CN102277176A - Chloroalkyl polyphosphate ester fire retardant and synthetic technology thereof - Google Patents
Chloroalkyl polyphosphate ester fire retardant and synthetic technology thereof Download PDFInfo
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- CN102277176A CN102277176A CN2011101223342A CN201110122334A CN102277176A CN 102277176 A CN102277176 A CN 102277176A CN 2011101223342 A CN2011101223342 A CN 2011101223342A CN 201110122334 A CN201110122334 A CN 201110122334A CN 102277176 A CN102277176 A CN 102277176A
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 46
- 229920000388 Polyphosphate Polymers 0.000 title claims abstract description 28
- 239000001205 polyphosphate Substances 0.000 title claims abstract description 28
- 235000011176 polyphosphates Nutrition 0.000 title claims abstract description 28
- 125000004965 chloroalkyl group Chemical group 0.000 title abstract 7
- 150000002148 esters Chemical class 0.000 title abstract 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- 150000007517 lewis acids Chemical group 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 3
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000463 material Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000000835 fiber Substances 0.000 abstract description 3
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 239000005060 rubber Substances 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 239000002649 leather substitute Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 230000006837 decompression Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003500 flue dust Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Landscapes
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses a chloroalkyl polyphosphate ester fire retardant and a synthetic technology thereof. The synthetic technology of the chloroalkyl polyphosphate ester fire retardant comprises that phosphorous oxychloride and diglycol are utilized as raw materials and undergo a reaction to produce an intermediate; and the intermediate reacts with epoxypropane in the presence of a catalyst to produce the chloroalkyl polyphosphate ester fire retardant. The chloroalkyl polyphosphate ester fire retardant and the synthetic technology have the advantages that a technology is simple; reaction processes are easy to be controlled; synthesized chloroalkyl polyphosphate ester is utilized mainly as a fire retardant of materials such as rubbers, polyurethanes, staple fibers, artificial leather and the like; flame retardant properties are stable; and chloroalkyl polyphosphate ester can be utilized as a fire retardant, a stabilizing agent, a fire retardant plasticizer and a cross-linking agent.
Description
Technical field
The present invention relates to a kind of fire retardant, specifically a kind of alkyl chloride Quito fire retardant of polyphosphate and synthetic method thereof belong to chemical field.
Background technology
The sixties in 20th century, the external fire retardant of exploitation at first is organic halogenated flame retardant, has advantages such as flame retarding efficiency height, consumption are few, little to the material property influence, moderate cost, occupies critical role in flame retardant area.Yet from 1986, the researchist found that organic halogenated flame retardant generates a large amount of flue dust and corrosive gases when hot tearing and burning, have certain pollution to environment.In the modern society that people more and more pay attention to environmental protection, the development of halogenated flame retardant thereby also be restricted.Particularly in recent years, under the situation of seeking environmental protection, safe fire retardant, phosphorus flame retardant had overcome the shortcoming of halogenated flame retardant effectively as a kind of BACN, had caused people's common concern.
For fire retardant develops rapidly, consumption and kind also sharply rise along with domestic, and be annual approximately with 6%～8% speed increment, and organic fire-retardant accounts for 45% of whole fire retardant consumption.The phosphoric acid ester fire retardant is widely used in plastics and chemical fibre field especially, and since the nineties, along with the further investigation of fire-retardant problem and the progress of flame-retarded technology, the phosphoric acid ester fire retardant is excessive to double focusing or polyphosphate class from phosplate.Especially polyphosphate class, owing to have suitable molecular weight, halogen and phosphorus have good synergism simultaneously, and have characteristics such as volatility is low, odorless, hydrolysis, low atomizing, low Huang Xin, thereby, be widely used in fields such as plastics and weaving in recent years.
Summary of the invention
The objective of the invention is to, a kind of alkyl chloride Quito fire retardant of polyphosphate and synthetic method thereof are provided, this fire retardant can be widely used in linings such as rubber, urethane, regenerated fiber, leatheroid, both can make fire retardant, can make flame-retardant plasticizer again.
Technical scheme of the present invention is:
Alkyl chloride provided by the invention Quito poly phosphate is a kind of novel polyphosphate class environmental protection fire retarding agent.
Structural formula is as follows:
Described fire retardant outward appearance is colourless or light yellow transparent viscous liquid; Molecular formula: C
16H
32Cl
4O
9P
2CAS:52186-00-2; Molecular weight: 572.18; Boiling point: 575.1 ± 50 ℃; Flash-point: 530 ± 37.7 ℃; Proportion: 1.322 ± 0.06g/cm
3(20 ℃); Viscosity: 800-1200mPas(25 ℃);
Be dissolved in organic solvents such as alcohols, be slightly soluble in water; Low smell, low volatility; Have good thermostability and oxidative stability.
The synthesis technique of alkyl chloride provided by the invention Quito fire retardant of polyphosphate comprises the steps:
(1) with phosphorus oxychloride and glycol ether in molar ratio 1.5～2.5 ratio join respectively in reactor and the scale tank, reactor stirs under 0～45 ℃, condition of negative pressure, and slowly drip glycol ether in the scale tank, after dropwising, till continuing to be stirred to no hydrogen chloride gas and producing; Negative pressure removes the hydrogenchloride of generation then, and reaction equation is as follows:
Obtain reaction intermediate (I);
(2) add catalyzer in the reactor in step (1), drip propylene oxide then, and reactor is heated up, keep 60 ~ 80 ℃ of temperature of reaction, preserving heat after reaction ends 1 hour, reaction equation is as follows:
Obtain crude product (II).
Described crude product is after washing, and underpressure distillation steams moisture, promptly gets the product of purifying after the cooling cooling.
The mol ratio of described propylene oxide and glycol ether is 3.5～5, and is wherein preferred 3.8～4.5, more preferably 3.9～4.2.
Described catalyzer is a Lewis acid.
Described Lewis acid consumption is 0.3%～1% of a phosphorus oxychloride quality, and wherein, preferred 0.5%～0.8%, 0.55%～0.65% is best.
Described Lewis acid is a kind of in titanium tetrachloride, iron trichloride, zinc chloride, magnesium chloride, aluminum trichloride (anhydrous), the titanium dioxide.
Described phosphorus oxychloride and glycol ether are in molar ratio 1.8 ~ 2.2 for more suitable, and wherein 1.9 ~ 2.1 is best.
Preferred 10～35 ℃ of the temperature of reaction of described step (1), the best is 25～30 ℃.
The dropping time of described step (1) is 0.5～3 hour, and preferred 1～2 hour, the best was 1.5.
Preferred 65～75 ℃ of the temperature of reaction of described step (2).
The dropping time of described step (2) is 1～6 hour, and preferred 2～5 hours, the best was 2.5～3.5 hours.
This fire retardant can use according to the fire retardant using method of routine, has and does not have special service requirements.
The invention has the advantages that: synthesis technique is simple, only needs for two steps can finish, and reaction process is convenient to control, reaction conditions gentleness; The hydrogen chloride gas that produces, environmentally safe; The product Heat stability is good, decomposition temperature height (500 ℃ of ﹥).Compare with other similar phosphate flame retardant, because alkyl chloride Quito poly phosphate has suitable molecular weight (572.18), halogen and phosphorus have better synergy simultaneously, and it is low to have volatility, characteristics such as odorless, hydrolysis, low atomizing, low Huang Xin, therefore foams can have more persistent flame retardant resistance, and the starting material abundance is fit to suitability for industrialized production simultaneously.
Embodiment
Below the preferred embodiments of the present invention are described, should be appreciated that preferred embodiment described herein only is used for description and interpretation the present invention, and be not used in qualification the present invention.
Except as otherwise noted, the percentage ratio that is adopted among the present invention is weight percentage.
Embodiment 1
The synthesis technique of a kind of alkyl chloride Quito fire retardant of polyphosphate comprises the steps:
(1) add 217.7g(1.42mol electric mixer, constant pressure funnel, thermometer being housed and being connected in the four-hole bottle of hydrochloric acid vacuum absorption device) POCl
3(phosphorus oxychloride), open electric mixer and hydrochloric acid vacuum absorption device, the water-bath controlled temperature is at 25～30 ℃, slowly drip 75g(0.71mol) glycol ether, there are a large amount of hydrogen chloride gas to produce, dropwised in 0.5～3 hour, dropwise and continue reaction to there being the hydrogen chloride gas generation, obtain reaction intermediate, intermediate is stayed in four-hole bottle, directly carry out next step and synthesize;
(2) four-hole bottle that fills intermediate in the above-mentioned steps (1) is adapted as have electric mixer, the reaction unit of constant pressure funnel, thermometer and spherical condenser, open electric mixer, under the room temperature, slowly in bottle, add catalyzer Lewis acid (titanium tetrachloride) 1.6g.Slowly heat up, the water-bath controlled temperature is 65～75 ℃, begin to drip 164.4g(2.83mol) propylene oxide, dripped off, and dropwised in 3 hours, 65～75 ℃ of insulations 1 hour, reaction finishes, and obtains crude product, and crude product is again after washing, decompression steams moisture, promptly gets alkyl chloride Quito fire retardant of polyphosphate of purifying after the cooling cooling.
Result: product yield 85%; Phosphorus content: 10.9%; Cl content: 23%.
Embodiment 2
With embodiment 1, replace the 1.6g titanium tetrachloride but go on foot the reacting middle catalyst Lewis acid with the 1.5g aluminum trichloride (anhydrous) second, product gets finished product after washing, decompression steam moisture.
Result: yield 82%, phosphorus content 10.9%; Cl content: 23%.
Embodiment 3
With embodiment 1, replace the 1.6g titanium tetrachloride but go on foot the reacting middle catalyst Lewis acid with the 1.5g magnesium chloride second, product gets finished product after washing, decompression steam moisture.
Result: yield 75%, phosphorus content 10.9%; Cl content: 23%.
Embodiment 4
With embodiment 1, in the first step reaction with 2molPOCl
3Replace the 1.42mol POCl in the example 1
3, product gets finished product after washing, decompression steam moisture.
Result: yield 89%, phosphorus content 10.9%; Cl content: 24%.
Embodiment 5
With embodiment 1, but in the second step reaction, replace the 2.83mol propylene oxide with the 3mol propylene oxide, product after washing, decompression steam moisture, finished product.
Result: yield 86%, phosphorus content 10.9%; Cl content: 22%.
Among each embodiment of the present invention, used chemical industry material is used material in the production of this area, all can obtain from market, and can not exert an influence for the production result; The equipment of using in each operation all adopts conventional equipment used in the current production, there is no special feature.
It should be noted that at last: the above only is the preferred embodiments of the present invention, be not limited to the present invention, although the present invention is had been described in detail with reference to previous embodiment, for a person skilled in the art, it still can be made amendment to the technical scheme that aforementioned each embodiment put down in writing, and perhaps part technical characterictic wherein is equal to replacement.Within the spirit and principles in the present invention all, any modification of being done, be equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. alkyl chloride Quito fire retardant of polyphosphate is characterized in that: the molecular formula of described fire retardant: C
16H
32Cl
4O
9P
2Chemical structural formula:
CAS：52186-00-2。
2. the described a kind of alkyl chloride of claim 1 Quito fire retardant of polyphosphate, it is characterized in that: described fire retardant outward appearance is colourless or light yellow transparent viscous liquid; Boiling point: 575.1 ± 50 ℃; Flash-point: 530 ± 37.7 ℃; Proportion: 1.322 ± 0.06g/cm
3Viscosity: 800～1200mPas.
3. the technology of the described alkyl chloride of synthetic claim 1 Quito fire retardant of polyphosphate is characterized in that: may further comprise the steps:
(1) phosphorus oxychloride is joined in the reactor, glycol ether phosphorus is joined in the scale tank, and reactor stirs under 0～45 ℃, condition of negative pressure, and slowly drips the glycol ether in the scale tank, after reaction finished, the hydrogenchloride that negative pressure removes generation obtained reaction intermediate;
(2) add catalyzer in the reactor in step (1), drip propylene oxide then, keep 65～75 ℃ of temperature of reaction, obtain product.
4. the synthesis technique of a kind of alkyl chloride according to claim 3 Quito fire retardant of polyphosphate is characterized in that: described step (2) obtains product after washing, and underpressure distillation steams moisture, obtains the product of purifying after the cooling cooling.
5. the synthesis technique of a kind of alkyl chloride according to claim 3 Quito fire retardant of polyphosphate is characterized in that: the mol ratio of described propylene oxide and glycol ether is 3.5～5 ﹕ 1.
6. the synthesis technique of a kind of alkyl chloride according to claim 3 Quito fire retardant of polyphosphate, it is characterized in that: described catalyzer is a Lewis acid.
7. the synthesis technique of a kind of alkyl chloride according to claim 6 Quito fire retardant of polyphosphate, it is characterized in that: described Lewis acid consumption is 0.3%～1% of a phosphorus oxychloride quality.
8. the synthesis technique of a kind of alkyl chloride according to claim 7 Quito fire retardant of polyphosphate is characterized in that: described Lewis acid is a kind of in titanium tetrachloride, iron trichloride, zinc chloride, magnesium chloride, aluminum trichloride (anhydrous), the titanium dioxide.
9. the synthesis technique of a kind of alkyl chloride according to claim 3 Quito fire retardant of polyphosphate is characterized in that: the dropping time of glycol ether is 0.5～3 hour in the described step (1).
10. the synthesis technique of a kind of alkyl chloride according to claim 3 Quito fire retardant of polyphosphate is characterized in that: the dropping time of propylene oxide is 1～6 hour in the described step (2).
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Cited By (6)
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| CN103351406A (en) * | 2013-06-19 | 2013-10-16 | 天津市联瑞阻燃材料有限公司 | Method of producing phosphoric acid alkyl aryl ester by using excess phosphorus oxychlorid method |
| CN103865100A (en) * | 2014-03-14 | 2014-06-18 | 安徽瑞邦橡塑助剂集团有限公司 | Rubber processing aid and preparation method thereof |
| CN108219196A (en) * | 2018-01-08 | 2018-06-29 | 浙江鸿浩科技有限公司 | A kind of preparation method of modified chlorinated phosphate ester fire retardant |
| CN109603437A (en) * | 2018-12-24 | 2019-04-12 | 厦门中科易工化学科技有限公司 | The method of separating hydrogen chloride and the methods and applications of chlorination hydrogen are separated and recovered in a kind of mixed gas from containing hydrogen chloride |
| CN117327343A (en) * | 2023-09-29 | 2024-01-02 | 安徽大学绿色产业创新研究院 | Chloroalkyl polyphosphate ester-EVA composite material and preparation method thereof |
| CN120904467A (en) * | 2025-10-11 | 2025-11-07 | 寿光卫东腾冠化工有限公司 | Chloroalkyl poly(s) Process for producing phosphoric acid esters |
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| CN117327343A (en) * | 2023-09-29 | 2024-01-02 | 安徽大学绿色产业创新研究院 | Chloroalkyl polyphosphate ester-EVA composite material and preparation method thereof |
| CN120904467A (en) * | 2025-10-11 | 2025-11-07 | 寿光卫东腾冠化工有限公司 | Chloroalkyl poly(s) Process for producing phosphoric acid esters |
| CN120904467B (en) * | 2025-10-11 | 2026-01-06 | 寿光卫东腾冠化工有限公司 | A method for preparing chloroalkyl polyphosphates |
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Application publication date: 20111214 |