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WO2003100395A1 - Procede de mesure de la concentration d'hydroperoxydes d'hydrocarbures alkylaromatiques - Google Patents

Procede de mesure de la concentration d'hydroperoxydes d'hydrocarbures alkylaromatiques Download PDF

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Publication number
WO2003100395A1
WO2003100395A1 PCT/US2003/014616 US0314616W WO03100395A1 WO 2003100395 A1 WO2003100395 A1 WO 2003100395A1 US 0314616 W US0314616 W US 0314616W WO 03100395 A1 WO03100395 A1 WO 03100395A1
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WO
WIPO (PCT)
Prior art keywords
concentration
hydroperoxide
sample
cumene
spectrometer
Prior art date
Application number
PCT/US2003/014616
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English (en)
Inventor
Randall Todd Bishop
John William Fulmer
Arkady Samuilovich Dykman
Andrey Vladimirovich Zinenkov
Original Assignee
General Electric Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from RU2002113195/28A external-priority patent/RU2231045C2/ru
Application filed by General Electric Company filed Critical General Electric Company
Priority to AU2003228961A priority Critical patent/AU2003228961A1/en
Publication of WO2003100395A1 publication Critical patent/WO2003100395A1/fr

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G01N21/35—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light
    • G01N21/359—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light using near infrared light
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G01N21/35—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light
    • G01N21/3577—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light for analysing liquids, e.g. polluted water
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00—Sampling; Preparing specimens for investigation
    • G01N1/02—Devices for withdrawing samples
    • G01N1/10—Devices for withdrawing samples in the liquid or fluent state
    • G01N1/20—Devices for withdrawing samples in the liquid or fluent state for flowing or falling materials
    • G01N1/2035—Devices for withdrawing samples in the liquid or fluent state for flowing or falling materials by deviating part of a fluid stream, e.g. by drawing-off or tapping
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N35/00—Automatic analysis not limited to methods or materials provided for in any single one of groups G01N1/00 - G01N33/00; Handling materials therefor
    • G01N35/08—Automatic analysis not limited to methods or materials provided for in any single one of groups G01N1/00 - G01N33/00; Handling materials therefor using a stream of discrete samples flowing along a tube system, e.g. flow injection analysis

Definitions

  • the present disclosure relates to the area of analytic control, namely to methods of measuring the concentration of hydroperoxides of alkylaromatic hydrocarbons in industrial streams, such as, for example, the measurement of the concentration of cumene hydroperoxide (CHP) in industrial streams obtained during the production of phenol and acetone by a cumene oxidation method.
  • CHP cumene hydroperoxide
  • the industrial two-stage method of producing phenol and acetone involves continuously oxidizing cumene (isopropylbenzene) with atmospheric oxygen to form an intermediate, cumene hydroperoxide (CHP), in a system of sequential reaction vessels as generally shown by reaction scheme (I).
  • cumene isopropylbenzene
  • CHP cumene hydroperoxide
  • reaction scheme (II) the intermediate CHP then undergoes acid decomposition with a protic acid to form the desired end products, i.e., phenol and acetone.
  • a protic acid i.e., phenol and acetone.
  • the mixture of phenol and acetone that is formed in the process is separated and purified, usually by rectification on several columns.
  • the yield of CHP obtained during continuous oxidation of cumene in a series of reaction vessels depends on its steady-state concentration, which is maintained in each of the reaction vessels.
  • samples of the reaction mixture should be taken as often as possible from all cumene oxidation reaction vessels.
  • the samples are typically hand-carried to the laboratory and analyzed for their CHP concentration by titration methods, which ensures the greatest accuracy and reliability.
  • the same method of manual sampling and titration in the analytic laboratory is used for determining the residual concentration of CHP after the stage of its acid decomposition. Since the stage of continuous decomposition of CHP is especially dangerous, laboratory analyses are done around the clock with a frequency of about 6 to about 12 times per day, which translates to about every 2 to about 4 hours.
  • Typical laboratory analytical methods of determining the CHP content under industrial production conditions include iodometric titration or a wet photometric method, which involves measuring the optical density after an additional reagent is added to the solution containing CHP.
  • iodometric titration or a wet photometric method, which involves measuring the optical density after an additional reagent is added to the solution containing CHP.
  • both of the indicated methods are rather complex, require the use of expensive reagents, and are not practical for continuous industrial processes, e.g., continuous "in process” or “online continuous applications.
  • Another method for monitoring the CHP content includes using an "on-line" industrial calorimeter analyzer.
  • the method includes adding sulfuric acid to a small stream taken off the main stream to completely decompose the CHP. In this method, heat is liberated and the corresponding temperature rise is recorded. The CHP concentration is then calculated from the magnitude of the temperature rise.
  • This method is not attractive for commercial use, since it requires a complex apparatus, uses a complex scheme of streams, and requires an added reagent, which needs to be precisely metered to obtain reproducible results as well as requires frequent replenishment.
  • this method is generally applicable only for very low concentrations of CHP.
  • this method is inconvenient for measurements in the stream at the cumene oxidation stage, since the analysis process consumes a significant quantity of CHP.
  • a "in process” method for measuring a concentration of a hydroperoxide of an alkylaromatic hydrocarbon in a process stream comprising immersing a probe into the process stream; wherein the probe is coupled to a spectrometer; collecting abso ⁇ tion data with the spectrometer at a wavelength of 13,000 cm “1 to 4,000 cm “1 ; and calculating a concentration of the hydroperoxide of the alkylaromatic hydrocarbon in the process stream.
  • a method for measuring a concentration of a hydroperoxide of an alkylaromatic hydrocarbon in a process stream comprising withdrawing a sample from a process stream; collecting absorption data of the sample with the spectrometer at a wavelength of 13,000 cm “1 to 4,000 cm “1 ; and calculating a concentration of the hydroperoxide of the alkylaromatic hydrocarbon in the sample.
  • Also disclosed herein is a process for monitoring a concentration of cumene hydroperoxide during a process for manufacturing phenol and acetone from cumene, wherein the process for manufacturing the phenol and the acetone comprises oxidizing the cumene in an oxidizing atmosphere to produce a process stream containing cumene hydroperoxide, and decomposing the cumene hydroperoxide with a protic acid to produce the phenol and the acetone, the process comprising immersing a probe into the process stream at one or more stages of the oxidizing atmosphere, wherein the probe is coupled to a spectrometer; collecting abso ⁇ tion data with the spectrometer at a wavelength of 13,000 cm "1 to 4,000 cm “1 ; and calculating a concentration of the cumene hydroperoxide in the process stream.
  • a concentration of hydroperoxides of alkylaromatic hydrocarbons in liquid industrial streams at any stages of processes be determined directly using a spectroscopic method.
  • the spectrometer employed in the spectroscopic method is calibrated according to a series of known concentrations of the hydroperoxide solutions, which correspond to a desired range of concentrations that are to be measured.
  • the calibration model obtained from the known concentrations is stored in the memory of a computer by appropriate software. Analysis of a sample for its hydroperoxide content can then be carried out directly in the stream, preferably in a near infrared spectrum, with the concentration of hydroperoxide in the stream being calculated using the calibration model.
  • the proposed method is based on direct measurement of the concentration of hydroperoxides in liquid industrial streams.
  • This new analytical method is instrumental, and, unlike the prior art, does not propose the use of additional reagents.
  • the given method is spectroscopic, uses the near infrared spectrum of wavelengths and therefore it is non-destructive and makes it possible to obtain precise values of the concentration of hydroperoxides in industrial streams quickly.
  • NIR near infrared
  • Suitable spectrometers include scanning spectrometers, with a Fourier transform, with sets of filters, and also Raman spectrometers. Other suitable spectrometer s will be apparent to those skilled in the art in view of this disclosure.
  • a spectrometer transmission probe made of an inert material is placed in process stream or in a sample.
  • the probe can be employed in a laboratory setting, or more preferably, is disposed in an appropriate pipe on an industrial system for direct measurement of a process stream.
  • the probe can be connected to the spectrometer using fiber-optic cables or the like.
  • the CHP concentration is measured by reading the spectrum and using the corresponding calibration of the device.
  • Special software for the NIR spectrometer calculates the CHP concentration from the signal that is measured.
  • the analytical procedure is completely finished in 2 to 5 minutes or less, depending on the device that is used, and does not require the use of additional reagents.
  • the NIR spectrometer, the fiber-optic probes, and the equipment connected with them were developed in such a way that they do not contain moving parts (or a minimum number of them), which makes service relatively inexpensive and makes the system highly reliable when installed under production conditions.
  • a critical requirement for measuring the CHP concentration is first to correctly calibrate the device using standard solutions containing known concentrations of CHP. Nevertheless, this procedure is easy to perform, and the calibration model that is obtained is stable over a long period of time.
  • the standard software for the NIR spectrometer can perform the required calculations on one wavelength at which the abso ⁇ tion is quantitatively connected with the CHP concentration in accordance with the Bouguer-Lambert-Beer law. Measurements at one wavelength are possible; however, it is preferable to use more complex models that are built on several wavelengths, since they ensure better accuracy and reproducibility. These models use several wavelengths, usually no fewer than two wavelengths, which are selected from the NIR spectrum.
  • a calculation algorithm can use multiple linear regression (MLR) or the method of partial least squares (PLS).
  • MLR linear regression
  • PLS partial least squares
  • An important factor in selecting the algorithm is its ability to exclude from the calculation abso ⁇ tion bands from other components that are present in the mixture, such as cumene, phenol, acetone, or the like; these absorption bands are superimposed on those of CHP.
  • air can also oxidize other hydrocarbons, for example sec-butylbenzene, diisopropylbenzene, and others, to form the corresponding hydroperoxides as intermediates in the production of methyl ethyl ketone, resorcinol, or hydroquinone, and other products.
  • hydrocarbons for example sec-butylbenzene, diisopropylbenzene, and others.
  • the method according to the disclosure is rather flexible and can be used both at the cumene oxidation stage and at the CHP decomposition stage.
  • the composition of samples and the component matrix differ significantly in these two cases.
  • the products of cumene oxidation include, in addition to CHP and cumene, which are present in large concentrations, components such as acetophenone, 2- phenyl-2-propanol (dimethylphenylcarbinol, DMPC), and water, while the concentration of CHP in the CHP decomposition reaction mixture is much lower and the basic components of this mixture are cumene, acetone, and phenol. Nevertheless, the CHP concentration can be analyzed quickly and precisely.
  • the advantages include rapid and precise non-destructive laboratory analysis of the content of cumene hydroperoxide (CHP), which saves time, labor, and reagent expenses; rapid and precise measurement of the CHP concentration at critical areas in the stream: at the cumene oxidation stage and at the stage where CHP is decomposed into phenol and acetone; measurements are made in real time and can be used by the process control system to fine-tune the process in order to obtain the best safety and efficiency indices; and the delay resulting from the necessity of delivering samples to the laboratory and waiting for manual analysis results is eliminated.
  • CHP cumene hydroperoxide
  • a sample of a reaction mixture obtained from the oxidation of cumene by atmospheric oxygen is collected from an industrial system and delivered to the laboratory.
  • Volumetric analysis is performed using iodometric titration as follows: a weighed amount of the sample from the cumene oxidation reaction mixture is placed in a flask having a volume of 200 ml; the weighed amount contained 5 to 10 g if the CHP concentration is 0 to 5%; 1 to 2 g if the CHP concentration is 5 to 25%; and 0.2 to 0.4 g if the CHP concentration is 25 to 85%. 40 ml of a saturated solution of potassium iodide in methanol is added to each sample.
  • a reflux condenser is connected to the flask and the contents are boiled for 5 minutes on a hot plate until the cumene hydroperoxide is completely decomposed.
  • the hydroperoxide reacts with the potassium iodine and an equivalent quantity of free iodine is liberated.
  • the flask is removed from the hot plate and is allowed to cool for 5 to 10 minutes.
  • the iodine that was liberated in the preceding step is titrated with a 0.1 N solution of sodium thiosulfate until the color disappears.
  • the number of milliliters of the 0.1 N sodium thiosulfate solution that were used for titration are used to calculate the CHP content according to the following formula.
  • the spectrometer used in this example was an Antaris Fourier Transform Near Infrared (NIR) spectrometer produced by Nicolet Instrument Co ⁇ oration in Madison, Wisconsin.
  • NIR Antaris Fourier Transform Near Infrared
  • To the spectrometer was connected a fiber-optic transmission probe made of stainless steel, model FPT-850, manufactured by Axiom Analytical Inco ⁇ orated, Irvine, California.
  • the probe was equipped with a head having sapphire windows and an optical path length of 2 cm.
  • the instrument's resolution is reported to be 8 cm "1 .
  • the Antaris FT-NIR spectrometer was first calibrated using a set of standards representing CHP solutions prepared by weight, which spanned the entire range of concentrations that needed to be measured. The calibration curve that was obtained was stored in memory by software.
  • the analysis of six samples of cumene oxidation reaction mixtures using the FT-NIR spectrometer was conducted directly (without sample preparation) and quickly, by placing the fiber-optic probe into the sample that was obtained directly from the factory. No sample preparation or addition of reagents was required. After the probe was placed in the volume containing the sample, the apparatus scanned the spectrum of the sample and measured the abso ⁇ tion at specified wavelengths.
  • the ranges are 6,640 to 7,010 cm “1 and 8,300 to 8,500 cm “1 .
  • These two spectral ranges use the partial least squares (PLS) algorithm for analysis.
  • PLS partial least squares
  • the software automatically calculates the value of the CHP concentration in the sample of the cumene oxidation reaction mixture.
  • the total analysis time for any of the samples was less than 5 minutes.
  • the results of the measurements of six samples are presented in Table 1. Table 1.
  • the same eight samples were also analyzed for their CHP content in the laboratory using an ⁇ IR spectrometer.
  • the spectrometer used was an Antaris Fourier transform near infrared ( ⁇ IR) spectrometer produced by ⁇ icolet Instrument Co ⁇ oration in Madison, Wisconsin in accordance with Example 1.
  • results demonstrate quantitative correlation between the analyses of CHP by the two methods.
  • results also show the sensitivity of the NIR spectroscopy method at low CHP concentrations.
  • the computer of the distributed control system took the CHP concentration data, which was obtained in-stream, and used it in real time as an input parameter for adjusting various process parameters, for example temperature, to achieve more precise control over the process. As such, it is now possible to increase the yield at the cumene oxidation stage and to conduct the process in a safer and more stable manner.
  • the introduction of in-stream measurement of the CHP concentration by the spectroscopic method realized a feedback loop in the control of the process. With the introduction of this mode of operation, it was found that there is no need to collect samples of the oxidation reaction mixture and transport them to the laboratory for manual iodometric titration of CHP.
  • Table 3 demonstrates that the spectrophotometric method can be successfully used as an online and precise method of analysis of CHP, which makes it possible to reduce fluctuations, increase the stability of process control, and, consequently, to increase the yield of the product and the economic efficiency of the process.
  • a transmission probe made of stainless steel which is analogous to those manufactured by Axiom Analytical Inco ⁇ orated, was placed in a pipe in a continuously operating CHP decomposition system.
  • the probe had a continuous stream of the CHP decomposition reaction mixture passing through it.
  • the CHP concentration was measured at a frequency of once every 2 to 3 minutes.
  • the spectrum was scanned, the obtained signal was processed, and the CHP concentration was calculated.
  • the spectral range that was used was 6,000 to 10,000 cm "1 . Approximately 400 measurements were performed per day, and the tests were carried out over a period of 3 days, i.e., 72 hours.
  • samples of various hydroperoxides were obtained in a pilot plant and quantitatively analyzed using the spectroscopic method.
  • the data obtained were compared with the data of iodometric titration.
  • the analysis used a spectral range of 5,000 to 10,000 cm "1 .
  • Analysis of the separate hydroperoxides used parts of this range depending on the nature of the hydroperoxide and other substances present in the mixture. Table 5 presents the results of this analysis.

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
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  • Analytical Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
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Abstract

Procédé de mesure de la concentration d'un hydroperoxyde d'un hydrocarbure alkylaromatique dans un flux industriel, qui consiste à introduire une sonde dans le flux industriel, ladite sonde étant couplée à un spectromètre, à recueillir des données d'absorption à l'aide dudit spectromètre à une longueur d'onde de 13 000 cm-1 à 4000 cm-1, et à calculer la concentration de l'hydroperoxyde d'hydrocarbure alkylaromatique dans le flux industriel. Dans un autre mode de réalisation, des échantillons sont prélevés dans le flux industriel et analysés de manière spectrométrique pour déterminer la concentration de l'hydroperoxyde d'hydrocarbure alkylaromatique dans l'échantillon.
PCT/US2003/014616 2002-05-20 2003-05-08 Procede de mesure de la concentration d'hydroperoxydes d'hydrocarbures alkylaromatiques WO2003100395A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003228961A AU2003228961A1 (en) 2002-05-20 2003-05-08 Method of measuring the concentration of hydroperoxides of alkylaromatic hydrocarbons

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
RU2002113195 2002-05-20
RU2002113195/28A RU2231045C2 (ru) 2002-05-20 2002-05-20 Способ измерения концентрации гидропероксидов алкилароматических углеводородов в жидких промышленных потоках
US10/425,909 2003-04-29
US10/425,909 US7012255B2 (en) 2002-05-20 2003-04-29 Method of measuring the concentration of hydroperoxides of alkylaromatic hydrocarbons

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016020879A1 (fr) * 2014-08-08 2016-02-11 Sabic Global Technologies B.V. Procédé de régulation du clivage d'hydroperoxydes d'hydrocarbures alkylaromatiques
WO2016065093A1 (fr) * 2014-10-24 2016-04-28 Sabic Global Technologies, B.V. Système et process pour le clivage d'hydroperoxyde de cumène avec une configuration en ligne améliorée

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WO1994027135A1 (fr) * 1993-05-17 1994-11-24 Ashland Oil, Inc. Procede et systeme d'analyse et d'echantillonnage
JP2000063352A (ja) * 1998-08-12 2000-02-29 Mitsui Chemicals Inc 芳香族アルキルヒドロペルオキシドの製造方法
WO2000062078A1 (fr) * 1999-04-12 2000-10-19 Texas Tech University Procedes et appareil de mesure d'hydroperoxydes
WO2002012969A1 (fr) * 2000-08-07 2002-02-14 Mitsui Chemicals, Inc. Procede de controle de production

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WO1994027135A1 (fr) * 1993-05-17 1994-11-24 Ashland Oil, Inc. Procede et systeme d'analyse et d'echantillonnage
JP2000063352A (ja) * 1998-08-12 2000-02-29 Mitsui Chemicals Inc 芳香族アルキルヒドロペルオキシドの製造方法
WO2000062078A1 (fr) * 1999-04-12 2000-10-19 Texas Tech University Procedes et appareil de mesure d'hydroperoxydes
WO2002012969A1 (fr) * 2000-08-07 2002-02-14 Mitsui Chemicals, Inc. Procede de controle de production

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DONG J ET AL: "STOICHIOMETRIC DETERMINATION OF HYDROPEROXIDES IN OILS BY FOURIER TRANSFORM NEAR-INFRARED SPECTROSCOPY", JOURNAL OF AOAC INTERNATIONAL, AOAC INTERNATIONAL, ARLINGTON, VA, US, vol. 80, no. 2, 1997, pages 345 - 352, XP000934084, ISSN: 1060-3271 *
FREW J E ET AL: "SPECTROPHOTOMETRIC DETERMINATION OF HYDROGEN PEROXIDE AND ORGANIC HYDROPEROXIDES AT LOW CONCENTRATIONS IN AQUEOUS SOLUTION", TROX REPORT, GORINCHEM, NL, vol. 155, 1983, pages 139 - 150, XP000934307 *
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 05 14 September 2000 (2000-09-14) *
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016020879A1 (fr) * 2014-08-08 2016-02-11 Sabic Global Technologies B.V. Procédé de régulation du clivage d'hydroperoxydes d'hydrocarbures alkylaromatiques
CN106536461A (zh) * 2014-08-08 2017-03-22 沙特基础工业全球技术有限公司 控制烷基芳族烃的氢过氧化物裂解的方法
KR20170041834A (ko) * 2014-08-08 2017-04-17 사빅 글로벌 테크놀러지스 비.브이. 알킬방향족 탄화수소의 하이드로퍼옥사이드의 개열 제어 방법
US10017440B2 (en) 2014-08-08 2018-07-10 Sabic Global Technologies B.V. Method for controlling cleavage of hydroperoxides of alkylaromatic hydrocarbons
KR102493951B1 (ko) * 2014-08-08 2023-01-31 사빅 글로벌 테크놀러지스 비.브이. 알킬방향족 탄화수소의 하이드로퍼옥사이드의 개열 제어 방법
WO2016065093A1 (fr) * 2014-10-24 2016-04-28 Sabic Global Technologies, B.V. Système et process pour le clivage d'hydroperoxyde de cumène avec une configuration en ligne améliorée
US10065171B2 (en) 2014-10-24 2018-09-04 Sabic Global Technologies B.V. System and process for cumene hydroperoxide cleavage with improved online instrumentation configuration

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