CN102188928A - Fluorocarbon cationic gemini and hybridized gemini surfactants and synthesis method thereof - Google Patents
Fluorocarbon cationic gemini and hybridized gemini surfactants and synthesis method thereof Download PDFInfo
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- UUIUQQKVXCCSEQ-UHFFFAOYSA-O CCCCC[NH+](C)CCN(C)C Chemical compound CCCCC[NH+](C)CCN(C)C UUIUQQKVXCCSEQ-UHFFFAOYSA-O 0.000 description 1
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Abstract
The invention relates to fluorocarbon cationic gemini and gemini surfactants and a synthesis method thereof. The structural formula of the fluorine carbon cationic gemini and gemini surfactants is as follows: the fluorine carbon surfactants are prepared by the following steps that: with perfluoroalkyl iodide as a raw material, after perfluoroalkyl iodide is condensed with butenoic acid, the condensation product is reduced and deiodinated through lithium aluminum hydride to obtain the compound fluorocarbon alcohol; and after the hydroxide radical of the fluorocarbon alcohol is protected, the fluorocarbon alcohol is substitution reaction with different secondary amines and is quaternized by bromomethane to respectively obtain fluorocarbon cationic gemini and gemini surfactants. The method provided by the invention has mild reaction conditions and simpleness and convenience for post-treatment and is applicable to further industrial amplification.
Description
Technical field
The present invention relates to a class fluorine carbocation Gemini surface active agent C
n FC
4-2-C
n FC
4And fluorine carbocation hydridization Gemini surface active agent C
n FC
4The new synthetic method of-2-12.
Wherein, n=4,6,8.
Wherein, n=4,6,8.
Background technology
Gemini surface active agent (gemini or dimeric surfactant) is to connect basic mode with chemical bond by one two conventional surfactant molecules are formed by connecting, and contains 2 hydrophilic radicals and 2 oleophylic chains in the molecule.The structure of Gemini surface active agent is typically expressed as m-s=m ', and wherein m, m ' represent the number of both sides hydrophobic chain institute carbon atoms, connects the number that base is gone up carbon atom in the middle of s represents.When m=m ', be called the symmetric form Gemini surface active agent, just our Gemini surface active agent that it has been generally acknowledged that; When m ≠ m ', just be referred to as the asymmetrical type Gemini surface active agent, comprise being uneven in length or different in kind of m, the latter also is the hydridization Gemini surface active agent.
1936, Kreimeier etc. have reported with acetylene as connecting parents' compound that base links together two pure molecules, this structure is known as Gemini surface active agent the earliest later age, but do not cause enough attention (Kreimeier, O.R.Process of preparing tertiary ethynyl carbinols and product thereby produced.US2106180) at that time.Up to 1971, Bunton etc. are just at first to alkyl-α, the research of aspects such as the synthetic and surface nature of the two methyl alkyl ammonium bromides of ω-two alkyl, critical micelle concentration has carried out reporting (C.A.Bunton, L.Robinson.Catalysis of nucleophilic substitutions by micelles of dieationic detergent.J.Org.Chem., 1971,36:2346-2352).Nineteen ninety, Japan Okahara be combined into one group of novel amphipathic molecule for a short time, the ion head respectively with one hydrocarbon connection of oil loving long-chain (Zhu, Y.P.; Masuyama, A.; Kirito, Y.I.; Okahara, M.Preparation and properties of double-or-triple-chain surfactants with two sulfonate groups devised from N-acyldiethanolamines.J.Am.Oil.Chem.Soc., 1991,68 (7): 539-543).1991, Menger etc. synthesized two alkyl surfactants, because its structure is similar to Gemini astronomically, therefore gave this amphiphile, amphiphilic molecule called after " Gemini (astronomically ' Gemini ') surfactant " (Menger, F.M.; Littau, C.A.Gemini surfactant:synthesis and properties.J.Am.Chem.Soc., 1991,113:1451-1452.).Afterwards, these naming systems of employing such as the Rosen group of USA New York City University and Zana group have been studied PEO and the PPO synthetic and surface property (Rosen as the Gemini surface active agent that is connected base, M.J.Geminis:A newGeneration of surfactants.J.Chem.Technol., 1993,30:23-33; Zana, R.; Talmon.Y.Dependence of aggregate morphology on structure of dimeric surfactants.Nature, 1993,362:228-229).
Fluorocarbon surfactant itself is exactly the special surfactant of a class, because its particular structure feature has determined it to have very unique character.Compare with conventional surfactant, fluorocarbon surfactant has higher surface activity, high heat-resistant stability, high chemical stability and not only hydrophobic but also hate the wet goods good characteristic.Therefore, the research of novel fluoro-carbon surface active agent has been subjected to whole world scientist's extensive concern.
As more special fluorine carbon hydridization surfactant, because the complexity of its structure is given the synthetic suitable difficulty of having brought.Up to the present, Abe research group (Abe, M. that Japan only arranged; Tobita, K.; Sakai, H.; Kamogawa, K.; Momozawa, N.; Kondo, Y.; Yoshino, N.Thermoresponsive viscoelasticity of concentrated solutions with a fluorinated hybrid surfactant.Colloids and Surfaces A:Physicochem.Eng.Aspects, 2000,167:47-60; Tobita, K.; Sakai, H.; Kondo, Y.; Yoshino, N.; Kamogawa, K.; Momozawa, N.; Abe, M.Temperature-induced critical phenomenon of hybrid surfactant as revealed by viscosity measurements.Langmuir, 1998, the research that 14:4753-4757) continues, they find that such surfactant has far above conventional carbon hydrogen meter the live surface-active of agent and unusual unique interface character.And, only have the Oda group of France to report its synthetic method and its correlated performance has been carried out studying (Oda, R. on one side as fluorine carbocation Shuangzi involved in the present invention and hydridization Shuangzi (tail chain is a fluorocarbon chain, on one side tail chain be alkyl chain) surfactant; Huc, I.; Danino, D.; Talmon, Y.Aggregation Properties and Mixing Behavior of Hydrocarbon, Fluorocarbon, and Hybrid Hydrocarbon-Fluorocarbon Cationic Dimeric Surfactants.Langmuir, 2000,16:9759-9769; Nishida, J.; Brizard, A.; Desbat, B.; Oda, R.Mixing behavior of fluorinated and hydrogenated gemini surfactants at the air-water interface.Journal of Colloid and Interface Science., 2005,284:298-305).The reagent tri-butyl tin hydride that iodine need be used costliness is taken off in (Scheme 1) reduction in the synthetic method of Oda group.The bromo-reaction operation is difficulty very, if with hydrobromic acid and concentrated sulfuric acid bromo, have a large amount of spent acid to need to handle again, and final quaterisation need reflux (3-4 days), has brought suitable difficulty for the industrialization amplification of this compound in the long reaction time.Therefore, we improve its synthetic method.
Scheme?1
Summary of the invention
One of purpose of the present invention provides a class fluorine carbocation Gemini surface active agent C
n FC
4-2-C
n FC
4With fluorine carbocation hydridization Gemini surface active agent C
n FC
4-2-12.
Two of purpose of the present invention provides a class fluorine carbocation Gemini surface active agent C
n FC
4-2-C
n FC
4With fluorine carbocation hydridization Gemini surface active agent C
n FC
4The synthetic method of-2-12.
Method of the present invention is to be initiation material with the perfluoroalkyl iodide, obtains required target product through taking off the protection of iodine, hydroxyl, the replacement of amido, quaterisation with the reduction of the coupling reaction of 1-butenoic acid, lithium aluminium hydride reduction.Its chemical equation following (Scheme 2):
Scheme?2
Wherein, n=4,6,8; Ts: p-toluenesulfonyl
1, coupling reaction; 2, reduction reaction; 3, esterification; 4, substitution reaction; 5, substitution reaction; 6, quaterisation; 7, quaterisation.
Synthetic method provided by the invention can specifically describe as follows:
1, coupling reaction: under the effect of AIBN (azodiisobutyronitrile), molecular formula is C
nF
2n+1The mol ratio of the perfluoroalkyl iodide of I and 1-butenoic acid is 1: 1～1: 5, and recommending mol ratio is 1: 1～1: 3, and reaction temperature is 0 ℃ to 100 ℃, recommended temperature is 50 ℃, reaction time is 4-14 hour, and the recommendation response time is 10-14 hour, and reaction is after or purify without post processing.
2, reduction reaction: in polar solvent, molecular formula is
Acid and the mol ratio of lithium aluminium hydride reduction be 1: 2～1: 10, recommending mol ratio is 1: 2～1: 5, reaction temperature is 0 ℃-100 ℃, the recommendation response temperature is 60 ℃, react 2-10 hour, the recommendation response time is 2-4 hour, reacts after or purify without post processing.
3, esterification: in polar solvent, molecular formula is
The mol ratio of alcohol, paratoluensulfonyl chloride and alkali be 1: 1: 1～1: 4: 10 successively, recommending mol ratio is 1: 2: 1～1: 4: 2, reaction temperature is 0 ℃-60 ℃, the recommendation response temperature is 0-40 ℃, reacted 1-15 hour, the recommendation response time is 2-4 hour, and reaction is after or purify without post processing.Described alkali is NaOH, potassium hydroxide, potash, triethylamine, pyridine etc.
4) substitution reaction: in polar solvent, reaction temperature is 0 ℃-100 ℃, and the recommendation response temperature is 80 ℃-100 ℃, and molecular formula is
Compound, N, the mol ratio of N '-dimethyl-ethylenediamine and alkali is 1: 0.2: 2～1: 1: 5 successively, and recommending mol ratio is 1: 0.3: 2～1: 0.6: 3, reaction time 2-24 hour, the recommendation response time is 6-10 hour, and reaction is after or purify without post processing.Described alkali is NaOH, potassium hydroxide, potash, triethylamine, pyridine etc.
5, substitution reaction: in polar solvent, reaction temperature is 0 ℃-100 ℃, and the recommendation response temperature is 80 ℃-100 ℃, and molecular formula is
The mol ratio of compound, N-methyl-N '-dodecyl ethylenediamine and alkali be 1: 1.5: 2～1: 5: 5 successively, recommending mol ratio is 1: 1.5: 3～1: 3: 4, reaction time 2-24 hour, the recommendation response time was 6-10 hour, and reaction is after or purify without post processing.Described alkali is NaOH, potassium hydroxide, potash, triethylamine, pyridine etc.
6, quaterisation: in polar solvent, reaction temperature is 0 ℃-100 ℃, and the recommendation response temperature is 50 ℃-100 ℃, and molecular formula is
Two tertiary amines and the mol ratio of Celfume be 1: 2～1: 10, recommending mol ratio is 1: 2～1: 5, reaction time 2-48h, the recommendation response time is 2-6 hour, obtaining product is fluorine carbocation Gemini surface active agent
Reaction is after or purify without post processing.
7, quaterisation: in polar solvent, when reaction temperature was 0 ℃-100 ℃, the recommendation response temperature was 50 ℃-100 ℃, and molecular formula is
Two tertiary amines and the mol ratio of Celfume be 1: 2～1: 10, recommending mol ratio is 1: 2～1: 5, reaction time 2-48h, the recommendation response time is 2-6 hour, obtaining product is fluorine carbocation Gemini surface active agent
Reaction is after or purify without post processing.
Solvent is C described in the above-mentioned 1-7 step
1-C
8Alcohol, alkyl halide, oxolane (THF), dioxane, acetonitrile, N, any or its mixed solvent in the dinethylformamide (DMF) etc.
The invention provides the preparation method again of fluorine carbocation Gemini surface active agent and fluorine carbocation hydridization Gemini surface active agent, than before synthetic civil engineering have mild condition, handling safety.Easy advantage has the extensive industrialized prospect.Simultaneously, object surface-active of the present invention is very good, with C
8 FC
4-2-C
8 FC
4Be example, its surface tension under critical micelle concentration is 18.76mN/m, and its critical micelle concentration is 0.0111wt%; C
8 FC
4-2-C
12H
25Critical micelle concentration under surface tension be 18.89mN/m, its critical micelle concentration is 0.0255wt%.
Description of drawings
Fig. 1 is fluorine carbocation Gemini surface active agent C of the present invention
8 FC
4-2-C
8 FC
4γ-C curve (25 ℃);
Fig. 2 is fluorine carbocation hydridization Gemini surface active agent C of the present invention
8 FC
4-2-C
12H
25γ-C curve (25 ℃).
The specific embodiment:
Following examples help to understand the present invention, but do not limit content of the present invention:
5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12, the preparation of 12-17 fluoro-positive dodecoic acid of 3-iodo
In 60mmol perfluor iodo-octane and 10.2ml3-butenoic acid and 1g azodiisobutyronitrile (AIBN) adding 100ml there-necked flask, under the Ar gas shiled, be warmed up to 50 ℃ of reactions 8 hours, the TLC demonstration reacts completely.Product is not done further processing and is directly used in next step reaction.
Embodiment 2
5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12, the preparation of 12-17 fluoro n-dodecanols
In the 500ml there-necked flask, add 100mlTHF, the ventilation operation, the Ar protection adds the 5g lithium aluminium hydride; use then dropping funel in 1 hour with 60mmol5,5,6,6; 7,7,8,8; 9,9,10; 10,11,11; 12,12,12-17 fluoro-positive dodecoic acid of 3-iodo (being dissolved among the 50mlTHF) adds wherein.Be warming up to 70 ℃ of reactions 6 hours subsequently, the TLC demonstration reacts completely.After recovering room temperature, carefully in reactant liquor add the 100ml shrend reaction of going out, filter wherein solid with cloth formula funnel, filtrate is used ethyl acetate extraction, organic layer saturated common salt water washing, drying is crossed thick silica gel, desolventizing obtains colourless transparent oil liquid 21.3g, yield 72.2%.
1HNMR(CDCl
3，300MHz，TMS)，δ(ppm)：3.69(m，2H)，2.10(m，2H)，1.76-1.60(m，4H).
19F?NMR(282MHz，CDCl
3)，δ(ppm)：-80.76(t，J
3＝9.2Hz，3F)，-114.4(m，2F)，-121.88(m，6F)，-122.66(m，2F)，-123.46(m，2F)，-126.05(m，2F)。
Embodiment 3
5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12, the preparation of 12-17 fluoro n-dodecanol p-methyl benzenesulfonic acid esters
With 5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro n-dodecanol 21.3g and 50ml chloroform join-250ml single port bottle in, add 21g paratoluensulfonyl chloride and 15ml pyridine then, be heated to 40-50 ℃ of reaction 1-6 hour, complete through the TLC detection reaction.Cooling adds the 100ml water washing, tells organic layer, uses the saturated common salt water washing, tells organic layer, drying, and desolventizing, use benzinum: the ethyl acetate volume ratio is 15: 1 a mixed solvent recrystallization, obtains white needle-like crystals 24.9g, yield 89%.
300MHz
1H?NMR(CDCl
3，TMS)，δ(ppm)：7.79(d，J＝8.2Hz，2H)，7.35(d，J＝8.36Hz，2H)，4.06(m，2H)，2.45(s，3H)，2.05(m，2H)，1.70(m，4)
19F?NMR(282.4MHz，CDCl
3)：-80.76(t，J3＝19.2Hz，3F)，-114.4(m，2F)，-121.88(m，6F)，-122.66(m，2F)，-123.46(m，2F)，-126.05(m，2F)。
Embodiment 4
N, N '-two (5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro dodecyls)-N, the preparation of N '-dimethyl-ethylenediamine
With 5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro n-dodecanol p-methyl benzenesulfonic acid ester 5.1g and 50ml ethanol join in the 100ml there-necked flask, add 0.4mlN again, N '-dimethyl-ethylenediamine and 2.3g potash are heated to 80-100 ℃ of stirring and spend the night, and is complete through the TLC detection reaction.Cooling is filtered, and solvent is deviate from decompression, adds 50ml ethyl acetate, with 50ml water washing twice, tells organic layer, drying, and desolventizing obtains pale yellow oily liquid body 3.25g, yield 83%.
300MHz
1HNMR(CDCl
3，TMS)，δ(ppm)：2.57(s，4H)，2.46(m，4H)，2.28(s，6H)，2.05(m，4H)，1.60(m，8H)。
19FNMR(282.4MHz，CDCl
3)：-80.89(t，J
3＝19.7Hz，6F)，-114.5(m，4F)，-121.91(m，12F)，-122.79(m，4F)，-123.6(m，4F)，-126.18(m，4F)。
Embodiment 5
N-dodecyl-N '-(5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro dodecyls)-N, the preparation of N '-dimethyl-ethylenediamine
With 5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro n-dodecanol p-methyl benzenesulfonic acid ester 2.57g and 50ml ethanol join in the 100ml there-necked flask, add 0.85gN-dodecyl-N again, N '-dimethyl-ethylenediamine and 1.533g potash are heated to 80-100 ℃ of stirring and spend the night, and is complete through the TLC detection reaction.Cooling is filtered, and solvent is deviate from decompression, adds 50ml ethyl acetate, with 50ml water washing twice, tells organic layer, drying, and desolventizing obtains pale yellow oily liquid body 2.03g, yield 84.2%.
300MHz
1HNMR(CDCl
3，TMS)，δ(ppm)：2.52(s，3H)，2.39(m，4H)，2.28(s，3H)，2.24(s，4H)，2.08(m，2H)，1.55(m，6H)，1.25(m，18H)，0.87(m，3H)。
19F?NMR(282.4MHz，CDCl
3)：-80.73(m，3F)，-114.43(m，2F)，-121.92(m，6F)，-122.71(m，2F)，-123.49(m，2F)，-126.08(m，2F)。
Embodiment 6
N, N '-two (5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro dodecyls)-N, N, N ', the preparation of N '-tetramethyl second dibrominated ammonium
With N, N '-two (5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro dodecyls)-N, N '-dimethyl-ethylenediamine 2.15g and 15ml isopropyl alcohol join in the 50ml there-necked flask, add the 0.455ml Celfume again.Be warming up to 50-75 ℃ of reaction and spend the night, the TLC detection reaction is complete.Solvent is deviate from cooling, obtains white solid powder 2.08g, yield 81% for twice with acetone recrystallization.
300MHz?
1H?NMR(90/10，CDCl
3/CD
3OD，TMS)，δ(ppm)：4.23(s，4H)，3.46(m，4H)，3.24(s，12H)，2.18(m，4H)，1.84(m，4H)，1.65(m，4H)。
19FNMR(282.4MHz，CDCl
3)：-81.04(t，J3＝19.7Hz，6F)，-114.6(m，4F)，-122.06(m，12F)，-122.92(m，4F)，-123.63(m，4F)，-126.32(m，4F)。
N-dodecyl-N '-(5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro dodecyls)-N, N, N ', the preparation of N '-tetramethyl second dibrominated ammonium
With N-dodecyl-N '-(5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-17 fluoro dodecyls)-N, N '-dimethyl-ethylenediamine 2g and 15ml isopropyl alcohol join in the 50ml there-necked flask, add the 0.6ml Celfume again.Be warming up to 50-75 ℃ of reaction and spend the night, the TLC detection reaction is complete.Solvent is deviate from cooling, obtains white solid powder 2.3g, yield 91% for twice with acetone recrystallization.
300MHz
1H?NMR(90/10，CDCl
3/CD
3OD，TMS)，δ(ppm)：4.27(s，4H)，3.53(m，4H)，3.25(s，12H)，1.87(m，2H)，1.69(m，4H)，1.26(m，18H)，0.79(m，3H)。
19F?NMR(282.4MHz，CDCl
3)：-80.83(t，J3＝19.7Hz，3F)，-114.52(m，2F)，-121.95(m，6F)，-122.05(m，2F)，-123.49(m，2F)，-126.22(m，2F)。
Claims (5)
1. the structural formula of a class fluorine carbocation Gemini surface active agent is as follows:
2. the structural formula of a class fluorine carbocation hydridization Gemini surface active agent is as follows:
3. a synthetic method for preparing fluorine carbocation Gemini surface active agent as claimed in claim 1 and the described fluorine carbocation of claim 2 hydridization Gemini surface active agent is characterized in that comprising the steps:
1) coupling reaction: under the effect of AIBN (azodiisobutyronitrile), 0 ℃ under 100 ℃, molecular formula is C
nF
2n+1The mol ratio of the perfluoroalkyl iodide of I and 1-butenoic acid is 1: 1-5, reacted 4-14 hour, and described n is described in the claim 1;
2) reduction reaction: in polar solvent and 0 ℃-100 ℃ the time, molecular formula is
Acid and the mol ratio of lithium aluminium hydride reduction be 1: 2-10, reacted 2-10 hour, described n is described in the claim 1;
3) esterification: in polar solvent and 0 ℃-60 ℃ the time, molecular formula is
The mol ratio of alcohol, paratoluensulfonyl chloride and alkali be 1 successively: 1-4: 1-10, reacted 1-15 hour, described n is described in the claim 1;
4) substitution reaction: in polar solvent and 0 ℃-100 ℃ the time, molecular formula is
Compound, N, the mol ratio of N '-dimethyl-ethylenediamine and alkali is 1 successively: 0.2-1: 2-5, reaction time 2-24 hour, described n was described in the claim 1;
5) substitution reaction: in polar solvent and 0 ℃-100 ℃ the time, molecular formula is
The mol ratio of compound, N-methyl-N '-dodecyl ethylenediamine and alkali be 1 successively: 1.5-5: 2-5, reaction time 2-24 hour, described n was described in the claim 1;
6) quaterisation: in polar solvent and 0 ℃-100 ℃ the time, molecular formula is
Two tertiary amines and the mol ratio of Celfume be 1: 2-10, behind the reaction time 2-48h, obtaining product is fluorine carbocation Gemini surface active agent
Described n is described in the claim 1;
7) quaterisation: in polar solvent and 0 ℃-100 ℃ the time, molecular formula is
Two tertiary amines and the mol ratio of Celfume be 1: 2-10, behind the reaction time 2-48h, obtaining product is fluorine carbocation Gemini surface active agent
Described n is described in the claim 1.
4. a synthetic method as claimed in claim 3 is characterized in that described polar solvent is C
1-C
8Alcohol, alkyl halide, oxolane (THF), dioxane, acetonitrile, N, dinethylformamide (DMF) or its mixed solvent.
5. a synthetic method as claimed in claim 3 is characterized in that step 1), 2), 3), 4), 5), 6), 7) product through concentrate, a step or a few step in desolventizing, neutralization, crystallization, filtration, dilution, extraction, washing, recrystallization or the drying handle.
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| CN103657513A (en) * | 2013-12-10 | 2014-03-26 | 衢州学院 | Gemini-type ampholytic surfactant based on perfluoroolefine and preparation method thereof |
| JP2015168680A (en) * | 2014-03-11 | 2015-09-28 | 東ソー株式会社 | Gemini type surfactant |
| CN106634894A (en) * | 2017-01-18 | 2017-05-10 | 中国石油大学(北京) | Dual-cation fluorocarbon surfactant and preparation method thereof, application of dual-cation fluorocarbon surfactant as hydrophobic and oleophobic wetting reversal agent, as well as drilling fluid and application thereof |
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| CN111117787A (en) * | 2019-12-23 | 2020-05-08 | 万华化学集团股份有限公司 | Bactericidal acaricidal surfactant, preparation method thereof and laundry detergent |
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| JP2015168680A (en) * | 2014-03-11 | 2015-09-28 | 東ソー株式会社 | Gemini type surfactant |
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