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Synthesis method for pentadecanoicacid

A cyclopentadecanolactone and synthesis method technology, applied in the field of compound synthesis, can solve problems such as immature process conditions, harsh production conditions, and long process flow, and achieve strong industrial operability, low environmental pollution, and simple process Effect

Inactive Publication Date: 2012-12-12
FUJIAN TIANFU BIOTECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0031] Using cyclohexanone as raw material, it reacts with hydrogen peroxide under acidic conditions to obtain 1,1-dihydroperoxide dicyclohexyl peroxide, then reacts with cyclopentanone, and then heats and decomposes it in decane to obtain ten Five-carbon lactones and macrocyclic hydrocarbons. This method has a short process route and easy-to-obtain raw materials, but the process conditions are immature and the yield is low, so it is difficult to industrialize
[0032] The above known synthetic technology routes all have their shortcomings, some raw materials are not easy to get, expensive, high cost; some have many reaction steps, long process flow, harsh production conditions, high investment, low yield and low cost. high

Method used

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  • Synthesis method for pentadecanoicacid
  • Synthesis method for pentadecanoicacid
  • Synthesis method for pentadecanoicacid

Examples

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preparation example Construction

[0044] The synthetic method of cyclopentadecanolide comprises the following steps:

[0045] (1) Forming pentadecanedioic acid diester from the reaction of pentadecanedioic acid;

[0046]

[0047] (2) Synthesize pentadecanedioic acid monoester salt from the pentadecanedioic acid diester obtained in step (1);

[0048]

[0049] (3) The pentadecanedioic acid monoester salt obtained in step (2) is acidified and treated to obtain pentadecanedioic acid monoester;

[0050]

[0051] (4) generating 15-hydroxypentadecanoic acid by reducing the ester group of the pentadecanedioic acid monoester obtained in step (3);

[0052]

[0053] (5) The 15-hydroxypentadecanoic acid solid obtained in step (4) is subjected to a bromination reaction to obtain 15-bromopentadecanoic acid;

[0054]

[0055] (6) Dissolve quantitative 15-bromopentadecanoic acid in an organic solvent, add a small amount of iodine, and perform a ring closure reaction to obtain crude pentadecalactone;

[0056]...

Embodiment 1

[0060] Mix 27.2 g of pentadecanedioic acid with 64 ml of n-butanol, add 4 g of sodium bisulfate and 10 ml of cyclohexane under stirring at 115° C., and the reaction time is 4 hours. After filtering and washing with water until neutral, the organic solvent was distilled off to obtain 34.7 g of dibutyl pentadecanoic acid. Dissolve 25g of barium hydroxide in methanol, slowly add it dropwise to 30g of dibutyl pentadecanedioate at room temperature, react for 14 hours, filter, wash with water, and generate pentadecanedioic acid monoester barium salt. After diluting with a small amount of water, the solution was adjusted to a pH of 2 with dilute hydrochloric acid, extracted with ethyl acetate, washed with water until neutral, and evaporated to remove the organic solvent to obtain 21.2 g of monobutyl pentadecanedioic acid as a solid.

[0061] At 0°C, weigh 10 g of monobutyl pentadecanedioic acid and dissolve it in 200 ml of methanol solution, add 3.3 g of sodium borohydride in batches...

Embodiment 2

[0065] Mix 27.2 g of pentadecanedioic acid with 50 ml of n-butanol, add 4 g of sodium bisulfate and 10 ml of cyclohexane with stirring at 110° C., and the reaction time is 6 hours. After filtering and washing with water until neutral, the organic solvent was distilled off to obtain 34.7 g of dibutyl pentadecanoic acid. Dissolve 18g of barium hydroxide in a mixed solution of methanol and water, slowly add it dropwise to 30g of dibutyl pentadecanedioate at room temperature, react for 24 hours, filter, wash with water, and generate pentadecanedioic acid mono ester barium salt. After diluting with a small amount of water, the solution was adjusted to a pH of 2 with dilute hydrochloric acid, extracted with toluene, washed with water until neutral, and evaporated to remove the organic solvent. 20.8 g of white pentadecanedioic acid monobutyl was obtained.

[0066] At 0°C, 10 g of monobutyl pentadecanedioic acid was weighed and dissolved in 200 ml of ethanol solution, and 3.3 g of so...

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Abstract

The invention discloses a synthesis method for pentadecanoicacid. The pentadecanedioate is mixed with an organic dissolvent, and dimethylpentadecanedioate is obtained via reaction of adding a catalyst NaHSO4 and cyclohexane in a stirring condition; hydroxide is dissolved in the organic dissolvent and is dropped into the dimethylpentadecanedioate, and pentadecanedioate monoethanolamine is obtained after reaction; acid solution is used for treating the pentadecanedioate monoethanolamine to obtain pentadecanedioate monoester; the pentadecanedioate monoester is dissolved in the organic solution, adding sodium borohydride in batches to distill the organic dissolvent, and then acetic ether is utilized to extract 15-oxhydryl pentadecanoic acid; the mixture is dissolved in mixing solution of hydrobromic acid and glacial acetic acid to obtain 15-bromine pentadecanoic acid; the mixture is dissolved in organic dissolvent, carbonate and iodine are added, and the organic dissolvent is distilled to obtain a crude product of pentadecanoicacid; and the crude product of pentadecanoicacid is subjected to distillation at a reduced pressure, and fraction of 130-140 DEG C / 2mmHg is collected to obtain a product of pentadecanoicacid. The preparation method has simple process, low energy consumption, low cost, little pollution and easiness in realization of industrialization.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a synthesis method of cyclopentadecanolide. Background technique [0002] Cyclopentadecanolide also known as marshmallow [7] , the molecular formula is C 15 h 28 o 2 , the molecular weight is 240.29, and its structural formula is as follows: [0003] [0004] Cyclopentadecanolide, an important macrocyclic musk, is naturally present in angelica root oil and has an intense, delicate and elegant musky aroma. In addition, it is also a very good fixative, which can keep the essence of fragrance for a long time. The appearance of this compound is white needle crystal, with a melting point of 36-37°C and a boiling point of 280°C. According to the information provided by RIFM, the acute toxicity data of cyclopentadecanolide: Oral LD 50 >5g / Kg (rat), skin test LD 50 >5g / Kg (rabbit). [0005] Due to the excellent performance and high added value of cyclopentadecanolide, scien...

Claims

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Application Information

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IPC IPC(8): C07D313/00
Inventor 戚一文
Owner FUJIAN TIANFU BIOTECH DEV CO LTD
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