GB864069A - Process for the manufacture of aromatic carboxylic acids - Google Patents
Process for the manufacture of aromatic carboxylic acidsInfo
- Publication number
- GB864069A GB864069A GB30161/57A GB3016157A GB864069A GB 864069 A GB864069 A GB 864069A GB 30161/57 A GB30161/57 A GB 30161/57A GB 3016157 A GB3016157 A GB 3016157A GB 864069 A GB864069 A GB 864069A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- pressure
- acid
- mixture
- tube
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/243—Tubular reactors spirally, concentrically or zigzag wound
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00094—Jackets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00101—Reflux columns
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00162—Controlling or regulating processes controlling the pressure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00164—Controlling or regulating processes controlling the flow
- B01J2219/00166—Controlling or regulating processes controlling the flow controlling the residence time inside the reactor vessel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
<PICT:0864069/IV (b)/1> In a process for the manufacture of aromatic carboxylic acids by the oxidation of aromatic compounds with dilute nitric acid (e.g. of 10 to 30% strength), the reaction is carried out by passing the reaction-mixture, at elevated temperature and under a pressure of at least 80 atm., through a horizontal tube; and the conditions are so chosen that the reaction-product, i.e. the required carboxylic acid, does not separate out from the reaction mixture. The process, which is particularly advantageous for making terephthalic acid and p-nitrobenzoic acid, enables high yields of the product per unit of space and time to be obtained; and the temperature-control is facilitated, e.g. by arranging heating and cooling jackets at different sections along the reaction tube. The tube may be repeatedly doubled back on itself to form a series of horizontal sections arranged one above the other. In order to keep the residence-time as low as possible, the velocity of flow of the reaction mixture through the tube should be at least five times the internal radius of the tube multiplied by the number of alkyl carbon atoms per molecule in the compound to be oxidised. The reaction may be initiated by bringing the material to be oxidised into contact with nitric acid which has been heated to about 170 DEG C., and ensuring that the heat of reaction raises the temperature of the reaction-mixture to above 230 DEG C. In Fig. 2 is shown a reaction tube wherein the heat of reaction is utilized to preheat the reaction-mixture by working on a countercurrent principle. When the reaction is complete, the pressure of the reaction-mixture is reduced to atmospheric pressure, preferably via a stage of intermediate pressure e.g. 15 atm., in the apparatus shown in Fig. 4. The reaction mixture is discharged from reaction tube 15 through a valve; and the mixture is cooled and diluted by pumping water, at a temperature of 100 DEG -200 DEG C., into it through pipe 14. The mixture then enters vessel 10 which is maintained at the intermediate pressure by means of the valve 13 connected to condenser 12. A suspension of well-developed crystals is formed in vessel 10; and after a residence-time of about 15 minutes, the suspension is discharged to atmospheric pressure through valve 18. The particle-size and purity of the crystals depends on the pressure and residence-time in vessel 10, the particle size being larger the higher the pressure (see Group III). In Example 1, p-xylene at room temperature and nitric acid of 15% strength at a temperature of 170 DEG C. were pumped through a tube having an internal diameter of 24 mm. and an overall length of 42 metres. The pressure was maintained at 100 atm., and the temperature at 250 DEG C. Upon expansion, terephthalic acid crystallized out with a purity of 95%. In Example 2, o-chlorobenzoic acid is obtained by oxidation of o-chlorotoluene. Example 3 relates to the oxidation of 2-chloro-4-nitrotoluene yielding 2-chloro-4-nitrobenxoic acid. In Example 5, p-nitrobenzoic acid is obtained by oxidation of p-nitrotoluene. The process may also be used for the preparation of isophthalic acid and of p-chlorobenzoic acid. Terephthalic acid may be obtained by oxidation of p-chloromethyl toluene. A list of other suitable starting materials is given. Specification 698,157 is referred to.ALSO:In a process for the manufacture of aromatic carboxylic acids by the oxidation of organic compounds with dilute nitric acid, the reaction being carried out by passing the reaction-mixture, at elevated temperature and under a pressure of at least 80 atmospheres, through a horizontal tube whereby the product is obtained in solution (see Group IV(b)), the carboxylic acid is obtained in the form of pure and readily-filterable crystals by discharging the solution into a vessel, preferably fitted with a stirrer and reflux-condenser, and first partially releasing the pressure to 1 to 50 atm. (gauge) and then, after a residence-time of 15 seconds to 60 minutes, during which the desired crystals are formed, releasing the pressure to atmospheric conditions. Example 6 describes the preparation of crystals of p-nitrobenzoic acid having a predominant particle size of 40 microns. Example 7 describes the preparation of crystalline terephthalic acid having an average particle size of 10-30 microns. For a given residence time, the particle size of the crystals depends on the pressure established in the crystallizing-vessel, the particle size being larger the higher the pressure. Specification 698,157 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE864069X | 1956-09-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB864069A true GB864069A (en) | 1961-03-29 |
Family
ID=6801602
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30161/57A Expired GB864069A (en) | 1956-09-25 | 1957-09-25 | Process for the manufacture of aromatic carboxylic acids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB864069A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011095786A1 (en) * | 2010-02-08 | 2011-08-11 | Renewable Holdings Limited | Method and apparatus for esterifying fatty acid |
CN115197068A (en) * | 2022-06-10 | 2022-10-18 | 浙江优创材料科技股份有限公司 | Continuous step-by-step production process for producing p-nitrobenzoic acid |
-
1957
- 1957-09-25 GB GB30161/57A patent/GB864069A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011095786A1 (en) * | 2010-02-08 | 2011-08-11 | Renewable Holdings Limited | Method and apparatus for esterifying fatty acid |
US20130030205A1 (en) * | 2010-02-08 | 2013-01-31 | Richard Davis Jackson | Method and apparatus for esterifying fatty acid |
US9120739B2 (en) | 2010-02-08 | 2015-09-01 | Renewable Holdings Limited | Method and apparatus for esterifying fatty acid |
AU2011212228B2 (en) * | 2010-02-08 | 2016-03-24 | Renewable Holdings Limited | Method and apparatus for esterifying fatty acid |
CN115197068A (en) * | 2022-06-10 | 2022-10-18 | 浙江优创材料科技股份有限公司 | Continuous step-by-step production process for producing p-nitrobenzoic acid |
CN115197068B (en) * | 2022-06-10 | 2024-01-30 | 浙江优创材料科技股份有限公司 | Production process for continuously and stepwise producing p-nitrobenzoic acid |
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