CN101624380A - Technical method for liquid phase synthesizing cyanuric acid - Google Patents
Technical method for liquid phase synthesizing cyanuric acid Download PDFInfo
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Abstract
The invention discloses a technical method for liquid phase synthesizing cyanuric acid, comprising the steps: (1) heating organic solvent, and adding urea or solution of the organic solvent of the urea into the organic solvent; after feeding materials, leading the urea to have condensation reaction, and obtaining hot sizing agent formed by the cyanuric acid and the organic solvent; the organic solvent contains N, N-dimetbyl formamide or N, N-dimetbyl acetamide; (2) cooling the hot sizing agent obtained in the step (1) to be room temperature; fully crystallizing and separating out the cyanuric acid, and then carrying out solid-liquid separation to obtain a cyanuric acid filter cake; (3) washing the filter cake by clean water until no residual organic solvent exists, drying the washed filter cake, and obtaining white cyanuric acid crystalline solid after drying. The method needs no acid-washing refining, and has the advantages of energy conservation, environmental protection, little equipment investment, low production cost and high yield of the product.
Description
Technical field
The present invention relates to a kind of processing method of liquid phase synthesizing cyanuric acid.
Background technology
Cyanuric acid (abbreviating CA as) is a kind of broad-spectrum organic chemical industry's product, series product by the CA exploitation have reached kind more than 500, wherein industrial goodsization has surpassed kind more than 20, be mainly used in sterilizing agent chlorated fulminuric acid compounds (trichloroisocyanuric acid, sodium dichloroisocyanate), tricarbimide lipoid substance (trihydroxyethyl isocyanuric acid ester, three propenyl isocyanuric acids etc.), Halogen and contain the production of nitrogen combustion inhibitor tricyanic acid-trimeric cyanamide (MCA), polyester powder coating solidifying agent dai serge gram (TGIC) and other organic compound.
The production of cyanuric acid mainly contains solid phase method and two kinds of technologies of liquid phase method.Solid phase method technology is to place tunnel furnace to obtain crude product the urea condensation process, 280～300 ℃ of temperature of reaction, crude product need obtain elaboration after mineral acid boil-off, this technology investment is little, cost is low, batch production, but there are shortcomings such as energy consumption height, length consuming time, environmental pollution are big, labour intensity is big simultaneously, at present large-scale promotion at home.Liquid phase method technology is to place organic solvent to carry out the urea condensation process, and crude product need not that mineral acid is refining can to reach the elaboration standard, and this technology continuous production, energy consumption is low, pollution is little.The organic solvent that liquid phase method uses mainly contains: tetramethylene sulfone, dodecylbenzene, silicone oil etc., and the common feature of above-mentioned solvent is to cost an arm and a leg, all more than 30,000 yuan/ton, the selection of expensive solvent makes liquid phase method technology cost high always; Simultaneously because the corrosion of higher reaction temperatures (200～220 ℃) and reaction process, cause the equipment material costliness, invest huge, on cost, compare and do not have any competitive power with solid phase method, greatly limited the process of industrialization of liquid phase method technology, the research major part of relevant this technology concentrates on laboratory stage.With the tetramethylene sulfone is the liquid phase method of solvent, can be up to standard on quality product, and the preindustrial major cause of technology is that solvent holds at high price, solvent cost accounts for more than 50% of whole cost; With dodecylbenzene, silicone oil is the liquid phase method of solvent, because the water-insoluble product postprocessing working procedures complexity that makes of solvent has further increased investment.Urea distillation phenomenon was aggravated after simultaneous temperature surpassed 180 ℃, directly influenced the yield of product.But liquid phase method technology impels numerous researchists to hanker after the improvement of liquid phase method in the advantage aspect reaction continuity, automatization control, product purity, the ammonia gas as byproduct deep processing.Therefore for liquid phase method cyanuric acid technology, selecting water-soluble solvent at a low price and the distillation of control urea will be the key factor that can this technology of decision industrialization amplify.
The present invention uses cheap N, dinethylformamide (6000 yuan/ton) and N, N-N,N-DIMETHYLACETAMIDE (11000 yuan/ton) has also adopted back reinforced novel process, realized that urea efficiently transforms, make temperature of reaction be reduced to 150～180 ℃ simultaneously, under this operating environment, equipment such as reactor can be selected common lass lining material for use, greatly reduce facility investment, glass lined use has simultaneously solved the etching problem of reactor, and the employing of the reduction of temperature and back charging technology has reduced the distillation of urea to the full extent.Make liquid phase method still all have real industrialized possibility in the investment from cost.
Summary of the invention
The processing method that the purpose of this invention is to provide a kind of liquid phase synthesizing cyanuric acid.
The present invention adopts the preparation method who comprises following steps to reach purpose of the present invention:
(1) organic solvent is heated to 150～165 ℃, under the agitation condition, at the uniform velocity add this organic solvent solution of urea or urea in above-mentioned organic solvent, the reinforced time spent is 1～6 hour, in above-mentioned feed liquid, the weight ratio of the total amount of urea and the total amount of organic solvent is 1: 1～1: 6; After reinforced the finishing, under stirring and 150～180 ℃ of conditions of temperature, make urea condensation reaction 1～5 hour, obtain the hot slurry of forming by cyanuric acid and organic solvent; Above-mentioned organic solvent is N, dinethylformamide or N,N-dimethylacetamide;
(2) under the agitation condition, with the hot slurry cool to room temperature that obtains in the step (1), treat that the cyanuric acid sufficient crystallising is separated out after, carry out solid-liquid separation, obtain the cyanuric acid filter cake;
(3) it is residual to organic solvent-free to wash above-mentioned filter cake with clean water, and the filter cake after the washing is carried out drying, and the material that obtains after the drying is the white pyruric acid xln.
The weight ratio of the total amount of the total amount of urea and organic solvent is 1: 2～1: 3 described in the step (1).
The used time of this organic solvent solution that at the uniform velocity adds urea or urea in described organic solvent is 2-4 hour.
In this organic solvent solution of described urea, the weight ratio of urea and organic solvent is 1: 1～1: 5.
In the step of the present invention, step (1) is carried out in reactor, and the cooling in the step (2) is carried out in cooling reactor, and the solid-liquid separation described in the step (2) can realize that the present invention carries out solid-liquid separation in strainer by centrifugal or filtration.Step (3) is carried out in washing still and drying machine.Aforesaid device is the known technology in present technique field, does not repeat them here.The implication of this organic solvent solution of urea is meant: if N with an organic solvent in the condensation course, dinethylformamide, urea are also selected N, and the dinethylformamide dissolving is made into urea soln; Equally, if N,N-dimethylacetamide with an organic solvent in the condensation course, urea also selects the N,N-dimethylacetamide dissolving to be made into urea soln.
The technology that liquid phase method is produced CA is failed industrialized limitation factor and mainly contained: (1) expensive solvent makes liquid phase method cost height, compares with solid phase method and lacks competitiveness; (2) temperature of reaction is greater than 200 ℃ and simultaneous corrosion, and the harshness (the lass lining heat-resisting ability is poor, and there is acid attack in stainless steel) that has caused equipment material to select has increased facility investment; (3) there is the phenomenon of urea distillation equally in liquid phase method, only reduces than solid phase method, and reason is the distillation phenomenon aggravation of temperature urea when being higher than 180 ℃.Based on the problems referred to above, in technological process of the present invention, select N cheap and easy to get for use, dinethylformamide or N, the N-N,N-DIMETHYLACETAMIDE at first greatly reduces the production cost of liquid phase method in price as solvent from solvent, make it that industrialized possibility be arranged economically; Secondly temperature of reaction is reduced to 150～180 ℃, has greatly reduced the distillation of urea, make reactor can select common glassed steel reaction vessels for use simultaneously on material, has both reduced the problem that facility investment has also solved acid attack; By the back feed way of urea or urea organic solvent solution, realized that urea participates in reaction in moment once more, improved transformation efficiency, further reduced the distillation of urea, one step of product quality reaches the premium grads standard.
The processing method of liquid phase synthesizing cyanuric acid provided by the present invention, effect has the following advantages:
At first, adopt improved liquid phase method technology directly to obtain the cyanuric acid premium grads, it is refining to need not pickling, belongs to the novel process of energy-saving and environmental protection.Secondly, cheap solvent N, the selection of dinethylformamide or N,N-dimethylacetamide greatly reduces the production cost of liquid phase method.Once more, lower temperature of reaction and back charging technology have suppressed the distillation of urea to the full extent, and product yield, purity improve greatly.
Embodiment
Further specify the processing method of liquid phase synthesizing cyanuric acid by the following examples, these embodiment only are used to the present invention is described and to the present invention without limits.
Embodiment 1
With 125 gram N, dinethylformamide is heated to 150 ℃ in reactor, keep refluxing.Under agitation condition, fusing urea 125 grams are added in the reactor, 125 gram urea were at the uniform velocity added through 1 hour, keep solvent refluxing in the reinforced process.The reinforced back that finishes makes urea condensation reaction 3 hours under stirring and 162 ℃ of conditions of temperature, obtain by cyanuric acid and N the hot slurry that dinethylformamide is formed.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is washed to there not being N with clean water, and dinethylformamide is residual, and the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtains the white CA of 69.86 grams.
Embodiment 2
With 600 gram N, dinethylformamide is heated to 152 ℃ in reactor, keep refluxing.Under agitation condition, solid urea 100 grams are added in the reactor, 100 gram urea were at the uniform velocity added through 3 hours, keep solvent refluxing in the reinforced process.The reinforced back that finishes makes urea condensation reaction 1 hour under stirring and 152 ℃ of conditions of temperature, obtain by cyanuric acid and organic solvent N the hot slurry that dinethylformamide is formed.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is washed to there not being N with clean water, and dinethylformamide is residual, and the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtains the white CA of 57.32 grams.
Embodiment 3
With 125 gram N, dinethylformamide is heated to 152 ℃ in reactor, keep refluxing.Under agitation condition, solid urea 50 grams are added in the reactor, 50 gram urea were at the uniform velocity added through 6 hours, keep solvent refluxing in the reinforced process.The reinforced back that finishes makes urea condensation reaction 2 hours under stirring and 160 ℃ of conditions of temperature, obtain by cyanuric acid and N the hot slurry that dinethylformamide is formed.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is washed to there not being N with clean water, and dinethylformamide is residual, and the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtains the white CA of 33.32 grams.
Example 4
100 gram N,N-dimethylacetamide are heated to 165 ℃ in reactor, keep refluxing.Under agitation condition, N with urea, N-dimethylacetamide solution 600 grams add in the reactor, in the N,N-dimethylacetamide solution of above-mentioned urea, urea is 100 gram N, the N-N,N-DIMETHYLACETAMIDE is 500 grams, the N,N-dimethylacetamide solution of 600 gram urea at the uniform velocity added through 2 hours, kept solvent refluxing in the reinforced process.The reinforced back that finishes makes urea condensation reaction 4 hours under stirring and 170 ℃ of conditions of temperature, obtain the hot slurry of being made up of cyanuric acid and N,N-dimethylacetamide.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is residual to there not being N,N-dimethylacetamide with the clean water washing, the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtain the white CA of 64.49 grams.
Embodiment 5
250 gram N,N-dimethylacetamide are heated to 165 ℃ in reactor, keep refluxing.Under agitation condition, solid urea 50 grams are added in the reactor, 50 gram urea at the uniform velocity added through 2 hours, kept solvent refluxing in the reinforced process.The reinforced back that finishes makes urea condensation reaction 3 hours under stirring and 168 ℃ of conditions of temperature, obtain the hot slurry of being made up of cyanuric acid and N,N-dimethylacetamide.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is residual to there not being N,N-dimethylacetamide with the clean water washing, the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtain the white CA of 29.38 grams.
Embodiment 6
With 100 gram N, dinethylformamide is heated to 152 ℃ in reactor, keep refluxing.Under agitation condition, with the N of 250 gram urea, dinethylformamide solution adds in the reactor, in the above-mentioned urea soln, urea is 100 grams, N, dinethylformamide is 150 grams, and 250 gram urea solns at the uniform velocity added through 2 hours, kept solvent refluxing in the reinforced process.The reinforced back that finishes makes urea condensation reaction 5 hours under stirring and 158 ℃ of conditions of temperature, obtain by cyanuric acid and N the hot slurry that dinethylformamide is formed.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is washed to there not being N with clean water, and dinethylformamide is residual, and the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtains the white CA of 65.92 grams.
Embodiment 7
100 gram N,N-dimethylacetamide are heated to 165 ℃ in reactor, keep refluxing.Under agitation condition, solid urea 100 grams are added in the reactor, 100 gram urea at the uniform velocity added through 3 hours, kept solvent refluxing in the reinforced process.The reinforced back reaction under stirring and 180 ℃ of conditions of temperature that finishes makes urea condensation reaction 2 hours, obtains the hot slurry of being made up of cyanuric acid and N,N-dimethylacetamide.Above-mentioned hot slurry is sent in the water cooler, under agitation condition, is cooled to room temperature, treat that the cyanuric acid sufficient crystallising is separated out after, send into strainer and filter, obtain the cyanuric acid filter cake.Above-mentioned filter cake is washed to no solvent residue with clean water, the cyanuric acid filter cake after the washing is sent in the drying machine, after under 100 ℃ of conditions of temperature dry 120 minutes, obtain the white CA of 64.49 grams.
Every quality index of the product of embodiment 1～7 system detects and sees the following form.
Embodiment 1～7 product quality indicator detects table
Annotate: 1.: urea is residual with reference to GB 2440-2001 " urea and measuring method thereof ".
2.: the assay of acid amides is with reference to " analytical procedure of melon in the cyanuric acid ", " Chinese chlor-alkali " No8 in 2005, P28-29.
3.: the cyanuric acid master contains with reference to " gravimetry is measured cyanuric acid purity ", " Chinese chlor-alkali " No8 in 2004, P25-27.
In the above-mentioned example, adopt the mode that filters to carry out solid-liquid separation; Adopt centrifugal mode to be suitable for the present invention too, and can obtain identical effect.
Claims (4)
1. the processing method of a liquid phase synthesizing cyanuric acid, it is characterized in that: this method may further comprise the steps:
(1) organic solvent is heated to 150～165 ℃, under the agitation condition, at the uniform velocity add this organic solvent solution of urea or urea in above-mentioned organic solvent, the reinforced time spent is 1～6 hour, in above-mentioned feed liquid, the weight ratio of the total amount of urea and the total amount of organic solvent is 1: 1～1: 6; After reinforced the finishing, under stirring and 150～180 ℃ of conditions of temperature, make urea condensation reaction 1～5 hour, obtain the hot slurry of forming by cyanuric acid and organic solvent; Above-mentioned organic solvent is N, dinethylformamide or N,N-dimethylacetamide;
(2) under the agitation condition, with the hot slurry cool to room temperature that obtains in the step (1), treat that the cyanuric acid sufficient crystallising is separated out after, carry out solid-liquid separation, obtain the cyanuric acid filter cake;
(3) it is residual to organic solvent-free to wash above-mentioned filter cake with clean water, and the filter cake after the washing is carried out drying, and the material that obtains after the drying is the white pyruric acid xln.
2. the processing method of liquid phase synthesizing cyanuric acid according to claim 1, it is characterized in that: the weight ratio of the total amount of the total amount of urea and organic solvent is 1: 2～1: 3 described in the step (1).
3. the processing method of liquid phase synthesizing cyanuric acid according to claim 1, it is characterized in that: the used time of this organic solvent solution that at the uniform velocity adds urea or urea in described organic solvent is 2-4 hour.
4. the processing method of liquid phase synthesizing cyanuric acid according to claim 1, it is characterized in that: in this organic solvent solution of urea, the weight ratio of urea and organic solvent is 1: 1～1: 5.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104910088A (en) * | 2015-05-12 | 2015-09-16 | 山东兴达化工有限公司 | Research and application of energy saving, emission reduction and energy system optimization technology for producing cyanuric acid from urea |
| CN105885682A (en) * | 2016-07-04 | 2016-08-24 | 铜陵方正塑业科技有限公司 | Flame-retardant film coating and preparation method thereof |
| CN112898212A (en) * | 2021-01-28 | 2021-06-04 | 山东大明消毒科技有限公司 | Method for preparing cyanuric acid by using ionic liquid |
| CN113549024A (en) * | 2021-06-09 | 2021-10-26 | 河北科技大学 | Method for synthesizing cyanuric acid by pyrolysis polycondensation of urea in mixed liquid phase |
-
2009
- 2009-08-01 CN CN200910017379A patent/CN101624380A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104910088A (en) * | 2015-05-12 | 2015-09-16 | 山东兴达化工有限公司 | Research and application of energy saving, emission reduction and energy system optimization technology for producing cyanuric acid from urea |
| CN105885682A (en) * | 2016-07-04 | 2016-08-24 | 铜陵方正塑业科技有限公司 | Flame-retardant film coating and preparation method thereof |
| CN112898212A (en) * | 2021-01-28 | 2021-06-04 | 山东大明消毒科技有限公司 | Method for preparing cyanuric acid by using ionic liquid |
| CN112898212B (en) * | 2021-01-28 | 2022-09-09 | 山东大明消毒科技有限公司 | Method for preparing cyanuric acid by using ionic liquid |
| CN113549024A (en) * | 2021-06-09 | 2021-10-26 | 河北科技大学 | Method for synthesizing cyanuric acid by pyrolysis polycondensation of urea in mixed liquid phase |
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