CN105016989B - A kind of synthetic method of adermykon - Google Patents
A kind of synthetic method of adermykon Download PDFInfo
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- CN105016989B CN105016989B CN201510509097.3A CN201510509097A CN105016989B CN 105016989 B CN105016989 B CN 105016989B CN 201510509097 A CN201510509097 A CN 201510509097A CN 105016989 B CN105016989 B CN 105016989B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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Abstract
The present invention relates to a kind of synthetic method of adermykon, directly with the propane diols of 3 chlorine 1,2, parachlorophenol for raw material, the strong chemical solvent of corrosivity is not introduced into, reaction is simple, high income, and yield can reach more than 95% under optimal reaction condition.Adding a small amount of phase transfer catalyst can promote reaction is quick effectively to carry out, and can at least shorten 2 hours of reaction time.
Description
Technical field
The present invention relates to a kind of method for synthesizing adermykon.
Background technology
Adermykon, also known as siccolam, Chlorphenesin, English trade name Chlorphenesin, chemical name 3-
(4- chlorophenoxies) -1,2-PD, structural formula is as follows：
Molecular formula is C9H11ClO3, it is white powder, bitter, almost odorless, molecular weight 202.63, are slightly soluble in water, readily soluble
In ethanol, 78 DEG C~81 DEG C of fusing point.
Chlorphenesin main application：
1. in terms of medicine, mainly as a kind of muscle relaxant, it can also be applied to as a kind of antifungal drug anti-true
The illnesss such as bacterium, bacterium, vagina mould, trichmonad, pharmaceutical dosage form is more；
2. in terms of cosmetics, Chlorphenesin can effectively resist Gram-positive and negative bacterium, especially to aspergillus niger
IMI149007 and thermophilic loose mould IMI87160 (fungi) have a stronger bactericidal activity, and to Candida albicans NCPF3179 and
Saccharomyces cerevisiae NCPF3275 (yeast) has good inhibiting effect.
International Cosmetic Ingredient Dictionary and Handbook Twelfth
Edition (2008) proposes that Chlorphenesin can be used as cosmetic biocides, China《Cosmetics health specification (2007 editions)》
Point out that Chlorphenesin can limit the use of preservative as cosmetics and use in 70th page directory, it is maximum allowable in cosmetics to use
Concentration is 0.3%.
Chlorphenesin is as cosmetics preservative, with advantages below：(1) concentration is relatively low in cosmetics；(2) no
Containing any free or mating type formaldehyde, local skin or mucosal tolerance is good；(3) oxidation of fat will not be increased,
And antiseptic phenols can then cause this effect often, while will not also make protein denaturation；(4) the anti-of effective hypotoxicity is belonged to
Bacterium, antifungal agent, while being also effective anti-psoriasis composition, expert group's demonstration is examined by cosmetic composition, and it is using being peace
Complete.
Global Cosmetic Market is annual to develop close to 10% growth rate, and cosmetics preservative is as in cosmetics
Main adding ingredient, its consumption is also increasing.The security that current cosmetics are used increasingly is valued by people, newly
Presentation is removed MIT, goes oxybenzene esters and removes formaldehyde by the limit value that regulation is used MIT and oxybenzene esters, following cosmetics preservative
Trend as releaser class, due to Chlorphenesin because its own product advantage will be widely used.
Chlorphenesin synthetic method is a lot, but is prepared from mostly by chemical synthesis, and BP GB628497 is with right
Chlorophenol is raw material with glycidol, is reacted under conditions of pyridine presence, post processing chloroform or ether-petroleum ether essence
System, obtains product, and this method application ether-petroleum ether is the dicyandiamide solution highly volatile, inflammable, explosive to post-process solvent, no
It is adapted to amplification production.Chinese patent CN101445436A discloses one kind using epoxychloropropane, parachlorophenol as raw material, and sulfuric acid is
The method of catalyst preparation Chlorphenesin, this method reaction raw materials are complicated, and chloro- 1, the 2- third of 3- are first prepared using dilute sulfuric acid as oxidant
Glycol, then Chlorphenesin is synthesized, two-step reaction certainly will reduce reaction yield, and the yield that experiment obtains product is repeated in the method
It is low, and first step reaction can not monitor, and so reaction process can not be controlled effectively, this method introduces the corruption such as organic acid in addition
Corrosion is strong, and the difficult chemical solvent of post processing, is not suitable for amplification production.
It is of the invention to be not introduced into the strong chemical solvent of corrosivity directly using 3- chlorine-1,2-propylene glycols, parachlorophenol as raw material,
Reaction is simple, high income, and yield can reach more than 95% under optimal reaction condition.Add a small amount of phase transfer catalyst i.e.
It can promote reaction is quick effectively to carry out, can at least shorten 2 hours of reaction time.Do not have even in such reaction
Researcher applies such catalyst.
The content of the invention
The present invention provides a kind of synthetic method of Chlorphenesin.
The synthetic method of the Chlorphenesin, using 3- chlorine 1,2-PD, parachlorophenol as raw material, in the basic conditions,
Add phase transfer catalyst synthesis Chlorphenesin；
The synthetic method of the Chlorphenesin, including two steps：
The first step, crude product synthesis
In the reactor, 3- chlorine 1,2-PD, parachlorophenol and phase transfer catalyst are added in aqueous slkali, stirring,
After heating, insulation, reaction 2h~14h, reactant mixture is cooled, pH value is adjusted, stood, a layer organic phase, gas phase are removed in layering
Chromatography is detected, calculates conversion rate of products.
Second step, product separation
Solvent is added in organic phase obtained by the above-mentioned first step, ice-water bath is placed in, stirring a period of time, suction filtration obtains chlorine
The sweet ether finished product of benzene, dries and can obtain Chlorphenesin product, weigh, and calculates product yield, determines product content.
The phase transfer catalyst is the quaternary ammonium salt Huo quaternary alkylphosphonium salts in salt phase transfer catalyst, preferably tetrabutyl bromine
Change ammonium, tetrabutylammonium chloride, methyltriphenylphosphonium bromide or 4-butyl ammonium hydrogen sulfate.
Wherein, the first step, crude product synthesis：
The mol ratio of the parachlorophenol and the chloro- 1,2- propane diols of 3- is 1:1.0~1:2.0, mol ratio preferably is 1:
1.65~1:1.90 (purity of purity >=98%, 3- chlorine 1,2-PD of parachlorophenol >=99%)；
The mol ratio of the parachlorophenol and phase transfer catalyst is 1:0.003~1:0.1；
The aqueous slkali is the aqueous solution of inorganic alkali solution, preferably sodium hydroxide or potassium hydroxide；
The alkaline concentration is 10%~25%, and preferably alkaline concentration is 12%~18%；
The mol ratio of the parachlorophenol and alkali is 1:0.8~1:2.1, the preferably mol ratio of parachlorophenol and alkali is 1:
1.5~1:1.9；
The reaction temperature is 75 DEG C~105 DEG C, and preferable reaction temperature is 95 DEG C~105 DEG C；
The chloro- 1,2- propane diols of parachlorophenol, 3- and aqueous slkali is added portionwise in the reaction；
The reaction time is 2h~14h, and preferred reaction time is 3h~10h；
It is described that reactant mixture cooling is cooled down into reaction system Temperature fall or manually room temperature (20 DEG C~25
℃)；
The regulation pH value, generally application aqueous hydrochloric acid solution regulation pH value is 6.0~8.0, is preferably adjusted to 6.8-
7.2；
Layering general organic phase and the inorganic phase natural layering in the reactor, lower floor is organic phase；
The gas chromatography detection, detection method is as follows：
Instrument：Gas chromatograph；
Detector：Fid detector；
Chromatographic column：HP-530m×320μm×0.25μm
GC conditions：Injector temperature：280 DEG C of split ratios：50:1
Detector temperature：300℃
Column temperature:100 DEG C retain 0 minute, with 10 DEG C/min rise to 200 DEG C keep 2 minutes, then 30 DEG C/min rise to 280
DEG C keep 5 minutes
Carrier gas flux：Nitrogen 5mL/min
Sample is determined：Remove a layer organic phase to be placed in gas phase sample bottle, sample size is 0.1 μ L；
Computational methods：Area normalization method
Second step, product separation：
The solvent is chloroform-aqueous systems, ethanol-water system or water solution system, preferably chloroform-water body
It is for post processing solvent；
The proportioning (volume) of the solvent, the i.e. proportioning of chloroform-water are 1:4~4:1, preferably 2:3~3:2；
The drying uses boulton process；
The assay method of described product content：
Reagent and material：Methanol (chromatographically pure), Chlorphenesin (standard items, purity 99.5%).Unless otherwise specified, it is used
Reagent is that analysis is pure, and water is one-level experimental water.
Instrument and equipment：High performance liquid chromatograph, with PDAD；Balance, sensibility reciprocal 0.0001g.
Solution is prepared：Standard working solution：Chlorphenesin reference substance about 0.1g (being accurate to 0.0001g) is weighed in 100mL to hold
In measuring bottle, scale is settled to after adding mobile phase, ultrasonic dissolution, is shaken up.
Sample working solution：Chlorphenesin sample about 0.1g (being accurate to 0.0001g) is weighed in 100mL volumetric flasks, is added
Scale is settled to after mobile phase, ultrasonic dissolution, is shaken up.
Determination step：
Chromatogram reference conditions
Chromatographic column：C18 posts, 250mm × 4.6mm, 5 μm；
Mobile phase：Methanol+water=55+45；
Flow velocity：1.0mL/min；
Detector：PDAD, Detection wavelength is 280nm；
Column temperature：25℃.
Sample is determined
Under setting chromatographic condition, enter 10 μ L standard working solutions and treat that sample measuring liquid carries out efficient liquid phase chromatographic analysis.
Calculate
In formula：X (Chlorphenesin) --- the mass fraction of Chlorphenesin, % in cosmetics；
M --- the quality of Chlorphenesin to be measured, g；
A --- the peak area of Chlorphenesin to be measured；
m0--- Chlorphenesin is with reference to the quality of product, g；
A0--- peak area of the Chlorphenesin with reference to product.
The inventive method can make to produce immiscible two-phase in course of reaction using phase transfer catalyst fully reacts,
In the reaction, product Chlorphenesin is slightly soluble in water, with the progress of reaction, has substantial amounts of product to be dissolved into organic phase, so that
Make aqueous phase and organic phase separation, so two kinds of reactants are difficult mutually to draw close concurrent biochemical reaction, what influence was reacted normally enters
OK, phase transfer catalyst is added in the system, the conversion ratio of such reaction can be improved.Art methods recrystallization is most
Using the aqueous solution or ethanol solution, present invention application chloroform-aqueous systems do recrystallization solution, can not only improve product
Yield is purified, and chloroform can be reclaimed and used, and reduced the discharge of waste liquid, also reduced cost of material.
Brief description of the drawings
Fig. 1 adermykon gas chromatograms
Embodiment
The present invention is described in further detail with reference to embodiment, but the present invention is not limited with this.
Comparative example 1
Reaction is added without phase transfer catalyst, once feeds intake.
500ml there-necked flasks are taken, 3- chlorine-1,2-propylene glycols 41.1g (content 99.5%) (0.37mol), parachlorophenol is added
The mol ratio of 25.6g (0.2mol), parachlorophenol and 3- chlorine-1,2-propylene glycols is 1:1.85, the NaOH solution of concentration 18%
The mol ratio of 82.4g, parachlorophenol and sodium hydroxide is 1:1.85,105 DEG C are heated to, 4h is reacted.20 DEG C are cooled to, is added dilute
PH value is adjusted to 6.0 by hydrochloric acid.Stand after a period of time, separate two-phase, remove a layer organic phase, gas-chromatography monitoring, conversion ratio is
81.9%, it is further continued for reacting 2h, cooling, layering add the volume ratio of 150ml chloroforms and 100ml water, chloroform and water
For 3:2, it is put into frozen water domain and stirs, there is white solid precipitation, stirs, suction filtration.40 DEG C of vacuum drying, obtain white solid
31.47g, yield 77.7%, content 96.28%
Embodiment 1
500ml there-necked flasks are taken, 3- chlorine-1,2-propylene glycols 36.6g (content 99.5%) (0.33mol), parachlorophenol is added
16.6g (0.13mol), the NaOH solution 34.0g of concentration 18%, reaction system are heated to 105 DEG C, react 1h.Add to chlorobenzene
Phenol 9.0g (0.07mol), 18% NaOH solution 48.4g, 3- chlorine-1,2-propylene glycol 4.5g (content 99.5%) (0.04mol),
Now, the mol ratio of parachlorophenol and the total addition of 3- chlorine-1,2-propylene glycols is 1 in system:1.85, parachlorophenol and hydroxide
The mol ratio of the total addition of sodium is 1:1.85, continue to react 2h, be cooled to 20 DEG C, add watery hydrochloric acid and pH value is adjusted to 6.0.It is quiet
Put after a period of time, separate two-phase, remove a layer organic phase, gas-chromatography is monitored, and conversion ratio is 89.3%, then adds 150ml
The volume ratio of chloroform and 100ml water, chloroform and water is 3:2, it is put into frozen water domain and stirs, there is white solid precipitation,
Stirring, suction filtration.40 DEG C of vacuum drying, weighing products 35.34g, yield is 87.2%, content 98.46%.
Embodiment 2
500ml there-necked flasks are taken, 3- chlorine-1,2-propylene glycols 36.6g (content 99.5%) (0.33mol), parachlorophenol is added
16.6g (0.13mol), the NaOH solution 34.0g of concentration 18%, TBAB 0.32g, reaction system is heated to 105 DEG C,
React 1h.Add parachlorophenol 9.0g (0.07mol), 18% NaOH solution 48.4g, 3- chlorine-1,2-propylene glycol 4.5g (contents
99.5%) (0.04mol), now, the mol ratio of parachlorophenol and the total addition of 3- chlorine-1,2-propylene glycols is 1 in system:
1.85, the mol ratio of parachlorophenol and the total addition of sodium hydroxide is 1:1.85, parachlorophenol and TBAB rub
You are than being 1:0.005, continue to react 2h, be cooled to 20 DEG C, add watery hydrochloric acid and pH value be adjusted to 6.0.Stand after a period of time,
Two-phase is separated, a layer organic phase is removed, gas-chromatography is monitored, and conversion ratio is 98.2%, and 150ml chloroforms are added in reaction solution
With 100ml water, the volume ratio of chloroform and water is 3:2, it is put into frozen water domain and stirs, there is white solid precipitation, stirs, take out
Filter.40 DEG C of vacuum drying, weighing products 38.18g, yield is 94.2%, content 99.53%
Embodiment 3
500ml there-necked flasks are taken, 3- chlorine-1,2-propylene glycols 35.6g (content 99.5%) (0.32mol), parachlorophenol is added
16.6g (0.13mol), the KOH solution 73.2g of concentration 12%, 4-butyl ammonium hydrogen sulfate 0.5g, reaction system is heated to 105
DEG C, react 1h.Add parachlorophenol 9.0g (0.07mol), 12% KOH solution 104.1g, 3- chlorine-1,2-propylene glycol 4.3g
(content 99.5%) (0.04mol), now, parachlorophenol and the mol ratio of the total addition of 3- chlorine-1,2-propylene glycols are in system
1:1.80, the mol ratio of parachlorophenol and the total addition of potassium hydroxide is 1:1.90, parachlorophenol and 4-butyl ammonium hydrogen sulfate
Mol ratio be 1:0.007, continue to react 2h, be cooled to 20 DEG C, add watery hydrochloric acid and pH value be adjusted to 6.0.Stand a period of time
Afterwards, two-phase is separated, a layer organic phase is removed, gas-chromatography is monitored, and conversion ratio is 97.8%, and 100ml trichlorines are added in reaction solution
The volume ratio of methane and 150ml water, chloroform and water is 2:3, it is put into frozen water domain and stirs, there is white solid precipitation, stirs,
Suction filtration.40 DEG C of vacuum drying, weighing products 37.24g, yield is 91.9%, content 99.34%..
Embodiment 4
500ml there-necked flasks are taken, 3- chlorine-1,2-propylene glycols 36.6g (content 99.5%) (0.33mol), parachlorophenol is added
16.6g (0.13mol), the NaOH solution 40.8g of concentration 15%, methyltriphenylphosphonium bromide 0.57g, reaction system is heated to
105 DEG C, react 1h.Add parachlorophenol 9.0g (0.07mol), 15% NaOH solution 58.1g, 3- chlorine-1,2-propylene glycol
4.5g (content 99.5%) (0.04mol), now, parachlorophenol and mole of the total addition of 3- chlorine-1,2-propylene glycols in system
Than for 1:1.85, the mol ratio of parachlorophenol and the total addition of sodium hydroxide is 1:1.85, parachlorophenol and methyl triphenyl
The mol ratio of bromide phosphine is 1:0.008, continue to react 2h, be cooled to 20 DEG C, add watery hydrochloric acid and pH value is adjusted to 6.0.Stand one
After the section time, two-phase is separated, a layer organic phase is removed, gas-chromatography is monitored, and conversion ratio is 96.8%, and 50ml is added in reaction solution
The volume ratio of ethanol and 200ml water, ethanol and water is 2:8, it is put into frozen water domain and stirs, there is white solid precipitation, stirs, take out
Filter.40 DEG C of vacuum drying, weighing products 37.12g, yield is 91.6%, content 99.35%
Embodiment 5
500ml there-necked flasks are taken, 3- chlorine-1,2-propylene glycols 74.8g (content 98.05%) (0.65mol), parachlorophenol is added
33.2g (0.26mol), the NaOH solution 68.0g of concentration 10%, TBAB 1.28g, reaction system is heated to 105 DEG C,
React 1h.Parachlorophenol 18.0g (0.14mol) is added, 10% NaOH solution 96.8g, 3- chlorine-1,2-propylene glycol 9.2g (contains
98.05%) (0.08mol), now, the mol ratio of parachlorophenol and the total addition of 3- chlorine-1,2-propylene glycols is 1 to amount in system:
1.85, the mol ratio of parachlorophenol and the total addition of sodium hydroxide is 1:1.85, parachlorophenol and TBAB rub
You are than being 1:0.005, continue to react 2h, be cooled to 20 DEG C, add watery hydrochloric acid and pH value is adjusted to 6.0.Stand after a period of time, point
Go out two-phase, remove a layer organic phase, gas-chromatography is monitored, and conversion ratio is 98.9% (see accompanying drawing 1), and 200ml is added in reaction solution
The volume ratio of water and 300ml chloroforms, chloroform and water is 3:2, it is put into frozen water domain and stirs, there is white solid precipitation,
Stirring, suction filtration.40 DEG C of vacuum drying, weighing products 77.08g, yield is 95.1%, content 99.64%.
Claims (11)
1. a kind of synthetic method of adermykon, it is characterised in that including：
The first step, crude product synthesis
In the reactor, 3- chlorine-1,2-propylene glycols, parachlorophenol and phase transfer catalyst are added in inorganic alkali solution, stirring,
After heating, insulation, reaction 2h~14h, reactant mixture is cooled, is 6.0~8.0 with aqueous hydrochloric acid solution regulation pH value, stands,
Layering, removes a layer organic phase, and gas chromatography detection calculates conversion rate of products；
The mol ratio of the parachlorophenol and the chloro- 1,2- propane diols of 3- is 1:1.0~1:2.0；
The mol ratio of the parachlorophenol and phase transfer catalyst is 1:0.003~1:0.1；
The phase transfer catalyst is the quaternary ammonium salt Huo quaternary alkylphosphonium salts in salt phase transfer catalyst；
The mol ratio of the parachlorophenol and inorganic base is 1:0.8~1:2.1；
The inorganic alkali solution concentration is 10%~25%；
Second step, product separation
Solvent is added in organic phase obtained by the above-mentioned first step, ice-water bath is placed in, stirring a period of time, suction filtration obtains chlorobenzene sweet
Ether finished product, dries and can obtain Chlorphenesin product, weigh, and calculates product yield, determines product content；The solvent is trichlorine
Methane-aqueous systems, the wherein volume proportion of chloroform-water are 1:4~4:1.
2. adermykon synthetic method according to claim 1, it is characterised in that the phase transfer catalyst is four fourths
Base ammonium bromide, tetrabutylammonium chloride, methyltriphenylphosphonium bromide or 4-butyl ammonium hydrogen sulfate.
3. adermykon synthetic method according to claim 1, it is characterised in that the parachlorophenol and 3- chloro- 1,
The mol ratio of 2- propane diols is 1:1.65~1:1.90.
4. adermykon synthetic method according to claim 1, it is characterised in that the inorganic alkali solution is hydroxide
The aqueous solution of sodium or potassium hydroxide.
5. adermykon synthetic method according to claim 4, it is characterised in that the alkaline concentration is 12%~
18%.
6. the adermykon synthetic method according to claim 1,4 or 5, it is characterised in that the parachlorophenol and alkali
Mol ratio be 1:1.5~1:1.9.
7. adermykon synthetic method according to claim 1, it is characterised in that the first step, the reaction temperature is
75 DEG C~105 DEG C；The reaction time is 2h~14h.
8. adermykon synthetic method according to claim 7, it is characterised in that the first step, the reaction temperature is
95 DEG C~105 DEG C；The reaction time is 3h~10h.
9. adermykon synthetic method according to claim 1, it is characterised in that the first step, the reaction adds in batches
Enter the chloro- 1,2- propane diols of parachlorophenol, 3- and aqueous slkali.
10. adermykon synthetic method according to claim 1, it is characterised in that the first step, the regulation pH value,
It is 6.8-7.2 with aqueous hydrochloric acid solution regulation pH value.
11. adermykon synthetic method according to claim 1, it is characterised in that second step, the chloromethane of solvent three
The volume proportion of chloroform-water is 2 in alkane-aqueous systems:3~3:2.
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| CN108440253A (en) * | 2018-05-09 | 2018-08-24 | 广西大学 | A kind of method of green high-efficient selectivity synthesis Chlorphenesin |
| CN109293483A (en) * | 2018-11-29 | 2019-02-01 | 湖北阿泰克生物科技股份有限公司 | A method of Chlorphenesin is prepared using microchannel continuous flow reactor |
| CN111056928A (en) * | 2019-12-30 | 2020-04-24 | 陕西省石油化工研究设计院 | Method for synthesizing chlorphenesin |
| CN111138250B (en) * | 2019-12-30 | 2022-07-01 | 陕西化工研究院有限公司 | Refining method of chlorphenesin |
| CN111153780B (en) * | 2019-12-30 | 2022-07-01 | 陕西化工研究院有限公司 | Green treatment process for dephenolization of chlorphenesin |
| CN112661616A (en) * | 2020-12-22 | 2021-04-16 | 陕西省石油化工研究设计院 | Method for drying and processing chlorphenesin |
| CN112661617A (en) * | 2020-12-29 | 2021-04-16 | 陕西省石油化工研究设计院 | Process for refining chlorphenesin by melt crystallization method |
| CN113149818B (en) * | 2021-03-15 | 2022-05-03 | 菏泽新东方日化科技有限公司 | Preparation process of chlorphenesin |
| CN113185384B (en) * | 2021-04-23 | 2023-11-07 | 渭南畅通药化科技有限公司 | High-purity odorless synthesis method of chlorphenyl glycinate |
| CN113979841A (en) * | 2021-11-17 | 2022-01-28 | 华阳新材料科技集团有限公司 | Method for continuously producing chlorphenesin |
| CN115015422B (en) * | 2022-06-06 | 2023-08-01 | 上海应用技术大学 | Liquid chromatography tandem mass spectrometry detection method for 3-chloro-1, 2-propanediol in soy sauce |
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