CN106268495B - A kind of N, N, N- cocoyl-ethoxy-methyl-N ', N ', N ' the double chlorination ammonium surfactants of-dihydroxy ethyl-methyl trimethylene and preparation method - Google Patents
A kind of N, N, N- cocoyl-ethoxy-methyl-N ', N ', N ' the double chlorination ammonium surfactants of-dihydroxy ethyl-methyl trimethylene and preparation method Download PDFInfo
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- CN106268495B CN106268495B CN201610633394.3A CN201610633394A CN106268495B CN 106268495 B CN106268495 B CN 106268495B CN 201610633394 A CN201610633394 A CN 201610633394A CN 106268495 B CN106268495 B CN 106268495B
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- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
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Abstract
A kind of N, N, the double chlorination ammonium surfactants of N cocoyl hydroxyethyl methyl N', N', N' dihydroxy ethyl methyl trimethylene, its structural formula are as follows：Wherein R is cocoyl.The advantages of present invention has good surface activity, and surface tension is small in aqueous.
Description
Technical field
The present invention relates to a kind of cationic surfactant and its preparation, and in particular to N, N, N- cocoyl-hydroxyl second
Double chlorination ammonium surfactants of base-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene and preparation method thereof.
Background technology
N- alkyl trimethylene diamines are a kind of important intermediates, and there are production, each life in larger fatty amine producer abroad
Production producer has made a large amount of works in simplified technique, raising product economy benefit and product deep processing, derivative development and application etc.
Make.But at home, the development of N- alkyl trimethylene diamines only has one, vicennial history, continue to use traditional primary amine and closed with acrylonitrile
It is outmoded stirred-tank reactor using equipment into technique, the country remains in the small lot trial production stage.
N- alkyl trimethylene diamines have cationic, available for synthesis polyfunctional surfactant glycine betaine-amine oxide, two
The excellent softening agent such as quaternary ammonium salt.It has been widely used abroad, type asphalt emulsifier, oil addition is split in being mainly used as
Agent, mineral flotation agent and flocculant, metal inhibitor, the agent of fabric pigment lubrication, the waterproofing agent of paper, biological bactericide etc..By
It is excellent in surface-active, thus have a wide range of applications, and diamines can further derive and be transformed into various other compounds, obtain
To further development and application.
The quaternary ammonium salt that generation is further alkylated by fat tertiary amine is a kind of common surfactant, and in cation
Very big proportion is occupied in surfactant.Since the presence of cationic hydrophilic head adds the general surface of solids in aqueous medium
Negative electrical charge often is carried, quaternary surfactant is readily adsorbed in the surface of solids, increases its hydrophobicity.This causes quaternary ammonium salt in crowd
It is multi-field to have a wide range of applications, fungicide can be used as, asphalt emulsifier can be used as in road construction or improves coagulation
The wetability and mobility of soil and mortar, are used as fabric softener in textile industry, are used to improve paper in paper industry
Feel or mould proof, in stock-dye be used for control dyeing it is uniform, in addition, quaternary surfactant is in pharmacy, flotation
Ore deposit, preparation medium and oil field development etc. are also widely used.
N, the double chlorinations of N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene are not found through retrieval
Ammonium surfactant and preparation method thereof.
The content of the invention
The present invention is intended to provide a kind of good surface activity, the small N of surface tension in aqueous, N, N- cocoyl-hydroxyl second
Double chlorination ammonium surfactants of base-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene and preparation method thereof.
The present invention is closed using N- cocoyl trimethylene diamines as raw material by ethoxylation and quaterisation two-step reaction
Into N, the double ammonium chlorides of N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene, which has good
Good surface-active and application potential.
N provided by the invention, N, the double chlorinations of N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene
Ammonium structural formula is as follows：
Wherein R is cocoyl
The preparation process of the present invention is as follows：
(1) ethoxylation
The uniform liquid obtained after N- cocoyl trimethylene diamines heat is melted is added in reaction kettle, uses N2In replacement reaction kettle
Air is warming up to 110-120 DEG C, control pressure is in 0.25-0.4MPa, Ran Houkai under agitation to exclude air in system
Beginning is continually fed into ethylene oxide gas and is reacted, and is passed through the time as 30-50 minutes, reaction temperature is controlled at 120-130 DEG C, is led to
2-3h is reacted after complete gas and obtains intermediate product N, N- cocoyl, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines；
Reaction is as follows：
(2) quaterisation
The intermediate product obtained in step (1) is put into reaction kettle, with Na2CO3For catalyst, isopropanol is solvent, is used
N2Air is warming up to 70-75 DEG C, is then held into reaction kettle under agitation to exclude air in system in replacement reaction kettle
It is continuous to be passed through methyl chloride gas and reacted, the time is passed through as 30-60 minutes, and control pressure is in 0.25-0.4MPa, reaction temperature control
System can obtain product N, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy second at 75-85 DEG C, reaction time 5-6h
The double ammonium chlorides of base-methyl trimethylene；
(3) Separation ＆ Purification of product
By the product liquid obtained in step (2) add anhydrous sodium sulfate remove moisture, be then filtered to remove sodium sulphate and
Catalyst, rotary evaporation remove solvent isopropanol；It is dried in vacuo after removing solvent with 3-5 rear rotary evaporation of petroleum ether extraction
24-48h；Then carried out with ethyl acetate after recrystallizing 3-5 times, vacuum drying 24-48h obtains final products.
Each material usage ratio relation is in above-mentioned steps (1)：N- cocoyl trimethylene diamines is with molar ratio：
1.0:3.3-3.6；
N in above-mentioned steps (2), N- cocoyls, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines are with chloromethanes molar ratio
1.0:2.1-2.4；The dosage of catalyst sodium carbonate is the 0.2-0.4wt% always to feed intake；Isopropanol dosage is added always to feed intake
48-52wt%.
The present invention has the characteristics that compared with prior art：
(1) this synthetic route combines traditional ethoxylation and quaterisation so as to which a kind of new N, N be made,
The double ammonium chlorides of N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene, possess conventional quaternary ammonium salts feature
Meanwhile possess the hydrophily of higher, it is water-soluble, and application performance is good.
(2) the synthetic method mild condition, it is easy to accomplish, reaction time is short, is applicable to extension production.
(3) this special single-stranded double end, the structure that two hydrophilic groups are connected by a propyl group, makes it hydrophilic
General quaternary ammonium product salt is different from terms of hydrophobicity, there is good Assembling Behavior, and good surface activity in aqueous,
Surface tension is small in aqueous.
Brief description of the drawings：
Fig. 1 is the nuclear magnetic resonance spectroscopy after the quaternary ammonium salt purification that embodiment 3 is prepared.
In Fig. 11H-NMR(CDCl3,ppm):δ0.89(t,3H,CH3-(CH2)7-CH2-CH2-N), 1.27 (d, 14H, CH3-
(CH2)7-CH2-CH2-N, 1.63 (t, 2H, CH3-(CH2)7-CH2-CH2-N-CH2-CH2-CH2N), 2.38 (s, 2H, N-CH2-CH2-
CH2- N, 3.16 (d, 6H, CH3-N-CH2-CH2-CH2-N-CH3),3.69(m,8H,CH3-(CH2)7-CH2-CH2-N-(CH2-
CH2OH)-CH2-CH2-CH2-N-(CH2-CH2OH)2),4.10(t,4H,N-CH2-CH2-CH2-N),4.95(t,6H,N-(CH2-
CH2OH)-CH2-CH2-CH2-N-(CH2-CH2OH)2)。
Fig. 2 is the infrared spectrum after the quaternary ammonium salt purification that embodiment 3 is prepared.
Shown in Fig. 2,3390cm-1(O-H stretching vibrations), 2924,2855cm-1(C-H stretching vibrations), 1468cm-1(C-H is curved
Qu Zhendong), 1124cm-1(C-N stretching vibrations), 1072cm-1(C-O stretching vibrations), and 721cm-1(C-H swing vibrations).
Fig. 3 is the aqueous solution surface tension curve figure after the quaternary ammonium salt purification that embodiment 3 is prepared.
According to Fig. 3 measurement results, the CMC of CTHDAC is 4.58mmol L-1, γCMCFor 39.12mNm-1。
Embodiment
Embodiment 1：
In the uniform liquid suction 1L reaction kettles obtained after 165gN- cocoyl trimethylene diamines low-grade fever is melted, N is used2Displacement
Twice to exclude air in system.110 DEG C are warming up under agitation, then start to be continually fed into 110g ethylene oxide gas
Reacted, control pressure is passed through the time as 30 minutes in 0.25MPa, and reaction temperature is controlled at 120 DEG C, lead to after gas instead
2h is answered to obtain intermediate product N, N- cocoyl, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines.
The product 38.1g obtained in above-mentioned steps is put into 500mL reaction kettles, with 0.30gNa2CO3For catalyst, 50g
Isopropanol is solvent, uses N2Air twice, is warming up to 70 DEG C, is then held into reaction kettle under agitation in replacement reaction kettle
It is continuous to be passed through 11.6g methyl chloride gas and reacted, the time is passed through as 30 minutes, and reaction pressure is controlled in 0.25MPa, reaction temperature
Control at 75 DEG C, reaction time 5h, can obtain product N, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-
The double ammonium chlorides of methyl trimethylene.(water/chloroform diphasic titration, bromophenol blue are indicator to chemical analysis, are dripped with tetraphenylboron sodium standard solution
It is fixed) measure, quaternary ammonium salt content is 58.47wt% in product.
Embodiment 2
In the uniform liquid suction 1L reaction kettles obtained after 165gN- cocoyl trimethylene diamines low-grade fever is melted, N is used2Displacement
Twice to exclude air in system.115 DEG C are warming up under agitation, then start to be continually fed into 113g ethylene oxide gas
Reacted, control pressure is passed through the time as 50 minutes in 0.35MPa, and reaction temperature is controlled at 125 DEG C, lead to after gas instead
2.5h is answered to obtain intermediate product N, N- cocoyl, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines.
The product 34.9g obtained in above-mentioned steps is put into 500mL reaction kettles, with 0.36gNa2CO3For catalyst,
42.8g isopropanols are solvent, use N2Air twice, is warming up to 75 DEG C under agitation in replacement reaction kettle, then to reaction
11.1g methyl chloride gas is continually fed into kettle to be reacted, is passed through the time as 40 minutes, and reaction pressure control is in 0.35MPa, instead
Temperature control is answered to can obtain product N, N, N- cocoyl-ethoxy-methyl-N', N', N'- at 80 DEG C, reaction time 5.5h
The double ammonium chlorides of dihydroxy ethyl-methyl trimethylene.(water/chloroform diphasic titration, bromophenol blue are indicator to chemical analysis, use tetraphenylboron sodium
Standard solution titrates) measure, quaternary ammonium salt content is 64.67wt% in product.
Embodiment 3
In the uniform liquid suction 1L reaction kettles obtained after 165gN- cocoyl trimethylene diamines low-grade fever is melted, N is used2Displacement
Twice to exclude air in system.120 DEG C are warming up under agitation, then start to be continually fed into 116g ethylene oxide gas
Reacted, control pressure is passed through the time as 50 minutes, reaction temperature is controlled at 130 DEG C, is reacted after having led to gas in 0.4MPa
3h obtains intermediate product N, N- cocoyl, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines.
The product 48.9g purified in above-mentioned steps is put into 500mL reaction kettles, with 0.28gNa2CO3For catalysis
Agent, 71.8g isopropanols are solvent, use N2Air twice, is warming up to 80 DEG C under agitation in replacement reaction kettle, then to anti-
Answer and 17.0g methyl chloride gas is continually fed into kettle is reacted, be passed through the time as 50 minutes, reaction pressure control in 0.4MPa,
Reaction temperature is controlled at 85 DEG C, reaction time 5h, can obtain product N, N, N- cocoyl-ethoxy-methyl-N', N', N'-
The double ammonium chlorides of dihydroxy ethyl-methyl trimethylene.(water/chloroform diphasic titration, bromophenol blue are indicator to chemical analysis, use tetraphenylboron sodium
Standard solution titrates) measure, quaternary ammonium salt content is 60.43wt% in product.
Embodiment 4
In the uniform liquid suction 1L reaction kettles obtained after 165gN- cocoyl trimethylene diamines low-grade fever is melted, N is used2Displacement
Twice to exclude air in system.115 DEG C are warming up under agitation, then start to be continually fed into 120g ethylene oxide gas
Reacted, control pressure is passed through the time as 50 minutes, reaction temperature is controlled at 120 DEG C, is reacted after having led to gas in 0.3MPa
2.5h obtains intermediate product N, N- cocoyl, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines.Obtained product was carried out
Filter, vacuum distillation purification.
The product 34.9g purified in above-mentioned steps is put into 500mL reaction kettles, with 0.33gNa2CO3For catalysis
Agent, 48.3g isopropanols are solvent, use N2Air twice, is warming up to 70 DEG C under agitation in replacement reaction kettle, then to anti-
Answer and 11.1g methyl chloride gas is continually fed into kettle is reacted, be passed through the time as 60 minutes, reaction pressure control in 0.3MPa,
Reaction temperature controls, and 80 DEG C, reaction time 6h, can obtain product N, N, N- cocoyl-dihydroxy ethyl-methyl-N', N', N'-
The double ammonium chlorides of dihydroxy ethyl-methyl trimethylene.(water/chloroform diphasic titration, bromophenol blue are indicator to chemical analysis, use tetraphenylboron sodium
Standard solution titrates) measure, quaternary ammonium salt content is 60.27wt% in product.
Embodiment 5
In the uniform liquid suction 1L reaction kettles obtained after 165gN- cocoyl trimethylene diamines low-grade fever is melted, N is used2Displacement
Twice to exclude air in system.110 DEG C are warming up under agitation, then start to be continually fed into 115g ethylene oxide gas
Reacted, control pressure is passed through the time as 40 minutes in 0.35MPa, and reaction temperature is controlled at 120 DEG C, lead to after gas instead
3h is answered to obtain intermediate product N, N- cocoyl, ethoxy-N', N'- dihydroxy ethyl trimethylene diamines.
The product 34.9g purified in above-mentioned steps is put into 500mL reaction kettles, with 0.23gNa2CO3For catalysis
Agent, 45.4g isopropanols are solvent, use N2Air twice, is warming up to 75 DEG C under agitation in replacement reaction kettle, then to anti-
Answer and 12.1g methyl chloride gas is continually fed into kettle is reacted, be passed through the time as 40 minutes, reaction pressure control in 0.35MPa,
Reaction temperature is controlled at 80 DEG C, reaction time 5h, can obtain product N, N, N- cocoyl-dihydroxy ethyl-methyl-N', N',
The double ammonium chlorides of N'- dihydroxy ethyls-methyl trimethylene.(water/chloroform diphasic titration, bromophenol blue are indicator to chemical analysis, use tetraphenylboron
Sodium standard solution titrates) measure, quaternary ammonium salt content is 57.78wt% in product.
Claims (6)
1. a kind of N, N, the double ammonium chloride surface-actives of N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl trimethylene
Agent, it is characterised in that structural formula is as follows：
Wherein R is cocoyl.
2. a kind of N as claimed in claim 1, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl-prop
The preparation method of the double chlorination ammonium surfactants of support, it is characterised in that include the following steps：
（1）Ethoxylation
The uniform liquid obtained after N- cocoyl trimethylene diamines heat is melted is added in reaction kettle, uses N2Air in replacement reaction kettle
To exclude air in system, 110-120 DEG C is warming up under agitation, then control pressure starts to hold in 0.25-0.4MPa
It is continuous to be passed through ethylene oxide gas and reacted, the time is passed through as 30-50 minute, and reaction temperature control has led to gas at 120-130 DEG C
2-3h is reacted after body and obtains intermediate product N, N- cocoyl-ethoxy-N', N'- dihydroxy ethyl trimethylene diamines；
（2）Quaterisation
By step（1）In obtain intermediate product input reaction kettle in, with Na2CO3For catalyst, isopropanol is solvent, uses N2Put
Air in reaction kettle is changed, to exclude air in system, to be warming up to 70-75 DEG C under agitation, then into reaction kettle persistently lead to
Enter methyl chloride gas to be reacted, be passed through the time as 30-60 minutes, control pressure exists in 0.25-0.4MPa, reaction temperature control
75-85 DEG C, reaction time 5-6h, obtain product N, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-first
The double ammonium chlorides of base trimethylene；
（3）The Separation ＆ Purification of product
By step（2）In obtained product liquid add anhydrous sodium sulfate and remove moisture, be then filtered to remove sodium sulphate and catalysis
Agent, rotary evaporation remove solvent isopropanol；24- is dried in vacuo after removing solvent with 3-5 rear rotary evaporation of petroleum ether extraction
48h；Then carried out with ethyl acetate after recrystallizing 3-5 times, vacuum drying 24-48h obtains final products.
3. a kind of N as claimed in claim 2, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl-prop
The preparation method of the double chlorination ammonium surfactants of support, it is characterised in that each material usage ratio is in step (1)：N- cocoyls third
Support diamines is with molar ratio：1.0:3.3-3.6.
4. a kind of N as claimed in claim 2, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl-prop
The preparation method of the double chlorination ammonium surfactants of support, it is characterised in that N in step (2), N- cocoyl-ethoxy-N', N'- bis-
Ethoxy trimethylene diamines is 1.0 with chloromethanes molar ratio:2.1-2.4.
5. a kind of N as claimed in claim 2, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl-prop
The preparation method of the double chlorination ammonium surfactants of support, it is characterised in that the dosage of catalyst sodium carbonate is always to feed intake in step (2)
0.2-0.4wt%.
6. a kind of N as claimed in claim 2, N, N- cocoyl-ethoxy-methyl-N', N', N'- dihydroxy ethyl-methyl-prop
The preparation method of the double chlorination ammonium surfactants of support, it is characterised in that it is the 48- always to feed intake that isopropanol dosage is added in step (2)
52wt%。
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