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Ube Industries : Patent Issued for Ester Production Method and Ester Production Device (USPTO 9776950)

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10/12/2017 | 09:50pm CEST

By a News Reporter-Staff News Editor at Life Science Weekly -- UBE INDUSTRIES, LTD. (Ube-shi, JP) has been issued patent number 9776950, according to news reporting originating out of Alexandria, Virginia, by NewsRx editors (see also UBE INDUSTRIES, LTD.).

The patent's inventors are Il, Hirofumi (Ube, JP); Fukui, Yuya (Ube, JP); Tanaka, Syuji (Ube, JP).

This patent was filed on July 3, 2015 and was published online on October 3, 2017.

From the background information supplied by the inventors, news correspondents obtained the following quote: "Carbonate esters are useful compounds as a raw material for synthesis of aromatic polycarbonates, and drugs and agricultural chemicals, etc. Oxalic esters are also useful compounds as a raw material for synthesis of glycols, dye intermediates, and drugs, etc. Methods for continuous mass production of these compounds have been previously proposed.

"As a process to continuously produce a carbonate ester, a process is known in which synthesis through gas phase reaction is performed by using carbon monoxide and a nitrite ester in the presence of a solid catalyst of a platinum group metal (e.g., see Patent Literature 1). In such a process, a carbonate ester can be obtained through the following reaction formula (i). CO+2RONO.fwdarw.ROC(.dbd.O)OR+2NO (i)

"NO obtained through the reaction represented by the formula (i) reacts with an alcohol in accordance with the following formula (ii) to form a nitrite ester in a reaction column (regeneration column). By reusing the nitrite ester obtained in the reaction and newly feeding carbon monoxide, a carbonate ester can be continuously produced. An oxalic ester can be also produced continuously in a similar process (e.g., see Patent Literature 2). Thus, carbonate esters and oxalic esters are produced by circulating nitrogen components such as a nitrite ester. 2NO+1/2O.sub.2+2ROH.fwdarw.2RONO+H.sub.2O (ii)

"In the process as described above, a reaction represented by the formula (iii) also proceeds in a reaction column. HNO.sub.3 formed in the reaction is extracted from the bottom of a reaction column. Patent Literature 3 proposes to introduce HNO.sub.3 thus formed into a nitric acid-concentrating column for effective use of nitric acid to reduce loss of nitrogen components. NO+3/4O.sub.2+1/2H.sub.2O.fwdarw.HNO.sub.3 (iii)"

Supplementing the background information on this patent, NewsRx reporters also obtained the inventors' summary information for this patent: "Technical Problem

"In the production methods described in the above Patent Literatures, a desired compound is produced through catalytic reaction while a nitrite ester is regenerated. Although such production methods enable mass production through scaling-up, it is required to establish a technique to continue production stably and efficiently. The reason is that, once continuous production is interrupted, cumbersome operation of an apparatus such as start-up operation and shutdown operation are required and in addition loss of opportunity due to the shutdown increases.

"To continue production stably, it is required to continue operation stably while the activity of a catalyst in a reactor is maintained. In such a reaction with a catalyst, the reaction rate decreases as the concentration of a component to react becomes excessively low to thereby decrease the production of an intended product. If the concentration of a nitrite ester in raw materials becomes excessively low, for example, the production of an ester including at least one of a carbonate ester and an oxalic ester, as an intended product, decreases. If the concentration of a nitrite ester becomes excessively high, on the other hand, safety in operation is expected to be deteriorated. Accordingly, it is required to suppress the variation of the composition of raw materials to be fed to a reactor.

"In view of this, an object of the present invention is to provide, in one aspect, a production method enabling stable production of an ester including at least one of a carbonate ester and an oxalic ester. In another aspect, an object of the present invention is to provide a production device enabling stable production of an ester including at least one of a carbonate ester and an oxalic ester.

"Solution to Problem

"The present invention provides, in one aspect, a method for producing an ester including at least one of a carbonate ester and an oxalic ester, the method comprising:

"introducing a first gas containing carbon monoxide, a nitrite ester, and nitric oxide into a first reactor and reacting the first gas in the presence of a catalyst to obtain a second gas containing an ester including at least one of a carbonate ester and an oxalic ester and nitric oxide;

"allowing the second gas to contact with an absorbing solution to obtain a condensate containing the ester and a noncondensable gas containing nitric oxide;

"introducing an alcohol and a mixed gas obtained by mixing the noncondensable gas with oxygen gas into a second reactor to obtain a third gas containing a nitrite ester and nitric oxide;

"distilling the condensate to obtain the ester;

"mixing the third gas with carbon monoxide to obtain the first gas;

"feeding the noncondensable gas and a bottom liquid discharged from the bottom of the second reactor and containing water, nitric acid, and an alcohol to a third reactor to form a fourth gas containing a nitrite ester, and feeding the fourth gas to the second reactor; and

"measuring the concentration of a nitrite ester in the first gas and/or the third gas, and at least one of adjusting the amount of the noncondensable gas to feed to the third reactor on the basis of the concentration and adjusting the amount of nitric acid to feed to the third reactor on the basis of the concentration.

"The production method includes obtaining a second gas containing an ester including at least one of a carbonate ester and an oxalic ester and nitric oxide from a first gas obtained by mixing a third gas containing nitric oxide and a nitrite ester with carbon monoxide by using a catalyst in a first reactor. Further, the production method includes measuring the concentration of a nitrite ester in the first gas and/or the third gas, and at least one of adjusting the amount of the noncondensable gas to feed to the third reactor on the basis of the concentration and adjusting the amount of nitric acid to feed to the third reactor on the basis of the concentration. These steps enable adjustment of the amount of a nitrite ester to be formed in the third reactor. By virtue of this, the variation of the concentration of a nitrite ester in the first gas and/or the third gas can be sufficiently reduced. Accordingly, lowering of the reaction rate in the first reactor is suppressed and at least one of a carbonate ester and an oxalic ester can be thus efficiently formed. In addition, the concentration of a nitrite ester in the first gas and the third gas is suppressed from excessively increasing and the safety can be thus enhanced.

"The present invention provides, in another aspect, a method for producing an ester including at least one of a carbonate ester and an oxalic ester, the method comprising:

"introducing a first gas containing carbon monoxide, a nitrite ester, and nitric oxide into a first reactor and reacting the first gas in the presence of a catalyst to obtain a second gas containing an ester including at least one of a carbonate ester and an oxalic ester and nitric oxide;

"allowing the second gas to contact with an absorbing solution to obtain a condensate containing the ester and a noncondensable gas containing nitric oxide;

"introducing an alcohol and a mixed gas obtained by mixing the noncondensable gas with oxygen gas into a second reactor to obtain a third gas containing a nitrite ester and nitric oxide;

"distilling the condensate to obtain the ester;

"mixing the third gas with carbon monoxide to obtain the first gas; and

"measuring the concentration of a nitrite ester in the first gas and/or the third gas and adjusting the amount of nitric oxide to mix with the noncondensable gas on the basis of the concentration.

"In the production method, a second gas containing at least one of a carbonate ester and an oxalic ester and nitric oxide is formed from a first gas obtained by mixing a third gas containing nitric oxide and a nitrite ester with carbon monoxide by using the catalyst in the first reactor. Then, the concentration of a nitrite ester in the first gas and/or the third gas is measured to adjust the amount of nitric oxide to mix with the noncondensable gas on the basis of the concentration. This enables adjustment of the amount of a nitrite ester to be formed in the second reactor. By virtue of this, the variation of the concentration of a nitrite ester in the first gas and/or the third gas can be sufficiently reduced. Accordingly, lowering of the reaction rate in the first reactor is suppressed and at least one of a carbonate ester and an oxalic ester can be thus efficiently formed. In addition, the concentration of a nitrite ester in the first gas and the third gas is suppressed from excessively increasing and the safety can be thus enhanced.

"In some embodiments, the concentration of a nitrite ester in the first gas and/or the third gas may be measured by using non-dispersive infrared analysis. Non-dispersive infrared analysis enables measurement of the concentration of a nitrite ester quicker than other analytical methods such as gas chromatography. By virtue of this, adjustment of the amount of the noncondensable gas to feed to the third reactor and/or adjustment of the amount of nitric oxide to feed for mixing with the noncondensable gas can be performed quickly. Accordingly, the variation of the concentration of a nitrite ester in the first gas can be further reduced.

"In the non-dispersive infrared analysis, an infrared analyzer including a measurement cell to allow the first gas and/or the third gas to flow therethrough and a detector encapsulating ammonia may be used to measure the concentration of a nitrite ester in the first gas and/or the third gas. Ammonia has absorption peaks in the same wavenumber regions as wavenumber regions including the infrared absorption peaks of a nitrite ester. In addition, ammonia is safer than nitrite esters. Thus, use of a detector encapsulating ammonia enables measurement of the concentration of a nitrite ester at a high precision concomitantly with enhancement of safety.

"In some embodiments, the production method may comprise measuring the concentration of nitric oxide in the first gas and/or the third gas and adjusting the amount of oxygen gas to mix with the noncondensable gas on the basis of the concentration. Because nitric oxide does not have an adverse effect on the activity of the catalyst in the first reactor, nitric oxide can be present in the first gas and the third gas at a concentration higher than that of oxygen gas. Thus, the concentration of nitric oxide in the first gas and the third gas can be detected at a higher precision than the concentration of (molecular) oxygen. In addition, the concentration of nitric oxide and the concentration of oxygen in the first gas and the third gas are closely related. Thus, the concentration of oxygen in the first gas can be monitored at a high precision by measuring the concentration of nitric oxide without directly measuring the concentration of oxygen in each of the first gas and the third gas. By virtue of this, lowering of the activity of the catalyst and deterioration of the catalyst caused by oxygen gas can be further suppressed.

"In the production method, the concentration of a nitrite ester in the first gas may be maintained at 5 to 25% by volume based on the total of the first gas. This enables sufficient utilization of the activity of the catalyst to efficiently produce at least one of a carbonate ester and an oxalic ester in combination with sufficient enhancement of the safety.

"In the production method, the concentration of a nitrite ester in the third gas may be maintained, for example, at 5 to 30% by volume based on the total of the third gas. This enables sufficient utilization of the activity of the catalyst to efficiently produce at least one of a carbonate ester and an oxalic ester in combination with sufficient enhancement of the safety.

"The present invention provides, in still another aspect, a device for producing an ester including at least one of a carbonate ester and an oxalic ester, the device comprising:

"a first reactor to react a first gas containing carbon monoxide, a nitrite ester, and nitric oxide in the presence of a catalyst to obtain a second gas containing an ester including at least one of a carbonate ester and an oxalic ester and nitric oxide;

"an absorption column to allow the second gas to contact with an absorbing solution to separate into a condensate containing the ester and a noncondensable gas containing nitric oxide;

"a second reactor to introduce an alcohol and a mixed gas containing the noncondensable gas and oxygen gas thereinto to obtain a third gas containing a nitrite ester and nitric oxide;

"a distillation column to distill the condensate to obtain the ester;

"a junction part to allow the third gas and carbon monoxide to join together to obtain the first gas;

"a third reactor to form a fourth gas containing a nitrite ester from the noncondensable gas and a bottom liquid discharged from the bottom of the second reactor and containing water, nitric acid, and an alcohol and to feed the fourth gas to the second reactor;

"a first measurement unit to measure the concentration of a nitrite ester in the first gas and/or the third gas; and

"at least one of a first flow rate-adjusting unit to adjust the amount of the noncondensable gas to feed to the third reactor on the basis of the concentration, and a second flow rate-adjusting unit to adjust the amount of nitric acid to feed to the third reactor on the basis of the concentration.

"The production device comprises a first reactor including a catalyst. In the first reactor, a second gas containing at least one of a carbonate ester and an oxalic ester and nitric oxide is obtained from a first gas obtained by allowing a third gas containing nitric oxide and a nitrite ester and carbon monoxide to join together. Further, the production device comprises a first measurement unit to measure the concentration of a nitrite ester in the first gas and/or the third gas, and at least one of a first flow rate-adjusting unit to adjust the amount of the noncondensable gas to feed to the third reactor on the basis of the concentration and a second flow rate-adjusting unit to adjust the amount of nitric acid to feed to the third reactor on the basis of the concentration.

"This enables adjustment of the amount of a nitrite ester to be formed in the third reactor. By virtue this, the variation of the concentration of a nitrite ester in the first gas and/or the third gas can be sufficiently reduced. Accordingly, lowering of the reaction rate in the first reactor is suppressed and at least one of a carbonate ester and an oxalic ester can be thus efficiently formed. In addition, the concentration of a nitrite ester in the first gas and the third gas is suppressed from excessively increasing and the safety can be thus enhanced.

"The present invention provides, in still another aspect, a device for producing an ester including at least one of a carbonate ester and an oxalic ester, the device comprising:

"a first reactor to react a first gas containing carbon monoxide, a nitrite ester, and nitric oxide in the presence of a catalyst to obtain a second gas containing an ester including at least one of a carbonate ester and an oxalic ester and nitric oxide;

"an absorption column to allow the second gas to contact with an absorbing solution to separate into a condensate containing the ester and a noncondensable gas containing nitric oxide;

"a second reactor to introduce an alcohol and a mixed gas containing the noncondensable gas and oxygen gas thereinto to form a third gas containing a nitrite ester and nitric oxide;

"a distillation column to distill the condensate to obtain the ester;

"a junction part to allow the third gas and carbon monoxide to join together to obtain the first gas;

"a first measurement unit to measure the concentration of a nitrite ester in the first gas and/or the third gas; and

"a third flow rate-adjusting unit to adjust the amount of nitric oxide to mix with the noncondensable gas on the basis of the concentration.

"The production device comprises a first reactor including a catalyst. In the first reactor, a second gas containing at least one of a carbonate ester and an oxalic ester and nitric oxide is formed from a first gas obtained by allowing a third gas containing nitric oxide and a nitrite ester and carbon monoxide to join together. Further, the production device comprises a first measurement unit to measure the concentration of a nitrite ester in the first gas and/or the third gas, and a first flow rate-adjusting unit to adjust the amount of nitric oxide to mix with the noncondensable gas on the basis of the concentration. This enables adjustment of the amount of a nitrite ester to be formed in the second reactor. By virtue of this, the variation of the concentration of a nitrite ester in the first gas and/or the third gas can be sufficiently reduced. Accordingly, lowering of the reaction rate in the first reactor is suppressed and at least one of a carbonate ester and an oxalic ester can be thus efficiently formed. In addition, the concentration of a nitrite ester in the first gas and the third gas is suppressed from excessively increasing and the safety can be thus enhanced.

"In some embodiments, the production device may comprise a control unit to control at least one of the first flow rate-adjusting unit, the second flow rate-adjusting unit, and the third flow rate-adjusting unit so that the concentration of a nitrite ester in the first gas becomes 5 to 25% by volume based on the total of the first gas. This enables sufficient utilization of the activity of the catalyst to efficiently produce at least one of a carbonate ester and an oxalic ester in combination with sufficient enhancement of the safety. In some other embodiments, the production device may comprise a control unit to control at least one of the first flow rate-adjusting unit, the second flow rate-adjusting unit, and the third flow rate-adjusting unit so that the concentration of a nitrite ester in the third gas becomes 5 to 30% by volume based on the total of the third gas. This enables sufficient utilization of the activity of the catalyst to efficiently produce at least one of a carbonate ester and an oxalic ester in combination with sufficient enhancement of the safety.

"The first measurement unit may be a non-dispersive infrared analyzer. A non-dispersive infrared analyzer can measure the concentration of a nitrite ester quicker than other analyzers such as gas chromatographs. Measurement of the concentration of a nitrite ester with a non-dispersive infrared analyzer enables quick adjustment with the flow rate-adjusting unit. Accordingly, the variation of the concentration of a nitrite ester in the first gas can be further reduced.

"The non-dispersive infrared analyzer may include a measurement cell to allow the first gas and/or the third gas to flow therethrough and a detector encapsulating ammonia, and may be configured to measure the concentration of a nitrite ester in the first gas and/or the third gas in the measurement cell. Ammonia is safer than nitrite esters as a subject to be measured. Ammonia has absorption peaks in the same wavenumber regions as wavenumber regions including the infrared absorption peaks of a nitrite ester. Thus, use of a detector encapsulating ammonia enables measurement of the concentration of a nitrite ester at a high precision concomitantly with enhancement of safety.

"In some embodiments, the production device may comprise: a second measurement unit to measure the concentration of nitric oxide in the first gas and/or the third gas; and a fourth flow rate-adjusting unit to adjust the amount of oxygen gas to mix with the noncondensable gas on the basis of the concentration. Because nitric oxide does not have an adverse effect on the activity of the catalyst in the first reactor, nitric oxide can be present in the first gas and the third gas at a concentration higher than that of oxygen. Thus, the concentration of nitric oxide in the first gas and the third gas can be measured at a higher precision than the concentration of oxygen gas. In addition, the concentration of nitric oxide and the concentration of (molecular) oxygen in the first gas and the third gas are closely related. Thus, the concentration of oxygen in the first gas can be monitored at a high precision by providing the second measurement unit to measure the concentration of nitric oxide without directly measuring the concentration of oxygen in each of the first gas and the third gas. By virtue of this, lowering of the activity of the catalyst and deterioration of the catalyst caused by oxygen gas can be further suppressed.

"Advantageous Effects of Invention

"The present invention can provide, in one aspect, a production method enabling stable production of an ester including at least one of a carbonate ester and an oxalic ester. In addition, the present invention can provide, in another aspect, a production device enabling stable production of an ester including at least one of a carbonate ester and an oxalic ester."

For the URL and additional information on this patent, see: Il, Hirofumi; Fukui, Yuya; Tanaka, Syuji. Ester Production Method and Ester Production Device. U.S. Patent Number 9776950, filed July 3, 2015, and published online on October 3, 2017. Patent URL: http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=9776950.PN.&OS=PN/9776950RS=PN/9776950

Keywords for this news article include: Pharmaceuticals, Anions, Esters, Ammonia, Alkalies, Chemicals, Carbonates, Chalcogens, Nitric Acid, Nitric Oxide, Carbonic Acid, Carbon Monoxide, Nitrogen Oxides, Nitrogen Compounds, UBE INDUSTRIES LTD, Noncarboxylic Acids, Reactive Nitrogen Species, Inorganic Carbon Compounds.

Our reports deliver fact-based news of research and discoveries from around the world. Copyright 2017, NewsRx LLC

(c) 2017 NewsRx LLC, source Health Newsletters

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Financials ( JPY)
Sales 2018 691 B
EBIT 2018 -
Net income 2018 27 262 M
Debt 2018 153 B
Yield 2018 1,89%
P/E ratio 2018 12,52
P/E ratio 2019 11,70
EV / Sales 2018 0,72x
EV / Sales 2019 0,69x
Capitalization 347 B
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Yuzuru Yamamoto President, Group CEO & Representative Director
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