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Method for preparing isononanoic acid from isononyl alcohol through green oxidation

A technology of isononyl alcohol and isononanoic acid, applied in the field of biomedicine, can solve the problems of high pressure, low activity and selectivity of phosphine compound ligands, complicated operation process, etc., achieves the improvement of reaction product yield, avoids excessive oxidation and Effects of explosion risk

Active Publication Date: 2021-04-06
GUANGDONG UNIV OF PETROCHEMICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In summary, the production method of isononanoic acid by oxidation method uses oxidant as oxygen. Although it is green and environmentally friendly, the oxygen in the oxidation process has the risk of explosion, and the conversion rate is often sacrificed to avoid excessive oxidation.
However, the pressure required for hydroformylation or hydromethylation in the existing production process is high, the operation process is complicated, and the activity and selectivity of the phosphine compound ligand are low.

Method used

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  • Method for preparing isononanoic acid from isononyl alcohol through green oxidation
  • Method for preparing isononanoic acid from isononyl alcohol through green oxidation
  • Method for preparing isononanoic acid from isononyl alcohol through green oxidation

Examples

Experimental program
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Effect test

Embodiment 1

[0038] In a 100mL two-necked round bottom flask equipped with a reflux condenser and a thermometer, add isononyl alcohol (14.42g, 100mmol), 30% H 2 o 2 (8.50g, 250mmol), Na 2 WO 4 2H 2 O (0.66g, 2mmol) and methyl trioctyl ammonium bisulfate (0.93g, 2mmol) were mixed uniformly, measured with precision pH test paper and adjusted to a pH value of about 1. Stir rapidly and heat to 90°C, maintain the reaction temperature of 90°C for 4 hours, add water and let it stand after cooling to room temperature, separate the supernatant and carry out vacuum distillation to obtain 14.40 g of isononanoic acid product with a yield of 91%. 1 H NMR (400MHz, CDCl 3 )δ0.87(s, 9H), 1.02(d, J=6.4Hz, 3H), 1.12-1.34(m, 2H), 2.06-2.40(m, 3H); 13 C NMR (100MHz, CDCl 3)δ22.6, 26.8, 29.9, 31.0, 43.7, 50.5, 179.4, the NMR spectrum is completely consistent with the standard spectrum.

Embodiment 2

[0040] In a 100mL two-necked round bottom flask equipped with a reflux condenser and a thermometer, add isononyl alcohol (14.42g, 100mmol), 30% H 2 o 2 (6.80g, 200mmol), Na 2 WO 4 2H 2 O (0.66g, 2mmol) and methyl trioctyl ammonium bisulfate (0.93g, 2mmol) were mixed uniformly, measured with precision pH test paper and adjusted to a pH value of about 1. Stir rapidly and heat to 90°C, maintain the reaction temperature of 90°C for 4 hours, add water and let it stand after cooling to room temperature, separate the supernatant and carry out vacuum distillation to obtain 11.07g of isononanoic acid product with a yield of 70%. 1 H NMR (400MHz, CDCl 3 )δ0.87(s, 9H), 1.02(d, J=6.4Hz, 3H), 1.12-1.34(m, 2H), 2.06-2.40(m, 3H); 13 C NMR (100MHz, CDCl 3 )δ22.6, 26.8, 29.9, 31.0, 43.7, 50.5, 179.4, the NMR spectrum is completely consistent with the standard spectrum.

Embodiment 3

[0042] In a 100mL two-necked round bottom flask equipped with a reflux condenser and a thermometer, add isononyl alcohol (14.42g, 100mmol), 30% H 2 o 2 (10.20g, 300mmol), Na 2 WO 4 2H 2 O (0.66g, 2mmol) and methyl trioctyl ammonium bisulfate (0.93g, 2mmol) were mixed uniformly, measured with precision pH test paper and adjusted to a pH value of about 1. Stir rapidly and heat to 90°C, maintain the reaction temperature of 90°C for 4h, add water after cooling to room temperature, separate the supernatant and carry out vacuum distillation to obtain 13.92g of isononanoic acid product with a yield of 88%. 1 H NMR (400MHz, CDCl 3 )δ0.87(s, 9H), 1.02(d, J=6.4Hz, 3H), 1.12-1.34(m, 2H), 2.06-2.40(m, 3H); 13 C NMR (100MHz, CDCl 3 )δ22.6, 26.8, 29.9, 31.0, 43.7, 50.5, 179.4, the NMR spectrum is completely consistent with the standard spectrum.

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Abstract

The invention relates to the technical field of biological medicines, and provides a method for preparing isononanoic acid from isononyl alcohol through green oxidation. The method is used for solving the problems of complex flow, long reaction time, fire blast danger in the reaction process, waste gas generation, low product yield and the like in the isononanoic acid preparation process in the prior art. According to the method, isononyl alcohol is used as a raw material, a hydrogen peroxide solution is used as an oxidant, and a co-oxidant and a phase transfer catalyst are added for one-step oxidation under acidic conditions to prepare isononanoic acid. According to the method, isononyl alcohol is used as a raw material, 30% hydrogen peroxide is used as an oxidant, a co-oxidant and a phase transfer catalyst are added, isononanoic acid is prepared through a reaction under an acidic condition, the reaction is rapid, safe, green and environmentally friendly, the highest yield of a reaction product can reach 91%, and the catalyst can be repeatedly used.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a method for preparing isononanoic acid from isononyl alcohol by green oxidation. Background technique [0002] Isononanoic acid is also known as 3,5,5-trimethylhexanoic acid, CAS No. 3302-10-1, melting point -70°C, boiling point 121°C (10mmHg), density 0.91g / cm 3 , Refractive index 1.4278-1.4298, flash point 125°C. The structure is shown in the figure below: [0003] [0004] Isononanoic acid has a wide range of uses and can be used as pharmaceutical intermediates, synthetic lubricant intermediates, raw materials for metalworking fluids, and can also be used for alkyd resin modification. Its ester can be used in the field of cosmetics, and its salt can be used in paint drier, vinyl stabilizer, polyvinyl chloride stabilizer and preservative, tire adhesive aid, etc. [0005] At present, the main process for producing isononanoic acid is to prepare isononanal by oxidation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/285C07C53/128
CPCC07C51/285C07C53/128
Inventor 蒋达洪张志华崔宝臣李磊王煦张桂禧
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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