Catalytic preparation method for phloroglucinol

A technology of phloroglucinol catalysis and acid catalyst, which is applied to the preparation of peroxygen compounds, chemical instruments and methods, and the preparation of organic compounds. safe effect

Inactive Publication Date: 2016-05-04
SUZHOU SUTONG PHARMA CO LTD
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  • Application Information

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Problems solved by technology

The TNT oxidation method is an ancient classic process, using 2,4,6-trinitrotoluene (TNT) as raw material to produce phloroglucinol industrially through 2,4,6-trinitrobenzoic acid and m-benzenetriamine. Cheap, mature technology, but difficult post-processing and serious environmental pollution, the raw material TNT has potential safety hazards and poor safety, especially the "three wastes" discharge is large and difficult to handle, and the production of each ton of products contains chromium salts (about 8%) and sodium Salt (5%) waste acid (containing about 40% sulfuric acid) 60 tons, iron sludge 15 tons and 40 tons of "three high and one poor" wastewater (that is, high chroma, high COD, high salt content, poor biochemical properties)
The raw material cost of etherification hydrolysis method is high and the process route is immature
There is also a process for preparing phloroglucinol through esterification, dechlorination, and hydrolysis with hexachlorobenzene, which is complicated and difficult for industrial production; aniline and bromine are used for benzene ring bromination and amino diazotization to synthesize phloroglucinol, The bromine consumption of this process is large, the pollution is serious, and the price of bromine is quite dynamic, and the industrialization has not been realized.
The cumene method has overcome the shortcoming of above method, is raw material with mesityl cumene, through secondary oxidation, once decomposition can obtain target product phloroglucinol, and cost is lower; But there is oxidation time too long, product The Obvious Problem of Lower Yields

Method used

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  • Catalytic preparation method for phloroglucinol

Examples

Experimental program
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Effect test

Embodiment 1

[0028] primary oxidation. Add 400g of TIP (96%, purity) and 400g of 2.5wt% NaOH aqueous solution, 32g of 4? molecular sieve, 10g of azobisisobutyronitrile, 7g of manganese dioxide, 2g of vanadium pentoxide and 1g of yttrium nitrate in a 2L autoclave. The stirring speed is 1250r / min, and the temperature is raised to 95°C. Add 200ml of 3.5wt% NaOH solution in the alkali dropping tank to keep the pH value of the reaction system at 9. Samples were taken every 4 hours, and after 20 hours of reaction, the material was discharged, cooled, and left to stand to obtain 748g of the aqueous phase and 482g of the organic phase (primary oxide).

[0029] Second stage oxidation. Remove the water from the primary oxide, weigh 30g and dissolve it in toluene to form a transparent solution, add it to a 500ml four-neck flask equipped with a stirrer, thermometer, and condenser, and heat up while stirring (stirring speed 1250r / min). When the temperature rises to 58°C, add H 2 SO 4 、H 2 o 2 A ...

Embodiment 2

[0033] primary oxidation. Add 400g of TIP (96%, purity) and 400g of 2wt% NaOH aqueous solution, 32g of 4? molecular sieve, 18g of cumene hydroperoxide and 2g of yttrium nitrate into a 2L autoclave, stirring at a speed of 1250r / min, and raising the temperature to 100°C. Add 200 g of 3.5wt% NaOH solution in the alkali dropping tank to keep the pH value of the reaction system at 9-10. Samples were taken every 4 hours. After 20 hours of reaction, the material was discharged, cooled, and left to stand to obtain 734 g of the aqueous phase and 489 g of the organic phase (primary oxide).

[0034] Second stage oxidation. Remove the water from the primary oxide, weigh 34g and dissolve it in toluene to form a transparent solution, add it to a 500ml four-neck flask equipped with a stirrer, thermometer, and condenser tube, and heat up under stirring (stirring speed 1200r / min). When the temperature rises to 58°C, add H 2 SO 4 、H 2 o 2 A homogeneous solution made of acid catalyst compo...

Embodiment 3

[0038] primary oxidation. In a 2L autoclave, add 400g TIP (96%, purity) and 400g 2wt% NaOH aqueous solution, 35g 4? min, the temperature was raised to 100°C. Add 200 g of 3.5wt% NaOH solution in the alkali dropping tank to keep the pH value of the reaction system at 9-10. Samples were taken every 4 hours. After 20 hours of reaction, the material was discharged, cooled, and left to stand to obtain 730 g of the aqueous phase and 492 g of the organic phase (primary oxide).

[0039] Second stage oxidation. Remove the water from the primary oxide, weigh 37g and dissolve it in toluene to form a transparent solution, add it to a 500ml four-neck flask equipped with a stirrer, a thermometer, and a condenser tube, and heat up while stirring (stirring speed 1250r / min). When the temperature rises to 58°C, add H 2 SO 4 、H 2 o 2 A homogeneous solution made of acid catalyst composed of water, ammonium persulfate and copper phthalocyanine, continue to react at 60°C for 1 hour, then sto...

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Abstract

The invention discloses a catalytic preparation method for phloroglucinol. Primary oxidation reaction is performed on 1,3,5-triisopropylbenzene in presence of a phase transfer catalyst to prepare isohydroxypropyl or cumene peroxide, the reaction time is shortened to 15 to 20h, the conversion rate of the 1,3,5-triisopropylbenzene is approximate to 100 percent, and the total molar selectivity reaches 62.0 percent. An oil phase obtained by the primary oxidation reaction is extracted with toluene to enter secondary oxidation in presence of an acid catalyst, the reaction temperature is 60 DEG C, the reaction time is 1h, and the yield of THPO is higher than 77 percent. A solid product and a toluene solution are separated after the secondary oxidation reaction, a certain amount of acetone is added to dissolve solids to obtain a transparent solution for acid decomposition reaction, the reaction time does not exceed 1h, the conversion rate of THPO reaches 88 percent, and the phloroglucinol selectivity is higher than 90 percent. A hydrothermal extraction method is adopted for separation and purification of the phloroglucinol, the total yield reaches 62 percent, the purity of a product is equal to or higher than 98 percent, and industrial application is facilitated.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a catalytic preparation method of phloroglucinol. Background technique [0002] Phloroglucinol (1,3.5-trihydroxybenzene) is an important fine chemical product. Phloroglucinol can be used as a fuel coupling agent and can be used in the synthesis of new phthalein fuels. Phloroglucinol can also be used as a variety of systems, such as glutaraldehyde solution, synthetic rubber, composite modified dual-fuel rocket propellant (CMDB) stabilizer; it can also be widely used in tire tackifiers and azo Composite ink and other raw materials. It is used as a dye coupler in the textile and leather dyeing process, in the production of plastic capsules, in place of silver iodide for artificial rainfall, and as a preservative for certain synthetic materials. [0003] In addition to its chemical value, phloroglucinol is mainly used as an intermediate in drug synthesis, such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/08C07C39/10
CPCC07C37/08C07C407/00C07C39/10C07C409/08
Inventor 罗嵬王辉娟李伟
Owner SUZHOU SUTONG PHARMA CO LTD
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