Resorcin synthetic process

A technology for resorcinol and synthesis process, which is applied in the field of synthesis technology of resorcinol, can solve the problems of relatively high requirements on process conditions, high cost, and a conversion rate of only 26%, and achieves guaranteed catalytic effect and low cost. , the effect of reducing catalyst cost

Inactive Publication Date: 2009-02-25
深圳泛胜塑胶助剂有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the route design of this process is catalytic oxidation dehydration, rather than direct catalytic dehydrogenation, and the yield of resorcinol is only about 80%, the process conditions are relatively high, and the cost is relatively high
British Patent GB1188387 discloses a 1,3-cyclohexanedione at a temperature of 150-300 ° C, using iodine, 5% palladium charcoal or 5% palladium-coated calcium carbonate as a catalyst, through catalytic dehydrogenation to obtain m-benzene The method of diphenol, but the transformation rate of this document embodiment only has 26%; U.S. Patent US4431848 has synthesized above-mentioned (2), (3) synthetic route, is raw material with δ-ketoester, and catalytic cyclization becomes cyclo Diketone or 3-hydroxycyclohexenone, and then catalytic dehydrogenation of cyclic diketone or oxidative dehydration of 3-hydroxycyclohexenone to obtain resorcinol, which provides a method using water as a solvent However, the overall conversion rate of cyclohexane-1,3 diketone is only about 80% (column 60-70, column 11, column 12, line 12, US4431848 specification), which is far lower than other 95-98% conversion under the same reaction conditions in the examples of organic solvents

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  • Resorcin synthetic process

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Experimental program
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Effect test

Embodiment 1

[0021] Add 1 liter of water and 10 grams of 5% Pd-C catalyst (which contains 8% potassium oxide promoter) in a 5-liter autoclave. After sealing, heat it to 190 ° C under stirring, and feed nitrogen or inert gas under the liquid surface. Keep the liquid surface pressure at about 1.2Mpa. 2 liters of aqueous solution having 180 grams of 1,3-cyclohexanedione dissolved therein was introduced into the reaction kettle within 2 hours from the liquid surface, the temperature was controlled at 180-185° C., and the reaction was continued for 6 hours. After the reaction is finished, cool down to normal temperature, filter and recover the catalyst, extract the reaction solution with butyl acetate to obtain crude resorcinol, distill the crude product resorcinol to recover butyl acetate, and then distill under reduced pressure to obtain a white product with a purity of 99.4%. Resorcinol 163.8 grams. The yield of resorcinol in this embodiment is 92.1%.

Embodiment 2

[0023] In a 5-liter autoclave, add 1 liter of water and 10 grams of 10% Pt-C catalyst (which contains a promoter of 6% magnesium oxide), after sealing, heat to 170 ° C under stirring, and feed nitrogen or inert gas under the liquid surface Keep the liquid surface pressure at about 1.0Mpa. 2 liters of aqueous solution containing 225 grams of 1,3-cyclohexanedione was introduced into the reaction kettle from under the liquid surface within 90 minutes, the temperature was controlled at 170-175° C., and the reaction was continued for 4 hours. After the reaction is finished, lower the temperature to normal temperature, filter and recover the catalyst, extract the reaction solution with isopropyl ether to obtain crude resorcinol, distill the crude product resorcinol to recover isopropyl ether, and then distill under reduced pressure to obtain a white product with a purity of 99.7%. Resorcinol 200 grams. The yield of resorcinol in this embodiment is 90.2%.

Embodiment 3

[0025] In a 5-liter autoclave, add 1 liter of water and 10 grams of 30% Ni-diatomite catalyst (promoter comprising 4% potassium sulfate), after sealing, heat to 180°C under stirring, and feed nitrogen or gas under the liquid surface The inert gas keeps the liquid surface pressure at about 1.4Mpa. 2 liters of aqueous solution having 150 grams of 1,3-cyclohexanedione dissolved in it was introduced into the reaction kettle within 2 hours from the liquid surface, the temperature was controlled at 180-185°C, and the reaction was continued for 4.5 hours. After the reaction is finished, cool down to normal temperature, filter and recover the catalyst, extract the reaction solution with a mixed solvent of butyl acetate and n-butanol to obtain crude resorcinol, distill the crude product resorcinol to recover the solvent, and then distill under reduced pressure to obtain a purity of 99.8 % white resorcinol 139.3 g. The yield of resorcinol in this embodiment is 94.4%.

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Abstract

The invention relates to a synthesis process of resorcinol, which takes cyclohexane with -OH substituent group or =O substituent group at the location 1 and the location 3 as raw material, and takes water as a solvent. The resorcinol is obtained by catalytic dehydrogenation at the temperature of 150 to 300 DEG C and the pressure of 0.1-1.7MPa for 3-10h; wherein, the water is taken as a reaction medium, and the dehydrogenation catalyst is chosen from Pd, Pt or Ni series. The process has simple synthetic route and simple process; the reaction is easily controlled; the water is taken as the solvent, so less three wastes are generated, and the synthesis process of the resorcinol is environmentally friendly and has less cost; meanwhile, as the catalyst is chosen from the Pd, the Pt or the Ni catalysts, the catalyst has the advantages of good catalytic selectivity, high activity and high reaction conversion rate, and the resorcinol obtained is easily purified with high yield.

Description

【Technical field】 [0001] The invention relates to an organic synthesis process, in particular to a synthesis process of resorcinol. 【Background technique】 [0002] Resorcinol is an important basic fine organic chemical raw material, which is widely used in many fields such as medicine, pesticide, dye, rubber, adhesive, electronic chemical and so on. The present industrialized resorcinol synthesis method mainly contains two: the one, the sulfonation alkali fusion method (sulfonation method) of benzene, and the 2nd is the oxidation method (oxidation method) that is raw material with m-dicumene. The sulfonation method uses benzene and sulfuric acid as raw materials, and the process includes sulfonation, neutralization, alkali fusion and acidification. This method has a simple process and low equipment requirements, but the production process is lengthy, there are many wastes, and the environmental friendliness is low; The oxidation method is to first oxidize m-dicumyl to dicumy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/07C07C37/06C07C39/08
CPCY02P20/584
Inventor 梁沛基傅健
Owner 深圳泛胜塑胶助剂有限公司
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