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“Development of new propylene oxide process by cumene recycling”

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The 8th Green and Sustainable Chemistry Award

第8界绿色与可持续化 学奖

Awarded by the Minister of Economy, Trade and Industry


Sumitomo Chemical Co., Ltd.

住友商事化学公司


“Development of new propylene oxide process by cumene recycling”

【清洁技术】循环使用异丙基苯的新PO工艺


Propylene oxide (PO) can be produced by conventional chlorohydrin or hydroperoxide process.
Each conventional process has the unsolvable disadvantage, such as producing a large amount of
valueless chloride salt or co-producing a huge amount of stylene or isobutene.

Sumitomo Chemical has developed a new PO only production process that does not produce any
co-products. Cumene is used and recycled as a reaction medium like “oxygen carrier” through three
reaction steps of oxidation, epoxidation and hydrogenation in the process (figure 1).

Most important problem was how to develop a highly active catalyst for the epoxidation using
such a large molecule like cumene hydroperoxide with propylene. Microporous Ti-silicate zeolite
such as TS-1 is well-known to be a very active epoxidation catalyst by the reaction with hydrogen
peroxide, but it showed extremely low activity for the epoxidation with cumene hydroperoxide. The
three factors are thought to be important for developing high performance catalyst, (1) to maximize
tertrahedral titanium active sites highly dispersed in a silica matrix, (2) to have mesoporous
structure (nano space) which a large molecule like cumene hydroperoxide can be easily diffused,
and (3) to have sufficient hydrophobic property for high propylene affinity. As a result of challenging
catalyst development especially focusing on how to make as many meso pores as possible, we have
succeeded in finding and industrializing a high performance Ti-silica epoxidation catalyst, which
have a characteristic “mesoporous structure”. Figure 2 shows a reaction image with a mesoporous
epoxidation catalyst. We think this is a first example of industrialized mesoporous catalyst.

In our process, all reaction steps proceed in especially high yields, and the usage of process energy
is very low since all exothermic reaction heat of oxidation, epoxidation and hydrogenation is
recovered and effectively utilized. Therefore, we think our PO cumene process is superior in raw
material consumption and energy consumption to other processes including the hydrogen peroxide
method. We can estimate that the energy saving effect of our new process against a conventional
process is equivalent to the carbon dioxide reduction of about 300,000 tons/y, based on a PO 200,000
tons/y plant. Our new PO process is very economical and “green”. The first plant using our new
technology was built in Japan and started up in 2003, and the second plant at Petro Rabigh in
Saudi Arabia is to start up this year.

Source: http://www.gscn.net/awardsE/images/GSC_aw2008_1.pdf

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