RU99100379A - TWO-STEP METHOD OF ALKYLATION OF BENZENE WITH FORMATION OF LINEAR ALKYLBENZENES - Google Patents

TWO-STEP METHOD OF ALKYLATION OF BENZENE WITH FORMATION OF LINEAR ALKYLBENZENES

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Publication number
RU99100379A
RU99100379A RU99100379/04A RU99100379A RU99100379A RU 99100379 A RU99100379 A RU 99100379A RU 99100379/04 A RU99100379/04 A RU 99100379/04A RU 99100379 A RU99100379 A RU 99100379A RU 99100379 A RU99100379 A RU 99100379A
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Russia
Prior art keywords
benzene
mordenite
fluorine
clay
contacting
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RU99100379/04A
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Russian (ru)
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RU2173677C2 (en
Inventor
Джон Ф. Нифтон
Пракаса Рао Анантанени
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Хантсмэн Петрокемикал Корпорейшн
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Priority claimed from US08/662,786 external-priority patent/US5777187A/en
Application filed by Хантсмэн Петрокемикал Корпорейшн filed Critical Хантсмэн Петрокемикал Корпорейшн
Publication of RU99100379A publication Critical patent/RU99100379A/en
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Publication of RU2173677C2 publication Critical patent/RU2173677C2/en

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Claims (22)

1. Способ, полезный для получения моноалкилированного бензола, включающий стадии: (а) контактирование бензола с олефином, содержащим от 5 до 30 атомов углерода, в присутствии фторсодержащего морденита, в таких условиях, что образуется линейный моноалкилбензол; и (b) контактирование продукта стадии (а) с бензолом в присутствии катализатора на основе фторсодержащей глины, так что продукт стадии (b) имеет бромное число, меньшее чем бромное число продукта стадии (а).1. A method useful for producing monoalkylated benzene, comprising the steps of: (a) contacting benzene with an olefin containing from 5 to 30 carbon atoms in the presence of fluorine-containing mordenite, under such conditions that linear monoalkylbenzene is formed; and (b) contacting the product of step (a) with benzene in the presence of a fluorine-containing catalyst, so that the product of step (b) has a bromine number lower than the bromine number of the product of step (a). 2. Способ по п. 1, в котором фторсодержащий морденит имеет мольное соотношение двуокись кремния/окись алюминия в интервале от 10:1 до 50:1, и где морденит обработан путем контактирования морденита с водным раствором фтористого водорода, где фтористый водород в водном растворе имеет концентрацию 0,1 - 5,0 мас.%. 2. The method according to p. 1, in which the fluorine-containing mordenite has a molar ratio of silicon dioxide / alumina in the range from 10: 1 to 50: 1, and where mordenite is processed by contacting mordenite with an aqueous solution of hydrogen fluoride, where hydrogen fluoride in an aqueous solution has a concentration of 0.1 to 5.0 wt.%. 3. Способ по п. 1 или 2, в котором олефин имеет от около 10 до около 14 атомов углерода. 3. The method according to claim 1 or 2, in which the olefin has from about 10 to about 14 carbon atoms. 4. Способ по пп. 1, 2 или 3, в котором моноалкилированный бензол содержит около 70%, или более, 2-фенилизомера. 4. The method according to PP. 1, 2 or 3, in which monoalkylated benzene contains about 70% or more of the 2-phenyl isomer. 5. Способ по пп.1-3 или 4, в котором морденит содержит фтор 0,1 - 4,0 мас.%. 5. The method according to claims 1 to 3 or 4, in which mordenite contains fluorine from 0.1 to 4.0 wt.%. 6. Способ по пп.1-4 или 5, в котором катализатор на основе глины изготовлен из монтмориллонитмой глины. 6. The method according to claims 1 to 4 or 5, in which the clay-based catalyst is made of montmorillonite clay. 7. Способ по пп.1-5 или 6, в котором содержание фтора в катализаторе на основе глины составляет 0,1 - 10,0 мас.%. 7. The method according to claims 1-5 or 6, in which the fluorine content in the clay catalyst is 0.1 to 10.0 wt.%. 8. Способ по пп.1-6 или 7, в котором бромное число продукта стадии (b) составляет менее чем 0,1. 8. The method according to claims 1-6 or 7, in which the bromine number of the product of stage (b) is less than 0.1. 9. Способ по пп.1-7 или 8, в котором стадия (2) проводится в непрерывном режиме. 9. The method according to claims 1 to 7 or 8, in which stage (2) is carried out continuously. 10. Способ, полезный для получения моноалкилированного бензола, включающий стадии: введение исходной смеси, содержащей олефин, имеющий от 5 до 30 атомов углерода, и бензол, в слой катализатора на основе фторсодержащего морденита, в таких условиях, что образуется линейный моноалкилированный бензол; предоставление бензолу, олефину и моноалкилбензолу возможности стекать в ребойлер из слоя катализатора; нагревание содержимого ребойлера таким образом, что бензол отгоняется, с тем чтобы далее вступить в контакт со слоем фторсодержащего морденита; удаление моноалкилированного бензола, имеющего некоторое бромное число, из ребойлера; контактирование моноалкилированного бензола, удаленного из ребойлера, с бензолом в присутствии катализатора на основе фторсодержащей глины, так, что бромное число моноалкилированного бензола, удаленного из ребойлера, понижается. 10. A method useful for producing monoalkylated benzene, comprising the steps of: introducing an initial mixture containing an olefin having 5 to 30 carbon atoms and benzene into a fluorine-containing mordenite catalyst bed under such conditions that a linear monoalkylated benzene is formed; allowing benzene, olefin and monoalkylbenzene to drain into the reboiler from the catalyst bed; heating the contents of the reboiler in such a way that the benzene is distilled off so as to further come into contact with the fluorine-containing mordenite layer; removing monoalkylated benzene having a certain bromine number from the reboiler; contacting monoalkylated benzene removed from the reboiler with benzene in the presence of a fluorine-based catalyst so that the bromine number of monoalkylated benzene removed from the reboiler is reduced. 11. Способ по п.10, в котором обработанный фтором морденит имеет мольное соотношение двуокись кремния/окись алюминия в интервале от 10:1 до 50:1, где морденит обработан путем контактирования морденита с водным раствором фтористого водорода, где фтористый водород в водном растворе имеет концентрацию в интервале от 0,1 до 5 мас.%. 11. The method according to claim 10, in which the fluorine-treated mordenite has a molar ratio of silicon dioxide / alumina in the range from 10: 1 to 50: 1, where mordenite is processed by contacting mordenite with an aqueous solution of hydrogen fluoride, where hydrogen fluoride in an aqueous solution has a concentration in the range from 0.1 to 5 wt.%. 12. Способ по п. 10 или 11, в котором олефин имеет от 10 до 14 атомов углерода. 12. The method according to p. 10 or 11, in which the olefin has from 10 to 14 carbon atoms. 13. Способ по пп.10, 11 или 12, отличающийся тем, что моноалкилированный бензол содержит около 70%, или более, 2-фенилизомера после контактирования с глиной. 13. The method according to PP.10, 11 or 12, characterized in that the monoalkylated benzene contains about 70% or more of the 2-phenylisomer after contacting with clay. 14. Способ по пп.10-12 или 13, в котором отношение бензола к олефину в исходной смеси составляет от 2:1 до 20:1, где температура слоя катализатора на основе глины поддерживается в диапазоне 75 - 200°С, и где исходная смесь вводится в слой катализатора с часовой скоростью подачи жидкости от около 0,1 ч-1 до около 1 ч-1.14. The method according to PP.10-12 or 13, in which the ratio of benzene to olefin in the initial mixture is from 2: 1 to 20: 1, where the temperature of the clay catalyst layer is maintained in the range of 75-200 ° C, and where the original the mixture is introduced into the catalyst bed with a fluid flow rate from about 0.1 h -1 to about 1 h -1 . 15. Способ по пп.10-13 или 14, дополнительно включающий, сбор воды над слоем катализатора на основе морденита в ловушке для воды. 15. The method according to claims 10-13 or 14, further comprising collecting water over the mordenite-based catalyst layer in a water trap. 16. Способ по пп.10-14 или 15, в котором морденит содержит фтор 0,1 - 4,0 мас.%. 16. The method according to PP.10-14 or 15, in which mordenite contains fluorine from 0.1 to 4.0 wt.%. 17. Способ по пп. 10-15 или 16, в котором катализатор на основе глины изготовлен из монтмориллонитовой глины. 17. The method according to PP. 10-15 or 16, in which the clay-based catalyst is made of montmorillonite clay. 18. Способ по пп.10-16 или 17, в котором содержание фтора в катализаторе на основе глины составляет 0,1 - 4,0 мас.%. 18. The method according to PP.10-16 or 17, in which the fluorine content in the clay catalyst is 0.1 to 4.0 wt.%. 19. Способ по пп. 10-17 или 18, в котором катализатор на основе глины прокаливают в интервале температур от 100 до 600°С. 19. The method according to PP. 10-17 or 18, in which the clay-based catalyst is calcined in the temperature range from 100 to 600 ° C. 20. Способ по пп. 10-18 или 19, в котором катализатор на основе глины имеет площадь поверхности более чем 30 м2/г.20. The method according to PP. 10-18 or 19, in which the clay-based catalyst has a surface area of more than 30 m 2 / g. 21. Способ по пп.10-19 или 20, в котором бромное число продукта снижается до значения менее чем около 0,1. 21. The method according to PP.10-19 or 20, in which the bromine number of the product is reduced to a value of less than about 0.1. 22. Способ по пп.10-20 или 21, в котором контактирование проводят в непрерывном режиме. 22. The method according to PP.10-20 or 21, in which the contacting is carried out continuously.
RU99100379/04A 1996-06-12 1997-05-08 Two-stage method of alkylating benzene to form linear alkyl benzenes RU2173677C2 (en)

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US08/662,786 US5777187A (en) 1996-02-08 1996-06-12 Two-step process for alkylation of benzene to form linear alkylbenzenes
US08/662,786 1996-06-12

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RU2173677C2 RU2173677C2 (en) 2001-09-20

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US (1) US5777187A (en)
EP (1) EP0918736B1 (en)
JP (1) JP2000511927A (en)
KR (1) KR20000016605A (en)
CN (1) CN1073539C (en)
DE (1) DE69705953T2 (en)
ES (1) ES2159397T3 (en)
ID (1) ID17942A (en)
RU (1) RU2173677C2 (en)
TW (1) TW426653B (en)
WO (1) WO1997047573A1 (en)

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