CN102417446A - Production method for zinc undecylenate - Google Patents

Production method for zinc undecylenate Download PDF

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Publication number
CN102417446A
CN102417446A CN2011103376200A CN201110337620A CN102417446A CN 102417446 A CN102417446 A CN 102417446A CN 2011103376200 A CN2011103376200 A CN 2011103376200A CN 201110337620 A CN201110337620 A CN 201110337620A CN 102417446 A CN102417446 A CN 102417446A
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Prior art keywords
zinc
undecylenic acid
undecylenate
water
zinc oxide
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CN2011103376200A
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CN102417446B (en
Inventor
覃旭
何政剑
冷承先
韦宾
黄敬洲
徐岸玲
梁燕萍
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Guangxi Yikang Pharmaceutical Co., Ltd.
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GUANGXI YIKANG PHARMACEUTICAL INDUSTRY Co Ltd
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Abstract

The invention discloses a production method for zinc undecylenate. The production method comprises the following steps: adding glacial acetic acid and zinc oxide into purified water, thereby preparing a zinc acetate aqueous solution; dropwise adding an undecylenate ethanol solution into the zinc acetate aqueous solution; heating, keeping the temperature at 40-80 DEG C, and reacting for 1-2 hours; and filtering, washing, crushing and drying, thereby obtaining a white or light yellow powder zinc undecylenate product.

Description

The working method of Zinc Undecylenate
Technical field
The present invention relates to a kind of working method of Zinc Undecylenate, specifically the working method of high quality Zinc Undecylenate.
Background technology
Zinc Undecylenate, phonetic name: Shiyixisuanxin, English name: Zinc Undecylenate, molecular formula C 22H 38O 4, structural formula [CH 2=CH (CH 2) 8COO] 2Zn, molecular weight 431.92.Fusing point 116-121 ℃.Proterties: white or little yellow amorphous powder.Water-soluble hardly and ethanol.Meet strong acid and be decomposed into undecylenic acid and corresponding zinc salt.Purposes: 1, aniorfic surfactant; The assistant for emulsifying agent of cream kind makeup particularly; 2, also can be used as emulsifying agent and sterilant, the sterilant of for example various makeup and perfumed soap.3, be used for medicine, antifungal drug, treatment is by fungus-caused tetter.
Be the 10 hendecenoic acid zinc salt.Contain C 22H 38O 4Zn should be 98.0%～102.0%.
[proterties] these article are white amorphous powder.Almost insoluble in water or ethanol.Fusing point is 116～121 ℃.
Traditional Zinc Undecylenate working method: (1) is to be raw material with undecylenic acid and zinc oxide, and direct heating to back flow reaction generates Zinc Undecylenate under in water or alcohol-water blending agent, stirring, and obtains the Zinc Undecylenate dry product through filtration, washing, drying; (2) be to be raw material with undecylenic acid and zinc sulfate, earlier zinc sulfate is dissolved in water after, directly add undecylenic acid and react the generation Zinc Undecylenate, obtain the Zinc Undecylenate dry product through filtration, washing, drying; (3) " Liaoning chemical industry " 1992; The improvement of the gloomy undecylenic acid zinc technology of delivering of (4) 43～61 woodss is to be raw material with zinc acetate, undecylenic acid and sodium hydroxide; Earlier undecylenic acid and sodium hydroxide reaction are generated undecylenic acid sodium; Add zinc acetate aqueous solution again and carry out replacement(metathesis)reaction and generate Zinc Undecylenate, obtain the Zinc Undecylenate dry product through filtration, washing, drying.The weak point of its existence is: A, method (1) raw material zinc oxide are water insoluble and the alcoholic acid white powder, and this reaction is the solid-liquid phase reaction, and the Zinc Undecylenate of generation is the white powder that is insoluble to the second alcohol and water; The difficult control of reaction end, the Zinc Undecylenate white powder that reaction process generates is often carried secretly and is enclosed with more unreacted zinc oxide and undecylenic acid, makes reaction not exclusively; Aftertreatment washing and drying be difficulty, and the undecylenic acid zinc powder that obtains is more coarse, and white is fine and smooth uniformly inadequately for the finished product outward appearance; The finished product plucked; And have the part block, cause when producing medicine and skin protection cosmetics, drug distribution is inhomogeneous; B, method (2) is raw materials used is zinc sulfate, generates a certain amount of strong acid H in the reaction process 2SO 4, to having relatively high expectations, and the vitriol in the product is higher, does not meet medicinal or the cosmetics quality standard; C, method (3) are raw materials used to be that the one-tenth undecylenic acid sodium of zinc acetate and preparation all can be water-soluble, is the liquid-liquid phase replacement(metathesis)reaction in water, reacts more complete; But owing to used sodium hydroxide in the technology; Aftertreatment is difficulty, basic metal in the resulting undecylenic acid zinc product and alkaline earth salt content overproof, and the product fusing point that obtains is merely 115～116 ℃; Be lower than 116～121 ℃ of the fusing points of the drug standard, be more difficult to get the undecylenic acid zinc product that meets medicinal and cosmetics quality standard.
Summary of the invention
The working method that the purpose of this invention is to provide the highly purified Zinc Undecylenate of the weak point that can overcome prior art.
Concrete production stage and process method are following:
Ratio of components:
Zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.5～1.7: 8 (W/W)
Undecylenic acid: ethanol=1: 1～5 (W/W)
(1) preparation of zinc acetate solution:
Accurately take by weighing zinc oxide by ratio of components; Again by zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.5～ratio of components dropped into purified water, Glacial acetic acid min. 99.5, zinc oxide in the retort respectively in 1.7: 8, and under agitation was heated to 80～100 ℃, reacted 1-2 hour; After zinc oxide is dissolved fully; Zinc acetate aqueous solution is filtered, obtain water white zinc acetate solution, subsequent use.
(2) preparation of undecylenic acid ethanolic soln:
Content >=96.0% undecylenic acid the elaboration that accurately takes by weighing above-mentioned steps (1) preparation drops in the retort; Again by undecylenic acid: it is 80～95% ethanol that the weight ratio of ethanol=1: 1 adds content; Fully stir, and heat temperature raising to 40～80 ℃, as clear as crystal undecylenic acid ethanolic soln obtained.
(3) preparation of Zinc Undecylenate:
In above-mentioned steps (2) undecylenic acid-ethanolic soln, under agitation, slowly splash in the zinc acetate solution of above-mentioned steps (1) preparation, dropwised in 30～60 minutes, and heat temperature raising to 70～80 ℃ reaction 1-2 hour, make it to generate fully white Zinc Undecylenate.
(4) filter: reactant is slowly put into whizzer get rid of filter, behind the filter fundatrix liquid, for several times earlier with the purified water washing; Flush away reacts water-soluble impurities such as incomplete zinc acetate; Use 70～95% washing with alcohol secondary again, flush away reacts oil-soluble impuritieses such as incomplete undecylenic acid, and material is dried.
(5) pulverize, dry: the block Zinc Undecylenate after will drying is ground into 80～100 orders with kibbler, contains in drip pan, and is dry in baking oven, and drying is 2～4 hours under 80 ± 2 ℃, obtains the Zinc Undecylenate dry product of white or micro-yellow powder shape.
It is following that above-mentioned Zinc Undecylenate respectively goes on foot chemical reaction:
Above-mentioned process using generates zinc acetate soluble in water with water-fast zinc oxide and acetic acid reaction earlier; Direct again and undecylenic acid ethanolic soln is mixed into the liquid-liquid phase reaction and generates Zinc Undecylenate, and reaction conditions is loose, is easy to control; Reaction end is obvious, and aftertreatment is simple.In the reaction mixture except that Zinc Undecylenate, water, ethanol; Also contain zinc acetate soluble in water, acetic acid and a small amount of water insoluble and be easy to alcoholic acid undecylenic acid impurity; Through ethanol and purified water alternately washing very easily remove, overcome the deficiency that traditional technology product impurity is many, yield is low, the undecylenic acid zinc product that obtains is pure white, fine and smooth; Powder is even, reaches medicinal fully and the cosmetics quality requirement.
Above-described undecylenic acid is to adopt three grades of short-path distillation methods to separate purification to obtain highly purified undecylenic acid, contains C 11H 20O 2>=98% (g/g).
The about 3g of these article is got in [discriminating] (1), adds water 20ml and dilute sulphuric acid 25ml, extracts 2 times with the ether jolting, and each 25ml merges ether extracted liquid, put boil off ether in the water-bath after, get and leave over liquid 1ml, according to undecylenic acid item discriminating (a 1) down test, apparent identical reaction.
(2) get the about 0.1g of these article, add water 10ml and strong ammonia solution 1ml dissolving after, add sodium sulphite test solution number droplet, promptly generate white precipitate.
(3) the infrared Absorption collection of illustrative plates of these article should with collection of illustrative plates " medicine ir spectra collection " the nineteen ninety-five version of contrast, light clef 18 figure is consistent.
[inspection] weight loss on drying is got these article, is dried to constant weight at 105 ℃, subtracts weight loss and must not cross 1.0% (appendix VIII L).
Basic metal and alkaline earth salt are got these article 1.5g, add water 50ml and hydrochloric acid 10ml, boil, and filter with moistening filter paper while hot, and do not show acid-reaction with hot wash to washing lotion; Merging filtrate and washing lotion are put in the 200ml measuring bottle, add ammonia solution and make alkalize, add the ammonium sulfide test solution again zinc is precipitated fully, are diluted with water to scale, shake up, and filter; Obtain filtrating 100ml, add sulfuric acid 0.5ml, evaporate to dryness, and ignition to constant weight are left over residue and must not be crossed 7.5mg.
[assay] got the about 0.5g of these article, and accurate the title decides, and adds 1mol/L hydrochloric acid soln 10ml and water 10ml; After boiling 10 minutes, filter while hot, filter residue is used hot wash; Merging filtrate and washing lotion are put coldly, add 1 of the ethanolic soln of 0.025% methyl red; Add ammonia solution in right amount to the micro-yellow of solution; Add water and make full dose be about 35ml, again ammonification-ammonium chloride buffer (pH10.0) 10ml and chromium black T indicator a little, become pure blue with Calcium Disodium Versenate vs (0.05mol/L) titration to solution from red-purple.Every 1ml Calcium Disodium Versenate vs (0.05mol/L) is equivalent to the C of 21.60mg 22H 38O 4Zn.
[classification] Cidex-7.
[storage] sealing is preserved.
[preparation] compound zinc undecylenate ointment
Compared with prior art, advantage of the present invention is:
1, the present invention has overcome undecylenic acid and the zinc oxide direct reaction gets the Zinc Undecylenate process method; Reaction end is not obvious; Package clip has more unreacted zinc oxide and undecylenic acid impurity in the undecylenic acid zinc powder that generates, and the aftertreatment washing is difficult, quality product cannot say for sure shortcomings such as card.
2, the present invention has overcome the reaction of employing undecylenic acid and zinc sulfate and has obtained in the Zinc Undecylenate process method, and the sulfuric acid of generation reaches more greatly to equipment corrosion that the sulfur impurity phosphate content exceeds standard seriously in the product, quality product cannot say for sure shortcomings such as card.
3, the invention solves employing and earlier undecylenic acid is carried out saponification reaction generation undecylenic acid sodium with sodium hydroxide solution earlier; Carry out in the replacement(metathesis)reaction process method with zinc acetate solution again, obtain the undecylenic acid zinc product basic metal and earth alkali metal salts contg severe overweight, fusing point is on the low side, quality product cannot say for sure shortcomings such as card.
4, process method of the present invention is simple to operation, controllable product quality.In the reaction mixture except that Zinc Undecylenate, water, ethanol; Other impurity have only zinc acetate, acetic acid, undecylenic acid; And zinc acetate, acetic acid is soluble in water and undecylenic acid is dissolved in and is prone in the ethanol be removed; The undecylenic acid zinc product that obtains is pure white, fine and smooth, and powder is even, reaches medicinal fully and the cosmetics quality requirement.
Description of drawings
Fig. 1 is the process flow sheet that Zinc Undecylenate of the present invention is produced.
See among Fig. 1; At first Glacial acetic acid min. 99.5 and zinc oxide adding pure water are prepared zinc acetate aqueous solution; And then the undecylenic acid ethanolic soln is added drop-wise in the zinc acetate aqueous solution; Heat tracing through filtering, wash, pulverize, drying, promptly obtains white or micro-yellow powder shape undecylenic acid zinc product after reacting 1～2 hour under 40～80 ℃.
Embodiment
Embodiment 1
Ratio of components:
Zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.5: 8 (W/W)
Undecylenic acid: ethanol=1: 1 (W/W)
By zinc oxide: Glacial acetic acid min. 99.5: water=ratio of components dropped into purified water 70.4kg, Glacial acetic acid min. 99.5 13.2kg, zinc oxide 8.8kg in the retort respectively in 1: 1.5: 8; And under agitation be heated to 80～100 ℃; Reacted 1 hour, zinc oxide is dissolved fully after, zinc acetate aqueous solution is filtered; Obtain water white zinc acetate solution, subsequent use.Accurately taking by weighing content is that 96.0% undecylenic acid elaboration 40kg drops in the retort; Again by undecylenic acid: it is 95% ethanol 40kg that the weight ratio of ethanol=1: 1 adds content, fully stir, and heat temperature raising to 70 ℃; Obtain as clear as crystal undecylenic acid ethanolic soln, subsequent use.In the undecylenic acid ethanolic soln, under agitation, slowly splash in the zinc acetate solution of above-mentioned preparation, dropwised in 30 minutes, and heat temperature raising to 70～80 ℃ reaction 1 hour, make it to generate fully white Zinc Undecylenate.Reactant is slowly put into whizzer get rid of filter, behind the filter fundatrix liquid, for several times earlier with the purified water washing; Flush away reacts water-soluble impurities such as incomplete zinc acetate; Use 70～95% washing with alcohol secondary again, flush away reacts oil-soluble impuritieses such as incomplete undecylenic acid, and material is dried.Block Zinc Undecylenate after drying is ground into 80～100 orders with kibbler, contains in drip pan, dry in baking oven, drying is 4 hours under 80 ± 2 ℃, obtains white or pulverous Zinc Undecylenate dry product 44.2kg.
Embodiment 2
Ratio of components:
Zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.6: 8 (W/W)
Undecylenic acid: ethanol=1: 2 (W/W)
Accurately take by weighing zinc oxide 9.2kg by ratio of components; Again by zinc oxide: Glacial acetic acid min. 99.5: water=ratio of components dropped into purified water 70.4kg, Glacial acetic acid min. 99.5 14.72kg, zinc oxide 9.2kg in the retort respectively in 1: 1.5: 8, and under agitation was heated to 80～100 ℃, reacted 1.5 hours; After zinc oxide is dissolved fully; Zinc acetate aqueous solution is filtered, obtain water white zinc acetate solution, subsequent use.Accurately taking by weighing content is that 96.0% undecylenic acid elaboration 40.0kg drops in the retort; Again by undecylenic acid: it is 80% ethanol 80kg that the weight ratio of ethanol=1: 2 adds content, fully stir, and heat temperature raising to 70 ℃; Obtain as clear as crystal undecylenic acid ethanolic soln, subsequent use.In the undecylenic acid ethanolic soln, under agitation, slowly splash in the zinc acetate solution of above-mentioned preparation, dropwised in 50 minutes, and heat temperature raising to 70～80 ℃ reaction 2 hours, make it to generate fully white Zinc Undecylenate.Reactant is slowly put into whizzer get rid of filter, behind the filter fundatrix liquid, for several times earlier with the purified water washing; Flush away reacts water-soluble impurities such as incomplete zinc acetate; Use 90% washing with alcohol secondary again, flush away reacts oil-soluble impuritieses such as incomplete undecylenic acid, and material is dried.Block Zinc Undecylenate after drying is ground into 80～100 orders with kibbler, contains in drip pan, dry in baking oven, drying is 3 hours under 80 ± 2 ℃, obtains the Zinc Undecylenate dry product 44.5kg of white powder.
Embodiment 3
Ratio of components:
Zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.7: 8 (W/W)
Undecylenic acid: ethanol=1: 4 (W/W)
It is subsequent use accurately to take by weighing zinc oxide 9.6kg by ratio of components.Again by zinc oxide: Glacial acetic acid min. 99.5: water=ratio of components dropped into purified water 70.4kg, Glacial acetic acid min. 99.5 16.32kg, zinc oxide 9.6kg in the retort respectively in 1: 1.7: 8; And under agitation be heated to 80～100 ℃; Reacted 2 hours, zinc oxide is dissolved fully after, zinc acetate aqueous solution is filtered; Obtain water white zinc acetate solution, subsequent use.Accurately taking by weighing content is that 96.0% undecylenic acid elaboration 40.0kg drops in the retort; Again by undecylenic acid: it is 80% ethanol 160kg that the weight ratio of ethanol=1: 2 adds content, fully stir, and heat temperature raising to 70 ℃; Obtain as clear as crystal undecylenic acid ethanolic soln, subsequent use.In the undecylenic acid ethanolic soln, under agitation, slowly splash in the zinc acetate solution of above-mentioned preparation, dropwised in 50 minutes, and heat temperature raising to 70～80 ℃ reaction 1.5 hours, make it to generate fully white Zinc Undecylenate.Reactant is slowly put into whizzer get rid of filter, behind the filter fundatrix liquid, for several times earlier with the purified water washing; Flush away reacts water-soluble impurities such as incomplete zinc acetate; Use 90% washing with alcohol secondary again, flush away reacts oil-soluble impuritieses such as incomplete undecylenic acid, and material is dried.Block Zinc Undecylenate after drying is ground into 80～100 orders with kibbler, contains in drip pan, dry in baking oven, drying is 3 hours under 80 ± 2 ℃, obtains the Zinc Undecylenate dry product 45.5kg of white powder.

Claims (3)

1. the working method of a Zinc Undecylenate, adopting zinc oxide, Glacial acetic acid min. 99.5, undecylenic acid is raw material, it is characterized in that: its concrete production stage and process method are following:
Ratio of components:
Zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.5～1.7: 8 (W/W)
Undecylenic acid: ethanol=1: 1～5 (W/W)
(1) preparation of zinc acetate solution:
Accurately take by weighing zinc oxide by ratio of components; Again by zinc oxide: Glacial acetic acid min. 99.5: water=1: 1.5～ratio of components dropped into purified water, Glacial acetic acid min. 99.5, zinc oxide in the retort respectively in 1.7: 8, and under agitation was heated to 80～100 ℃, reacted 1-2 hour; After zinc oxide is dissolved fully; Zinc acetate aqueous solution is filtered, obtain water white zinc acetate solution, subsequent use;
(2) preparation of undecylenic acid ethanolic soln:
Accurately taking by weighing content drops in the retort for >=96.0% undecylenic acid elaboration; Again by undecylenic acid: it is 80～95% ethanol that the weight ratio of ethanol=1: 1～5 adds content; Fully stir, and heat temperature raising to 40～80 ℃, as clear as crystal undecylenic acid ethanolic soln obtained;
(3) preparation of Zinc Undecylenate:
In above-mentioned steps (2) undecylenic acid-ethanolic soln; Under agitation, slowly splash in the zinc acetate solution of above-mentioned steps (1), dropwised in 30～60 minutes; And heat temperature raising to 70～80 ℃ reaction 1-2 hour, make it to generate fully white Zinc Undecylenate;
(4) filter: reactant is slowly put into whizzer get rid of filter; Behind the filter fundatrix liquid; With the purified water washing for several times, flush away reacts water-soluble impurities such as incomplete zinc acetate, uses 70～95% washing with alcohol secondary more earlier; Flush away reacts oil-soluble impuritieses such as incomplete undecylenic acid, and material is dried;
(5) pulverize, dry: the block Zinc Undecylenate after will drying is ground into 80～100 orders with kibbler, contains in drip pan, and is dry in baking oven, and drying is 2～4 hours under 80 ± 2 ℃, obtains the Zinc Undecylenate dry product.
2. the production stage of Zinc Undecylenate according to claim 1 and process method is characterized in that: described undecylenic acid is to adopt three grades of short-path distillation methods to separate the high purity undecylenic acid of purifying and obtaining, C 11H 20O 2Weight content>=98%.
3. the production stage of Zinc Undecylenate according to claim 1 and process method is characterized in that: described step (1), (2), (3), (4), (5) resulting product are white or yellowish high quality Zinc Undecylenate.
CN201110337620.0A 2011-10-31 2011-10-31 Production method for zinc undecylenate Active CN102417446B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3228843A (en) * 1960-10-13 1966-01-11 Shannalta Beauty Products Ltd Zinc salt of olefinic acid antidandruff preparation
GB1373002A (en) * 1972-01-25 1974-11-06 Unilever Ltd Process for the manufacture of zinc citrate
CN1059196C (en) * 1997-12-30 2000-12-06 徐同香 Prepn. tech. of zinc acetate
CN1861065A (en) * 2005-07-08 2006-11-15 方南 Formula and prepn. method for compound ointment contg. zinc undecenate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3228843A (en) * 1960-10-13 1966-01-11 Shannalta Beauty Products Ltd Zinc salt of olefinic acid antidandruff preparation
GB1373002A (en) * 1972-01-25 1974-11-06 Unilever Ltd Process for the manufacture of zinc citrate
CN1059196C (en) * 1997-12-30 2000-12-06 徐同香 Prepn. tech. of zinc acetate
CN1861065A (en) * 2005-07-08 2006-11-15 方南 Formula and prepn. method for compound ointment contg. zinc undecenate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
林森: "十一烯酸锌工艺的改进", 《辽宁化工》 *

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Patentee before: Guangxi Yikang Pharmaceutical Industry Co., Ltd.