Illa International, L.l.c.

General Electric Company

Sabic Innovative Plastics IP B.v.

Vladimir Mikhailovitch Zakoshansky

Irina Ivanovna Vassilieva

Andrei K Griaznov

Andrey Budarev

John William Fulmer

William D Kight

Yuri Ivanovitch Malov

Vasiliy Trubaev

Yuri Nikolaevich Koshelev

Sergey Korchagin

The purpose of the present invention is to provide an advantageous method for accelerating the cumene oxidation reaction without the drawbacks of the above-described previously known approaches by utilizing one or more airlift-type tray installed in one or more conventional commercial reactors utilized during the cumene oxidation process. Such a method is of great use in process configurations where it is desirable to achieve a controlled acceleration of the cumene oxidation process without decreasing process selectivity.

Method for acceleration of cumene oxidation

The purpose of the present invention is to provide an advantageous non-barbotage method for oxidation of hydrocarbons, that, when implemented in various embodiments thereof, provides significantly higher selectivity, a greater level of safety, lower capital costs, etc., than conventional oxidation processes utilizing the barbotage technique. The essence of the inventive non-barbotage oxidation process is ensuring that the oxidizing agent delivered to the process reactor undergoes continued contact only with exposed surfaces of the liquid phase of the hydrocarbons being oxidized configured as at least one of: formed liquid phase thin film(s), liquid phase continuous stream(s), and/or liquid phase globule (e.g., droplets, etc.) stream(s), preferably, with the surface area(s) of the exposed surface(s) being maximized to increase contact with an oxidizing agent being directed thereto, to ensure that the inventive oxidation reaction occurs at the border between liquid and gas phases, such that the oxidation reaction effectively occurs by way of contact of the oxidizing agent (e.g., oxygen) from the gas phase with exposed surface(s) of the liquid phase of the hydrocarbons being oxidized. The inventive non-barbotage oxidation process may be implemented in a single reactor, or in plural sequential reactors, and may be implemented both in a stand-alone configuration, and in combination with various conventional barbotage methods for oxidation of hydrocarbons.

Non-barbotage method for oxidation of hydrocarbons by forming and utilizing liquid phase thin film

A desalting method for extracting salt from phenol production waste of a phenol process, comprising the steps of:

Method for high efficiency salt removal from phenol process byproducts

A two-step method of crude phenol treatment from impurities, wherein a first step comprises oxidizing hydroxyacetone and aldehydes impurities, in phenol medium by air oxygen with the use of a heterogeneous catalyst which contains transition metals, and a second step comprises treating the unoxidized impurities with the use of a heterogeneous acidic catalyst. The separation of treatment by-products compounds produced during said phenol treatment may then be carried out by a conventional fractionation, distillation, or equivalent method, to produce highly purified product phenol.

Method for removing impurities from phenol

A method for the enhanced decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone which comprises decomposing cumene hydroperoxide in a non-isothermal manner in the presence of excess acetone whereby the molar ratio of acetone to phenol in a decomposition reactor is from about 1.1:1 to 1.5:1. A method for the selectivity of the decomposition of dicumyl peroxide to alpha methylstyrene also phenol and acetone in the presence of an acidic catalyst which comprises carrying out the decomposition at a temperature of from about 80&#xb0; to 110&#xb0; C. A method for carrying out the decomposition of dicumyl peroxide with an acidic catalyst system which comprises performing such decomposition in the presence of the reaction product of (1) an amine with (2) an acidic material which can catalyze the decomposition of CHP. A method for preparing phenol and acetone from the decomposition of CHP with an acidic catalyst which comprises (a) decomposing CHP at a specific acidic catalyst concentration and temperature thereby forming a composition comprising phenol, acetone and dicumyl peroxide, (b) transferring dicumyl peroxide to a plug flow reactor wherein decomposition of dicumyl peroxide to phenol acetone and AMS occurs at a lower acidic catalyst concentration and a higher temperature than the catalyst concentration and temperature in step (a). A method for the decomposition of CHP and producing CHP decomposition products therefrom which comprises recycling the CHP decomposition products to a CHP feedstream in the quantity of from about 10-25 times the weight of the CHP feedstream.

Method for the decomposition of cumene hydroperoxide by acidic catalyst to phenol and acetone

A continuous method of cumene oxidation in a gas-liquid system is provided, where the liquid phase is represented by cumene and its oxidation products and the gas phase is represented by air. The oxidation process can be carried out either in a reactor series or in a single reactor at least one of which is preferably equipped with at least two airlift-type trays. When specific CHP concentration is achieved, the oxidation products are discharged from the to reaction zone and treated in a mixing device with aqueous ammonia or water to remove organic acids such as formic acid, benzoic acid, etc. and to remove phenol, which is an inhibitor of oxidation reaction. The cumene oxidation product stream, free of organic acids and phenol is recycled to the same reactor in the case of single reactor, or is passed to the next reactor of the series in the case of reactor series. In all cases, the oxidation products treated with water or aqueous ammonia is first directed to a unit for separation of aqueous phase from organic products and then anhydrous organic product stream is forwarded to the next reactor of the series, or recycled to the single reactor for the continued cumene oxidation until the required CHP concentration is achieved. The airlift-type trays in at least one process reactor accelerate the cumene oxidation reaction therein while increasing the process selectivity and enabling the process to be conducted at lower temperature, improving safety thereof. Advantageously, lower quality cumene having impurities such as sulfur-containing trace elements, can be used in the inventive process while maintaining a high process selectivity.

Method for production of cumene hydroperoxide

A cumene process of producing phenol and acetone comprises the joint oxidation of aldehydes and dimethylbenzene alcohol by aqueous hydrogen peroxide solutions in presence of 16 wt % to 94 wt % of cumene hydroperoxide by contacting of mutually insoluble phases of the organic products from a cumene oxidation stage and hydrogen peroxide containing water with optional addition of acidic catalysts in a conversion reactor for the purpose of conversion of aldehydes into organic acids and dimethylbenzene alcohol into cumene hydroperoxide and therefore significantly simplifying the process of fractionation of organic conversion products into high quality product phenol and product acetone.

High selective method of producing cumene hydroperoxide, phenol and acetone in an oxidation by-product conversion process

Disclosed is a method for the production of product acetone of higher oxidation stability where the product acetone is produced by a multi-step rectification process in the presence of alkali catalyst. The embodiments of the method of present invention utilize a two-column and a one-column scheme of product acetone rectification from an acetone stream. In a two-column embodiment of the present invention, acetone is taken off in a vapor phase as a side-draw in a first column and directed to a partial condenser wherein it is separated into liquid and vapor phases with a simultaneous feed of aqueous sodium hydroxide solution to the first column above the feed tray. The vapor phase of the partial condenser is forwarded to a second column where the product acetone is rectified and then removed overhead, the bottom products are recycled to the first column feed, and the liquid phase of the partial condenser is treated with alkali and recycled either to the first column or to a neutralization stage of cumene hydroperoxide cleavage products. In a one-column embodiment of the present invention, acetone is taken off in the vapor phase overhead and directed to the partial condenser with the simultaneous feed of the aqueous sodium hydroxide solution above the feed tray. Product acetone is then condensed from the vapor phase and removed.

Method of production of product acetone of high stability to oxidation

A new phenol and acetone production process reduces the amount of necessary stages for obtaining phenol and acetone, results in higher yield of desired products and requires less complex equipment implementation and less energy than current processes of a similar type. The new process comprises a stage of cumene hydroperoxide production via cumene oxidation, a stage of cumene oxidation products concentration to produce technical cumene hydroperoxide and recycle of unreacted cumene to oxidation stage after treatment, a stage of separation of cumene oxidation products in a continuous or cycle adsorption-desorption with the purpose of producing CHP that is free from DMBA and AP utilizing predetermined adsorbents and desorbents, a stage of heterogeneous or homogeneous cumene hydroperoxide cleavage with the use of acidic catalysts to produce at least phenol and acetone, a stage of AP fractionation from AP-cumene fraction and return of cumene to the separation stage, a stage of catalytic DMBA hydrogenation into cumene, and a stage of separating phenol, acetone, and desorbent to produce required product phenol and acetone. This results in (1) elimination of formation of by-products at the CHP cleavage stage and the fractionation stage; (2) simplification and reduced complexity of CHP cleavage products fractionation; and (3) a significant decrease in energy expenses compared to the conventional phenol and acetone production processes.

Wasteless economic method of production of phenol and acetone

Purification of cumene hydroperoxide cleavage products from hydroxyacetone and carbonyl compounds is accomplished via extraction of hydroxyacetone and carbonyl compounds from cleavage products with a circulating water-salt solution in an extractor during an extraction stage and subsequent conversion of hydroxyacetone and other carbonyl compounds into deep condensation products in a HAC reactor operating as a plug-flow reactor or mixing reactor or as their combination. The conversion/condensation process is conducted in the water-salt solution by treating the hydroxyacetone and carbonyl compounds with alkaline agents. Various homogenous and/or heterogeneous alkaline catalysts may be used. Optionally multiple sequential extraction stages may be connected to the HAC reactor for improved performance.

Method of purifying cumene hydroperoxide decomposition products from

Disclosed is a process for the cleavage of technical cumene hydroperoxide (CHP) into phenol, acetone and .alpha.-methylstyrene. In a first stage, the CHP cleavage process is conducted in such a way to maintain the heat generation rate and the heat removal rate balanced in each of the CHP cleavage reactors. The cleavage of the CHP is conducted under substantially isothermal conditions at a temperature in the range of 47-50.degree. C. In the second stage of the process dicumylperoxide (DCP) and dimethylbenzene alcohol (DMBA) cleavage is carried out in a multi-section plug-flow reactor under non-isothermal conditions at a controlled temperature increase. The temperature is controlled with the use of thermocouples installed in each section of the reactor. The obtained temperature profile is compared with the temperature profile required by the kinetic model based on .DELTA.T in each section of the reactor. Based on any obtained fluctuations at least one of the amount of water additionally fed to the reactor, the temperature and the degree of sulfuric acid conversion into NH.sub.4 HSO.sub.4 are adjusted.

High selective method of phenol and acetone production

The present invention is an improved method for the recovery of phenol from a cleavage mass resulting from the sulfuric acid cleavage of cumene hydroperoxide comprising neutralizing the cleavage mass, forming an aqueous phase and an organic phase, separating the organic phase into an acetone-rich stream and a phenol-rich stream, removing phenol tars from the phenol-rich stream and cracking the phenol tars wherein the improvement comprises maintaining the pH of the cleavage mass during neutralization between 4.0 and about 4.9 whereby the sulfuric acid is converted to the bisulfate salt and substantially no free sulfuric acid remains in the cleavage mass and corrosion of process equipment is reduced. As a result of this improved process, a phenol tar waste stream containing less than about 4 parts per million by weight of chromium is obtained.

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Mt. Vernon, IN, United States of America

Vladimir Mikhailovitch Zakoshansky