CN100532366C - Climbazole synthesizing process - Google Patents
Climbazole synthesizing process Download PDFInfo
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- CN100532366C CN100532366C CNB2007100206714A CN200710020671A CN100532366C CN 100532366 C CN100532366 C CN 100532366C CN B2007100206714 A CNB2007100206714 A CN B2007100206714A CN 200710020671 A CN200710020671 A CN 200710020671A CN 100532366 C CN100532366 C CN 100532366C
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Abstract
The climbazole synthesizing process includes the following steps: adding alkali and imidazole into organic solvent; adding chloroether ketone; adding water before collecting lower water phase and leaving organic phase; adding water and hydrochloric acid and leaving the upper organic phase; adding water and sodium hydroxide into the left organic phase and leaving organic phase; recovering toluene from the organic phase at normal pressure and leaving remanent liquid; cooling the remanent liquid to 0+/-3 deg.c, suction filtering and stoving to obtain the climbazole product; cooling the mixed water phase to below 25 deg.c, regulating pH with 30 % concentration alkali solution to 12-13 and recovering catalyst. The climbazole synthesizing process has low cost, environment friendship and high product purity.
Description
One, technical field
The invention belongs to a kind of synthetic method of compound, particularly a kind of synthetic method of climbazole.
Two, background technology
Prior art: sterilization, thimerosal and sterilization, sterilization aerosol are to be specifically designed to human body.Fruit, vegetables, article and environment carry out degerming, the special daily chemical products of disinfectant, and to killing human body, food and environment germ and virus, the blocking-up infectious disease transmission has vital role.It is the product that recent people need in a hurry.Sterilant and washing composition are synergistic, and consistency is fine, can join sterilant in the washing composition, when cleaning; Play germ-resistant effect.When special occasions such as hospital, dining room clean, must add people's sterilant in the scavenging solution.Because people strengthen suddenly to sterilization, disinfectant consciousness in the recent period.Sterilization, thimerosal and sterilization, sterilization aerosol class daily chemical products have had great demand.The relevant expert of health and epidemic prevention department recommends to use Peracetic Acid, chloride sterilant (as 84 thimerosals), aqueous hydrogen peroxide solution, ozonize and uviolizing etc., and virus, germ are had preferable killing action, and its shortcoming is not have long-lasting.Be critically ill colony and place of flowabilities such as hospital, school, shop, public transport lacked and continue killing action.Recently exploitation be that efficient, wide spectrum, long-acting type disinfection solution and the disinfecting aerosol agent of main sterilization component has lasting killing action to germ, virus with sterilant such as triclosan, two para-chlorophenols, use separately or be used killing and suppressing all kinds of germs, virus, prevent that the infectious disease transmission effect is better with above-mentioned disinfection sanitizer.At present, to pathogenic agent further deeply under the prerequisite of understanding, also answer emphasis to strengthen all kinds of efficient, wide spectrums, long-acting type disinfection solution and disinfecting aerosol agent Products Development and production.Sterilization, sterilization are that daily product is used and the critical function that develops, and the disinfection function of daily product is generally realized by adding an amount of disinfection sanitizer.An ideal sterilant should possess following condition: the drug effect that, the microorganism of occurring in nature is had wide spectrum; Two, on a small quantity can be effectively; Three, excellent compatibility is arranged; Four, solvability, dispersed good does not influence the basic usefulness of product; Five, safe, nontoxic to human body, non-stimulated, can not produce allergy; Have no side effect.In fact, the sterilant that meets fully above-mentioned requirements seldom.Most use range are narrower.The used for cosmetic sanitas of China regulation has 66 kinds, be usually used in the daily chemical products only have ten surplus kind.Sterilization, the sanitas of at present domestic and international popular outbalance: climbazole, have another name called active climbazole, diazolones, English name: Climbazole, chemical name :-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazoles-1-yl)-2-butanone, white or canescence crystal, fusing point: 95～97 ℃, be called as the efficient anti-dandruff and itching-relieving agent of the s-generation.Climbazole is the efficient germicide new product of German Bayer company exploitation listing in 1977, domesticly develops the beginning of the nineties in last century.Significant anti-dandruff and itching-relieving function of this product tool and excellent compatibility energy, shampoo with its preparation can not produce drawbacks such as precipitation, layering, variable color, skin irritation, has multiple anti-fungal property, to produce the human body dandruff main fungi---avette bud is embraced bacterium and is had unique effect, the white beads seedling that causes human oral cavity dental caries inflammation, periodontitis is also had obvious restraining effect.Become one of first-selected sterilant of cosmeticses of everyday use such as medium-to-high grade Ji hair-care shampoo, perfumed soap, medicated soap, medicated toothpaste and rinse liquid.Recommending working concentration in shampoo etc. is 0.5%～0.8%, dissolves in and uses in alcoholic solvent or the nonionogenic tenside, 70 ℃ of solvent temperatures.Climbazole is commonly used for the preparation of agricultural chemicals, personal care articles, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazoles-1-yl)-2-butanone belongs to s-generation dandruff sterilant, is made by cloroecther ketone and the reaction of excessive imidazoles usually, because of the imidazoles large usage quantity, cost an arm and a leg,, and produce a large amount of imidazoles waste liquids so synthetic cost is higher, do not meet the cleaner production requirement, big to environmental influence.
Three, summary of the invention
The present invention is directed to above-mentioned technical problem, provide a kind of production cost low, the product purity height, it is few to produce waste liquid, the synthetic method of eco-friendly climbazole.
Technical solution of the present invention is: a kind of synthetic method of climbazole, preparation process is: the cloroecther ketone that takes by weighing 1 molar part, in organic solvent, drop into organic bases or mineral alkali earlier as catalyzer, drop into imidazoles again, wherein the input amount of catalyzer and imidazoles is respectively 1～1.1 times of cloroecther ketone molfraction, 60～100 rev/mins are stirred intensification dehydration in 1～3 hour after 120 ℃, and 60～100 rev/mins of stirrings were cooled to 60 ℃ in 1～3 hour again, got reaction system a; Add the 1 molar part cloroecther ketone that takes by weighing in above-mentioned reaction system a, 60～100 rev/mins of stirrings are warming up to 110～120 ℃ and refluxed 3～6 hours, and 60～100 rev/mins of stirrings are cooled to 60 ± 5 ℃, get reaction system b; In reaction system b, add 10～16 molar part water,, collect lower floor's water, leave and take upper organic phase at 60 ℃ of standing demix; Upwards go on foot organic addition 10～16 molar part water and 0.1～0.2 molar part hydrochloric acid of leaving and taking, stir and be warming up to 60 ± 5 ℃ of standing demix, collect lower floor's water, leave and take upper organic phase; Upwards go on foot organic addition 10～16 molar part water and 0.2～0.3 molar part sodium hydroxide of leaving and taking, 60～100 rev/mins are stirred intensification 1～2 hour, refluxed 1～3 hour, 60 ± 5 ℃ of standing demix, upper organic phase adds 10～16 molar part water, 60 ± 5 ℃ of standing demix, 60 ℃ of standing demix are left and taken upper organic phase; The organic phase that the last step was left and taken stirs the dehydration in 1～3 hour that heats up for 60～100 rev/mins to 120 ℃ of normal pressures recovery toluene, leaves and takes remaining liq; To go up step 60～100 rev/mins of remaining liqs and stir 1～5 hour frozen cooling to 0 ± 3 ℃, suction filtration, oven dry, the product climbazole; The water of mixed collection, 60～100 rev/mins are stirred cooling 1～4 hour, are cooled to below 25 ℃, with 30% liquid adjusting PH with base to 12～13, behind the standing demix, divide sub-cloud water, reclaim the upper strata catalyzer and apply mechanically.Organic solvent is the toluene solution of toluene or mass percent 3～10% climbazoles.Organic bases is triethylamine, pyridine, N, N-dimethyl benzylamine, N, accelerine or N, N-Diethyl Aniline.The synthetic method of climbazole as claimed in claim 1 is characterized in that described mineral alkali is Na
2CO
3, NaHCO
3, NaOH or K
2CO
3The structural formula of climbazole is:
The beneficial effect that the present invention produces: use processing method of the present invention and produce climbazole, the imidazoles consumption is few, has reduced production cost, has reduced the discharging of imidazoles waste liquid, environmental friendliness; And behind utilization the present invention, product purity obviously improves as can be seen after testing.
Four, embodiment
Embodiment 1
In the 2000ml there-necked flask, throw toluene or mother liquor 900 grams, N, N-dimethyl benzylamine 260 grams, imidazoles 125 grams stir the dehydration that heats up to 120 ℃ of end, stir and are cooled to 60 ℃, throw cloroecther ketone 450 grams, stirred temperature rising reflux 4 hours, qualitative end, stirring is cooled to 60 ℃, adds water 400 grams, 60 ℃ of standing demix, lower floor's water is collected, and upper organic phase adds water 400 grams, and concentration is mass percent 30% hydrochloric acid 26 grams, 60 ℃ of standing demix, lower floor's water is collected, and upper organic phase adds water 400 grams, concentration is mass percent 30% liquid caustic soda 60 grams, stirs temperature rising reflux 1 hour, 60 ℃ of standing demix, upper organic phase adds water 400 grams, 60 ℃ of standing demix, and upper organic phase stirs the dehydration that heats up to 120 ℃, finish, normal pressure reclaims toluene 300 grams, stirs frozen cooling to 0 ℃, suction filtration, oven dry, get product 432 grams, yield 96%, content reaches 99%.
A collection of water stirs, and is cooled to below 25 ℃, and 30% liquid caustic soda is transferred PH=12-13, layering sub-cloud water, and the upper strata catalyzer is applied mechanically.
Yancheng City product quality supervision and testing institute assay:
| Sequence number | Test item | Unit | Technical requirements | Detected result | Individual event is judged |
| 1 | Content | ％ | ≥99.0 | 99.9 | Qualified |
| 2 | Para-chlorophenol | ％ | ≤0.1 | <0.1 | Qualified |
| 3 | Fusing point | ℃ | 96.0～98.0 | 97.2 | Qualified |
| 4 | Moisture | ％ | ≤0.5 | 0.1 | Qualified |
Embodiment 2
In the 2000ml there-necked flask, throw toluene or mother liquor 900 grams, N, accelerine 240 grams, imidazoles 125 grams stir the dehydration that heats up to 120 ℃ of end, stir and are cooled to 60 ℃, throw cloroecther ketone 450 grams, stirred temperature rising reflux 4 hours, qualitative end, stirring is cooled to 60 ℃, adds water 400 grams, 60 ℃ of standing demix, lower floor's water is collected, and upper organic phase adds water 400 grams, and concentration is mass percent 30% hydrochloric acid 26 grams, 60 ℃ of standing demix, lower floor's water is collected, and upper organic phase adds water 400 grams, concentration is mass percent 30% liquid caustic soda 60 grams, stirs temperature rising reflux 1 hour, 60 ℃ of standing demix, upper organic phase adds water 400 grams, 60 ℃ of standing demix, and upper organic phase stirs the dehydration that heats up to 120 ℃, finish, negative pressure reclaims toluene 300 grams, stirs frozen cooling to 0 ℃, suction filtration, oven dry, get product 418 grams, yield 93%, content reaches 99%.
A collection of water stirs, and is chilled to below 25 ℃, and 30% liquid caustic soda is transferred PH=12-13, layering sub-cloud water, and the upper strata catalyzer is applied mechanically.
Embodiment 3
Throw toluene 900 grams in the 2000ml there-necked flask, imidazoles 125 grams stir the temperature rising reflux dehydration to 120 ℃ of end, be cooled to 60 ℃, throw triethylamine 200 grams, cloroecther ketone 450 grams, stirred temperature rising reflux 6 hours, qualitative end is cooled to 60 ℃, add water 400 grams, 60 ℃ of layerings, lower floor's water is collected, organic addition water 400 grams, 30% hydrochloric acid, 26 grams, 60 ℃ of standing demix, lower floor's water is collected, organic addition water 400 grams, 30% liquid caustic soda, 60 grams, stirred temperature rising reflux 1 hour, 60 ℃ of standing demix, upper organic phase adds water 400 grams, 60 ℃ of standing demix, upper organic phase stirs the dehydration that heats up to 120 ℃, finishes, and negative pressure reclaims toluene 300 grams, stir frozen cooling to 0 ℃, suction filtration, oven dry gets product 427 grams, yield 95%, content 99%.
A collection of water stirs, and is chilled to below 25 ℃, and 30% liquid caustic soda is transferred PH=12-13, adds toluene 200 grams simultaneously, layering sub-cloud water, and upper organic phase rectifying is told catalyzer and is applied mechanically.
Embodiment 4
Throw toluene 900 grams in the 2000ml there-necked flask, imidazoles 125 grams stir the temperature rising reflux dehydration to 120 ℃ of end, be cooled to 60 ℃, throw sheet alkali 80 grams, the PTC50 gram, cloroecther ketone 450 grams stirred temperature rising reflux 10 hours, qualitative end, be cooled to 60 ℃, add water 400 grams, 60 ℃ of layerings, organic addition water 400 grams, 30% hydrochloric acid, 26 grams, 60 ℃ of standing demix, organic addition water 400 grams, 30% liquid caustic soda, 60 grams stirred temperature rising reflux 1 hour, 60 ℃ of standing demix, upper organic phase adds water 400 grams, 60 ℃ of standing demix, and upper organic phase stirs the dehydration that heats up to 120 ℃, finish, negative pressure reclaims toluene 300 grams, stirs frozen cooling to 0 ℃, suction filtration, oven dry, get product 405 grams, yield 90%, content 85%.
Embodiment 5
Throw toluene 900 grams in the 2000ml there-necked flask, imidazoles 125 grams stir the temperature rising reflux dehydration to 120 ℃ of end, be cooled to 60 ℃, throw sodium bicarbonate 120 grams, the PTC50 gram, cloroecther ketone 450 grams stirred temperature rising reflux 10 hours, qualitative end, be cooled to 60 ℃, add water 400 grams, 60 ℃ of layerings, organic addition water 400 grams, 30% hydrochloric acid, 26 grams, 60 ℃ of standing demix, organic addition water 400 grams, 30% liquid caustic soda, 60 grams stirred temperature rising reflux 1 hour, 60 ℃ of standing demix, upper organic phase adds water 400 grams, 60 ℃ of standing demix, and upper organic phase stirs the dehydration that heats up to 120 ℃, finish, negative pressure reclaims toluene 300 grams, stirs frozen cooling to 0 ℃, suction filtration, oven dry, get product 410 grams, yield 91%, content 85%.
Embodiment 6
In the 2000ml there-necked flask, throw toluene or suction filtration mother liquid obtained (composition mainly is the climbazole of toluene and about 3-10%) 900 grams, N, N-dimethyl benzylamine 260 grams, imidazoles 125 grams, 60-100 rev/min of stirring, dehydration was to 120 ℃ of end in intensification 1-3 hour, 60-100 rev/min is stirred cooling 1-3 hour to 60 ℃, throw cloroecther ketone 450 grams, 60-100 rev/min of stirring was warming up to 110-120 ℃ of backflow 3-6 hour, insulation finishes, stirring is cooled to 60 ± 5 ℃, add water 400 ± 100 grams, 60-100 rev/min of stirring is cooled to 60 ± 5 ℃ of standing demix, lower floor's water is collected (water 1), upper organic phase adds water 400 ± 100 grams, and 30% hydrochloric acid 25-30 gram stirs and is warming up to 60 ± 5 ℃ of standing demix, lower floor's water is collected (water 2), upper organic phase adds water 400 ± 100 grams, 30% liquid caustic soda 50-70 gram, and 60-100 rev/min is stirred intensification 1-2 hour, backflow 1-3 hour, 60 ± 5 ℃ of standing demix, upper organic phase add water 400 ± 100 grams, 60 ± 5 ℃ of standing demix, upper organic phase 60-100 rev/min is stirred intensification dehydration in 1-3 hour to 120 ℃, finish, normal pressure reclaims toluene 250-350 gram, and 60-100 rev/min of stirring was cooled to 0 ± 3 ℃ in freezing 1-5 hour, suction filtration, oven dry gets product 432 grams, yield 96%, content reaches 99%, mother liquid recycle.
Water 1 and water 2 mix, and 60-100 rev/min is stirred cooling 1-4 hour, is cooled to below 25 ℃, and 30% liquid caustic soda is transferred PH=12-13, layering sub-cloud water, and upper strata N, the N-dimethyl benzylamine is applied mechanically.
Comparative Examples 1
In the 2000ml there-necked flask, throw toluene 900 grams, cloroecther ketone 450 grams, imidazoles 250 grams, stirred temperature rising reflux 4 hours, qualitative end is cooled to 60 ℃, add water 500 grams, 60 ℃ of layering sub-cloud waters, upper organic phase adds water 400 grams, 30% hydrochloric acid, 26 grams, 60 ℃ of layering sub-cloud waters add water 400 grams, 30% liquid caustic soda, 60 grams stirred temperature rising reflux 1 hour, 60 ℃ of standing demix, upper organic phase adds water 400 grams, 60 ℃ of standing demix, upper organic phase stir the dehydration that heats up to 120 ℃, finish, negative pressure reclaims toluene 300 grams, stir frozen cooling to 0 ℃, suction filtration, oven dry, get product 405 grams, yield 95%.Content 95%.
Claims (3)
1. the synthetic method of a climbazole is characterized in that preparation process is:
A. take by weighing the cloroecther ketone of 1 molar part, in organic solvent, drop into organic bases or mineral alkali earlier as catalyzer, drop into imidazoles again, wherein the input amount of catalyzer and imidazoles is respectively 1～1.1 times of cloroecther ketone molfraction, 60～100 rev/mins are stirred intensification dehydration in 1～3 hour after 120 ℃, 60～100 rev/mins of stirrings were cooled to 60 ℃ in 1～3 hour again, got reaction system a, and described organic solvent is the toluene solution of toluene or mass percent 3～10% climbazoles;
B. add the 1 molar part cloroecther ketone that takes by weighing in above-mentioned reaction system a, 60～100 rev/mins of stirrings are warming up to 110～120 ℃ and refluxed 3～6 hours, and 60～100 rev/mins of stirrings are cooled to 60 ± 5 ℃, get reaction system b;
C. in reaction system b, add 10～16 molar part water,, collect lower floor's water, leave and take upper organic phase at 60 ℃ of standing demix;
D. upwards go on foot organic addition 10～16 molar part water and 0.1～0.2 molar part hydrochloric acid of leaving and taking, stir and be warming up to 60 ± 5 ℃ of standing demix, collect lower floor's water, leave and take upper organic phase;
E. organic addition 10～16 molar part water and 0.2～0.3 molar part sodium hydroxide of leaving and taking to steps d, 60～100 rev/mins are stirred intensification 1～2 hour, refluxed 1～3 hour, 60 ± 5 ℃ of standing demix, upper organic phase adds 10～16 molar part water, 60 ± 5 ℃ of standing demix, 60 ℃ of standing demix are left and taken upper organic phase;
F. the organic phase that step e is left and taken stirs dehydration in 1～3 hour to the 120 ℃ of normal pressures that heat up for 60～100 rev/mins and reclaims toluene, leaves and takes remaining liq;
G. will go up step 60～100 rev/mins of remaining liqs and stir 1～5 hour frozen cooling to 0 ± 3 ℃, suction filtration, oven dry, the product climbazole;
H. the water of mixed collection, 60～100 rev/mins are stirred cooling 1～4 hour, are cooled to below 25 ℃, with 30% liquid adjusting PH with base to 12～13, behind the standing demix, divide sub-cloud water, and recovery upper strata organic alkali catalyst is applied mechanically.
2. the synthetic method of climbazole as claimed in claim 1 is characterized in that described organic bases is triethylamine, pyridine, N, N-dimethyl benzylamine, N, accelerine or N, N-Diethyl Aniline.
3. the synthetic method of climbazole as claimed in claim 1 is characterized in that described mineral alkali is NaOH.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100206714A CN100532366C (en) | 2007-03-20 | 2007-03-20 | Climbazole synthesizing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2007100206714A CN100532366C (en) | 2007-03-20 | 2007-03-20 | Climbazole synthesizing process |
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| Publication Number | Publication Date |
|---|---|
| CN101020663A CN101020663A (en) | 2007-08-22 |
| CN100532366C true CN100532366C (en) | 2009-08-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2007100206714A Expired - Fee Related CN100532366C (en) | 2007-03-20 | 2007-03-20 | Climbazole synthesizing process |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107501189A (en) * | 2017-08-28 | 2017-12-22 | 江苏绿叶农化有限公司 | A kind of preparation method of high-purity climbazole |
| CN107739341A (en) * | 2017-10-31 | 2018-02-27 | 江苏绿叶农化有限公司 | A kind of preparation method of climbazole |
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2007
- 2007-03-20 CN CNB2007100206714A patent/CN100532366C/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| 活性甘宝素－新型高效去屑剂. 陆缵明等.上海轻工业，第4期. 1996 |
| 活性甘宝素－新型高效去屑剂. 陆缵明等.上海轻工业，第4期. 1996 * |
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