CN102491923A - Method for continuous chemosynthesis of perfluoro surfactant with water as solvent - Google Patents
Method for continuous chemosynthesis of perfluoro surfactant with water as solvent Download PDFInfo
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Abstract
The invention relates to a method for continuous chemosynthesis of a perfluoro surfactant with water as solvent. Perfluoroalkyl sulfonyl chloride is adopted as a starting material, water is adopted as the solvent, and a halogen hydride catcher is added to react with N,N-alkyl propane diamine for 8 to 16 hours with the reaction temperature of 40 to 80 DEG C; solvent distillation and temperature reduction are not needed; an aqueous solution of sodium chloroacetate is directly added for reaction for 10 to 24 hours with the reaction temperature of 80 to 110 DEG C; and dilution is carried directly after the reaction to prepare a solution, without the need of aftertreatment. The invention further relates to an aqueous film forming foam fire extinguisher prepared through the method, wherein perfluoroalkyl betaine accounts for 30 to 80 percent, hydrocarbon surfactant foaming of type 1 accounts for 6 to 10 percent, hydrocarbon surfactant foaming of type 2 accounts for 2 to 6 percent, and a lather stabilizer accounts for 5 to 15 percent. The invention has the advantages of avoiding the problem of three-waste pollution caused in the traditional method adopting toluene or the like as solvent, achieving the goal of environment-friendly production, and reducing cost.
Description
Technical field
The invention belongs to fine chemistry and fire-fighting fire extinguishing solvent technology, particularly a kind of is the method for solvent continuous processing chemosynthesis perfluorinated surfactant with water.
Background technology
Mainly by electrochemical process, oligomerisation method, the synthetic manufacturing of three kinds of methods of telomerization method, wherein perfluoro octyl sulfonic acid salt (PFOS) prepares by electrochemical process is synthetic fluorochemical surfactant, and PFOS possibly have following properties:
1, persistence: transformation period, the biodegradability of research fluorochemical surfactant.
2, biological accumulation property: the experimental study fluorochemical surfactant is built up in the organic-biological body.
3, toxicity: make acute, inferior chronic and chronic the contact and the inferior chronic contact fluorochemical surfactant of monkey of mouse, and can draw the toxic evidence of this material to the two generations research of mouse.
4, long-distance transmissions: whether fluorochemical surfactant has the ability and the pollution range of long distance environment transmission.
Sweden has proposed to ban use of the suggestion of PFOS according to " Convention of Stockholm " to United Nations, so that reduce the discharging of persistence organic pollutant.Simultaneously, Sweden also proposes to hope to include PFOS in national forbid in the decree to European Commission.International " about the Convention of Stockholm examination board of persistence organic pollutant " holds a meeting, and review will comprise that five kinds of compounds of PFOS list " about the Convention of Stockholm of persistence organic pollutant " (being called for short POPs pact) in.In case PFOS is put into this pact, the use of PFOS and verivate thereof will be closed down comprehensively, meets with restriction in the world and uses, until forbidding fully.PFOS has been classified as the persistence organic pollutant Black List.
The research and extension of China's aqueous film-forming foam extinguishing agent is started late; Approximately had only for 10 years by China's fire-fighting circle understanding and the also a large amount of uses of acceptance; But usage quantity increases year by year; Nineteen ninety-five whole nation aqueous film-forming foam extinguishing agent usage quantity every year is about 500 tons, and usage quantity in 2006 is about 6000 tons, and many industries such as group companies such as Sinopec, CNPC all send the documents and stipulate that clearly project begun newly must use aqueous film-forming foam extinguishing agent.
Yet China has the 40 tame factories of surpassing to be to use perfluoro octyl sulfonic acid salt (PFOS) in the 50 tame aqueous film-forming foam extinguishing agent manufacturers nearly at present, moreover all the other also only are to use the product of import less than 10 tame factories.The production of present domestic fluorine surfactant mainly is the production of PFOS class fluorocarbon surfactant.
China is as the signatory of " about the Convention of Stockholm of persistence organic pollutant "; Also take active action; Research China PFOS service condition and Corresponding Countermeasures, the forbidding of PFOS is imperative in fire-fighting, and new substitute products and the technology of active research.
In view of this, seeking a kind of is that solvent continuous processing chemosynthesis perfluorinated surfactant method becomes pursuing one's goal of these those skilled in the art with water.
Summary of the invention
It is solvent continuous processing chemosynthesis perfluorinated surfactant method with water that task of the present invention provides a kind of; It has overcome above-mentioned existing in prior technology shortcoming; Having avoided tradition is that solvent causes the three-waste pollution problem with toluene etc., has realized the target that environmental protection is produced, and has avoided with the technology that be solvent distill the removal solvent with the synthetic back of amine reaction such as toluene; Realize the target of safety in production, reduced cost.
Technical solution of the present invention is following:
A kind of is solvent continuous processing chemosynthesis perfluorinated surfactant method with water, is starting raw material with the perfluoroalkyl SULPHURYL CHLORIDE, is solvent with water; Add the hydrogen halide trapping agent, with N, the reaction of N-alkyl tn; 40 ℃～80 ℃ of temperature of reaction, 8～16 hours reaction times; Need not solvent distillation, need not cooling; Directly add the sodium chloroacetate aqueous solution through reaction; Temperature of reaction is 80 ℃～110 ℃, and the reaction times is 10～24 hours; Directly dilution was mixed with solution after reaction was accomplished, and need not aftertreatment.
A kind of aqueous film-forming foam extinguishing agent of preparation as stated above, the recipe ingredient content of foam solution is by weight percentage:
Perfluoroalkyl trimethyl-glycine 3%～8%, hc-surfactant 1 type 6%～10% that foams, hc-surfactant 2 types 2%～6% that foam, suds-stabilizing agent 5%～15%, sanitas 0.1%～1%, urea 0.2%～1%, water 60%～80%.
The recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 5%, hc-surfactant 1 type 6% that foams, hc-surfactant 2 types 4% that foam, suds-stabilizing agent 8%, sanitas 0.2%, urea 0.8%, water 76%.
The recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 8%, hc-surfactant 1 type 8% that foams, hc-surfactant 2 types 2% that foam, suds-stabilizing agent 15%, sanitas 0.5%, urea 0.2%, water 66.3%.
The recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 3%, hc-surfactant 1 type 10% that foams, hc-surfactant 2 types 3% that foam, suds-stabilizing agent 5%, sanitas 0.3%, urea 1%, water 77.7%.
The recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 6%, hc-surfactant 1 type 7% that foams, hc-surfactant 2 types 6% that foam, suds-stabilizing agent 13%, sanitas 1%, urea 0.8%, water 66.2%.
Method of the present invention is starting raw material as the chemical synthesis process of perfluoroalkyl trimethyl-glycine with the perfluoroalkyl SULPHURYL CHLORIDE, is solvent with water; Add the hydrogen halide trapping agent, with N, the reaction of N-alkyl tn; Reacted not treated, directly added the sodium chloroacetate aqueous solution and after reacting, make.
Of the present invention a kind of be that the advantage of solvent continuous processing chemosynthesis perfluorinated surfactant method is with water: having avoided tradition is that solvent causes the three-waste pollution problem with toluene etc.; Realized the target that environmental protection is produced; Having avoided with toluene etc. is the technology that solvent is removed in solvent and amine reaction synthetic back distillation; Realize the target of safety in production, reduced cost.Product has been proved conclusively its structure through mass spectroscopy, and the surface tension of 0.1% and 0.05% solution reaches 16 dynes per centimeter, confirms and can be widely used at aqueous film-forming foam extinguishing agent through fire-extinguishing test.
Description of drawings
Fig. 1 be by of the present invention a kind of be the assay map that solvent continuous processing chemosynthesis perfluorinated surfactant method makes the perfluorinated surfactant product with water.
Embodiment
Make telogen with PFEI in the industry, telomerize monomer with tetrafluoroethylene, under the peroxide initiator effect, carry out telomerization, final product is a perfluoroalkyl iodide.Perfluoroalkyl iodide can be produced various types of fluorocarbon surfactants through all kinds of reactions.The great advantage of telomerization method is an ability synthetic intermediate perfluoroalkyl iodide, and further is converted into another important intermediate perfluor alcohol, from then on sets out and can synthesize various types of fluorocarbon surfactants.Making employed second main production of fluorochemicals is telomerization, and this technology just is being used to synthetic fluorine-containing telomer base product at present by other mechanism's research and development of E.I.Du Pont Company.These products do not contain PFOS and verivate thereof, do not contain PFOA yet.Therefore, the sub product of PFOS and fluorine-containing telomer based compound can not be produced.
Telomerization is under the effect of catalysts for radical polymerization, telogen (claiming the end group thing again) and unsaturated double-bond monomer generation polyaddition reaction.The telomerization process is following:
The advantage of telomerization method is the perfluor carbochain that can obtain linear chain structure, and surfactivity is high.
The present invention is intended to utilize the synthetic perfluorinated surfactant that does not contain PFOS, PFOA of telomerization method; Change and generally use benzene, toluene etc. to cause the complicacy of production technique to reach pollution abroad environment as reaction solvent.Method of the present invention is that the solvent two-step reaction is carried out continuously with water, need not carry out aftertreatment, both enhances productivity, and reduces again and pollutes.
By of the present invention a kind of be solvent continuous processing chemosynthesis perfluorinated surfactant method with water, be starting raw material with the perfluoroalkyl SULPHURYL CHLORIDE, be solvent with water; Add the hydrogen halide trapping agent, with N, the reaction of N-alkyl tn; 40 ℃～80 ℃ of temperature of reaction, 8～16 hours reaction times; Need not solvent distillation, need not cooling; Directly add the sodium chloroacetate aqueous solution through reaction; Temperature of reaction is 80 ℃～110 ℃, and the reaction times is 10～24 hours; Directly dilution was mixed with solution after reaction was accomplished, and need not aftertreatment.
Following table has been listed the surface tension test result of perfluorinated surfactant product, and the perfluorinated surfactant product has been proved conclusively its structure through mass spectroscopy.
As shown in Figure 1, the surface tension of 0.1% and 0.05% solution reaches 16 dynes per centimeter, confirms and can be widely used at aqueous film-forming foam extinguishing agent through fire-extinguishing test.
Below in conjunction with experimental result and analysis, specifically describe by of the present invention a kind of be the embodiment that solvent continuous processing chemosynthesis perfluorinated surfactant method makes the perfluorinated surfactant product with water.
Use instrument: the Ross2Miles Latherometer of ASMT standard, surface tension instrument, IR.
Synthesizing of fluorocarbon surfactant:
Reagent: perfluoroalkyl SULPHURYL CHLORIDE, N, N alkyl tn (analytical pure); Virahol; Hexanaphthene (analytical pure); Absolute ethyl alcohol (analytical pure); Zero(ppm) water.
1, the perfluoroalkyl sulphonyl is synthetic
F(CF2)n(CH2)mSO2Cl+(CH3)2NCH2CH2CH2NH2→
F(CF2)n(CH2)mSO2NHCH2CH2CH2N(CH3)2
n：4～10，m：0～4
Reactions step is:
Take by weighing a certain amount of N, N alkyl tn is dissolved in the suitable quantity of water; Adding has in the 250mL there-necked flask of magnetic agitation, slowly adds perfluor sulfonyl chlorine while stirring in batches, and temperature keeps below 40 ℃ in adition process; After adding finishes, be warming up to 65 ℃, reaction is 8 hours under this temperature.
2, the building-up reactions formula of FS perfluorinated surfactant is following:
(CF2)n(CH2)mSO2NHCH2CH2CH2N(CH3)2+ClCH2COONa
→(CF2)n(CH2)mSO2NHCH2CH2CH2N+(CH3)2CH2COO-
Reactions step is:
In the above-mentioned perfluoroalkyl sulphonyl aqueous solution, directly drip the sodium chloroacetate aqueous solution, be warming up to 90 ℃, reacted 20 hours.Reaction finishes, and cools to 40 ℃ naturally, adds an amount of ethanol and water, is deployed into the surfactant soln of desired concn.
By of the present invention a kind of be solvent continuous processing chemosynthesis perfluorinated surfactant method with water, can prepare aqueous film-forming foam extinguishing agent, the recipe ingredient content of foam solution is by weight percentage:
Perfluoroalkyl trimethyl-glycine 3%～8%, hc-surfactant 1 type 6%～10% that foams, hc-surfactant 2 types 2%～6% that foam, suds-stabilizing agent 5%～15%, sanitas 0.1%～1%, urea 0.2%～1%, water 60%～80%.
First embodiment of the foam solution of said aqueous film-forming foam extinguishing agent prescription, its component concentration is by weight percentage: perfluoroalkyl trimethyl-glycine 5%, hc-surfactant 1 type 6% that foams; Hc-surfactant 2 types 4% that foam, suds-stabilizing agent 8%, sanitas 0.2%; Urea 0.8%, water 76%.
Second embodiment of the foam solution prescription of said aqueous film-forming foam extinguishing agent; Its component concentration is by weight percentage: perfluoroalkyl trimethyl-glycine 8%, hc-surfactant 1 type 8% that foams, hc-surfactant 2 types 2% that foam; Suds-stabilizing agent 15%; Sanitas 0.5%, urea 0.2%, water 66.3%.
The 3rd embodiment of the foam solution of said aqueous film-forming foam extinguishing agent prescription, its component concentration is by weight percentage: perfluoroalkyl trimethyl-glycine 3%, hc-surfactant 1 type 10% that foams; Hc-surfactant 2 types 3% that foam, suds-stabilizing agent 5%, sanitas 0.3%; Urea 1%, water 77.7%.
The 4th embodiment of the foam solution of said aqueous film-forming foam extinguishing agent prescription, its component concentration is by weight percentage: perfluoroalkyl trimethyl-glycine 6%, hc-surfactant 1 type 7% that foams; Hc-surfactant 2 types 6% that foam, suds-stabilizing agent 13%, sanitas 1%; Urea 0.8%, water 66.2%.
The foam solution of processing is according to its performance of GB15308-2006 test.The foam solution performance is following:
Surface tension: 15.6 dynes per centimeter; Spread coefficient: 4.2; Foam expansion: 7.8; Drainage time: 3.2 minutes; Attack time: 2.1 minutes; The anti-burning time: 11.3 minutes.
In sum; Of the present invention a kind of be that the advantage of solvent continuous processing chemosynthesis perfluorinated surfactant method is with water: having avoided tradition is that solvent causes the three-waste pollution problem with toluene etc.; Realized the target that environmental protection is produced; Having avoided with toluene etc. is the technology that solvent is removed in solvent and amine reaction synthetic back distillation, has realized the target of safety in production, has reduced cost.Product has been proved conclusively its structure through mass spectroscopy, and the surface tension of 0.1% and 0.05% solution reaches 16 dynes per centimeter, confirms and can be widely used at aqueous film-forming foam extinguishing agent through fire-extinguishing test.
Certainly; Those skilled in the art in the present technique field will be appreciated that; The foregoing description only is to be used for explaining the present invention; And be not with opposing qualification of the present invention, as long as in connotation scope of the present invention, all will drop in the scope of claim of the present invention the variation of the foregoing description, modification etc.
Claims (6)
1. one kind is solvent continuous processing chemosynthesis perfluorinated surfactant method with water, and it is characterized in that: with the perfluoroalkyl SULPHURYL CHLORIDE is starting raw material, is solvent with water; Add the hydrogen halide trapping agent, with N, the reaction of N-alkyl tn; 40 ℃～80 ℃ of temperature of reaction, 8～16 hours reaction times; Need not solvent distillation, need not cooling; Directly add the sodium chloroacetate aqueous solution through reaction; Temperature of reaction is 80 ℃～110 ℃, and the reaction times is 10～24 hours; Directly dilution was mixed with solution after reaction was accomplished, and need not aftertreatment.
2. press the aqueous film-forming foam extinguishing agent that the said method of claim 1 prepares for one kind, it is characterized in that the recipe ingredient content of foam solution is by weight percentage:
Perfluoroalkyl trimethyl-glycine 3%～8%, hc-surfactant 1 type 6%～10% that foams, hc-surfactant 2 types 2%～6% that foam, suds-stabilizing agent 5%～15%, sanitas 0.1%～1%, urea 0.2%～1%, water 60%～80%.
3. aqueous film-forming foam extinguishing agent according to claim 2 is characterized in that, the recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 5%; Hc-surfactant 1 type 6% that foams; Hc-surfactant 2 types 4% that foam, suds-stabilizing agent 8%, sanitas 0.2%; Urea 0.8%, water 76%.
4. aqueous film-forming foam extinguishing agent according to claim 2 is characterized in that, the recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 8%; Hc-surfactant 1 type 8% that foams; Hc-surfactant 2 types 2% that foam, suds-stabilizing agent 15%, sanitas 0.5%; Urea 0.2%, water 66.3%.
5. aqueous film-forming foam extinguishing agent according to claim 2 is characterized in that, the recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 3%; Hc-surfactant 1 type 10% that foams; Hc-surfactant 2 types 3% that foam, suds-stabilizing agent 5%, sanitas 0.3%; Urea 1%, water 77.7%.
6. aqueous film-forming foam extinguishing agent according to claim 2 is characterized in that, the recipe ingredient content of said foam solution is by weight percentage: perfluoroalkyl trimethyl-glycine 6%; Hc-surfactant 1 type 7% that foams; Hc-surfactant 2 types 6% that foam, suds-stabilizing agent 13%, sanitas 1%; Urea 0.8%, water 66.2%.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103721365A (en) * | 2012-10-15 | 2014-04-16 | 湖北中科博策新材料研究院 | Perfluorooctyl-free nonpolar aqueous film-forming foam extinguishing agent |
| CN110478846A (en) * | 2019-09-23 | 2019-11-22 | 中国科学技术大学 | A kind of environment-friendly type aqueous film-forming foam extinguishing agent based on C6 type fluorocarbon surfactant |
| CN111111550A (en) * | 2019-12-27 | 2020-05-08 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103721365A (en) * | 2012-10-15 | 2014-04-16 | 湖北中科博策新材料研究院 | Perfluorooctyl-free nonpolar aqueous film-forming foam extinguishing agent |
| CN103721365B (en) * | 2012-10-15 | 2016-05-18 | 湖北中科博策新材料研究院 | A kind of nonpolar aqueous film-forming foam extinguishing agent that does not contain perfluoro capryl class |
| CN110478846A (en) * | 2019-09-23 | 2019-11-22 | 中国科学技术大学 | A kind of environment-friendly type aqueous film-forming foam extinguishing agent based on C6 type fluorocarbon surfactant |
| CN110478846B (en) * | 2019-09-23 | 2021-08-13 | 中国科学技术大学 | Environment-friendly aqueous film-forming foam extinguishing agent based on C6 type fluorocarbon surfactant |
| CN111111550A (en) * | 2019-12-27 | 2020-05-08 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
| CN111111550B (en) * | 2019-12-27 | 2021-11-30 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
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Application publication date: 20120613 |