CN101333339B - Preparation method for enhancing yield of edible sunset yellow - Google Patents
Preparation method for enhancing yield of edible sunset yellow Download PDFInfo
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- CN101333339B CN101333339B CN2007100426818A CN200710042681A CN101333339B CN 101333339 B CN101333339 B CN 101333339B CN 2007100426818 A CN2007100426818 A CN 2007100426818A CN 200710042681 A CN200710042681 A CN 200710042681A CN 101333339 B CN101333339 B CN 101333339B
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- sunset yellow
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Abstract
The invention provides a high-yield method for preparing Sunset yellow. Through the introduction of phase transfer catalyst in the process, the method improves reaction effect, improving the reaction percent conversion to be 98% and improving the HPLC purity of the Sunset yellow in the coupled liquid from the original 85.5% to 93.4%. The method can prepare high purity Sunset yellow with high yield and is of good economic and social benefits.
Description
Technical field
The present invention relates to a kind of preparation method of food dye, relate to the preparation method who improves edible sunset yellow reaction total conversion rate particularly.
Background technology
Sunset yellow, FD﹠amp; C Yellow No.6, E110, C.I.15985, CAS No.2783-94-0, molecular formula C
16H
10N
2O
7S
2Na
2Orange red powder or particle, azo-type structure (seeing formula 1).Sunset yellow is one of important monochrome of edible synthesized coloring matter, also is to be allowed in the world to be used for food color one of synthetic colour the most widely, accounts for 1 15 of global synthetic colour total amount.It is widely used in fields such as food, medicine, makeup, medical apparatus, tobacco, feed, edible packing, daily use chemicals product, toy.
The preparation technology of domestic current Sunset yellow is simple relatively, generates diazonium salt by Sulphanilic Acid through diazonium, and (have another name called: coupling under alkaline condition beta naphthal-6-sodium sulfonate) neutralizes, saltouts, makes with extra care, dry and get with Schaffer's acid sodium.
The synthetic route of Sunset yellow is as follows:
1 doazo reaction
2 coupled reactions
Wherein in the doazo reaction outside the demineralizing acid, also can use sulfuric acid, cross mineral acids such as chloric acid and fluoroboric acid.
Because the coupled reaction of Sulphanilic Acid diazonium salt and Schaffer's acid sodium is an inhomogeneous reaction, so yield is relatively low, total reaction conversion ratio is about 93%, Sunset yellow HPLC purity also has only 85-86.5% (239nm) in the coupling solution, post-processed is only rough to saltout, the making beating washing is made with extra care in the salt solution, and total recovery is at 85-87%.And we know, transformation efficiency is low, mean that final product yield can be not high yet, simultaneously, also influenced the purity and the quality of the finished product.So be necessary to carry on technical development, improve total reaction conversion ratio.
Summary of the invention
The objective of the invention is to improve Sunset yellow diazonium, the total reaction conversion ratio of coupled reaction, obtain a kind of Sunset yellow preparation method of high yield.
The inventor is through extensive and deep research, and down auxiliary in the liquid-phase chromatographic analysis technology filtered out a kind of suitable, phase-transfer catalyst efficiently, forms the process for cleanly preparing of high yield edible sunset yellow.
The preparation method of raising yield of edible sunset yellow disclosed by the invention, its step is as follows:
The first step, with Sulphanilic Acid weight (hereinafter referred to as to acid) than being in the presence of the phase-transfer catalyst of 1-6%, Sulphanilic Acid carries out doazo reaction, generates the Sulphanilic Acid diazonium salt; Second step had been in the presence of the phase-transfer catalyst of 1-5% with beta naphthal-6-sodium sulfonate weight ratio, and beta naphthal-6-sodium sulfonate and Sulphanilic Acid diazonium salt carry out coupled reaction, and reaction system pH8.5～12 generate Sunset yellow.
Above-mentioned phase-transfer catalyst is selected from a kind of in auxiliary agents such as ethanol, Si Ban-tween series, polyoxyethylene glycol series, peregal 0 or emulsifying agent, the dispersion agent and their combination.The consumption of phase-transfer catalyst is the 0.1-2.0% of whole reaction system weight.
Above-mentioned Si Ban-tween series comprises the 40-of class of department polysorbate40, the 60-of class of department polysorbate60, the 80-of class of department tween 80 or the like.
Above-mentioned polyoxyethylene glycol series comprises poly(oxyethylene glycol) 400, cetomacrogol 1000, polyethylene glycol 6000, polyoxyethylene glycol 8000 etc.
In the present invention's one preferred embodiment, phase-transfer catalyst is a cetomacrogol 1000.
Beta naphthal-6-sodium sulfonate and all minimum to the solubleness in water under the sour diazonium salt room temperature, be suspension, so both coupled reactions are inhomogeneous reaction.Phase-transfer catalyst should add when diazotization reaction and coupled reaction.To help when phase-transfer catalyst is added to doazo reaction the diazonium salt particles that generates thinner, avoid acid is wrapped into wherein simultaneously, make the diazonium unit process complete.When phase-transfer catalyst is added to coupled reaction, help to improve the collision effect of diazonium salt and beta naphthal-6-sodium sulfonate molecule, reduce the occurrence probability that side reaction and diazonium salt decompose, thereby improve total reaction conversion ratio.
The preparation method of raising yield of edible sunset yellow disclosed by the invention and former technology are relatively, improved reaction effect, total reaction conversion ratio brings up to 98% from original 93%, make the HPLC purity of Sunset yellow in the coupling solution bring up to 93.4% from 85% of former technology, prepare high yield high purity Sunset yellow product, have good economic and social benefit.
Embodiment
Below in conjunction with specific embodiment, further illustrate the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.The experimental technique of unreceipted actual conditions in the following example, usually according to normal condition, or the condition of advising according to manufacturer.Ratio and per-cent are based on weight, unless stated otherwise.
Embodiment 1
In 500mL four neck flasks, add 180mL hot water (60 ℃), add 2g cetomacrogol 1000 (PEG-1000) then, stir adding 35g99.0% Sulphanilic Acid (0.2mol) down fast, stirred ten minutes, be chilled to room temperature, add technical hydrochloric acid.Continue to be chilled to 0～5 ℃, liquid drips down 47.3g30% sodium nitrite solution (0.202mol), and 5～12 ℃ of holding temperatures (keep congo-red test paper blueness, potassium iodide starch test paper light blue.Continue to stir 20min after finishing, add the excessive nitrous acid of little ammonia sulfonic acid cancellation.
Add 500ml water and 2.5g cetomacrogol 1000 (PEG-1000) in the 1000ml beaker, stir adding 57.6g87.1% Schaffer's acid sodium (0.204mol) down.Slowly be sprinkled into yellow soda ash again, stir 15min.Be cooled to 12～15 ℃, the thick pulpous state that is creamy white, pH10～11.Slowly add diazonium salt under stirring, 45min adds, 10～15 ℃ of controlled temperature, pH 〉=8.5.Saltout and ooze that circle is colourless through H acid test, the test of m-nitraniline diazonium salt is orange red.Continue to stir 2 hours.Saltout and ooze circle and test shallow orange red through the m-nitraniline diazonium salt.The about 800mL of volume.Survey its total reaction conversion ratio 99.1% (in to acid), Sunset yellow HPLC purity 93.4% (239nm) in the coupling solution.
Embodiment 2
Replace 2g cetomacrogol 1000 (PEG-1000) with the 0.5g cetomacrogol 1000, all the other are with embodiment 1.Survey its total reaction conversion ratio 98.7% (in to acid), Sunset yellow HPLC purity 92.6% (239nm) in the coupling solution.
Embodiment 3
Replace 2.5g cetomacrogol 1000 (PEG-1000) with the 0.8g cetomacrogol 1000, all the other are with embodiment 1.Survey its total reaction conversion ratio 97.8% (in to acid), Sunset yellow HPLC purity 91.2% (239nm) in the coupling solution.
Embodiment 4
Replace cetomacrogol 1000 (PEG-1000) with poly(oxyethylene glycol) 400 (PEG-400), all the other are with embodiment 1.Survey its total reaction conversion ratio 98.6% (in to acid), Sunset yellow HPLC purity 92.5% (239nm) in the coupling solution.
Embodiment 5
Replace 2g, 2.5g cetomacrogol 1000 (PEG-1000) with 15g, 20g5% polysorbate60-Si Ban 60 (20:1) aqueous solution respectively, all the other are with embodiment 1.Total reaction conversion ratio 97.8% (in to acid), Sunset yellow HPLC purity 93.7% (239nm) in the coupling solution.
Embodiment 6
Replace 2g, 2.5g cetomacrogol 1000 (PEG-1000) with 15g, 20g5% tween 80-Si Ban 80 (20:1) aqueous solution respectively, all the other are with embodiment 1.Total reaction conversion ratio 98.3% (in to acid), Sunset yellow HPLC purity 92.0% (239nm) in the coupling solution.
Embodiment 7
Replace 2g cetomacrogol 1000 (PEG-1000) with 15g5% tween 80-Si Ban 80 (20:1) aqueous solution, all the other are with embodiment 1.Total reaction conversion ratio 98.7% (in to acid), Sunset yellow HPLC purity 92.3% (239nm) in the coupling solution.
Embodiment 8
Replace 2.5g cetomacrogol 1000 (PEG-1000) with 20g5% tween 80-Si Ban 80 (20:1) aqueous solution, all the other are with embodiment 1.Total reaction conversion ratio 98.5% (in to acid), Sunset yellow HPLC purity 92.1% (239nm) in the coupling solution.
Embodiment 9
15g5% tween 80-Si Ban 80 (20:1) aqueous solution replaces 2g cetomacrogol 1000 (PEG-1000), and all the other are with embodiment 1.All the other are with embodiment 1.Total reaction conversion ratio 98.6% (in to acid), Sunset yellow HPLC purity 92.4% (239nm) in the coupling solution.
Embodiment 10
Replace cetomacrogol 1000 (PEG-1000) with paregal O, all the other are with embodiment 1.Total reaction conversion ratio 99.2% (in to acid), Sunset yellow HPLC purity 93.5% (239nm) in the coupling solution.
All quote in this application as a reference at all documents that the present invention mentions, just quoted as a reference separately as each piece document.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after having read above-mentioned teachings of the present invention, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Claims (6)
1. one kind is improved the preparation method that edible sunset yellow reacts total conversion rate, it is characterized in that:
The first step being that Sulphanilic Acid carries out doazo reaction in the presence of 1～6% the phase-transfer catalyst with the Sulphanilic Acid weight ratio, generates the Sulphanilic Acid diazonium salt; Second step, be in the presence of 1～5% the phase-transfer catalyst and water with beta naphthal-6-sodium sulfonate weight ratio, stir and add beta naphthal-6-sodium sulfonate, slowly be sprinkled into yellow soda ash again, stir 15min, be cooled to 12～15 ℃, thick pulpous state is creamy white, slowly add the Sulphanilic Acid diazonium salt under stirring and carry out coupled reaction, reaction system pH 8.5～12, generate Sunset yellow.
2. the method for claim 1 is characterized in that, described phase-transfer catalyst is a kind of and combination between them in ethanol, Si Ban-tween, polyoxyethylene glycol, the peregal 0.
3. method as claimed in claim 2 is characterized in that, described phase-transfer catalyst is cetomacrogol 1000 or poly(oxyethylene glycol) 400.
4. method as claimed in claim 3 is characterized in that, the cetomacrogol 1000 consumption is 5-6% for the Sulphanilic Acid weight ratio in doazo reaction, and the cetomacrogol 1000 consumption is that beta naphthal-6-sodium sulfonate weight ratio is 3-5% in coupled reaction.
5. method as claimed in claim 2 is characterized in that, described phase-transfer catalyst is department's class's 60-polysorbate60 or the 80-of class of department tween 80.
6. as each described method of claim 1～5, it is characterized in that the scope of the reaction system pH of described coupled reaction is 8.5～9.5.
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| CN2007100426818A CN101333339B (en) | 2007-06-26 | 2007-06-26 | Preparation method for enhancing yield of edible sunset yellow |
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| CN101333339B true CN101333339B (en) | 2010-12-08 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102313806A (en) * | 2011-02-01 | 2012-01-11 | 天津百鸥瑞达生物科技有限公司 | Method and enzyme-linked immunosorbent assay (ELISA) kit for detecting sunset yellow |
| CN102286211B (en) * | 2011-08-08 | 2013-06-19 | 天津市化学试剂研究所 | Method for preparing acid orange-12 |
| CN104016881B (en) | 2014-06-10 | 2015-12-30 | 苏州大学张家港工业技术研究院 | For the solvent medium of diazotization reaction |
| CN106752063A (en) * | 2016-12-06 | 2017-05-31 | 浙江力禾集团有限公司 | A kind of method of one pot process AZOpigments |
| CN106893355A (en) * | 2017-01-10 | 2017-06-27 | 泉州市希姆色彩研究院有限公司 | A kind of dispersed black dye of water fastness high and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1952015A (en) * | 2005-10-19 | 2007-04-25 | 上海染料研究所有限公司 | Process for preparing lemon chrome |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1952015A (en) * | 2005-10-19 | 2007-04-25 | 上海染料研究所有限公司 | Process for preparing lemon chrome |
Non-Patent Citations (1)
| Title |
|---|
| 杨新玮等.染料（第四版）.染料（第四版）.化学工业出版社,2005,(第4版),454页. * |
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