CN107434790A - A kind of crosslinking agent TAIC manufacture method - Google Patents
A kind of crosslinking agent TAIC manufacture method Download PDFInfo
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- CN107434790A CN107434790A CN201610358871.XA CN201610358871A CN107434790A CN 107434790 A CN107434790 A CN 107434790A CN 201610358871 A CN201610358871 A CN 201610358871A CN 107434790 A CN107434790 A CN 107434790A
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- taic
- sodium chloride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D3/00—Halides of sodium, potassium or alkali metals in general
- C01D3/04—Chlorides
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/80—Compositional purity
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- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of crosslinking agent TAIC manufacture method, and it includes TAIC synthesis, the recovery of sodium chloride crystal, distillation is refined and post-processes.During substitution, cyclisation two step continuous chemicals reaction synthesis TAIC occur for chloropropene and alkali metal cyanate, appropriate crystallizing agent is added into reaction mass, by the crystallization temperature and crystallization time that control sodium chloride, the powdery sodium chloride byproduct for making to separate out in course of reaction changes into the larger crystalloid sodium chloride of particle diameter, and the solid sodium chloride accessory substance in reaction system is isolated with simple filtering unit operations mode.Filtrate removes DMF solvent through being evaporated under reduced pressure, and obtains the TAIC crude products of maroon, is refined by molecule short-path distillation, obtains the TAIC products of clear, colorless.Beneficial effects of the present invention are：It is on the premise of TAIC yields are ensured, there is provided it is a kind of simply, economically to separate the method for sodium chloride byproduct in reactant, and avoid and produce brine waste in process of production, greatly save the post processing expense of brine waste.
Description
Technical field
The present invention relates to crosslinking agent preparing technical field, more particularly to a kind of crosslinking agent TAIC manufacture method.
Background technology
Crosslinking agent TAIC, scientific name triallyl isocyanurate（Triallyl isocyanurate, abbreviation TAIC）, point
Minor is C12H15N3O3.
TAIC outward appearances are colourless oil liquid or crystal, 24 DEG C of fusing point, are a kind of multi-functional olefinic monomers containing triazine ring.
TAIC main applications are thermoplastic macromolecule material（Polyethylene, polyvinyl chloride, haloflex, EVA, polystyrene etc.）Friendship
Join modifying agent, during heat cross-linking, TAIC additions are amount of resin 1~3%, it is necessary to it is possible to additionally incorporate 0.2~1% cumyl peroxide
（DCP）；During crosslinking with radiation, TAIC additions are the 0.5~2% of amount of resin, can not add DCP in addition.Thermoplastic macromolecule material passes through
Cross TAIC it is cross-linking modified after, heat resistance, solvent resistance, mechanical strength and electrical property of product etc. are improved, now extensively use
In polyethylene, polyethylene/haloflex, polyethylene/EVA crosslinked cables and the high and low foaming product of polyethylene etc..
TAIC industrial product route is broadly divided into two kinds of techniques of isocyanuric acid Aqueous phase and Zassol solvent method：（1）It is different
Cyanuric acid Aqueous phase, using isocyanuric acid as initiation material, using sodium hydrate aqueous solution as reaction medium, in catalyst and fire-bar
Under part, with chloropropene nucleophilic substitution occurs for isocyanuric acid, and TAIC is made；（2）Cyanate solvent method, with alkali metal cyanate
For initiation material, using higher boiling aprotic solvent as reaction medium, in anhydrous conditions, Zassol passes through with chloropropene and substituted,
Two step tandem reaction sequences are cyclized, TAIC is made.
In above-mentioned two kinds of process routes, due to route（1）Isocyanuric acid Aqueous phase allyl chloride hydrolysis side reaction be present,
The unit consumption of chloropropene is high, about the 200% of theoretical amount, and cost of material is higher, just gradually by route（2）Zassol solvent method
Instead of.
Zassol solvent method uses higher boiling to dredge proton-organic solvent as reaction medium, avoids chloropropene with water in high temperature
Under hydrolytic side reactions, the unit consumption of chloropropene has become the key industry production line of TAIC crosslinking agents close to theoretical amount,
Its chemical equation is：
3CH2=CH-CH2Cl+3NaOCN→3CH2=CH-CH2NCO+3NaCl
3CH2=CH-CH2NCO→TAIC
Production process is by aprotic solvent dimethylformamide（DMF）, catalyst of triethylamine, dehydrating agent anhydrous calcium chloride and cyanogen
The mixture of sour sodium is heated to 110~140 DEG C under agitation, and chloropropene insulation reaction is added dropwise, and Zassol takes with chloropropene
Generation, the continuous two steps chemical reaction of cyclisation, generate TAIC.After reaction terminates, material reclaims DMF solvent by being evaporated under reduced pressure, then adds
Enter water and dissolve side product chlorinated sodium, stratification, separate sodium chloride aqueous phase, obtain TAIC organic phase crude product.Crude product
Through overpickling, alkali cleaning and washing, water-solubility impurity is removed, content about more than 95% is made, outward appearance is light reddish brown color transparency liquid shape
TAIC products.
It was found from the chemical equation of Zassol solvent method, 1 ton of TAIC product is often produced, about generates 0.7 ton of chlorination
Sodium accessory substance.These sodium chloride byproducts are generally in muddy, it is difficult to are separated by filtration from reactant.It is i.e. enabled to be separated by filtration,
Also because the feed liquid entrainment of muddy sodium chloride filter cake is excessive, TAIC yield can be made to decline excessively.
The production technology of existing Zassol solvent method takes the method for aqueous phase dissolved inorganic salts to remove the chlorine in reactant
Change sodium.The method of this Isolating chlorinated sodium can produce largely gives up to the high concentration saliferous of Sewage Disposal biochemistry pool harmful microorganism
Water, it is impossible to be directly entered Sewage Disposal house steward.Some manufacturing enterprises use the environmental practice such as multiple-effect evaporation, UF membrane, to containing
Salt waste water discharges after carrying out desalting processing, adds producing cost.
The content of the invention
In order to solve the problems of the prior art, it is an object of the invention to provide a kind of crosslinking agent TAIC manufacture method,
It is on the premise of TAIC yields are ensured, there is provided a kind of method for simply, economically separating sodium chloride byproduct in reactant,
And avoid and produce brine waste in process of production, greatly save the post processing expense of brine waste.
To achieve these goals, the Isolating chlorinated sodium method of aqueous phase dissolved of TAIC production technologies is changed to filter by the present invention
Separation method, the problem of avoiding discharge and the high processing cost of brine waste, and TAIC crude products are passed through into molecule short distance
Colourless TAIC products are made in distilation.The technical solution adopted by the present invention is：
A kind of crosslinking agent TAIC manufacture method, it comprises the following steps：
S1, TAIC synthesis：A certain amount of aprotic solvent, alkali metal cyanate, dehydrating agent and catalyst are added into reactor
It is interior, after being warming up to 90~120 DEG C, a certain amount of chloropropene liquid is added dropwise into reactor, then adds compound crystal agent,
Insulation reaction 3~4 hours at a temperature of 120~140 DEG C, while cyclization, make sodium chloride sufficient crystallising complete；
S2, sodium chloride crystal recovery：Reaction solution obtained by step S1 is cooled to less than 50 DEG C, filters to isolate sodium chloride crystalline substance
Body, after washing and drying, the white crystalline sodium chloride byproduct that purity is more than 95% is obtained, filtrate and cleaning solution are merged
Obtain mixed solution；
S3, distillation are refined：Mixed solution is subtracted at a temperature of 100~120 DEG C, under -0.08MPa extremely -0.095MPa pressure
Pressure is distilled to recover solvent, is down to room temperature after desolvation, the hydrochloric acid solution for being respectively 2% with mass concentration, mass concentration are 1%
Sodium hydroxide solution and water washing remove water-solubility impurity, obtain outward appearance be light reddish brown color transparency liquid, purity be more than 95%
TAIC crude products, TAIC crude products are distilled with molecule short-distance distiller refined, obtain outward appearance as colorless and transparent liquid or crystal, pure
Spend the target product TAIC for more than 97%；
S4, post-processing unit.
Preferable scheme, the parts by weight of each component are needed for the synthesis of the TAIC：The weight of aprotic solvent 70~110
Part；The parts by weight of alkali metal cyanate 40~55；The parts by weight of dehydrating agent 0.3~1.5；The parts by weight of catalyst 0.3~1.5；Chloropropene
45~60 parts by weight；The parts by weight of compound crystal agent 1.0~5.0.
Further preferred scheme, the aprotic solvent are selected from dimethylformamide, dimethyl sulfoxide, acetonitrile or methyl second
One kind in acid amides, preferably dimethylformamide.
Scheme still more preferably, the preferably one kind of the alkali metal cyanate in Zassol or potassium cyanate, cyanogen
Sour sodium.
Scheme still further preferably, the one kind of the dehydrating agent in calcium oxide or anhydrous calcium chloride.Dehydrating agent
Effect is to remove the trace water in reaction mass, reduces the side reaction of chloropropene and reaction intermediate isocyanates and water.
One or more of the catalyst in triethylamine, KBr, stannous chloride.
The compound crystal agent is sodium chloride or is the mixture of sodium chloride and quaternary amine.
The compound crystal agent is the mixture of sodium chloride and quaternary amine, wherein, the mass ratio of sodium chloride and quaternary amine is
1:1, the quaternary ammonium salt is selected from TEBA, benzyl trimethyl ammonium chloride, tricaprylmethyl ammonium chloride, tetrabutyl chlorine
Change the one or more in amine.
The effect of crystallizing agent is to make the sodium chloride that is separated out in course of reaction homogeneously crystallized, and the sodium chloride that generation is easy to filtering is brilliant
Body, while avoid suction-operated of the fine powdery sodium chloride to reaction mass.The present invention uses the mixing of sodium chloride and quaternary amine
With the more preferable effect for promoting crystallization when thing is as crystallizing agent.
The time for adding of chloropropene liquid is 3~4 hours.
TAIC molecules contain three active allyl functionalities, and hot radical polymerisation easily occurs at high temperature,
Generate the insoluble thermosetting polymer not melted.In conventional distillation subtractive process, part autohemagglutination often occurs for TAIC, cause bottom or
Condenser ramming material.And in molecule short-path distillation operating process, TAIC materials heated time and distillation path are short, are adapted to thermal sensitivity
The separation and purification of material.By content about 95%, outward appearance is light reddish brown color transparency liquid shape TAIC products, with molecule short-path distillation
Device is refined, and it is colorless and transparent, the TAIC products of content about 98% to obtain outward appearance.
By using above technical scheme, a kind of crosslinking agent TAIC manufacture method of the present invention compared with prior art, its
Have the beneficial effect that：
1st, the present invention, can be easily from reaction solution by controlling sodium chloride particle crystallization process and solid liquid phase filtering unit operations
In isolate solid sodium chloride, by washing, being dried to obtain content as more than 95%, the white crystalline for having industrial application value
Sodium chloride byproduct.
2nd, present invention can ensure that original technique TAIC yield, it is not necessary to increase multi-effect evaporating device or UF membrane in addition
Equipment handles brine waste, reduces energy consumption or equipment investment expense.
3rd, outward appearance is purified for pale yellow red liquid product by molecule short-path distillation method, the present invention, has been made colourless
Transparence TAIC products, the high polymer material that can be used for requiring transparency is cross-linking modified, and use range is wider.
4th, the present invention controls the precipitation crystallization process of side product chlorinated sodium on the premise of TAIC yields are kept, it may be difficult to
The sticky pulpous state sodium chloride being separated by filtration is transformed into advantages of good crystallization, carries the sodium chloride crystal that reaction mass is few, is easily separated by filtration secretly,
Operated by common suction filtration or press filtration, content can be directly isolated from reaction solution more than 95%, there is industrial application value
Sodium chloride byproduct, solve the problems, such as to produce a large amount of high-concentration salt-containing wastewaters in TAIC production processes that there is obvious ring
Guarantor and economic benefit.
Embodiment
To make the object, technical solutions and advantages of the present invention of greater clarity, with reference to instantiation, to the present invention
It is further described.It should be understood that these descriptions are merely illustrative, and it is not intended to limit the scope of the present invention.In addition,
In illustrating below, the description to known features and technology is eliminated, to avoid unnecessarily obscuring idea of the invention.
Below in conjunction with embodiment, the present invention will be further described.
In chloropropene and alkali metal cyanate substitution, cyclisation two step continuous chemicals reaction synthesis triallyl occur for the present invention
Chlorinated isocyanurates（TAIC）During, appropriate crystallizing agent is added into reaction mass, by the crystallization temperature for controlling sodium chloride
With crystallization time etc., the powdery sodium chloride byproduct for making to separate out in course of reaction changes into the larger crystalloid sodium chloride of particle diameter,
The solid sodium chloride accessory substance in reaction system is isolated with simple filtering unit operations mode.Filtrate removes through being evaporated under reduced pressure
DMF solvent, the TAIC crude products that outward appearance is maroon are obtained, are refined by molecule short-path distillation, obtain described clear, colorless
Shape TAIC products.
Embodiment 1：
In the 500L stainless steel cauldrons equipped with thermometer, agitator and reflux condenser, 184kg dimethylformamides are added
（DMF）, 1.8kg calcium chloride, 88kg Zassols（Content 95%）, 1.4kg triethylamines, 110 DEG C are heated under stirring, by 96.0kg
Chloropropene（Content 98%）Be slowly added dropwise in 3 hours to reactor, chloropropene add after by 1.5kg sodium chloride crystals and
1.5kg tetrabutylammonium chlorides add reactor, continue stirring reaction at 120 DEG C 3 hours, and reaction is down to room temperature after terminating.Pressure
The solid sodium chloride in reaction solution is isolated in filter, elutes sodium chloride filter cake with fresh or circulation and stress DMF40kg, cleaning solution is simultaneously
Enter filtrate and obtain mixed solution.Sodium chloride is dried by vacuum desiccator and reclaims DMF solvent simultaneously, and it is white to obtain outward appearance
Crystalloid sodium chloride byproduct 73.1kg, content 95.7%, the rate of recovery 94% of sodium chloride.
Mixed solution is distilled to removing DMF solvent under 110 DEG C, 0.09MPa vacuums, products therefrom is successively with 40 DEG C of matter
The hydrochloric acid solution of concentration 2%, the sodium hydroxide solution of mass concentration 1% and each 50L washings of water are measured, water-solubility impurity is removed, divides and go
Water layer, obtain the TAIC that outward appearance is light reddish brown color transparency liquid shape.Purified with molecule short-path distillation, obtain described clear, colorless
TAIC product 95.8kg, purity 97.5%, with chloropropene rate of collecting 92.1%.
Embodiment 2：
Equipped with thermometer, in the 500L stainless steel cauldrons of agitator and reflux condenser, 190kg DMF, 2.0kg chlorine is added
Change calcium, 88kg Zassols（Content 95%）, 1.0kg KBrs, 115 DEG C are heated under stirring, by 96.0kg chloropropenes（Content
98%）Be added dropwise in 3 hours in reactor, chloropropene add after by 2.0kg sodium chloride crystals and 2.0kg benzyl triethyl ammonium chlorine
Change amine and add reactor, continue stirring reaction at 130 DEG C 3 hours, reaction is down to room temperature after terminating.Reaction solution is isolated in press filtration
In solid sodium chloride, washed 1 time with fresh DMF40kg, cleaning solution is incorporated to filtrate and obtains mixed solution.By filtration cakes torrefaction, obtain
Sodium chloride byproduct 74.0kg to outward appearance for white, content 96.0%, the rate of recovery 96% of sodium chloride.
Mixed solution is distilled to recover DMF under 110 DEG C, 0.09MPa vacuums, products therefrom is dense with 45 DEG C of quality successively
The hydrochloric acid solution of degree 2%, the sodium hydroxide solution of mass concentration 1% and each 50L washings of water, removing water-solubility impurity, branch vibration layer,
Outward appearance is purified for the TAIC molecules short-path distillation of light reddish brown color transparency liquid shape, obtains described clear, colorless TAIC products
94.6kg, purity 98.0%, with chloropropene rate of collecting 92.3%.
Comparative example 1：
Equipped with thermometer, in the 500L stainless steel cauldrons of agitator and reflux condenser, 150kg DMF, 1.0kg chlorine is added
Change calcium, 70kg Zassols（Content 95%）, 1.4kg triethylamines, 120 DEG C are heated under stirring, by 78.1kg chloropropenes（Content
98%）It was added dropwise in 3 hours in reactor, 4.0kg sodium chloride crystals is added into reactor after chloropropene methane, at 130 DEG C
Continue stirring reaction after 3 hours, be evaporated under reduced pressure and reclaim DMF, obtain sticky mud shape product.Then to the residual after distillation
250L water is added in thing, is heated to 40 DEG C, is stirred 30 minutes, dissolves solid sodium chloride salt.
Stand, divide and remove saliferous water layer, the organic phase liquid layer containing TAIC is respectively with the hydrochloric acid solution of 45 DEG C of mass concentrations 2%, matter
The sodium hydroxide solution and each 50L of water for measuring concentration 1% wash 1 time, remove water-solubility impurity, stand to divide and remove water, are steamed with molecule short distance
Purification is evaporated, obtains clear, colorless TAIC product 78.8kg, purity 97.0%, with chloropropene rate of collecting 92.0%, TAIC purity
97.4%。
Embodiment 1, embodiment 2 and comparative example 1 contrast visible, embodiments of the invention 1, embodiment 2 can lead to
Cross and be simply separated by filtration operation, obtain the solid-like sodium chloride by-product that purity is 96.0%, the rate of recovery of sodium chloride reaches 94%
More than.In addition, the separation solid by-product sodium chloride method of the present invention does not influence on TAIC yield or yield.
Above-mentioned embodiment is exemplary, is to preferably make skilled artisans appreciate that originally
Patent, it is impossible to be not understood as the limitation for including scope to this patent；As long as times made of spirit according to disclosed in this patent
How with change or modification, the scope that this patent includes is each fallen within.
Claims (9)
1. a kind of crosslinking agent TAIC manufacture method, it is characterised in that it comprises the following steps：
S1, TAIC synthesis：A certain amount of aprotic solvent, alkali metal cyanate, dehydrating agent and catalyst are added into reactor
It is interior, after being warming up to 90~120 DEG C, a certain amount of chloropropene liquid is added dropwise into reactor, then adds compound crystal agent,
Insulation reaction 3~4 hours at a temperature of 120~140 DEG C, while cyclization, make sodium chloride sufficient crystallising complete；
S2, sodium chloride crystal recovery：Reaction solution obtained by step S1 is cooled to less than 50 DEG C, filters to isolate sodium chloride crystalline substance
Body, after washing and drying, the white crystalline sodium chloride byproduct that purity is more than 95% is obtained, filtrate and cleaning solution are merged
Obtain mixed solution；
S3, distillation are refined：Mixed solution is subtracted at a temperature of 100~120 DEG C, under -0.08MPa extremely -0.095MPa pressure
Pressure is distilled to recover solvent, is down to room temperature after desolvation, the hydrochloric acid solution for being respectively 2% with mass concentration, mass concentration are 1%
Sodium hydroxide solution and water washing remove water-solubility impurity, obtain outward appearance be light reddish brown color transparency liquid, purity be more than 95%
TAIC crude products, TAIC crude products are distilled with molecule short-distance distiller refined, obtain outward appearance as colorless and transparent liquid or crystal, pure
Spend the target product TAIC for more than 97%；
S4, post processing.
2. a kind of crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that in the synthesis of the TAIC
The parts by weight of required each component are：The parts by weight of aprotic solvent 70~110；The parts by weight of alkali metal cyanate 40~55；Dehydration
The parts by weight of agent 0.3~1.5；The parts by weight of catalyst 0.3~1.5；The parts by weight of chloropropene 45~60；The weight of compound crystal agent 1.0~5.0
Measure part.
A kind of 3. crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that the aprotic solvent choosing
One kind from dimethylformamide, dimethyl sulfoxide, acetonitrile or methylacetamide, preferably dimethylformamide.
A kind of 4. crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that the alkali metal cyanate
One kind in Zassol or potassium cyanate, preferably Zassol.
5. a kind of crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that the dehydrating agent is selected from oxygen
Change one kind in calcium or anhydrous calcium chloride.
6. a kind of crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that the catalyst is selected from three
One or more in ethamine, KBr, stannous chloride.
7. a kind of crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that the compound crystal agent is
Sodium chloride is sodium chloride and the mixture of quaternary amine.
8. a kind of crosslinking agent TAIC according to claim 7 manufacture method, it is characterised in that the compound crystal agent is
The mixture of sodium chloride and quaternary amine, wherein, the mass ratio of sodium chloride and quaternary amine is 1:1, the quaternary ammonium salt is selected from benzyl three
One or more in ethylmercury chloride amine, benzyl trimethyl ammonium chloride, tricaprylmethyl ammonium chloride, tetrabutylammonium chloride.
A kind of 9. crosslinking agent TAIC according to claim 1 manufacture method, it is characterised in that the dropwise addition of chloropropene liquid
Time is 3~4 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253329A (en) * | 2020-04-14 | 2020-06-09 | 湖南方锐达科技有限公司 | Preparation process of triallyl isocyanurate |
| CN111848532A (en) * | 2020-07-23 | 2020-10-30 | 山东海益化工科技有限公司 | Process for producing triallyl isocyanurate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102775364A (en) * | 2012-07-31 | 2012-11-14 | 合肥工业大学 | Preparation method of cross linking agent triallyl isocyanurate |
-
2016
- 2016-05-27 CN CN201610358871.XA patent/CN107434790A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102775364A (en) * | 2012-07-31 | 2012-11-14 | 合肥工业大学 | Preparation method of cross linking agent triallyl isocyanurate |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111253329A (en) * | 2020-04-14 | 2020-06-09 | 湖南方锐达科技有限公司 | Preparation process of triallyl isocyanurate |
| CN111253329B (en) * | 2020-04-14 | 2022-11-29 | 湖南方锐达科技有限公司 | Preparation process of triallyl isocyanurate |
| CN111848532A (en) * | 2020-07-23 | 2020-10-30 | 山东海益化工科技有限公司 | Process for producing triallyl isocyanurate |
| WO2022016635A1 (en) * | 2020-07-23 | 2022-01-27 | 山东海益化工科技有限公司 | Production process of triallyl isocyanurate |
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