CN105523956A - Dendritic tetrameric quaternary ammonium salt surfactant preparation method - Google Patents
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Abstract
The invention provides a novel dendritic tetrameric quaternary ammonium salt surfactant preparation method. The method comprises the following steps: (1) 2-hydroxy-1,3-propanediamine is subjected to a Michael addition reaction with excessive methyl acrylate, such that a compound (I) is obtained; (2) the compound (I) is subjected to an amidation reaction with excessive N,N-dimethyl-1,3-propanediamine, such that a compound (II) is obtained; and (3) the compound (II) is subjected to a quaternization reaction with bromododecane, such that a final product compound (III) is obtained. With the method provided by the invention, the prepared surfactant has excellent properties, and has good application prospects in the fields of daily chemicals, water treatment, papermaking, oil field development and the like.
Description
Technical field
The present invention relates to a kind of preparation method of quaternary surfactant, be specifically related to the preparation method of a kind of polyamide-amide (PAMAM) dendroid quaternary surfactant, belong to oligo surfactant synthesis technical field.
Background technology
Dendroid oligo surfactant is a kind of novel surfactant with special construction, two or more parents' group to link together form by connecting base by it, its relative molecular mass is usually between conventional surfactant and polymeric surface active agent, and it has filled up blank between the two.Compared with traditional tensio-active agent, oligo surfactant has the features such as the rheological property of lower micelle-forming concentration, higher surfactivity and uniqueness.The superiority of its each side character comprehensive, oligo surfactant has a good application prospect in novel substance synthesis, letex polymerization, inhibition sterilization, the process of leather coloring waste water decoloring and tertiary oil recovery etc.
The modal traditional preparation methods of quaternized polyamide-amide (PAMAM) dendritic surface promoting agent is core with quadrol, synthesize 1.0 generation pamam dendrimer macromole.PAMAM periphery-NH
2there is very strong nucleophilicity, then introduce quaternary ammonium group thereon.At present, be also in the starting stage by the research of quaternised modified PAMAM synthesis of oligonucleotides tensio-active agent, many problems need to solve, such as, the initiator reaction core of synthesis PAMAM is more single, and be that four of nucleosynthesis gathers type surfactants with quadrol mostly, morphological structure is single.
Summary of the invention
Quoting a kind of new initiator in the present invention is that core successively carries out Michael reaction and amidate action, obtains 1.0 generation PAMAM, then carries out quaterisation with bromo alkyl, obtain a kind of novel hydroxyl dendroid four polyquaternium tensio-active agent.
In the present invention, novel surfactant is prepared by core with 2-hydroxyl-1,3-propylene diamine, and concrete preparation method comprises the steps:
Step (1), wraps lucifuge by there-necked flask masking foil and is placed in ice-water bath, first logical nitrogen, by 2-hydroxyl-1,3-propylene diamine is dissolved in solvent, adds in there-necked flask fast, stirs, then methyl acrylate is slowly added dropwise to flask, dropwises, heat temperature raising continues stirring reaction.Reaction end final vacuum revolves to boil off and desolventizes and unnecessary methyl acrylate, obtains compound (I).
Step (2), there-necked flask masking foil is wrapped lucifuge and is placed in ice-water bath, first logical nitrogen, then adds solvent, N is added under stirring, N-dimethyl-1,3-propylene diamine, continues to stir a little while, compound (I) obtained in step (1) is dissolved in certain solvent and is slowly added dropwise to flask, dropwise, treat that temperature rises to room temperature naturally, then heat temperature raising continues stirring reaction.Reaction end final vacuum revolves to boil off and desolventizes and unnecessary N, N-dimethyl-1,3-propylene diamine, obtains compound (II).
Step (3), first passes into nitrogen, is dissolved in by bromododecane in solvent, adds in there-necked flask in there-necked flask, is then also dissolved in solvent by gained compound (II) in step (2), is slowly added dropwise in there-necked flask, intensification stirring reaction.Revolve after reaction terminates and steam except desolventizing, wash away excessive bromododecane with sherwood oil, it is dry that last vacuum revolves evaporate to dryness, obtains faint yellow solid (III).
In above-mentioned preparation method; the described 2-hydroxyl-1 of step (1); the mol ratio of 3-propylene diamine and methyl acrylate can be 1:(4 ~ 24); solvent is methyl alcohol, is suitable for continuing stirring 10 ~ 20min after dropping into 2-hydroxyl-1,3-propylene diamine; temperature of reaction can be 20 ~ 40 DEG C (just having started from reacting in ice-water bath); reaction times is 1 ~ 2 day, and methyl acrylate rate of addition can be and drips/2 ~ 4s, reacts and carries out under nitrogen protection and lucifuge.
In above-mentioned preparation method; the mol ratio of step (2) described compound (I) and N, N-dimethyl-1,3-propylene diamine can be 1:(16 ~ 30); solvent is methyl alcohol; be suitable for continuing stirring 10 ~ 20min after dropping into N, N-dimethyl-1,3-propylene diamine; temperature of reaction can be 20 ~ 40 DEG C (just having started from reacting in ice-water bath); reaction times is 4 ~ 6 days, and compound (I) rate of addition can be and drips/2 ~ 4s, reacts and carries out under nitrogen protection and lucifuge.
In above-mentioned preparation method; step (3) described compound (II) can be 1:(6 ~ 20 with the mol ratio of bromododecane), solvent is methyl alcohol or acetone/methanol (1:3), and temperature of reaction can be 30 ~ 40 DEG C; reaction times can be 4 ~ 6 days, and reaction is carried out under nitrogen protection.
The preparation method provided in the present invention has the following advantages:
1, raw material is easy to get, and synthesis is simple, provides prerequisite for being applied to suitability for industrialized production.
2, each step reaction conditions is gentleer, and become at a lower temperature and can react, the such as synthesis of compound (I) and compound (II) becomes at 30 DEG C can be carried out.
3, each step productive rate is all higher, and the present invention will extend one day the reaction times when synthetic compound (II), make it react completely, and obtain being close to absolutely productive rate.
4, in the building-up process of compound (II), increase N, the ratio of N-dimethyl-1,3-propylene diamine, the amount of exceeding in fact, compound (I) can be made to react more complete, for productive rate has made contribution.
5, new initiator 2-hydroxyl-1 is introduced in the present invention, 3-propylene diamine is core, a kind of hydroxyl dendroid four polyquaternium tensio-active agent is obtained after reaction, prove that this kind of tensio-active agent has very low micelle-forming concentration compared with conventional surfactant by experiment, the good characteristics such as higher surfactivity.
These characteristics is indicated, the present invention is applicable to multiple suitability for industrialized production, is with a wide range of applications.
Accompanying drawing explanation
Fig. 1 is the structural formula of compound (I), (II), (III).
Fig. 2 is the concrete synthetic route of quaternized polyamide-amide dendritic surface promoting agent.
Fig. 3 is compound (I)
1h-NMR spectrogram.
Fig. 4 is compound (II)
1h-NMR spectrogram.
Fig. 5 is compound (III)
1h-NMR spectrogram.
Embodiment
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Following reagent all can obtain from commercial channels, and does not do further process:
2-hydroxyl-1,3-propylene diamine (99%, Beijing lark prestige Science and Technology Ltd.), methyl acrylate (99.5%, Beijing lark prestige Science and Technology Ltd.), bromododecane (98%, Beijing lark prestige Science and Technology Ltd.).
Following reagent also obtains from commercial channels, and is further purified process:
Methyl alcohol (analytical pure, Tianjin Guang Cheng chemical reagent company limited), acetone (analytical pure, economic and technological development zone, Laiyang Fine Chemical Works), sherwood oil, (analytical pure, Tianjin is large chemical reagent development centre forever), reference
purificationofLaboratoryChemicals, 5the days(Chai, C.L.L.; Armarego, W.L.F., Butterwirth-Heinemann:NewYork, 2003.) the rear use of process.
The preparation of embodiment 1, a kind of quaternized polyamide-amide dendritic surface promoting agent
(1) preparation of compound (I)
50mL there-necked flask is placed in ice-water bath, and first logical nitrogen 3 ~ 5min, takes 0.9g(10mmol) 2-hydroxyl-1,3-propylene diamine, be dissolved in 10ml methyl alcohol, add in there-necked flask, continue to stir 20min, then 17.2g(200mmol is measured) methyl acrylate, dripping/speed of 3s is added dropwise to flask, dropwises, treat that temperature rises to room temperature naturally, then 30 DEG C are heated to, N
2protection is lower continues stirring reaction 36h.Repeatedly add methyl alcohol after reaction terminates to carry out vacuum and revolve steaming, remove excessive methyl acrylate, finally revolve and steam removing solvent methanol, vacuum is revolved and is steamed temperature and control at 30 ~ 35 DEG C, and when vacuum revolves steaming, pressure will little by little increase, and prevents sample bumping.Finally obtain the orange-yellow liquid of 4.18g thickness, i.e. compound (I) shown in upper figure, productive rate >=96.4%.
(2) preparation of compound (II)
50mL there-necked flask is placed in ice-water bath, and first logical nitrogen 3 ~ 5min, measures 5.63g(55.2mmol) N, N-dimethyl-1,3-propylene diamine, adds in there-necked flask, add 2ml methyl alcohol again, stirring 20min, then take 1g(2.3mmol) compound (I) is dissolved in 2ml methyl alcohol, dripping/speed of 3s is added dropwise to flask, dropwise, treat that temperature rises to room temperature naturally, be then heated to 30 DEG C, N
2protection is lower continues stirring reaction 5 days.Repeatedly add methanol in vacuo and revolve steaming after reaction terminates, remove excessive N, N-dimethyl-1,3-propylene diamine, last vacuum is revolved to boil off and is desolventized methyl alcohol, and vacuum is revolved and steamed temperature and control at 30 ~ 40 DEG C, and when vacuum revolves steaming, pressure will little by little increase, and prevents sample bumping.Finally obtain 1.68g thick yellow liquid, i.e. compound (II) shown in upper figure, productive rate >=100%.
(3) preparation of compound (III)
First in 250mL there-necked flask, pass into nitrogen, by 42.4g(10.6mmol) bromododecane is dissolved in 20mL acetone/methanol (1:3) solvent, add in there-necked flask, then 7.6g(10.6mmol is taken) compound (II) is dissolved in 20mL acetone/methanol (1:3) solvent, dripping/speed of 3s is added dropwise in there-necked flask, is warming up to 40 DEG C of stirring reactions 5 days.Revolve after reaction terminates and steam the most of solvent of removing, then wash away excessive bromododecane with sherwood oil, after washing twice altogether, it is dry that last vacuum revolves evaporate to dryness, and vacuum is revolved and steamed temperature and control at 30 ~ 40 DEG C, and when vacuum revolves steaming, pressure will little by little increase, and prevents sample bumping.Obtain 16.12g yellow solid, i.e. compound (III) shown in upper figure, productive rate >=88.57%.
The preparation of embodiment 2, a kind of quaternized polyamide-amide dendritic surface promoting agent
(1) preparation of compound (I)
As described in Example 1, difference changes the quality of methyl acrylate into 5.16g(60mmol), the quality of gained compound (I) is 4.23g, productive rate is 97.74%, point liberation of hydrogen composes known gained non-targeted product, does not connect four chains, and doubtful is the mixture of three chains and two chains.
(2) preparation of compound (II)
As described in Example 1, difference changes the quality of N, N-dimethyl-1,3-propylene diamine into 4.22g(41.4mmol), reaction 5, sky compound (I) react completely not yet.
(3) preparation of compound (III)
As described in Example 1, difference changes the quality of compound (II) into 0.77g(1.08mmol), the volume being dissolved in solvent is 6mL, change the quality of bromododecane into 3.23g(13mmol), the volume being dissolved in solvent is 8mL, react in 50ml there-necked flask, the quality of gained compound (III) is 1.65g, and productive rate is 87.18%.
The preparation of embodiment 3, a kind of quaternized polyamide-amide dendritic surface promoting agent
(1) as described in Example 1, difference is by 2-hydroxyl-1, the quality of 3-propylene diamine changes 0.18g(2mmol into), change the quality of methyl acrylate into 2.06g(24mmol), the quality of gained compound (I) is 0.41g, and productive rate is 96%, divide liberation of hydrogen spectrum known, along with the ratio of methyl acrylate increases, product is doubtful is partial target product, part three chain product.
(2) as described in Example 1, difference is that temperature of reaction is risen to 40 DEG C, and the reaction times is 4 ~ 5 days, but finds out there is assorted peak from hydrogen spectrum, and product is impure.
(3) as described in Example 1, difference changes the quality of compound (II) into 0.79g(1.1mmol), the volume being dissolved in solvent is 6mL, change the quality of bromododecane into 4.4g(17.7mmol), the volume being dissolved in solvent is 8mL, temperature of reaction is the quality of 30 DEG C of gained compounds (III) is 1.49g, and productive rate is 79.26%.
Claims (7)
1. the invention provides a kind of preparation method of novel dendritic four polyquaternium tensio-active agent, wherein, compound
for the hydroxyl dendroid four polyquaternium tensio-active agent of the present invention's synthesis;
Comprise the steps:
Step (1), 2-hydroxyl-1,3-propylene diamine and excessive methyl acrylate carry out Michael reaction, prepare compound (I);
Step (2), compound (I) and excessive N, N-dimethyl-1,3-propylene diamine obtain compound (II) by amidate action;
Step (3), compound (II) obtains final product compound (III) with bromododecane generation quaterisation again;
According to claim 1, it is characterized in that, introducing new initiator 2-hydroxyl-1,3-propylene diamine in the present invention is core, obtains a kind of hydroxyl four polyquaternium tensio-active agent after reaction.
2. according to claim 1-2, it is characterized in that, first in there-necked flask, nitrogen is led in the preparation process of the middle compound (I) of step (1), then 2-hydroxyl-1,3-propylene diamine is dissolved in solvent and adds flask fast, continue stirring 10 ~ 20min, then methyl acrylate is slowly added dropwise to flask, dropwise, treat that temperature rises to room temperature naturally, be then heated to 20 ~ 40 DEG C and continue stirring reaction.
3. according to claim 1-3; it is characterized in that; N in step (1); N-dimethyl-1; the mol ratio of 3-propylene diamine and methyl acrylate is 1:(4 ~ 24), solvent is methyl alcohol, and temperature of reaction is 20 ~ 40 DEG C (just having started from reacting in ice-water bath); reaction times is 1 ~ 2 day, reacts under nitrogen protection also lucifuge and carries out.
4. according to claim 1-2, it is characterized in that, in the preparation process of the middle compound (II) of step (2), there-necked flask is placed in ice-water bath, first logical nitrogen, then add solvent, under stirring, add N, N-dimethyl-1,3-propylene diamine, continue stirring 10 ~ 20min, then compound (I) obtained in (1) is slowly added dropwise to flask, dropwises, treat that temperature rises to room temperature naturally, be then heated to 20 ~ 40 DEG C and continue stirring reaction.
5. according to claim 1-2,5; it is characterized in that; compound (I) and N in step (2); N-dimethyl-1; the mol ratio of 3-propylene diamine can be 1:(16 ~ 30), solvent is methyl alcohol, and temperature of reaction can be 20 ~ 40 DEG C (just having started from reacting in ice-water bath); reaction times is 4 ~ 6 days, and reaction is carried out under nitrogen protection.
6. according to claim 1-2, it is characterized in that, first in there-necked flask, nitrogen is passed in the preparation process of the middle compound (III) of step (3), then bromododecane is dissolved in solvent, add in there-necked flask, then gained compound (II) in (2) is also dissolved in solvent, is slowly added dropwise in there-necked flask, is warming up to 30 ~ 40 DEG C of stirring reactions.
7. according to claim 1-2,7; it is characterized in that; in step (3), compound (II) can be 1:(6 ~ 20 with the mol ratio of bromododecane); solvent is methyl alcohol or acetone/methanol (1:3); temperature of reaction can be 30 ~ 40 DEG C; reaction times is 4 ~ 6 days, and reaction is carried out under nitrogen protection.
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| US11685709B2 (en) | 2018-08-29 | 2023-06-27 | Ecolab Usa Inc. | Multiple charged ionic compounds derived from polyamines and compositions thereof and use thereof as reverse emulsion breakers in oil and gas operations |
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