Method for production of phenol

 

(57) Abstract:

Use: as a reagent in organic synthesis. The inventive product is phenol. Reagent 1: cumene. Reagent 2: molecular oxygen. Reaction conditions: 60 - 150°C, 1-10 kgf/cm2alkaline compound pH of 8.5 to 10.5. table 1.

The invention relates to the production of phenol/ more specifically to a method for production of phenol/ which may lead to the formation of propylene byproduct of acetone/ and recycling the regenerated propylene as the starting material.

In this area is well known interaction of benzene with propylene to obtain cumene/ oxylene cumene with obtaining cumene hydroperoxide and acid cleavage of cumene hydroperoxide to phenol and acetone. The traditional method for production of phenol/ containing these combined stage/ generally known as a method for the production of cumene.

A well-known technique is the hydrogenation of acetone to isopropanol. This technique is widely used at present for the catalytic activity of hydrogenating catalyst and for other purposes. For example/ activity of skeletal Nickel hydrogenation catalysts often willows.

However, never offered a receipt from isopropanol acetone by-product during the production of phenol in accordance with Komolova way/ as well as dehydration of isopropanol to propylene.

There are similar ways/ for example obtaining ethylene from ethanol and obtaining isobutene from tert-butanol. However, these alainpantyhose methods cannot be used to obtain propylene from isopropanol for the following reasons. Since propylene is substantially different in reactivity from ethylene or isobutylene/ impossible dehydration of isopropanol as the terms and conditions of the synthesis of ethylene from ethanol/ or terms and conditions of the synthesis of isobutylene from tert-butanol.

As for the re-use of acetone/ which is a by-product in Komolova the way/ such as/ due to its conversion into propylene/ so far there have been no useful suggestions.

Method for production of phenol/ usually known as comology way/ is production of acetone by-product/ which one reasons is favorable/ however/ from other causes is unfavorable. More specifically/ advantage is the separate receiving in different settings. In turn, if the ratio of the produced phenol and acetone is unbalanced with respect to their business requirements/ one of the products in which there is less need/ is obtained substantially in excess of/ and this is a disadvantage.

As is well known in the art/ acetone abundantly available in recent years. Therefore, the production of acetone by-product is considered as a drawback of the method of production of cumene. Although acetone finds most of its use as starting material to obtain the methyl ester of methacrylic acid/ need in acetone is reduced due to failover, the source material for the production of methyl methacrylate.

Thus/ there is a need to develop a method for production of phenol/ which deprived the production of acetone and other by-products. Although proposed several ways/ not one of them leads to the production of phenol with sufficient outputs.

In addition/ impurities in the propylene often cause another disadvantage is that during the process of cumene from benzene and propylene in the method of production of cumene for the production of phenol. And have the ve source material. However, crude oil contains sulfur compounds and heavy metals/ and these impurities are sometimes transferred to propylene as pollutants - traces of/ in the course of its production. For example/ seraikis carbon (COS) as the sulfur compound or as a mixture of heavy metal in the propylene inhibits the function of catalyst (complex luminiare - HCl) used in the preparation of cumene/ thereby disrupting the normal process of synthesis of cumene. Therefore/ to eliminate pollution of propylene these impurities/ carry out simple cleaning. The types and amounts of these contaminants vary not only from a source of crude oil, but also from differences in the process conditions to obtain propylene (from crude oil). This extraordinary burdens method of purification of propylene extremely complex and hard stages.

Thus/ there is a need to create a method of producing propylene from sustainable clean/ do not contain any of the specified impurities/ to reduce the number of stages in the method cleanse propylene.

The aim of the invention is to provide a new and improved method for the production of phenol with commercially satisfactory is the generation of large quantities of by - product - acetone/ but not low interest yield of the obtained phenol. To solve this problem, the authors developed a way/ to turn the acetone by-product propylene/ ie method/ which allows to obtain propylene following receipt of phenol. In addition/ propylene/ obtained by dehydration of isopropanol/ which is made from acetone using hydrogenization/ contains no listed sulphur compounds and heavy metals. The purity of the propylene/ consequently/ quite enough/ to use it as raw material for the synthesis of cumene. Such high purity leads to a decrease burdensome stages in the process of purification of propylene and/ thus/ provides significant industrial rationalization method for the production of cumene.

The above and other objectives can be achieved in accordance with the present invention by combining the following stages.

In accordance with one embodiments of the present invention proposes a method of production of phenol/ in which (A) benzene is subjected to interaction with propylene for the synthesis of cumene/(B) oxidizing the cumene stage (A)/ to turn it into cumene hydroperoxide. (C) carry out Atithi it in isopropanol/ (E) carry out the dehydration of isopropanol stage (D) in propylene (F)/ recyclist propylene from step (E) to the step (A).

In accordance with the method of the present invention, the phenol can be obtained from benzene/ oxygen and hydrogen with carbon/ having 3 carbon atoms/ as a cross-cutting element compounds (see scheme) is shown in the drawing. Note to the drawing: [] raw material/ product or byproduct; <> - auxiliary substance; ()-intermediate product).

In practice, the present invention/ i.e. stage of implementation of the methods And/and/ can be performed in accordance with the traditional method of production of cumene.

Typical examples of the method of production of cumene suggest the following:

Example 1. Alkylation of benzene with propylene.

A glass autoclave of 1 liter/ equipped with an agitator with Teflon coating and a thermometer in the shell/ load 78 g of benzene and aluminofluoride complex. The number of downloaded aluminofluoride complex is 0/08 g in terms of aluminofluoride/ which corresponds to a molar ratio aluminofluoride complex to propylene/ equal to 1/1000. The autoclave was immersed in an oil bath and the contents of the autoclave support at the 100With careful stirring. In the car is the super 90 min/ maintaining the internal pressure of the autoclave at the level of 3 kgf/cm2. The reaction end with the completion of the feed of propylene and the reaction mixture is then removed from the autoclave. The reaction mixture was analyzed by gas chromatography and found that it contains 25/1 wt.% cumene/ 13/3 wt.% meta-diisopropylbenzene/ 7/4 wt.% para-diisopropylbenzene and 7/9 wt. % triisopropylbenzene. The total yield of cumene/ diisopropylbenzene and triisopropylbenzene 99 % by weight of propylene download.

The reaction mixture is separated by distillation in unreacted benzene/ cumene/ vysokomineralizovannye products. Vysokoizbiratelnoe products return to the initial stage or phase alkylation to parallelomania with the/ to turn them into cumene.

The oxidation of cumene

In an autoclave with a capacity of 500 ml stainless steel/ equipped blower tube/ hole to feed alkali/ nozzle for removal of samples/ thermometer in the shell/ reflux condenser and an intensive mixer/ load 120 g of cumene/ 30 g of a 5% aqueous solution of sodium carbonate and 0/5 g /- azobisisobutyronitrile as an initiator. The air in the autoclave displace nitrogen and the initial pressure is set to 5 kgf/cm2with nitrogen before heating with stirring the om air supply rotation of the agitator increase in order to provide sufficient gas-liquid interaction. the cumene oxidized by air blowing at a speed of 30 l/h When carrying out oxidation reactions are taken on samples of the reaction mixture at intervals through the nozzle for sampling to study the pH of the reaction mixture. Small portions of 5% aqueous sodium carbonate solution is pumped into the reactor through the feed slot with the alkali to maintain the pH of the reaction mixture at the level of 9-10. The reaction is complete when it takes 10 hours from the beginning of the purge air. The reaction mixture is discharged from the autoclave and separated into oil and water phases. The oil phase is subjected to liquid chromatography to determine the content of cumene hydroperoxide and find/ that the oil phase contains 26 % by weight of cumene hydroperoxide.

Acid cleavage of cumene hydroperoxide.

The oil phase/ result of oxylene cumene/ concentrated under 100C and a vacuum of 160 mm RT.art./ fending off the unreacted cumene. Concentrating finish/ when the concentration of the oil phase is increased by about 3 times. Then the oil phase contains about 78 % by weight of cumene hydroperoxide.

In chetyrehosnuju flask with a capacity of 500 ml equipped with a mixer/ drip funnel/ thermometer GU funnel load of 100 g of the concentrate of cumene hydroperoxide. The flask placed in a water bath at a temperature of 80With the/ to the acetone was continuously delegirovali/ under stirring contents of the flask.

At reflux distilled acetone concentrate of cumene hydroperoxide are added dropwise into the flask through a funnel. The rate of addition of the concentrate regulate/ watching the number deleverage acetone. After the addition of the full amount of the concentrate of cumene hydroperoxide reaction additionally continue for 30 minutes At the end of the reaction, the reaction mixture was analyzed liquid chromatography/ detecting/ what remains a small part of cumene hydroperoxide/ i.e. conversion of approximately 100 %. It is found that phenol is produced in quantity/ corresponding 95 % converted gidroperekisi cumene.

In the reaction mixture is added powdery sodium carbonate with the/ in order to neutralize the acid catalyst. Solid particles are removed from the neutralized reaction mixture by filtration and the filtrate concentrated with the/ to remove the acetone. The number of extracted includes acetone acetone download and 28/5 g of acetone/ resulting from the acid cleavage of cumene hydroperoxide.

Gidrogenit is 500 mm/ load in the middle part 100 (48 ml) lumpy alloy skeletal Nickel catalyst (Raney Nickel) hydrogenation (R-20L/ manufactured by Nikko Rika K. K). The reactor is filled with water and then 20% aqueous solution of caustic soda/ which slowly pump in the reactor tube for the manifestation of skeletal Nickel catalyst for hydrogenation. The internal temperature of the reactor increases/ as a manifestation of the catalyst causes an exothermic heat. The volumetric rate of solution of caustic soda is adjusted to the temperature inside the reactor did not exceed 60C. After discharge 0/5 l of a solution of caustic soda supplied raw materials to replace water in order to rinse the reactor nozzle. Washing is continued until/ until the flow of water from the reactor will not become neutral. At the end of the washing forced feeding material to be replaced by isopropanol to fill the reactor. Begin heating the reactor.

When the temperature inside the reactor reaches 100With/ reaction begins by the filing of acetone and hydrogen in the reactor from the top with bulk velocity 59/0 g/h and 40.2 l/h, respectively. The pressure in the reactor is maintained at a level of 20 kgf/cm2.

The reaction mixture/ leaving the reactor bottom/ share on the reaction liquid, and gaseous hydrogen using gas-liquid separator. The reaction liquid and getobjecta 9 h with continuous feeding of acetone and hydrogen. The reaction liquid and gaseous hydrogen, respectively analyzed by gas chromatography. Found/ what 0/2 wt.% acetone remains in the reaction liquid, and the other component consists exclusively of isopropanol. Analysis of the gas discharge shows no methane/ ethane and propane. Reaction efficiency is calculated on the basis of these analytical results/ finding/ the way isopropanol is 99/8 %.

Dehydration of isopropanol

The vertical reactor tube of stainless steel having an inner diameter 25/4 mm and a length of 500 mm/ load in the middle part 20 ml of a commercially available alumina/ finely ground to a size of 8 to 14 mesh. The air in the reactor was rinsed with nitrogen, after which the reactor is heated under pressure nitrogen/ 100 kgf/cm2. When the temperature inside the reactor reaches 320With/ isopropanol fed into the reactor from above with flow rate 40 ml/h the Reaction continued for 8 hours maintaining the reaction pressure at 10 kg/cm2.

Liquid product with the prevailing water content and a gaseous product with a predominant content of propylene obtained in the course of the reaction in the amount of 9/5 g/h 2/2 l/h, respectively. Liquid and rcia isopropanol is 99/6 % and the yield of propylene is 99/3 %. The gaseous product contains propylene purity 99/9 %.

The resulting gaseous product/ ie propylene/ ready for recirculation through alkilirovanija benzene without special treatment.

Alkylation using gaseous product resulting from the dehydration of isopropanol.

In a glass autoclave with a capacity of 1 l equipped with a blade stirrer with Teflon coating and a thermometer in the shell/ load 78 g of benzene and aluminofluoride complex. The number of downloaded aluminofluoride complex is 0/08 g in terms of aluminofluoride/ which corresponds to a molar ratio aluminofluoride complex to propylene/ equal to 1/1000. The autoclave was immersed in an oil bath and the contents of the autoclave support at the 100With careful stirring.

In the autoclave add portions of the gaseous product obtained in the preceding dehydration of isopropanol (which is collected by liquefaction in the trap/ cooled with dry ice)/ while the internal pressure in the autoclave is maintained at the level of 3 kgf/cm2. The gaseous product was served within 90 min/ in number/ corresponding 25/2 g of propylene. Soda/ it contains 25/1 wt.% cumene/ 13/3 wt. % meta-diisopropylbenzene/ 7/4 wt. % paradiseprivate and 7/9 wt.% triisopropylbenzene. The total yield of cumene/ diisopropylbenzene and triisopropylbenzene 99 % by weight of propylene feed.

Therefore demonstrated that phenol can be obtained from benzene as the primary reagent and oxygen and hydrogen as secondary reagents without the production of acetone by-product by combining a number of stages: (A) the interaction of benzene with propylene to the fact/ to synthesize cumene. (C) oxidation of cumene stage (A) in the cumene hydroperoxide/ (C) acid cleavage of cumene hydroperoxide to phenol and acetone.(D) hydrogenation of acetone stage (S) in isopropanol/ (E) dehydration of isopropanol stage (D) in the propylene/ (F) recycling propylene stage (E) in stage (A).

In accordance with the present invention, the phenol can be effectively obtained from benzene using hydrocarbon/ having 3 carbon atoms/ as intermediate compounds/ by combining the above-mentioned steps (A) - (F).

Propylene can be obtained from the acetone by-product/ produced during the production of phenol/ by combining the above stages (a) through (E)accelerate the procedure for the hydrogenation of acetone in example 1, except that the hydrogenation reactor load 100 ml alloy of Raney Nickel (R - 20L/ produced by firm Nikko Rika K. K.)/ acetone hydronaut under the reaction conditions/ are given in table.1/ a as the source material serves a mixture of acetone and isopropanol in the ratio of 1:1. The reaction mixture is analyzed as/ as in example 1. The results are shown in table.1

Examples 3/4 and 5. Repeat the hydrogenation reaction of acetone according to the method of example 2, except that instead of Nickel alloy Raney use 70 ml of a copper-chromium catalyst (N 201/ manufactured by a company "Nikki chemical Co/ Ltd)/ 100 ml of the catalyst/ made of Nickel deposited on hard-shelled land (N 112/ produced by firm "Nikki chemical Co/ Ltd) or 70 ml of catalyst/ made of ruthenium/ deposited on alumina (produced by firm "H.E. Chemcat Corporation"). Thus obtained results are shown in table.1.

Physical and chemical parameters of the used catalysts are the following:

The alloy of Raney Nickel (Ra-Ni/ before the development process)

Form - sponge.

The Content Of Ni 50 1%.

Mass density 1/9-2/1 g/cm3.

The particle size of 3-6 mm

Copper-Chromium (si-CR)

The form - cylinders with a diameter of 5 mm and a length of 5 mm

Mass density 1/4 tablepanel > 180 kg/cm2.

The catalyst/ made of Nickel on hard-shelled land (Ni/Diatom)

The form - cylinders with a diameter of 3 mm and a length of 3 mm

Mass density 1/1-1/2 g/cm3.

Composition/ % : 45-47 Ni, 2-3 Cr, 2-3 Cu, 4-5 carbon/ 27-29 hard-shelled land.

The average tensile fracture crush > 220 kg/cm2.

The catalyst/ made of ruthenium on aluminum oxide (Ru/alumina)

Form tablets.

The content of ruthenium 0/5 %.

The particle size of 3/2 mm

The specific surface area of 90-100 m2/g

Mass density 0/9-1/1 g/cm3.

Examples 6 and 7 and 8. Repeat the hydrogenation of acetone in example 1 except that the reaction temperature change/ as shown in the table.2. The resulting reaction mixture was analyzed as in example 1. The data obtained are shown in table.2.

Examples of 9/10 and 11/ Dehydration of isopropanol carried out by the same method/ as a process of dehydration of isopropanol/ described in example 1/ with the exception/ what to change the temperature of the reaction/ as shown in the table.3. The obtained reaction mixture was analyzed as in example 1. The results are shown in table.3.

edowski.

The average pore size: 30-150

Composition: -aluminium oxide 90 wt.%

the silicon oxide 10 wt.%

Strength acid: pKa = +up to 6/8 3/3

The total amount of acid 3/5 mEq/g

Examples 12/ 13 and 14. Carry out the dehydration of isopropanol well as/ as in the process of dehydration of isopropanol/ described in example 1/ with the exception/ what change pressure as shown in the table.4. The resulting reaction mixture was analyzed as in example 1. The results are shown in table. 4.

Examples 15. Carry out the dehydration of isopropanol by the same method/ that dehydration of isopropanol in example 1, except/ that replace the catalyst on H-Mordenite and the reaction is carried out at 250C. the resulting reaction mixture was analyzed as in example 1/ found a conversion towards isopropanol 96/6% and the yield of propylene 70/8 % when the frequency of the thus obtained propylene 99/5 %.

Physical and chemical parameters of the used catalyst are as follows:

H-Mordenite

Form: tablets.

The effective pore size :7 .

Composition: the molar ratio of SiO2/Al2O3, 10 to 25.

Apparent density: 0/5 to 0/6 g/cm3.

Size casterline can be made essentially the same results when using different catalysts (described in detail the physical and chemical parameters of the used catalysts).

Experimental data in examples 6-8 show that the hydrogenation of acetone in the stage (d) can be satisfactorily confirmed by examples in a wide temperature range.

Additional experimental data in examples 9 and 10 show that the dehydration reaction in stage (e) can be satisfactorily confirmed by the examples in the temperature range of/ present in new claims. Physical and chemical parameters-oxindolimine catalyst is also described.

Experimental data of examples 12 to 14 show/ the rehydration reaction in stage (e) can be satisfactorily carried out in a wide range of pressures.

METHOD for production of PHENOL by liquid-phase oxidation of cumene at 60 - 150oFrom 1 to 10 kgf/cm2molecular oxygen in the presence of alkaline compounds at pH of 8.5 to 10.5 with receipt of cumene hydroperoxide and its subsequent decomposition to phenol and acetone with the preliminary concentration of the reaction mixture to increase the concentration of cumene hydroperoxide in the specified reaction mixture to 60 to 85 wt.%, dilution of the concentrated reaction mixture at least one solvent that acts rol is varicel selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, lower aliphatic alcohols, lower aliphatic ketones and lower aliphatic ethers, and acid cleavage solution of cumene hydroperoxide in 30 - 120oWith 1 to 5 kgf/cm2in the presence of at least one acidic compound as a catalyst, selected from the group consisting of mineral acids, heteropolyacids and solid acids, characterized in that, to simplify the technological process at the stage of oxidation of cumene to cumene hydroperoxide the cumene synthesized by the interaction of benzene with propylene by mixing benzene with propylene in a molar ratio of respectively 1 to 10 : 1 at 30 - 200oFrom 1 to 15 kgf/cm2in the presence as catalyst aluminofluoride complex, which is produced by absorption of gaseous hydrogen chloride solution aluminium chloride in a solvent, and aluminofluoride complex take in an amount of 0.01 - 5 wt.% from aluminium chloride, stage after acid cleavage of cumene hydroperoxide to phenol and acetone acetone hydronaut in the liquid phase in a stationary layer of a heterogeneous catalyst at 60 - 150oFrom 5 to 50 kgf/cm2, use the - 0 : 1, and as a heterogeneous catalyst is at least one catalyst selected from the group consisting of Raney-Nickel, copper-chromium catalyst, Raney copper, copper-zinc catalyst of Nickel on hard-shelled land, Nickel on alumina, Nickel on silica, and platinum, palladium, rhenium and rhodium deposited on activated carbon or alumina, optionally in the presence of at least one solvent selected from the group consisting of lower aliphatic alcohols, glycols, lower aliphatic ethers, aprotic polar solvents and saturated hydrocarbons suitable for the production of isopropanol, followed by dehydration of isopropanol at 100 450oFrom 1 to 40 kgf/cm2in the presence of at least one catalyst selected from the group consisting of mineral acids, haloperoxidase researched, solid acids, metal oxides, zeolites and zeolites modified with metal ions, with the aim of increasing propylene, which is optionally subjected to recirculation on the stage of the interaction of benzene with propylene, and propylene in this case, pre-cooled and compressed to obtain a liquefied product, maple.

 

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