CN100551896C - A kind of synthetic method of 10-hydroxydecanoic acid - Google Patents
A kind of synthetic method of 10-hydroxydecanoic acid Download PDFInfo
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- CN100551896C CN100551896C CNB200710029017XA CN200710029017A CN100551896C CN 100551896 C CN100551896 C CN 100551896C CN B200710029017X A CNB200710029017X A CN B200710029017XA CN 200710029017 A CN200710029017 A CN 200710029017A CN 100551896 C CN100551896 C CN 100551896C
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- hydroxydecanoic acid
- secondary octanol
- synthetic method
- alkali
- viscotrol
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Abstract
The invention discloses a kind of synthetic method of 10-hydroxydecanoic acid, this method is added dropwise to Viscotrol C and Zhong Xin alcohol mixture earlier in the mixed system of the secondary octanol of microwave radiation and alkali, reaction at high temperature then, product obtains the 10-hydroxydecanoic acid through washing, water extraction, acidifying, filtering separation.The present invention adopts microwave to synthesize 10-hydroxydecanoic acid mode, can be to the heating of target compound selectivity, and heating efficiency height, saving energy have the remarkable shortening reaction times, lower energy consumption, and for normal pressure reaction down, improve security production, obtain good economic benefit.
Description
Technical field
The invention belongs to chemosynthesis technical field, particularly a kind of method of utilizing the synthetic 10-hydroxydecanoic acid of microwave.
Background technology
The 10-hydroxydecanoic acid is a kind of important fine-chemical intermediate, and market demand is bigger, is that raw material can prepare multiple high value-added product with it, is widely used in fields such as medicine, food, healthcare products, spices, makeup.It is the synthesizing efficient active substance---10-hydroxyl-2-decylenic acid, 6-(10-hydroxydecanoic acid)-2,3, and the important intermediate of dimethoxy-5-methylbenzoquinone, megacyclic musk, and can directly be added in the makeup as the sebum secretion inhibitor.
The 10-hydroxydecanoic acid can be made by ricinoleate acid glyceryl ester high temperature alkali cracking, and Mikhaibor, M. etc. adopt after-souring method separating and cracking product, and productive rate only is 32%; Diamond, M.J. add the n-Octanol productive rate and bring up to 69% in reaction, but the separated product condition needs deep cooling to-23 ℃ of crystallizations.Usefulness such as Li Kai 95% ethanol under high pressure cracking productive rate is 70%; 6 hours productive rates of secondary octanol of employings such as Huang Xiaofeng and the acidifying of moisture section can reach 75%, the first kind, and reaction process is loaded down with trivial details and productive rate is low, though back three's reaction yield is higher, exists or equipment requirement of withstand voltage height or characteristics such as long reaction time, process complexity.
The industrial production technology condition of present existing 10-hydroxydecanoic acid is: 200 ± 5 ℃ of temperature, pressure 3～4Mpa, and the 12 hours reaction times of early stage, therefore, exist the shortcoming that temperature of reaction height, pressure are big, the time is long equally, make production security poor, power consumption is big, and production efficiency is low.
Summary of the invention
In order to solve above-mentioned the deficiencies in the prior art part, the object of the present invention is to provide a kind of synthetic method of 10-hydroxydecanoic acid, the present invention adopts microwave to synthesize 10-hydroxydecanoic acid mode, can heat the target compound selectivity, heating efficiency height, saving energy have the remarkable shortening reaction times, lower energy consumption, and are normal pressure reaction down, improve security production, obtain good economic benefit.
Purpose of the present invention realizes by following technical proposals: a kind of synthetic method of 10-hydroxydecanoic acid, comprise the steps: mixing with Viscotrol C and secondary octanol, the mass ratio of described Viscotrol C and secondary octanol is 1: 0.3～1, then the mixture of above-mentioned Viscotrol C and secondary octanol is added dropwise in the mixture of the secondary octanol of microwave radiation to 110～150 ℃ and alkali, the mass ratio of described secondary octanol and alkali is 1: 1～1.75, evenly stir, be added dropwise to complete the back and continue microwave radiation, making the synthetic system temperature is 150～190 ℃, reflux 1～3h then, after reaction finishes, add entry, remove water layer after evenly stirring by 2～3 times of quality that add alkali; Oil reservoir extracts with 75～90 ℃ equal-volume water, combining water layer, more than 80 ℃, be acidified to PH6.0～6.5 with acid, remove the residual oil reservoir in top as far as possible after, be cooled to 30～40 ℃, continue to be acidified to congo-red test paper and become blue, leave standstill more than the 4h suction filtration, drying obtains product solid 10-hydroxydecanoic acid.
In order to realize the present invention better, the mass ratio of particularly preferred Viscotrol C and secondary octanol is 1: 0.5～1, and the mass ratio of secondary octanol and alkali is 1: 1～1.3.
Described alkali can adopt sodium hydroxide or potassium hydroxide etc.
Described microwave frequency is 2450MHz; Microwave power is 200～500W; Particularly preferred microwave power is 200～400W.
The rate of addition that the mixture of described Viscotrol C and secondary octanol is added dropwise in the mixture of the secondary octanol of microwave radiation to 110～150 ℃ and alkali is 1～3mL/min.
Described acid is hydrochloric acid or sulfuric acid etc.
Described product 10-hydroxydecanoic acid chemical structure is identified: MS has C through this compound of library searching
10H
20O
3Molecular composition, IR proves characteristic group: 3250cm
-1Be the OH absorption peak; 2900cm
-1Be CH
3The C-H stretching vibration absorb 1690cm
-1Charateristic avsorption band for C=O; 1470cm
-1Be CH
3Absorption peak; 1300cm
-1Absorption peak for OC-OH;
1H,
13C NMR proves that the exactness of its carbon skeleton: δ=179ppm is the carbonyl characteristic peak, and δ=62ppm is the peak of carbon of linking to each other with hydroxyl, and except that containing a carbonyl, all the other carbon all are CH in the molecule
2, do not have CH
1And CH
3
Principle of the present invention is earlier Viscotrol C to be mixed with secondary octanol, joins in the mixed system of the secondary octanol of microwave radiation and alkali, at high temperature reacts then, and product obtains the 10-hydroxydecanoic acid through washing, water extraction, acidifying, filtering separation.
The present invention and prior art mutually this, have following advantage and beneficial effect:, can save the energy because the microwave radiation controlled temperature is lower than prior synthesizing method temperature; Simultaneously, owing to the prior synthesizing method reaction times is 6～12h, and the time of microwave synthetic reaction is 1.5～3h, and microwave is synthetic can save reaction energy greatly, and enhances productivity; The prior synthesizing method reaction pressure is 3～4Mpa, and microwave synthetic reaction pressure is a normal pressure, and microwave is synthetic can to reduce dangerous hidden danger, safety in production, and cut down the consumption of energy.The present invention adopts the mode of the synthetic 10-hydroxydecanoic acid of microwave, can be to the heating of target compound selectivity, and heating efficiency height, saving energy, have the remarkable shortening reaction times, lower energy consumption, and for normal pressure reaction down, improve security production, can obtain good economic benefit.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
The present invention is described in further detail below in conjunction with embodiment and accompanying drawing, but embodiments of the present invention are not limited thereto.
Embodiment 1
The secondary octanol of 14g Viscotrol C and 6g is mixed, and the mixture of above-mentioned Viscotrol C and secondary octanol is at the uniform velocity splashed into microwave with the 1mL/min rate of addition, and (microwave frequency is 2450MHz; Microwave power is 300W) be radiated in the mixture of secondary octanol and 75% (mass percent) sodium hydroxide of the 15g 20g under 120 ℃, evenly stir, keep same microwave frequency and power, it is 150～180 ℃ that the continuation microwave radiation makes temperature of reaction, keeps backflow 1h.Reaction finishes the back and adds 60mL washing lixiviating, removes water layer; Oil reservoir extracts respectively 4 times with 80～85 ℃ hot water, is cooled to 30～40 ℃ with 60～70% (mass percent) sulfuric acid acidation to PH6.0～6.5 behind the combining water layer, continues to be acidified to congo-red test paper and becomes blue.Leave standstill 4h, suction filtration 65 ℃ of dryings, obtains solid 10-hydroxydecanoic acid, and output is: 4.5g, productive rate is: 65%.With obtaining white crystal behind the benzene recrystallization, the mensuration fusing point is: 74～75 ℃.
Embodiment 2
The secondary octanol of Viscotrol C 14g and 14g is mixed, and the mixture of above-mentioned Viscotrol C and secondary octanol is at the uniform velocity splashed into microwave with the 3mL/min rate of addition, and (microwave frequency is 2450MHz; Microwave power is 200W) be radiated in secondary octanol and 70% (mass percent) sodium hydroxide of the 21g 25g mixture under 110 ℃, evenly stir, (microwave frequency is 2450MHz to continue microwave; Microwave power is 400W) radiation makes temperature of reaction be: 160～190 ℃, keep backflow 1.5h.Reaction finishes the back and adds 50mL washing lixiviating, branch vibration layer; Oil reservoir is with 75～85 ℃ of water hot extractions 4 times, and combining water layer is cooled to 30～40 ℃ with 60～70% (mass percent) sulfuric acid acidation to PH6.0～6.5, continues to be acidified to congo-red test paper and becomes blue.Leave standstill 4h, suction filtration 65 ℃ of dryings, obtains solid 10-hydroxydecanoic acid, and output is: 5.1g, productive rate is: 75%.With obtaining white crystal behind the benzene recrystallization, the mensuration fusing point is: 74.5～75.5 ℃.
Embodiment 3
The secondary octanol of Viscotrol C 14g and 4.2g is mixed, and the mixture of above-mentioned Viscotrol C and secondary octanol is at the uniform velocity splashed into microwave with the 1mL/min rate of addition, and (microwave frequency is 2450MHz; Microwave power is 400W) be radiated in secondary octanol and 70% (mass percent) sodium hydroxide of the 21g 20g mixture under 150 ℃, evenly stir, keep same microwave frequency and power, continue microwave radiation and make temperature of reaction be: 150～190 ℃, keep backflow 2.5h.Reaction finishes the back and adds 40mL washing lixiviating, branch vibration layer; Oil reservoir is with 75～85 ℃ of water hot extractions 4 times, and combining water layer is cooled to 30～40 ℃ with 60～70% (mass percent) sulfuric acid acidation to PH6.0～6.5, continues to be acidified to congo-red test paper and becomes blue.Leave standstill 4h, suction filtration 65 ℃ of dryings, obtains solid 10-hydroxydecanoic acid, and output is: 4.6g, productive rate is: 68%.With obtaining white crystal behind the benzene recrystallization, the mensuration fusing point is: 75～76 ℃.
Embodiment 4
The secondary octanol of Viscotrol C 14g and 11g is mixed, and the mixture of above-mentioned Viscotrol C and secondary octanol is at the uniform velocity splashed into microwave with the 2mL/min rate of addition, and (microwave frequency is 2450MHz; Microwave power is 200W) be radiated in the secondary octanol of 18g and 25g 75% (mass percent) potassium hydroxide mixture under 130 ℃, evenly stir, (microwave frequency is 2450MHz to microwave; Microwave power is 300W) radiation makes temperature of reaction be: 150～180 ℃, keep backflow 2.8h.Reaction finishes the back and adds 30mL washing lixiviating, branch vibration layer; Oil reservoir extracts respectively 4 times with 85～90 ℃ of hot water, is cooled to 30～40 ℃ with 60～70% (mass percent) sulfuric acid acidation to PH6.0～6.5 behind the combining water layer, continues to be acidified to congo-red test paper and becomes blue.Leave standstill 6h, suction filtration 65 ℃ of dryings, obtains the 10-hydroxydecanoic acid, and output is: 4.9g, productive rate is: 72%.With measuring fusing point behind the benzene recrystallization be: 74.5～75.5 ℃.
Embodiment 5
The secondary octanol of Viscotrol C 14g and 7g is mixed, and the mixture of above-mentioned Viscotrol C and secondary octanol is at the uniform velocity splashed into microwave with the 2mL/min rate of addition, and (microwave frequency is 2450MHz; Microwave power is 200W) be radiated in the secondary octanol of 18g and 31.5g 75% (mass percent) potassium hydroxide mixture under 130 ℃, evenly stir, (microwave frequency is 2450MHz to microwave; Microwave power is 500W) radiation makes temperature of reaction be: 150～180 ℃, keep backflow 2h.Reaction finishes the back and adds 50mL washing lixiviating, branch vibration layer; Oil reservoir extracts respectively 5 times with 85～90 ℃ of hot water, arrives PH6.0～6.5 with hcl acidifying behind the combining water layer, is cooled to 30～40 ℃, continues to be acidified to congo-red test paper and becomes blue.Leave standstill 5h, suction filtration 65 ℃ of dryings, obtains the 10-hydroxydecanoic acid, and output is: 4.5g, productive rate is: 65%.With obtaining white crystal behind the benzene recrystallization, the mensuration fusing point is: 74.5～75.5 ℃.
The foregoing description is a preferred implementation of the present invention; but embodiments of the present invention are not restricted to the described embodiments; other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (7)
1, a kind of synthetic method of 10-hydroxydecanoic acid, it is characterized in that comprising the steps: mixing with Viscotrol C and secondary octanol, the mass ratio of described Viscotrol C and secondary octanol is 1: 0.3～1, then the mixture of above-mentioned Viscotrol C and secondary octanol is added dropwise in the mixture of the secondary octanol of microwave radiation to 110～150 ℃ and alkali, the mass ratio of described secondary octanol and alkali is 1: 1～1.75, evenly stir, be added dropwise to complete the back and continue microwave radiation, making the synthetic system temperature is 150～190 ℃, reflux 1～3h then, after reaction finishes, add entry, remove water layer after evenly stirring by 2～3 times of quality that add alkali; Oil reservoir extracts with 75～90 ℃ equal-volume water, and combining water layer more than 80 ℃, is acidified to PH6.0～6.5 with acid, after removing the residual oil reservoir in top, be cooled to 30～40 ℃, continue to be acidified to congo-red test paper and become blue, leave standstill more than the 4h, suction filtration, drying obtains solid 10-hydroxydecanoic acid.
2, the synthetic method of a kind of 10-hydroxydecanoic acid according to claim 1 is characterized in that: the mass ratio of described Viscotrol C and secondary octanol is 1: 0.5～1, and the mass ratio of secondary octanol and alkali is 1: 1～1.3.
3, the synthetic method of a kind of 10-hydroxydecanoic acid according to claim 1 is characterized in that: described alkali is sodium hydroxide or potassium hydroxide.
4, the synthetic method of a kind of 10-hydroxydecanoic acid according to claim 1 is characterized in that: described microwave frequency is 2450MHz; Microwave power is 200～500W.
5, the synthetic method of a kind of 10-hydroxydecanoic acid according to claim 4 is characterized in that: described microwave power is 200～400W.
6, the synthetic method of a kind of 10-hydroxydecanoic acid according to claim 1 is characterized in that: the rate of addition that the mixture of described Viscotrol C and secondary octanol is added dropwise in the mixture of the secondary octanol of microwave radiation to 110～150 ℃ and alkali is 1～3mL/min.
7, the synthetic method of a kind of 10-hydroxydecanoic acid according to claim 1 is characterized in that: described acid is hydrochloric acid or sulfuric acid.
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| CNB200710029017XA CN100551896C (en) | 2007-07-04 | 2007-07-04 | A kind of synthetic method of 10-hydroxydecanoic acid |
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| CNB200710029017XA CN100551896C (en) | 2007-07-04 | 2007-07-04 | A kind of synthetic method of 10-hydroxydecanoic acid |
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| CN106496010B (en) * | 2016-09-13 | 2018-11-16 | 成都师范学院 | A kind of new method of high-temperature catalytic cracking castor oil synthesis 10- hydroxydecanoic acid |
| JP7176801B2 (en) * | 2019-08-22 | 2022-11-22 | 株式会社山田養蜂場本社 | CONVERSION METHOD, CONVERTING AGENT, PROCESS FOR PRODUCING ROYAL JELLY COMPOSITION, AND LACTOBACILLUS BACTERIA |
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Non-Patent Citations (2)
| Title |
|---|
| 从蓖麻油制取10-羟基硅酸的研究. 黄小凤.有机化学，第16期. 1996 |
| 从蓖麻油制取10-羟基硅酸的研究. 黄小凤.有机化学，第16期. 1996 * |
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