Ester production method and ester production device

Patent metadata

Field	Value
Publication number	US-9776950-B2
Application number	US-201515323838-A
Country	US
Kind code	B2
Filing date	Jul 3, 2015
Priority date	Jul 4, 2014
Publication date	Oct 3, 2017
Grant date	Oct 3, 2017

Abstract

Provided is a production device including: a first reactor to form a second gas containing an ester and nitric oxide from a first gas containing carbon monoxide, a nitrite, and nitric oxide; an absorption column to separate the second gas and an absorbing solution into a condensate containing the ester and a noncondensable gas; a second reactor to introduce an alcohol, the noncondensable gas, and oxygen gas thereinto to form a third gas containing nitric oxide and a nitrite; a third reactor to form a fourth gas containing a nitrite from the noncondensable gas and a bottom liquid from the second reactor and to feed the fourth gas to the second reactor; a first measurement unit to measure the concentration of a nitrite in the first gas; and a first flow rate-adjusting unit to adjust the amount of the noncondensable gas to the third reactor based on the concentration.

First claim

The invention claimed is:

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

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

3. The method according to claim 1 , wherein the concentration of a nitrite ester in the first gas and/or the third gas is measured by using non-dispersive infrared analysis.

4. The method according to claim 3 , wherein 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 is used in the non-dispersive infrared analysis.

5. The method according to claim 1 , comprising measuring a concentration of nitric oxide in the first gas and/or the third gas and adjusting an amount of the oxygen gas to mix with the noncondensable gas on a basis of the concentration.

6. The method according to claim 1 , wherein the concentration of the nitrite ester in the first gas is maintained at 5 to 25% by volume based on a total of the first gas.

7. The method according to claim 1 , wherein the concentration of the nitrite ester in the third gas is maintained at 5 to 30% by volume based on a total of the third gas.

8. 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 a 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 a 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 a 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 an amount of the noncondensable gas to feed to the third reactor on a basis of the concentration, and a second flow rate-adjusting unit to adjust an amount of nitric acid to feed to the third reactor on a basis of the concentration.

9. 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 a 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 a concentration of a nitrite ester in the first gas and/or the third gas; and
a third flow rate-adjusting unit to adjust an amount of nitric oxide to mix with the noncondensable gas on a basis of the concentration.

10. The device according to claim 8 , comprising a control unit to control at least one of the first flow rate-adjusting unit and the second flow rate-adjusting unit so that the concentration of a nitrite ester in the first gas becomes 5 to 25% by volume based on a total of the first gas.

11. The device according to claim 8 , comprising a control unit to control at least one of the first flow rate-adjusting unit and the second flow rate-adjusting unit so that the concentration of a nitrite ester in the third gas becomes 5 to 30% by volume based on a total of the third gas.

12. The device according to claim 9 , comprising a control unit to control 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 a total of the first gas.

13. The device according to claim 9 , comprising a control unit to control 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 a total of the third gas.

14. The device according to claim 8 , wherein the first measurement unit includes a non-dispersive infrared analyzer.

15. The device according to claim 14 , wherein the non-dispersive infrared analyzer includes a measurement cell to allow the first gas and/or the third gas to flow therethrough, and a detector

Assignees

• Ube Industries

Inventors

• Il Hirofumi
• FUKUI Yuya
• Tanaka Syuji

Classifications

• C07C67/36 Primary

  by reaction with carbon monoxide or formates (C07C67/02, C07C67/03, C07C67/10 take precedence) · CPC title

• B01J2219/00231

  at the reactor inlet · CPC title

• B01J2219/00211

  comparing a sensed parameter with a pre-set value · CPC title

• B01J2219/00198

  at the reactor inlet · CPC title

• B01J2219/00186

  controlling the composition of the reactive mixture · CPC title