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1

Young, Jay A. "Cumene." Journal of Chemical Education 83, no. 7 (July 2006): 989. http://dx.doi.org/10.1021/ed083p989.

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2

Yang, Wei-Jun, Can-Cheng Guo, Neng-Ye Tao, and Jun Cao. "Aerobic oxidation of cumene to cumene hydroperoxide catalyzed by metalloporphyrins." Kinetics and Catalysis 51, no. 2 (March 2010): 194–99. http://dx.doi.org/10.1134/s0023158410020047.

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3

Shen, Hai M., Hong L. Ye, Qin Wang, Meng Y. Hu, Lei Liu, and Yuan B. She. "Efficient oxidation of cumene to cumene hydroperoxide with ambient O2 catalyzed by metalloporphyrins." Journal of Porphyrins and Phthalocyanines 25, no. 04 (March 31, 2021): 314–22. http://dx.doi.org/10.1142/s1088424621500310.

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A novel and efficient protocol for oxidation of cumene to cumene hydroperoxide was presented using ambient O2 catalyzed by very simple metalloporphyrins. The selectivity toward cumene hydroperoxide reached 98.3% in the cumene conversion of 28.1% with T(4-COOH)PPCu as a catalyst at 80[Formula: see text]C. The origin of the higher performance of T(4-COOH)PPCu was mainly ascribed to the low catalytic performance of copper(II) in the cumene hydroperoxide decomposition, and the ability of T(4-COOH)PP in stabilizing cumene hydroperoxide through hydrogen-bond interactions between them. Compared with current industrial processes and academic research in oxidation of cumene to cumene hydroperoxide with O2, the main superiorities of this protocol were the high selectivity, high conversion, simple catalysts, solvent-free, additive-free and mild conditions which made this work an appealing reference for the industrial oxidation of cumene to cumene hydroperoxide, as well as the oxidative functionalization of other C-H bonds in various hydrocarbons.
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4

Di Somma, Ilaria, Raffaele Marotta, Roberto Andreozzi, and Vincenzo Caprio. "Detailed thermal and kinetic modeling of cumene hydroperoxide decomposition in cumene." Process Safety and Environmental Protection 91, no. 4 (July 2013): 262–68. http://dx.doi.org/10.1016/j.psep.2012.07.001.

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5

Duh, Y. S., C. S. Kao, C. Lee, and S. W. Yu. "Runaway Hazard Assessment of Cumene Hydroperoxide From the Cumene Oxidation Process." Process Safety and Environmental Protection 75, no. 2 (May 1997): 73–80. http://dx.doi.org/10.1205/095758297528832.

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6

Matsui, S., and T. Fujita. "New cumene-oxidation systems." Catalysis Today 71, no. 1-2 (November 2001): 145–52. http://dx.doi.org/10.1016/s0920-5861(01)00450-3.

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7

Ishida, T., and T. Matsumoto. "Enantioselective metabolism of cumene." Xenobiotica 22, no. 11 (January 1992): 1291–98. http://dx.doi.org/10.3109/00498259209053157.

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8

Hou, Ching T., Thomas A. Seymour, and Marvin O. Bagby. "Microbial oxidation of cumene." Journal of Industrial Microbiology 13, no. 2 (March 1994): 97–102. http://dx.doi.org/10.1007/bf01584105.

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9

Hsu, Ying Fang, and Cheu Pyeng Cheng. "Polymer supported catalyst for the effective autoxidation of cumene to cumene hydroperoxide." Journal of Molecular Catalysis A: Chemical 120, no. 1-3 (June 1997): 109–16. http://dx.doi.org/10.1016/s1381-1169(96)00442-6.

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10

Liao, Shixia, Feng Peng, Hao Yu, and Hongjuan Wang. "Carbon nanotubes as catalyst for the aerobic oxidation of cumene to cumene hydroperoxide." Applied Catalysis A: General 478 (May 2014): 1–8. http://dx.doi.org/10.1016/j.apcata.2014.03.024.

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11

Jankowska, Agnieszka, and Sławomir Czerczak. "Cumene Documentation of proposed values of occupational exposure limits (OELs)." Podstawy i Metody Oceny Środowiska Pracy 33, no. 1(91) (May 28, 2017): 63–95. http://dx.doi.org/10.5604/1231868x.1232634.

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Cumene is a clear, colourless liquid with a strong aromatic gasoline-like odour. Cumene is used for the synthesis of phenol and acetone and as a solvent in paints, varnishes and res-ins. It is also used in the printing and rubber industries. According to data from Polish Chief Sanitary Inspectorate, in 2010, no workers were occupa-tionally exposed to cumene in concentrations exceeding Polish OEL values (100 mg/m3). In 2014, 51 workers were exposed to cumene in concentrations from 0.1 to 0.5 MAC value (from 10 mg/m3 to 50 mg/m3). Cumene vapours are irritating to the respira-tory tract. In humans, high concentrations of cumene cause painful irritation to the eyes and the respiratory tract. In animals, cumene caus-es mainly CNS depression. Chronic exposure to cumene can cause hepatotoxicity. In vitro tests indicated no mutagenic and no genotoxic potential of cumene. Intraperitoneal injection of cumene induced micronuclei in bone marrow of rats. Dose-related increases in DNA damage were observed in liver cells of male rat and lung cells of female mouse. A metabolite of cumene, α-methylstyrene, was not mutagenic in bacterial tests but induced chromosomal damage in cell cultures and ro-dent cells. IARC experts classified cumene in group 2.B – chemicals possibly carcinogenic to humans based on sufficient evidence in experimental animals for the carcinogenicity of cumene. Exposure of mice to cumene by inhalation in-creased the incidence of alveolar/bronchiolar adenoma and carcinoma in males and females mice, haemangiosarcoma of the spleen in male mice and hepatocellular adenoma in female mice. Exposure of rats to cumene by inhalation increased the incidence of nasal adenoma in males and females and renal tubule adenoma and carcinoma in male rats. Cumene is well absorbed. It is a lipophilic substance which is well distributed in the whole body. Cytochrome P-450 is involved in cumene me-tabolism. Main metabolite identified in urine was 2-phenyl-2-propanol and in exhaled air α-methylstyrene. In 2014, Scientific Committee for Occupational Exposure Limits to Chemical Agents (SCOEL) prepared change of indicative OEL for cumene – reduction of concentration from 100 mg/m3 (directive 2000/39/WE) to 50 mg/m³, STEL value 250 mg/m3 remain unchanged. The compound was included in SCOEL carcino-genicity group D (not genotoxic and not affect-ing DNA chemicals), for which a health-based OEL may be derived on the basis of NOAEL value. Poland did not submit any comments on SCOEL proposal during public consultations in 2014. A new indicative OEL was derived on the basis of 3-month NTP inhalation studies in rats and mice. SCOEL established 310 mg/m³ (62.5 ppm) level as a NOAEC for hepatotoxici-ty. A STEL of 250 mg/m3 (50 ppm) have been recommended to protect against respiratory tract irritation and behavioural effects. More-over, a “skin notation” was recommended because of its probable skin penetration. BLV recom-mended by SCOEL is 7 mg 2-phenyl-2-propanol per gramme of creatinine in urine (after hydrolysis). To determine MAC value for cumene hepato-toxicity and nephrotoxicity were adopted as a critical effect. The Expert Group for Chemi-cals Agents established 310 mg/m³ as NOAEC based on 3-month NTP inhalation studies in rats and proposed reduction of the current MAC value from 100 to 50 mg/m3. It was agreed that the previous STEL value of 250 mg/m3 should remain unchanged, which is also in accordance with the value recom-mended by SCOEL. Recommended BEI value is 7 mg 2-phenyl-2-propanol per gramme of creatinine in urine (after hydrolysis), sampled immediately after work shift. It was recom-mended to remain “I” (irritant) and “Sk” (sub-stance can penetrate skin) labelling of cumene.
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12

Herman, John P., Lauren Redfern, Christopher Teaf, Douglas Covert, Peter R. Michael, and Thomas M. Missimer. "Cumene Contamination in Groundwater: Observed Concentrations, Evaluation of Remediation by Sulfate Enhanced Bioremediation (SEB), and Public Health Issues." International Journal of Environmental Research and Public Health 17, no. 22 (November 12, 2020): 8380. http://dx.doi.org/10.3390/ijerph17228380.

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Isopropylbenzene (cumene) is commonly encountered in groundwater at petroleum release sites due to its natural occurrence in crude oil and historical use as a fuel additive. The cumene concentrations detected at these sites often exceed regulatory guidelines or standards for states with stringent groundwater regulations. Recent laboratory analytical data collected at historical petroleum underground storage tank (UST) release sites have revealed that cumene persists at concentrations exceeding the default cleanup criterion, while other common petroleum constituents are below detection limits or low enough to allow natural attenuation as a remediation strategy. This effectively makes cumene the driver for active remediation at some sites. An insignificant amount of research has been conducted for the in-situ remediation of cumene. Sulfate Enhanced Biodegradation (SEB) is evaluated in a field case study. The results from the field case study show an approximate 92% decrease in plume area following three rounds of SEB injections. An additional objective of this research was to determine the cumene concentration in fuels currently being used to determine future impacts. A review of safety data sheets from several fuel suppliers revealed that cumene concentrations in gasoline are reported typically as wide ranges due to the proprietary formulations. Several fuels from different suppliers were analyzed to determine a baseline of cumene concentration in modern fuels. The results of the analysis indicated that cumene accounts for approximately 0.01% (diesel) to 0.13% (premium gasoline) of the overall fuel composition. Cumene generally is considered to be of low human health toxicity, with the principal concern being eye, skin, and respiratory irritation following inhalation of vapors in an occupational setting, but it has been regulated in Florida at very low concentrations based on organoleptic considerations.
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13

Rider, Cynthia V., Po Chan, Ron A. Herbert, Grace E. Kissling, Laurene M. Fomby, Milton R. Hejtmancik, Kristine L. Witt, Suramya Waidyanatha, Greg S. Travlos, and Maria B. Kadiiska. "Dermal Exposure to Cumene Hydroperoxide." Toxicologic Pathology 44, no. 5 (March 16, 2016): 749–62. http://dx.doi.org/10.1177/0192623316636712.

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14

Occhiogrosso, R. N., and M. A. McHugh. "Critical-mixture oxidation of cumene." Chemical Engineering Science 42, no. 10 (1987): 2478–81. http://dx.doi.org/10.1016/0009-2509(87)80124-0.

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15

Tsai, Tseng-Chang, Chin-Lan Ay, and Ikai Wang. "Cumene disproportionation over zeolite β." Applied Catalysis 77, no. 2 (October 1991): 199–207. http://dx.doi.org/10.1016/0166-9834(91)80065-5.

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16

Tsai, Tseng-Chang, and Ikai Wang. "Cumene disproportionation over zeolite β." Applied Catalysis 77, no. 2 (October 1991): 209–22. http://dx.doi.org/10.1016/0166-9834(91)80066-6.

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17

Kharlampidi, Kh E., T. Sh Nurmurodov, N. V. Ulitin, К. A. Tereshchenko, N. P. Miroshkin, D. A. Shiyan, N. A. Novikov, et al. "Design of cumene oxidation process." Chemical Engineering and Processing - Process Intensification 161 (April 2021): 108314. http://dx.doi.org/10.1016/j.cep.2021.108314.

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18

Yang, Man, Guo Qiu, Chongpin Huang, Xiaomeng Han, Yingxia Li, and Biaohua Chen. "Selective Oxidation of Cumene to the Equivalent Amount of Dimethylbenzyl Alcohol and Cumene Hydroperoxide." Industrial & Engineering Chemistry Research 58, no. 43 (October 14, 2019): 19785–93. http://dx.doi.org/10.1021/acs.iecr.9b03476.

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19

Zhang, Meiying, Lefu Wang, Hongbing Ji, Bing Wu, and Xiaoping Zeng. "Cumene Liquid Oxidation to Cumene Hydroperoxide over CuO Nanoparticle with Molecular Oxygen under Mild Condition." Journal of Natural Gas Chemistry 16, no. 4 (December 2007): 393–98. http://dx.doi.org/10.1016/s1003-9953(08)60010-9.

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20

Duh, Yih-Shing. "Chemical kinetics on thermal decompositions of cumene hydroperoxide in cumene studied by calorimetry: An overview." Thermochimica Acta 637 (August 2016): 102–9. http://dx.doi.org/10.1016/j.tca.2016.06.003.

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21

Mathew, Sanyo M., Ankush V. Biradar, Shubhangi B. Umbarkar, and Mohan K. Dongare. "Regioselective nitration of cumene to 4-nitro cumene using nitric acid over solid acid catalyst." Catalysis Communications 7, no. 6 (June 2006): 394–98. http://dx.doi.org/10.1016/j.catcom.2005.12.022.

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22

Corma, A., J. L. G. Fierro, R. Montan˜ana, and F. Tomas. "On the mechanism of cumene dealkylation: the interaction of cumene molecules on silica-alumina surfaces." Journal of Molecular Catalysis 30, no. 3 (June 1985): 361–72. http://dx.doi.org/10.1016/0304-5102(85)85046-x.

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23

Setínek, Karel, Stanislava Drapáková, and Zdeněk Prokop. "Oxidation of cumene by molecular oxygen on heterogenized cobalt catalysts." Collection of Czechoslovak Chemical Communications 51, no. 9 (1986): 1958–63. http://dx.doi.org/10.1135/cccc19861958.

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In the oxidation of cumene to cumene hydroperoxide by molecular oxygen in the liquid phase, the cobalt(II) catalysts heterogenized on organic cation exchangers are active only if acid functional groups of the exchanger which bind cobalt ions show medium or weak acidity. The catalysts based on strongly acidic ion exchangers are inactive and, contrary to the above catalysts, they catalyze decomposition of the cumene hydroperoxide present in the reaction mixture to phenol and acetone.
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24

Ha, Dong-Myeong. "Measurement and Prediction of the Combustible Properties of Cumene." Korean Chemical Engineering Research 54, no. 4 (August 1, 2016): 465–69. http://dx.doi.org/10.9713/kcer.2016.54.4.465.

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25

Chudinova, Alena, Anastasiya Salischeva, Elena Ivashkina, Olga Moizes, and Alexey Gavrikov. "Application of Cumene Technology Mathematical Model." Procedia Chemistry 15 (2015): 326–34. http://dx.doi.org/10.1016/j.proche.2015.10.052.

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26

Duh, Yih-Shing, Chen-Shan Kao, Her-Huah Hwang, and William W. L. Lee. "Thermal Decomposition Kinetics of Cumene Hydroperoxide." Process Safety and Environmental Protection 76, no. 4 (November 1998): 271–76. http://dx.doi.org/10.1205/095758298529623.

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27

Zakoshanskii, V. M., and A. V. Budarev. "RETRACTED ARTICLE: Mechanism of cumene oxidation." Russian Journal of General Chemistry 79, no. 6 (June 2009): 1311. http://dx.doi.org/10.1134/s1070363209060462.

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28

Wittenberg, R., M. A. Pradera, and J. A. Navio. "Cumene Photo-oxidation over Powder TiO2Catalyst." Langmuir 13, no. 8 (April 1997): 2373–79. http://dx.doi.org/10.1021/la961055a.

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29

Małecka, Anna. "Cumene Cracking on Dodecatungstosilicic Acid Catalyst." Journal of Catalysis 165, no. 2 (January 1997): 121–28. http://dx.doi.org/10.1006/jcat.1997.1485.

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30

Ivanov, A. A., and A. A. Berlin. "Inhibition of cumene oxidation by polyarylenes." Journal of Polymer Science: Polymer Symposia 40, no. 1 (March 8, 2007): 93–100. http://dx.doi.org/10.1002/polc.5070400113.

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31

MEIMA, G. R. "ChemInform Abstract: Advances in Cumene Production." ChemInform 29, no. 48 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199848296.

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32

Miyake, Atsumi, Takashi Uchida, Terushige Ogawa, and Yuzo Ono. "Thermal Decomposition Characteristics of Cumene Hydroperoxide." KAGAKU KOGAKU RONBUNSHU 21, no. 2 (1995): 312–18. http://dx.doi.org/10.1252/kakoronbunshu.21.312.

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33

Garibov, E. N., I. A. Rzaeva, N. G. Shykhaliev, A. I. Kuliev, V. M. Farzaliev, and M. A. Allakhverdiev. "Cyclic thioureas as cumene oxidation inhibitors." Russian Journal of Applied Chemistry 83, no. 4 (April 2010): 707–11. http://dx.doi.org/10.1134/s1070427210040245.

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34

Novitskaya, N. N., F. Z. Galin, V. V. Shereshovets, Yu V. Tomilov, and G. A. Tolstikov. "p-(Chloro-tert-butyl)cumene hydroperoxide." Russian Chemical Bulletin 47, no. 6 (June 1998): 1218–20. http://dx.doi.org/10.1007/bf02503500.

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35

Hao, Yuzhi, Longxiang Tao, and Lubin Zheng. "Cumene dehydrogenation on silica-pillared rectorite." Applied Catalysis A: General 120, no. 1 (December 1994): 179–86. http://dx.doi.org/10.1016/0926-860x(94)80341-2.

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36

Chen, Chujun. "Modeling of a gas-liquid phase cumene oxidation process for efficient synthesis of cumene hydroperoxide (HPOC)." IOP Conference Series: Earth and Environmental Science 330 (November 8, 2019): 042062. http://dx.doi.org/10.1088/1755-1315/330/4/042062.

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37

Darmer, Kenneth I., Teresa L. Neeper-Bradley, Janette R. Cushman, Carl R. Morris, and Barbara O. Francis. "Developmental Toxicity of Cumene Vapor in Cd Rats and New Zealand White Rabbits." International Journal of Toxicology 16, no. 2 (March 1997): 119–39. http://dx.doi.org/10.1080/109158197227224.

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The potential developmental toxicity of cumene vapor (99.9% pure) was assessed in pregnant CD (Sprague-Dawley) rats and New Zealand White rabbits exposed for 6 h per day by inhalation, the most relevant route of potential human exposure. Groups of 25 rats were exposed on gestational days (GD) 6–15 to concentrations of 0 (filtered air), 100, 500, or 1200 ppm, and groups of 15 rabbits were exposed on GD 6–18 to 0, 500, 1200, and 2300 ppm cumene vapor. In rats, reduced maternal body weight gain and increased relative liver weight was observed at 1200 ppm cumene. In rats and rabbits, reduced food consumption was observed at concentrations of 500 and 1200 ppm. A t 2300 ppm, 2 rabbits died, body weight gain and food consumption were reduced during the exposure period, and relative liver weights were increased. None of the gestational parameters, including numbers of viable implantations per litter, sex ratio, and fetal body weights, were affected at any exposure level in rats or rabbits. There were no treatment-related increases in incidences of external, visceral, or skeletal malformations or in the incidences of variations at any level. Thus, in rats, the no observable adverse effect level (NO A EL) for maternal toxicity was 100 ppm and the NO A EL for developmental toxicity was 1200 ppm, the highest concentration of cumene vapor tested. In rabbits, there was no NO A EL for maternal toxicity, but the NO A EL for developmental toxicity was 2300 ppm for cumene, the highest concentration tested. Therefore, even at exposure levels associated with maternal toxicity, cumene was not a developmental toxicant by inhalation exposure in either rats or rabbits.
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38

Safin, D. Kh, R. T. Zaripov, M. G. Khayrullin, V. A. Smolko, and V. I. Gaynullin. "Benefits of zeolite catalysts implementation at a cumene production plants." Plasticheskie massy, no. 5-6 (July 17, 2021): 50–51. http://dx.doi.org/10.35164/0554-2901-2021-5-6-50-51.

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The main stages of revamping of the cumene production plant of Kazanorgsintez PJSC for the implementation of technology based on zeolite catalysts are described. The changes in the main technical and economic indicators of production process are described. Also, a brief description of existing cumene production technologies is presented.
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39

Luňák, Stanislav, Růžena Chmelíková, and Pavel Lederer. "Oxidation of cumene by dioxygen. The effect of radical initiators on the rate of the reaction catalyzed by 3d-transition metal 2,4-pentanedionates." Collection of Czechoslovak Chemical Communications 56, no. 2 (1991): 344–50. http://dx.doi.org/10.1135/cccc19910344.

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The effect of cumene hydroperoxide, benzoin ethyl ether and dibenzoyl peroxide on the oxidation of cumene by dioxygen catalyzed by VO(II), Cr(III), Mn(II), Fe(III), Co(II), Co(III) and Cu(II) 2,4-pentanedionates was studied. The rate of the catalyzed oxidation of cumene by dioxgen can not only be increased but also decreased by the presence of radical initiators, whereas in the absence of the catalyst the oxidation rate is always increased by the radical initiators. Which effect takes actually place is determined by the kind and oxidation state of the transition metal ion catalyst as well as by the kind of the radical initiator.
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40

Pedrosa, G. C., J. A. Salas, and M. Katz. "Excess Molar Volumes ofn-Pentanol + Cumene,n-Pentanol + 1,4-Dioxane and Cumene + 1,4-Dioxane at Different Temperatures." Physics and Chemistry of Liquids 21, no. 4 (August 1990): 207–16. http://dx.doi.org/10.1080/00319109008028486.

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41

Zakoshansky, V. M. "Phenomenology of oxidation of a cumene feed containing hydroperoxide: I. Two paths of cumene hydroperoxide formation reaction." Russian Journal of General Chemistry 81, no. 5 (May 2011): 845–64. http://dx.doi.org/10.1134/s1070363211050082.

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42

Wang, Er Qiang, Cheng Yue Li, Lang You Wen, Ze Xue Du, and Yong Qiang Zhang. "Simulation of Cumene Synthesis by Suspension Catalytic Distillation." Advanced Materials Research 557-559 (July 2012): 2243–48. http://dx.doi.org/10.4028/www.scientific.net/amr.557-559.2243.

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This paper deals with alkylation of benzene with propylene to produce cumene by Suspension Catalytic Distillation (SCD) which, as a new technology of process intensification, has been developed from traditional catalytic distillation. In this SCD process, the supported heteropolyacid catalysts are suspended inside the liquid phase on the column tray and flow with them, while in traditional catalytic distillation the catalyst pellets are generally fixed somewhere inside the column. SCD processes have been investigated for alkylation reaction of benzene with olefins in laboratorial scale. A pilot plant of SCD process for cumene synthesis had been run for several months. It has shown more advantageous characteristics for cumene synthesis compared with conventional process consisting of a reactor followed by distillation train. Based on experimental data and the reactive kinetic parameters of cumene synthesis using the supported heteropolyacid catalysts, numerical simulation of SCD process of the pilot plant was performed by an equilibrium stage model to study the effects of operation conditions on the process performance. The simulation results could agree, to a great extent, with the data acquired from the pilot plant experiment.
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43

Luyben, William L. "Design and Control of the Cumene Process." Industrial & Engineering Chemistry Research 49, no. 2 (January 20, 2010): 719–34. http://dx.doi.org/10.1021/ie9011535.

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44

Suppes, Galen J., Ronald N. Occhiogrosso, and Mark A. McHugh. "Oxidation of cumene in supercritical reaction media." Industrial & Engineering Chemistry Research 28, no. 8 (August 1989): 1152–56. http://dx.doi.org/10.1021/ie00092a006.

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45

Tur'ev, A. V., I. N. Grishina, and Yu M. Sivergin. "Kinetics of the Decomposition of Cumene Hydroperoxide." International Polymer Science and Technology 28, no. 1 (January 2001): 31–35. http://dx.doi.org/10.1177/0307174x0102800107.

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46

Zakoshansky, V. M. "The cumene process for phenol-acetone production." Petroleum Chemistry 47, no. 4 (July 2007): 273–84. http://dx.doi.org/10.1134/s096554410704007x.

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47

Zakoshansky, V. M. "The Cumene Process for Phenol—Acetone Production." Petroleum Chemistry 47, no. 4 (July 2007): 307. http://dx.doi.org/10.1134/s0965544107040135.

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48

Gera, Vivek, Mehdi Panahi, Sigurd Skogestad, and Nitin Kaistha. "Economic Plantwide Control of the Cumene Process." Industrial & Engineering Chemistry Research 52, no. 2 (December 19, 2012): 830–46. http://dx.doi.org/10.1021/ie301386h.

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49

Zhu, Qing-cai, Ben-xian Shen, Hao Ling, and Rong Gu. "Cumene hydroperoxide hydrogenation over Pd/C catalysts." Journal of Hazardous Materials 175, no. 1-3 (March 2010): 646–50. http://dx.doi.org/10.1016/j.jhazmat.2009.10.057.

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50

Andre, J. C., and M. Bouchy. "Kinetics of photochemically induced benzaldehyde-cumene cooxidation." Reaction Kinetics and Catalysis Letters 28, no. 2 (September 1985): 379–84. http://dx.doi.org/10.1007/bf02062968.

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