CN101781327B - Silicate ester compound, preparation method and application thereof - Google Patents
Silicate ester compound, preparation method and application thereof Download PDFInfo
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- CN101781327B CN101781327B CN2009100447391A CN200910044739A CN101781327B CN 101781327 B CN101781327 B CN 101781327B CN 2009100447391 A CN2009100447391 A CN 2009100447391A CN 200910044739 A CN200910044739 A CN 200910044739A CN 101781327 B CN101781327 B CN 101781327B
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- ester compound
- silicate ester
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- mineral ice
- therapeutic mineral
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Abstract
The invention relates to a new silicate ester compound, and also relates to a preparation method of the compound and application of the compound as a coolant agent. The silicate ester compound provided by the invention is menthol orthosilicate with the chemical structural formula shown as (I). The invention has the advantage of no odor, and since the new silicate ester compound has very high boiling point and can be released slowly, the new silicate ester compound is suitable for being used as the coolant agent of tobacco.
Description
Technical field
The present invention relates to a kind of new silicate ester compound; The invention still further relates to preparation method and it of this compound purposes as coolant agent.
Background technology
Coolant agent is all general names that can produce the not strong chemical substance of cooling effect and the property of medicine.Modal coolant agent is a Therapeutic Mineral Ice, but because its strong smell and to the intense stimulus property of skin, mucous membrane tissue and eye, so should not use in a large number; And peppermint has the characteristics of distillation, unsuitable storage and transport, and cool flavor does not continue.Therefore, many scientists seek the substitute products and the derived product of Therapeutic Mineral Ice always, have had some to think that the compound of comparison safety is applied in the industries such as tobacco, food, chemical industry.
In recent years, the demand of coolant agent is constantly increased, and require increasingly highly, do not have smell, the convenient interpolation discharges slowly, therefore all seeking new coolant agent.
Summary of the invention
The object of the invention just provides a kind of silicate ester compound, and the purposes as coolant agent of this compound is provided.
Silicate ester compound provided by the invention is silicic acid three menthyl ester, and its chemical structural formula is:
Above-mentioned substance chemical name of the present invention is silicic acid three menthyl ester, and the preparation method reacts through silicon tetrachloride and Therapeutic Mineral Ice, and its reaction formula is:
In the above-mentioned reaction; The consumption mol ratio of silicon tetrachloride and Therapeutic Mineral Ice is between 1: 3 to 1: 4, and acid binding agent can be triethylamine, pyridine, hexahydropyridine, N, accelerine; The consumption mol ratio of Therapeutic Mineral Ice and acid binding agent is between 3: 4 to 1: 1; Solvent is selected from methylene dichloride, trichloromethane, hexanaphthene, normal hexane, and hydrolysising condition can be acidic solution: Hydrogen chloride, dilute sulphuric acid, acetic acid can be basic soln: sodium hydroxide solution, potassium hydroxide solution, ammoniacal liquor.
NaOH is a catalyzer, and having reacted the back is catalyst neutralisation NaOH with the salt acid elution earlier, is in order to remove water miscible unnecessary soda acid with the sodium hydrogencarbonate washing again; Yellow liquid is the toluene solution of silicic acid three menthyl ester, because silicic acid three menthyl ester are insoluble to ethanol, so will separate out insolubles silicic acid three menthyl ester to the ethanol adding; Last water and washing with alcohol white solid are pure for assurance silicic acid three menthyl ester, and final drying gets pure article.
According to embodiments of the invention, the structure of prepared silicate ester compound is the structure of above-mentioned formula (I), i.e. silicic acid three menthyl ester.
The advantage of silicic acid three menthyl ester provided by the invention has no smell, because boiling point is very high, release to birth ratio is slower, so it has two big purposes: 1, be suitable for adding in the tobacco, can promote the quality of tobacco, improve the suction flavor of tobacco; 2,, become the staple of novel sanitation ball as anophelifuge and wormer.
Description of drawings
Fig. 1 is the gas chromatogram of compound provided by the invention;
Fig. 2 is the mass spectrograph figure of compound provided by the invention;
Fig. 3 is the 1H NMR figure of compound provided by the invention.
Embodiment
Embodiment one
In the there-necked flask that has TM and mechanical stirring 500mL, add 100g CH
2Cl
2And 0.4mol (62.5g) Therapeutic Mineral Ice, slowly drip 0.1mol (17g) SiCl in 10 ℃
4With the 0.4mol triethylamine, triethylamine is made acid binding agent, because reaction can be emitted acidic substance HCl, drips off in 40 minutes, and reflux 2 hours adds the 80g hexanaphthene again behind the desolventizing, and reflux 1h adds 50g toluene reflux 2h again behind the desolventizing.Filter, organic phase adds the NaOH solution of 50g 30%, stirs and is warming up to 60 ℃, constant temperature 4h; Earlier, use saturated sodium hydrogencarbonate washed twice again, become neutrality, separatory with distilled water wash at last with hydrochloric acid lotion agitator treating three times; Precipitation gets yellow liquid, adds absolute ethyl alcohol, separates out white solid; Filter, ethanol and distilled water wash repeatedly, 80 ℃ dry must 50g.Content is 99.5%.
Product silicic acid three menthyl ester are the white powder solid.
Synthetic characterization data as a result:
GC/MS analyzes:
Gas chromatography-mass spectrum logotype instrument model (HP 5973/6890GC/MS), test condition: pillar, HP-5MS, 30m * 0.25mm * 0.25um; 80 ℃ kept 3 minutes, and temperature rise rate is 30 ℃/min, warm eventually; 280 ℃, vaporization temperature, 250 ℃, ion source temperature; 230 ℃, quadrupole temperature, 150 ℃;
Mass spectrometry results is seen Fig. 2: 509 (molecular ion peaks of silicic acid three menthyl ester), 139 (peppermint sloughs the daughter ion peak of a hydroxyl).
Nuclear magnetic resonance spectroscopy:
NMR (VARIAN Oncology Systems, Varian INOVA-300): instrument model: VarianINOVA-300,
1H NMR (CDCl
3),
13C NMR (CDCl
3).
The nuclear magnetic resonance spectroscopy result sees Fig. 3: 1H NMR, and δ: 5.1ppm (1H-OH), 3.6ppm (3H ,-Si-O-CH-have such H on the Therapeutic Mineral Ice) verifies SiCl with this
4On the chlorine atom have one to be hydrolyzed, other three with menthol reaction.
Claims (2)
1. the preparation method of a silicate ester compound, its reaction formula is:
Wherein the consumption mol ratio of silicon tetrachloride and Therapeutic Mineral Ice is between 1: 3 to 1: 4, and said acid binding agent is a triethylamine, and the consumption mol ratio of said Therapeutic Mineral Ice and acid binding agent is between 3: 4 to 1: 1, and said solvent is a methylene dichloride; Concrete preparation process is following:
In the dichloromethane solution of Therapeutic Mineral Ice, slowly drip SiCl in 10 ℃
4Triethylamine solution, drip off post-heating and reflux, add cyclohexane solvent behind the desolventizing again, reheat refluxes, and adds the toluene solution reflux behind the desolventizing again; Filter then, organic phase adds alkaline solution, stirs and is warming up to 60 ℃, constant temperature for some time; Successively, become neutral with distilled water wash at last, separatory with hydrochloric acid lotion and saturated sodium hydrogencarbonate washing; Precipitation gets yellow liquid, adds absolute ethyl alcohol; Separate out white solid, filter, the washing back is drying to obtain product in 80 ℃.
2. the preparation method of silicate ester compound according to claim 1 is characterized in that the consumption mol ratio of silicon tetrachloride and Therapeutic Mineral Ice is 1: 4, and the consumption mol ratio of said Therapeutic Mineral Ice and acid binding agent is 1: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2009100447391A CN101781327B (en) | 2009-11-11 | 2009-11-11 | Silicate ester compound, preparation method and application thereof |
Applications Claiming Priority (1)
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| CN2009100447391A CN101781327B (en) | 2009-11-11 | 2009-11-11 | Silicate ester compound, preparation method and application thereof |
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| CN2011104454866A Division CN102558211A (en) | 2009-11-11 | 2009-11-11 | Silicate ester compound and preparation method and use thereof |
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| CN101781327A CN101781327A (en) | 2010-07-21 |
| CN101781327B true CN101781327B (en) | 2012-04-18 |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321116B (en) * | 2011-06-07 | 2013-11-27 | 湖南中烟工业有限责任公司 | Triple refined peppermint titanate-ethyl ester, and preparation and application methods thereof |
| CN105324041B (en) * | 2013-06-18 | 2018-12-04 | 日本烟草产业株式会社 | Tobacco product containing natural (L)-menthol refined substance |
| CN107628623A (en) * | 2017-09-29 | 2018-01-26 | 四川绿源聚能环保科技有限责任公司 | A kind of method for handling chlorosilane slurry raffinate |
-
2009
- 2009-11-11 CN CN2009100447391A patent/CN101781327B/en active Active
Non-Patent Citations (5)
| Title |
|---|
| )-bornoxy)silanol and tetrakis((− |
| )-menthoxy)silane.《Journal of Organometallic Chemistry 》.2002,第648卷(第1-2期),188–192. |
| Jens Beckmann,et al..Chiral trialkoxysilanols derived from terpene alcohols.Molecular structures of tris([(1S)-endo]-(− |
| Jens Beckmann,et al..Chiral trialkoxysilanols derived from terpene alcohols.Molecular structures of tris([(1S)-endo]-(−)-bornoxy)silanol and tetrakis((−)-menthoxy)silane.《Journal of Organometallic Chemistry 》.2002,第648卷(第1-2期),188–192. * |
| 吴奇林等.凉味剂的研究进展.《香料香精化妆品》.2008,(第6期),33-39. * |
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| CN101781327A (en) | 2010-07-21 |
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