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Preparation method of isobutyl 3,5-diamino-4-chlorobenzoate

A technology of isobutyl chlorobenzoate and diamino, applied in the field of preparation of chemical raw materials, can solve the problems of large environmental pollution, difficult treatment, high production cost, etc., and achieve the effects of reducing production cost, increasing reaction rate, and low production cost

Inactive Publication Date: 2017-03-08
中农发河南农化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 3,5-diamino-4-chlorobenzoic acid isobutyl ester is a kind of organic acid ester chemical additive with promising market prospect, its molecular formula C 11 h 15 N 2 o 2 Cl, molecular weight 242.5, brown crystalline powder under normal temperature and pressure, avoid contact with oxidants during storage, easily soluble in alcohols, ethers, carbon tetrachloride, methylene chloride and other organic solvents, insoluble in water, mainly used for Polyurethane chain extender or chain extender, the traditional production process uses p-chlorobenzoic acid as raw material to obtain dinitro-p-chlorobenzoic acid through nitration under the action of sulfuric acid, and undergoes esterification reaction with isobutanol through sulfuric acid catalysis, and the obtained esterified product Under the action of alcohols, the final product is obtained by reduction with special powder, and the reduction with iron powder has post-processing difficulties and large environmental pollution.
Moreover, the production cost is high and the yield is low, which is the target of the industry.

Method used

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  • Preparation method of isobutyl 3,5-diamino-4-chlorobenzoate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. Raw materials: 20g of esterified product, 100mL of isobutanol, 4g of Raney nickel, 1g of morpholine.

[0026] 2. Operation process:

[0027] 1) Put 20g of the esterified product, 4g of Raney nickel, 100mL of isobutanol, and 1g of morpholine into the autoclave to seal in turn, and replace the autoclave with 0.2-0.3MPa nitrogen and hydrogen for 3 times respectively;

[0028] 2) Fill the hydrogen pressure to 3.0MPa, raise the temperature to 90-100℃ and keep it warm, and replenish the pressure to 3.0MPa in time when the pressure in the kettle drops to 2.0Mpa;

[0029] 3) Continue to replenish and maintain the pressure in the kettle at 2.0-3.0MPa to react for 2.5 hours, the system will no longer absorb hydrogen, the reaction is over, and cool down;

[0030] 4) Suction filtration, solid Raney nickel recycling;

[0031] 5) The filtrate was concentrated under reduced pressure to a viscous state, placed in the refrigerator, and frozen for crystallization.

[0032] Experime...

Embodiment 2

[0034] 1. Raw materials: 20g of esterified product, 100mL of ethanol, 4g of Raney nickel, 1g of morpholine.

[0035] 2. Operation process:

[0036] 1) Put 20g of the esterified product, 4g of Raney nickel, 100mL of ethanol, and 1g of morpholine into the autoclave to seal, and use 0.2-0.3MPa nitrogen and hydrogen to replace the autoclave 3 times;

[0037] 2) Fill the hydrogen pressure to 3.0MPa, raise the temperature to 90-100℃ and keep it warm, and replenish the pressure to 3.0MPa in time when the pressure in the kettle drops to 2.0Mpa;

[0038] 3) Continue to replenish and maintain the pressure in the kettle at 2.0-3.0MPa to react for 1.5 hours, the system will no longer absorb hydrogen, the reaction is over, and cool down;

[0039] 4) Suction filtration, solid Raney nickel recycling;

[0040] 5) The filtrate was concentrated under reduced pressure to a viscous state, placed in the refrigerator, and frozen for crystallization.

[0041] Experimental results: the reaction is...

Embodiment 3

[0043] 1. Raw materials: 20g of esterified product, 100mL of ethanol, 2.5g of Raney nickel, 1g of morpholine.

[0044] 2. Operation process:

[0045] 1) Put 20g of esterified product, 2.5g of Raney nickel, 100mL of ethanol, and 1g of morpholine into the autoclave to seal, and use 0.2-0.3MPa nitrogen and hydrogen to replace the autoclave 3 times;

[0046] 2) Fill the hydrogen pressure to 3.0MPa, raise the temperature to 90-100℃ and keep it warm, and replenish the pressure to 3.0MPa in time when the pressure in the kettle drops to 2.0Mpa;

[0047] 3) Continue to replenish and maintain the pressure in the kettle at 2.0-3.0MPa to react for 1.5 hours, the system will no longer absorb hydrogen, the reaction is over, and cool down;

[0048] 4) Suction filtration, solid Raney nickel recycling;

[0049] 5) The filtrate was concentrated under reduced pressure to a viscous state, placed in the refrigerator, and frozen for crystallization.

[0050] Experimental results: the reaction wa...

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Abstract

A preparation method of isobutyl 3,5-diamino-4-chlorobenzoate comprises the following basic steps: step 1, putting raw material ester compound, a solvent, a catalyst Raney nickel and a dehalogenation inhibitor into a high pressure reaction kettle at one time, sealing, and adopting 0.2-0.3 MPa of nitrogen gas and hydrogen gas for replacing gas in the high pressure reaction kettle for 3 times respectively; step 2, after completely sealing in the step 1, adding the hydrogen gas pressure to 3.0 MPa, increasing the temperature of the high pressure reaction kettle, carrying out a reaction, and timely replenishing the hydrogen gas pressure to ensure that the pressure in the high pressure reaction kettle in the reaction process is maintained at 3.0 MPa; step 3, adding hydrogen gas to maintain the pressure at 3.0 MPa in the step 2, carrying out a reaction for about 1.5-2 hours, finishing the reaction after the system absorbs hydrogen gas no longer, and overall cooling; step 4, after the step 3 is finished, recycling the catalyst Raney nickel; step 5, carrying out reduced pressure concentration of a filtrate to be viscous, putting into a refrigerator, and cooling and crystallizing at low temperature; and step 6, desolventizing the solvent alcohol and the dehalogenation inhibitor, recycling and reusing. The method is low in cost, safe and feasible.

Description

technical field [0001] The invention relates to a method for preparing chemical raw materials, in particular to a method for preparing isobutyl 3,5-diamino-4-chlorobenzoate. Background technique [0002] 3,5-diamino-4-chlorobenzoic acid isobutyl ester is a kind of organic acid ester chemical additive with promising market prospect, its molecular formula C 11 h 15 N 2 o 2 Cl, molecular weight 242.5, brown crystalline powder under normal temperature and pressure, avoid contact with oxidants during storage, easily soluble in alcohols, ethers, carbon tetrachloride, methylene chloride and other organic solvents, insoluble in water, mainly used for Polyurethane chain extender or chain extender, the traditional production process uses p-chlorobenzoic acid as raw material to obtain dinitro-p-chlorobenzoic acid through nitration under the action of sulfuric acid, and undergoes esterification reaction with isobutanol through sulfuric acid catalysis, and the obtained esterified prod...

Claims

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Application Information

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IPC IPC(8): C07C227/04C07C227/40C07C229/60
CPCY02P20/584C07C227/04C07C227/40C07C229/60
Inventor 王军营
Owner 中农发河南农化有限公司
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