which involves extraction and treatment of the heavy epoxidate fraction with an alkali solution and treatment of the resultant spent alkaline stream with an extractant. The invention proposes addition of a ligand which forms a molybdenum organometallic complex to the spent alkaline stream and extraction from the spent alkaline stream of a fraction containing propylene glycol, acetophenone, ethylbenzene, phenol, methyl phenyl carbinol and the molybdenum organometallic complex formed, treatment with an extractant at T≥Tcr and P≥Pcr with subsequent splitting of the extract into fractions through stepped reduction of pressure from Pextr to P<Pcr with number of pressure reduction steps equal to the number of fractions of the components which should be obtained, taking into account the molybdenum organometallic complex, where Tcr, Pcr are critical temperature and pressure values of the extractant and Pextr is extraction pressure.

EFFECT: maintaining high degree of extracting molybdenum from the spent alkaline stream regardless of its composition and possibility of extracting fractions of components contained in the spent alkaline stream.

1 dwg, 3 tbl, 8 ex

 

The invention relates to the field of petrochemical industry, specifically to the process of neutralization of waste catalytic epoxidation of olefins with organic hydroperoxides.

A known method of disposal of heavy residue separation of epoxidated by returning part of it to the epoxidation reactor. The disadvantage of this method is to reduce the efficiency of the recycle catalyst and the formation of benzoic acid, which places high demands on corrosion resistance equipment [Kirpichnikov P.A., Beresnev V.V., Popova L. Album technological schemes of the main industries of synthetic rubber: - Textbook. manual for schools. - 2nd ed., Rev., Leningrad: Khimiya, 1986 - 224].

A known method of disposal of waste containing hydrocarbons, combustion at the facility thermal treatment of liquid wastes, including cyclone furnace with tangentially arranged gas burners, nozzles for supplying liquid waste, flue connected to a device for cleaning exhaust gases and flue (the book "Fire recycling and disposal of industrial waste". - M.: Chemistry, 1990, s-208). The disadvantage of this method is the necessity of using fuel, an irreversible loss of the raw materials contained in waste and environmental harm to the environment.

A known method of disposal of the waste is in by thermal treatment in ozonopause environment (see Pat. Of the Russian Federation No. 2289066, CL F23G 7/04 from 10.03.2005, publ. 10.12.2006. Bull. No. 34). The disadvantage of this method is the need of the use of fuel, ozone generator and irrecoverable loss of the raw materials contained in waste.

The method for extracting 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. As a precipitator trisulde molybdenum use of sulfur-alkaline wastewater production of olefins by the pyrolysis of hydrocarbons (see U.S. Pat. Of the Russian Federation No. 2268885, CL 07D 301/19, 15.11.2004, publ. 27.01.2006. Bulletin No. 3).

The disadvantage of this method is the dependence of the degree of extraction from the composition of sulfur-alkaline waste water and the composition of the spent alkaline stream and the inability to extract other components of the waste.

The known method of wastewater treatment petrochemical and oil refineries from dissolved phenols and petroleum products by processing a pulsed high voltage discharges with subsequent sedimentation, characterized in that, to improve the efficiency of dissolved phenols and oil products, the waste water is subjected to a combined treatment Vysokomol time pulsed discharges with specific energy 7-15 kJ/DM 3with the subsequent flotation, biological treatment and sorption on coal and sand filters (see U.S. Pat. Of the Russian Federation No. 96105609, CL C02F 1/48, from 22.03.1996, publ. 10.06.1998).

The disadvantage of this method is its multi-stage and high energy costs.

Closest to the present invention is a method of disposal of waste process for the catalytic epoxidation of olefins with organic hydroperoxides, including the selection and processing of heavy fractions of epoxide alkali solution, treatment of the resulting waste alkaline extractant stream with subsequent precipitation of the molybdenum-containing compounds. As a precipitator trisulde molybdenum use of sulfur-alkaline wastewater production of olefins by the pyrolysis of hydrocarbons (see U.S. Pat. Of the Russian Federation No. 2268885, CL 07D 301/19, 15.11.2004, publ. 27.01.2006. Bulletin No. 3).

The disadvantage of this method is the dependence of the degree of extraction from the composition of sulfur-alkaline waste water and the composition of the spent alkaline stream, and the impossibility of extraction of other components of the waste. Because sulfur-alkaline runoff and spent alkaline stream is a waste, its composition and quantity are not regulated and the real degree of extraction may vary from 100 to 0%, for industrial applications is unacceptable.

Object of the invention is the preservation of a high degree isplace the Oia molybdenum from spent alkaline stream regardless of the latter and the ability to extract propilenglikolem, etilbenzene, acetophenones, phenolic, methylphenylcarbinol fractions with subsequent fractionation.

The tasks are solved due to the fact that the method of disposal of waste process for the catalytic epoxidation of olefins with organic hydroperoxides, including the selection and processing of heavy fractions of epoxide alkali solution, treatment of the resulting waste alkaline extractant stream with subsequent precipitation of the molybdenum-containing compound is carried out by adding a ligand, forming the ORGANOMETALLIC complex of molybdenum and the selection of the departure of propylene glycol, ethylbenzol, acetophenones, phenolic, methylphenylcarbinol fractions and the resulting ORGANOMETALLIC complex of molybdenum processing extractant at T≥Tkrand R≥Rkrwith the subsequent separation of the extract into fractions by stepwise pressure reduction from Pthe extrasto R<Rkrwith the number of stages of pressure reduction, equal to the number of fractions of the components that you want to retrieve, given the ORGANOMETALLIC complex of molybdenum, where Tkr, Rkrcritical values of temperature and pressure of the extractant, Rthe extras- pressure extraction.

The method is as follows. The reaction products of the epoxidation olefinverbund 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 (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 salts, primarily sodium molybdate (Na2MoO4). For separation of molybdenum in THAT type ligand, forming ORGANOMETALLIC complex with molybdenum in a molar ratio of 1:1 to the molybdenum. The molybdenum content is determined by photocolorimetric method.

As extractant for the extraction process components of the waste and the complex formed of molybdenum well suited carbon dioxide, propane-n-butane mixture, a mixture of ethane to n-butane, n-pentane, n-heptane, n-octane and others, mixtures of methane, n-butane, n-pentane, n-hexane, n-heptane, n-octane and other Substances contained in these compounds and having a "relationship" with the molybdenum complex with different ligands and components of waste, provide high solvent method is ity to last.

As a ligand can be used ethylenediaminetetraacetic acid, salts of ethylenediaminetetraacetic acid (DNATA), oksihinolina-8, CYANEX-272 (..Opalovsky, I.I.Tychinskaya, Z.M.Kuznetsova, P.P.Samoilov, Molybdenum Halogenides-Nauka Publishing House, Siberian Division of the USSR Academy of Sciences, Novosibirsk, 1972, p.260) or other complexing compounds, soluble in the above extractants. Molybdenum forms stable complexes with ethylenediaminetetraacetic acid, disodium salt of ethylenediaminetetraacetic acid at pH 5 to 8, with the formation of compounds corresponding to the formula Na2Mo2O12H12C10N2×H2(A. I. busev Analytical chemistry of molybdenum. - M. Publishing house of the USSR Academy of Sciences, 1962. - 302 C.). In tables 1, 2, 3 shows the dependence of the solubility of the complexes of molybdenum from the pressure of the extraction and the content of components in the original solution and subjected to extraction at different pressures.

Diagram of the device for carrying out the extraction process shown in the drawing, 1 is a cylinder with liquefied carbon dioxide, 2,4,6 - valves, 3 - compressor or pump, 5 - extractor, 7 collections of extract, 8 - throttling device.

The following examples describe the method of disposal of waste process for the catalytic epoxidation of olefins.

Example 1. THAT is loaded into the extractor 5. Extractor hermetism the comfort and heated to temperature T≥T krwhile the valves 4 and 6 are closed. From the container 1 into the compressor or pump 3 serves extractant by opening valve 2. Then the extractor serves extractant under pressure R≥Rkrfrom the compressor or pump 3, by opening the valves 4, 6 and closing the valve 2. Passing through the solution, the extractant dissolves in themselves components of the waste. Further, the extractant dissolved substances passes through the throttle device 8. After the throttle device, the pressure drops, the dissolving ability of the extractant is reduced, thus there is a separation of the extractant from the dissolved substances. In proceedings of the extract 7 separated substances precipitate and the solvent evaporates. In the extractor remains water and resinous substances. Molybdenum in the extract.

Example 2. Differs from example 1 in that in THAT is added to the ligand of DNATA. The extraction process is conducted according to the procedure described in example 1. In proceedings of the extract components fall retreat (propylene glycol, ethylbenzene, acetophenone, phenolic, methylphenylcarbinol faction) and the complex of molybdenum. In the extractor after extraction remains thick resinous mass containing sodium salts of organic acids, heavy resin, unreacted ligand and water. The degree of extraction of molybdenum from waste at a ratio of solvent : waste =35:1 was 98,36%.

<> Example 3. Differs from example 2 in that the quality of the ligand in QUESTION is added CYANEX-272. In the extractor after extraction remains thick resinous mass containing sodium salts of organic acids, heavy resin, unreacted ligand and water.

Example 4. Differs from example 2 in that the quality of the ligand in QUESTION is added to the oksihinolina-8. In the extractor after extraction remains thick resinous mass containing sodium salts of organic acids, heavy resin, unreacted ligand and water.

Example 5. Differs from examples 1, 2, 3 and 4 so that the extractant dissolved substances throttled speed, passing two or more of the collection. In the collections of the extract falls mainly the component, the solubility of which is at a pressure in the collection is minimal. Thus, the extract can be divided into fractions. In the extractor remains after extraction, the water containing the sodium salt of the acid, a small amount of heavy resin and unreacted ligand.

Example 6. Differs from examples 1, 2, 3, 4 and 5 so that the pressure of the extractant fed to the extractor, increase gradually (stepwise), since Rkrwhen this solution is extracted mainly the component, the solubility of which at a given maximum pressure. In proceedings of the extract falls fractions of the components is now waste and complex molybdenum. In the extractor after extraction remains a small amount of water, heavy resin and unreacted ligand. The degree of extraction of molybdenum from waste at a ratio of solvent : waste =35:1 was 98%.

Example 7. Differs from examples 1, 2, 3, 4, 5 and 6 so that the pressure of the extractant dissolved ORGANOMETALLIC complex and components of the waste supplied from the extractor in the collections of the extract reduces gradually (stepwise), since Rthe extrasto R<Pkrwhile in the corresponding collection of the extract falls mainly the component, the solubility of which at a given pressure is minimal. In the extractor after extraction remains a small amount of water, heavy resin and unreacted ligand.

Example 8. Differs from examples 1, 2, 3, 4, 5, 6 and 7 so that THAT prior to being fed into the extractor handle alcohol solution (methanol, ethanol and others) or acetone in a molar ratio of 1:1 complex of molybdenum. In the extract, in addition to the components of the waste and of the complex of molybdenum, contains used in the processing of alcohol or acetone. In the extractor after extraction remains a small amount of water, heavy resin, the remnants of the alcohol or acetone and unreacted ligand. The degree of extraction of molybdenum from waste at a ratio of solvent : waste =35:1 was 98,48%.

As can be seen from t the blitz 3, the main components contained in the waste, are extracted almost completely. After extraction remains pasty substance and water, containing salts, acids, glycols and a small amount of aromatic hydrocarbons.

As studies have shown, the solubility of the molybdenum complex with different ligands depends only on the pressure and temperature of extraction and does not depend on the composition of raw materials. The solubility may be affected by factors that prevent the formation of a complex of molybdenum with ligand (strongly alkaline or strongly acidic environment, the binding of molybdenum in other, more durable organic complexes with high molecular weight).

Table 1
Change the solubility of the complex of molybdenum in the UK CO2depending on the pressure (at temperature 65°C)
no experienceThe pressure P, MPaSolubility, g Mo/ml of CO2
DITACYANEX-272The oksihinolina-8
1to 12.00,50×10-50,35×10-50,1×10 -5
215,00,83×10-50,41×10-50,12×10-5
320,0of 1.03×10-50,42×10-50,2×10-5
425,00,93×10-50,44×10-50,2×10-5

Table 2
Change the solubility of the complex of molybdenum in the propane-butane (50×50 wt.%) depending on the pressure (at temperature 160°C)
no experienceThe pressure P, MPaSolubility, g Mo/ml of CO2
DITACYANEX-272The oksihinolina-8
140,00,60×10-50,4×10-5<0,1×10-5
242,0 to 0.63×10-50,4×10-50,1×10-5

The method of disposal of waste process for the catalytic epoxidation of olefins with organic hydroperoxides, including the selection and processing of heavy fractions of epoxide alkali solution, treatment of the resulting waste alkaline extractant stream, characterized in that the spent alkaline stream type ligand, forming the ORGANOMETALLIC complex of molybdenum, and separated from spent alkaline stream fraction comprising propylene glycol, acetophenone, ethyl benzene, phenol, methylphenylcarbinol and the resulting ORGANOMETALLIC complex of molybdenum, processing extractant at T≥Tkrand R≥Rkrwith the subsequent separation of the extract into fractions by stepwise pressure reduction from Pthe extrasto R<Pkrwith the number of stages of pressure reduction, equal to the number of fractions of the components that you want to retrieve, given the ORGANOMETALLIC complex of molybdenum, where Tkr, Rkrcritical values of temperature and pressure of the extractant, Rthe extras- pressure extraction.



 

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2 cl, 3 dwg

FIELD: chemistry.

SUBSTANCE: method involves treatment of heavy olefin fraction by an alkali solution, processing of obtained discharge alkali flow by extragent, and further precipitation of molybdenum trisulfide by precipitator. According to invention, sodium hydrosulfide is applied as molybdenum trisulfide precipitator. The method allows regulation of molybdenum trisulfide precipitator feed, reduction of precipitation reactor dimensions and energy consumption of heating and stirring, significant reduction waste and hydrogen sulfide discharge at high molybdenum extraction degree of 90.5-97.6%.

EFFECT: improved method of molybdenum extraction from products of catalytic olefin epoxidation by organic hydroperoxides.

6 ex

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