AU2018100841A4 - Organic synthetic intermediate hexanoic acid synthesis method - Google Patents

Organic synthetic intermediate hexanoic acid synthesis method Download PDF

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AU2018100841A4
AU2018100841A4 AU2018100841A AU2018100841A AU2018100841A4 AU 2018100841 A4 AU2018100841 A4 AU 2018100841A4 AU 2018100841 A AU2018100841 A AU 2018100841A AU 2018100841 A AU2018100841 A AU 2018100841A AU 2018100841 A4 AU2018100841 A4 AU 2018100841A4
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hexanoic acid
synthesis method
synthetic intermediate
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AU2018100841A
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genan guan
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Chengdu Qianye Longhua Petroleum Engineering Technology Consulting Co Ltd
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Chengdu Qianye Longhua Petroleum Engineering Technology Consulting Co Ltd
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation

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  • Organic Chemistry (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Organic synthetic intermediate hexanoic acid synthesis method Abstract 5 The present invention discloses organic synthetic intermediate hexanoic acid synthesis method, comprises the following steps: 1-amidogen-2-bromine-heptane is added into the reaction vessel and then stirring is conducted, then potassium chloride solution is added and the temperature is increased and then keep still; then praseodymium oxide powder is added and the temperature is increased, then 10 glycerinum sodium acetate solution is added and reaction is made continuously, then the temperature is decreased, leading to solution stratification, washing is made through sodium nitrate for several times, washing is made through 3-hexanone and N-methyl aniline solution for several times, then re-crystallization is made in the pentaerythritol tetranitrate solution, finally, dehydration is carried out by virtue of 15 dehydrating agent and finished hexanoic acid is produced. Figure 1

Description

The present invention discloses organic synthetic intermediate hexanoic acid synthesis method, comprises the following steps: l-amidogen-2-bromine-heptane is added into the reaction vessel and then stirring is conducted, then potassium chloride solution is added and the temperature is increased and then keep still; then praseodymium oxide powder is added and the temperature is increased, then glycerinum sodium acetate solution is added and reaction is made continuously, then the temperature is decreased, leading to solution stratification, washing is made through sodium nitrate for several times, washing is made through 3-hexanone and N-methyl aniline solution for several times, then re-crystallization is made in the pentaerythritol tetranitrate solution, finally, dehydration is carried out by virtue of dehydrating agent and finished hexanoic acid is produced.
Figure 1
2018100841 20 Jun 2018
Organic synthetic intermediate hexanoic acid synthesis method
FIELD OF THE INVENTION
The present invention relates to a method for preparing a pharmaceutical 5 intermediate which belongs to the field of organic synthesis, more particularly, relates to organic synthetic intermediate hexanoic acid synthesis method.
GENERAL BACKGROUND
Hexanoic acid is mainly used for organic synthesis and manufacture artificial flavors and natural rubber and paint drier that are made from esters. By most of the existing synthesis methods, 2-octanol is instilled into nitric acid, and the distillation is carried out under reduced pressure. And after further dehydration is made, 158°C(8.0kPa) fraction is collected and finally hexanoic acid is produced. By this synthesis method, nitric acid will be used as chemical reaction. However, the corrosion capacity of nitric acid is rather strong and thus the demand for the corrosion-resistance capacity of the equipment is high. As a result, the equipment maintenance cost increases, which isn’t beneficial to the decrease in production cost. What’s more, when the 158°C fraction is collected through reduced-pressure distillation, the reaction energy consumption is high, which is also not beneficial to the decrease in production cost. And the technology of this kind of synthesis method is very complicated.
Therefore, it is necessary to propose a new synthesis method.
SUMMARY
Based on the technical problems of the background technology, the purpose of the present invention is to provide organic synthetic intermediate hexanoic acid synthesis method, comprises the following steps:
A: l-amidogen-2-bromine-heptane is added into the reaction vessel and then stirring is conducted at speed of 210-250 rpm, then within 50-70 min, potassium chloride solution is added and the temperature is increased to the level between 40-46 °C and then keep still for 30-50 min;
B: then praseodymium oxide powder is added and the temperature is increased to
2018100841 20 Jun 2018 the level between 60-67°C within 3-4 hours, then glycerinum sodium acetate solution is added and reaction is made continuously for 60-90min, then the temperature is decreased to the level between 10-15°C, leading to solution stratification, washing is made through sodium nitrate for several times, washing is made through 3-hexanone and N-methyl aniline solution for several times, then re-crystallization is made in the pentaerythritol tetranitrate solution, finally, dehydration is carried out by virtue of dehydrating agent and finished hexanoic acid is produced.
Preferably, the potassium chloride solution has a mass fraction of 15-21%.
Preferably, the mass fraction of glycerinum sodium acetate solution is 15-21%.
Preferably, the sodium nitrate solution has a mass fraction of 20-27%.
Preferably, the 3-hexanone solution has a mass fraction of 40-46%.
Preferably, the mass fraction of N-methyl aniline solution is 60-65%.
Preferably, the pentaerythritol tetranitrate solution has a mass fraction of 80-87%. Throughout the reaction process can be the following reaction formula:
NH,
I
CH3(CH2h,CHCH2 + PhjOn + C9H,4O6 -CH3(CH2)4COOH
Br
Compared with the synthesis method disclosed in the background art, the invention provides organic synthesis intermediate hexanoic acid synthesis method, it is unnecessary to use nitric acid, avoiding the strong corrosion of nitric acid to the equipment, reducing equipment maintenance costs, not using vacuum distillation to collect 158 °C fractions, reducing the reaction energy consumption, reducing production costs, reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield, at the same time, the present invention provides a new synthetic route which has laid a good foundation for further enhancing the yield of the reaction.
DESCRIPTION OF THE DRAWINGS
Figure 1 is the 'HNMR analysis spectrum of finished product hexanoic acid.
Figure 2 is a hydrogen atom marker map of hexanoic acid molecules.
2018100841 20 Jun 2018
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invention are further illustrated:
Embodiment 1
Organic synthetic intermediate hexanoic acid synthesis method, comprises the following steps:
A: 2mol l-amidogen-2-bromine-heptane is added into the reaction vessel and then stirring is conducted at speed of 210 rpm, then within 50 min, 800ml potassium chloride solution with a mass fraction of 15% is added and the temperature is increased to the level between 40 °C and then keep still for 30min;
B: then 2 mol praseodymium oxide powder is added and the temperature is increased to the level between 60 °C within 3 hours, then 4 mol glycerinum sodium acetate solution with a mass fraction of 15% is added and reaction is made continuously for 60min, then the temperature is decreased to the level between 10°C, leading to solution stratification, washing is made through sodium nitrate with a mass fraction of 20% for 2 times, washing is made through 3-hexanone with a mass fraction of 40% for 6 times and N-methyl aniline solution with a mass fraction of 60% for 4 times, then re-crystallization is made in the pentaerythritol tetranitrate solution with a mass fraction of 80%, finally, dehydration is carried out by virtue of anhydrous calcium sulphate dehydrating agent and finished hexanoic acid 206.48g is produced, yield of 89%.
Embodiment 2
Organic synthetic intermediate hexanoic acid synthesis method, comprises the following steps:
A: 2mol l-amidogen-2-bromine-heptane is added into the reaction vessel and then stirring is conducted at speed of 230 rpm, then within 60 min, 800ml potassium chloride solution with a mass fraction of 18% is added and the temperature is increased to the level between 43 °C and then keep still for 40min;
B: then 2.5 mol praseodymium oxide powder is added and the temperature is
2018100841 20 Jun 2018 increased to the level between 63.5 °C within 3.5 hours, then 4.5 mol glycerinum sodium acetate solution with a mass fraction of 18% is added and reaction is made continuously for 75min, then the temperature is decreased to the level between 12.5 °C, leading to solution stratification, washing is made through sodium nitrate with a mass fraction of 23.5% for 3 times, washing is made through 3-hexanone with a mass fraction of 43% for 7 times and N-methyl aniline solution with a mass fraction of 62.5% for 5 times, then re-crystallization is made in the pentaerythritol tetranitrate solution with a mass fraction of 83.5%, finally, dehydration is carried out by virtue of anhydrous potassium carbonate dehydrating agent and finished hexanoic acid 213.44g is produced, yield of 94%.
Embodiment 3
Organic synthetic intermediate hexanoic acid synthesis method, comprises the following steps:
A: 2mol l-amidogen-2-bromine-heptane is added into the reaction vessel and then 15 stirring is conducted at speed of 250 rpm, then within 70 min, 800ml potassium chloride solution with a mass fraction of 21% is added and the temperature is increased to the level between 46 °C and then keep still for 50min;
B: then 3 mol praseodymium oxide powder is added and the temperature is increased to the level between 67 °C within 4 hours, then 5 mol glycerinum sodium acetate solution with a mass fraction of 21% is added and reaction is made continuously for 90min, then the temperature is decreased to the level between 15 °C, leading to solution stratification, washing is made through sodium nitrate with a mass fraction of 27% for 4 times, washing is made through 3-hexanone with a mass fraction of 46% for 8 times and N-methyl aniline solution with a mass fraction of 65% for 6 times, then re-crystallization is made in the pentaerythritol tetranitrate solution with a mass fraction of 87%, finally, dehydration is carried out by virtue of anhydrous calcium sulphate dehydrating agent and finished hexanoic acid 222.72g is produced, yield of 96%.
13HNMR analysis of finished product hexanoic acid, 13HNMR spectrum is shown in figure 1, the analysis of data is shown in table 1.
2018100841 20 Jun 2018
Table 1 Peak data
Atomic Chemical shift
number (PPm)
A 11.2
B 2.348
C 1.639
D 1.33
E 0.902
The embodiments of the present invention are merely preferred embodiments of the present invention, but the range of the present invention is not limited this, and any person who is familiar with those skilled in the arts, within the technical range of the present invention. It is intended that the technical solution and its inventive concept be replaced or modified equivalently with reference to the range of the invention.
2018100841 20 Jun 2018

Claims (4)

  1. Claims
    1. Organic synthetic intermediate hexano ic acid synthesis method, comprises the following steps:
    5 A: l-amidogen-2-bromine-heptane is added into the reaction vessel and then stirring is conducted at speed of 210-250 rpm, then within 50-70 min, potassium chloride solution is added and the temperature is increased to the level between 40-46 °C and then keep still for 30-50 min;
    B: then praseodymium oxide powder is added and the temperature is increased to 10 the level between 60-67°C within 3-4 hours, then glycerinum sodium acetate solution is added and reaction is made continuously for 60-90min, then the temperature is decreased to the level between 10-15°C, leading to solution stratification, washing is made through sodium nitrate for several times, washing is made through 3-hexanone and N-methyl aniline solution for several times, then re-crystallization is made in the
    15 pentaerythritol tetranitrate solution, finally, dehydration is carried out by virtue of dehydrating agent and finished hexanoic acid is produced.
  2. 2. Organic synthetic intermediate hexanoic acid synthesis method according to claim 1 wherein the potassium chloride solution has a mass fraction of 15-21%.
  3. 3. Organic synthetic intermediate hexanoic acid synthesis method according to 20 claim 1 wherein the mass fraction of glycerinum sodium acetate solution is 15-21%.
  4. 4. Organic synthetic intermediate hexanoic acid synthesis method according to claim 1 wherein the sodium nitrate solution has a mass fraction of 20-27%.
    1/1
    2018100841 20 Jun 2018
    Figure 1 ppm
    COOI I (B) H2C 'ch2 (D) h2C.
    (A) (C)
    CH2 (D)
    CH3 (E)
    Figure 2
AU2018100841A 2017-08-19 2018-06-20 Organic synthetic intermediate hexanoic acid synthesis method Ceased AU2018100841A4 (en)

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CN201710714682.6A CN108238925A (en) 2017-08-19 2017-08-19 The synthetic method of organic synthesis intermediate caproic acid

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