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Process of producing 1,1 diaryl alkanes and derivatives thereof

A technology for diarylalkanes and aromatic compounds, applied in the field of manufacturing 1,1-diarylalkanes, can solve the problems of poor isomer selectivity, unsatisfactory reaction yield and the like

Inactive Publication Date: 2011-07-20
EVONIK DEGUSSA GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] A problem with the prior art mentioned above is the reported poor isomer selectivity when reactions involving substituted aromatic compounds such as xylenes
In addition, the reaction yield is unsatisfactory

Method used

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  • Process of producing 1,1 diaryl alkanes and derivatives thereof
  • Process of producing 1,1 diaryl alkanes and derivatives thereof
  • Process of producing 1,1 diaryl alkanes and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A tubular reactor (2.54 cm x 38.1 cm stainless steel) was filled with 18.01 grams of solid-supported perfluorosulfonic acid resin (Nafion® SAC-13). The catalyst bed was dried by heating to 150°C overnight under a nitrogen purge. The filled reactor was cooled to ambient temperature and a back pressure regulator set at 1379 kPa was attached to the outlet of the reactor. The system was primed with o-xylene at a flow rate of 0.89 mL / min and the reactor bed was heated to 170°C. Once the reactor bed was at temperature, the pure ortho-xylene feed was replaced with 6 wt% DMM in ortho-xylene and the flow rate was maintained at 0.89 mL / min. Analysis of the product stream leaving the tubular reactor showed that in 79 mol% yield, and with about 75% selection of the isomer 3,3',4,4'-tetramethyldiphenylmethane Proactively produces di(xylyl)methane (DXM).

Embodiment 2

[0042] The synthesis of DXM from DMM and o-xylene using solid-supported perfluorosulfonic acid resin (Nafion® SAC-13) was carried out using equipment similar to that described in Example 1.

[0043]A catalyst-packed tube reactor was prepared by heating at 150° C. overnight under a nitrogen purge. The tube reactor was cooled to room temperature. Turn on the pump and establish a flow of the DMM / o-xylene mixture at 1.0 mL / min. The tube furnace temperature was set at 40°C and the reactor temperature was increased by 15°C every 0.5-2.0 hours. An increase in the molar yield of DXM was observed with temperature up to 140 °C. DMM was detected in the product stream until the reaction temperature reached 180°C. For airspeed 2.9hr -1 (1.0 mL / min) and 6 wt% DMM concentration, the best molar yield (85%), selectivity (70-75%) and DMM conversion (100%) occurred at 180 °C.

Embodiment 3

[0045] The synthesis of DXM from DMM and o-xylene using perfluorosulfonic acid resin was carried out using equipment similar to that described in Example 1.

[0046] A catalyst-packed tube reactor was prepared by heating at 150° C. overnight under a nitrogen purge. The tube reactor was cooled to room temperature. Turn on the pump and establish a flow of the DMM / o-xylene mixture at 1.0 mL / min. The tube furnace temperature was set at 40°C and the reactor temperature was increased until the reaction temperature reached 160°, 170° or 180°C, then held at this temperature for a period of 8-10 hours while periodically sampling the product stream. Analysis showed a constant DXM molar yield of 60%. It is also observed that the isoselectivity is sustained at 70% in this range.

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Abstract

The invention relates to a process of producing 1,1 diaryl alkanes and derivatives thereof. A process of producing a 1,1-diaryl alkane comprises a condensation reaction of an aromatic compound having at least one aromatic hydrogen with an acetal, in the presence of a perfluorinated sulfonic acid in polymeric form as catalyst.

Description

technical field [0001] The present invention relates to a process for the production of 1,1-diarylalkanes by condensation of aromatic compounds with acetals using perfluorosulfonic acid in polymer form as a catalyst. Background technique [0002] Methods of making diarylalkanes are known in the art. [0003] JP 02-134332A discloses a process for producing diarylmethanes comprising reacting aromatic hydrocarbons with formaldehyde in the presence of a sulfuric acid catalyst and in the presence of a surfactant. [0004] FR 2745285 A1 discloses the C-alkylation of aromatics using special catalysts comprising rare earth metals on clay, silica and / or alumina supports. [0005] US 4,814,537 A discloses a process for the preparation of methyl-substituted diphenylmethanes by coupling methyl-substituted benzenes via contact with solid heterogeneous catalytic oxides of vanadium, molybdenum, rhenium and / or tungsten. [0006] US 4,895,988 A discloses the condensation of aromatic compou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/16C07C2/86
CPCC07C2531/10C07C2/862C07C15/16
Inventor J·H·迪米特M·D·卡格勒
Owner EVONIK DEGUSSA GMBH
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