CN107162918A - 2 chlorinations, the synthetic method of 3 poly- hydroxypropyl isopropylamine quaternary surfactants - Google Patents
2 chlorinations, the synthetic method of 3 poly- hydroxypropyl isopropylamine quaternary surfactants Download PDFInfo
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- CN107162918A CN107162918A CN201710321262.1A CN201710321262A CN107162918A CN 107162918 A CN107162918 A CN 107162918A CN 201710321262 A CN201710321262 A CN 201710321262A CN 107162918 A CN107162918 A CN 107162918A
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- isopropylamine
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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
- C07C213/02—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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/141—Amines; Quaternary ammonium compounds
- C23F11/142—Hydroxy amines
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Abstract
The invention discloses a kind of 2 chlorination, the synthetic method of 3 poly- hydroxypropyl isopropylamine quaternary surfactants.It is that intermediate of the reaction synthesis with double chlorine substituents is first carried out with isopropylamine and epoxychloropropane, recycles the intermediate to react the final product that synthesis obtains belonging to Quaternary ammonium gemini surfactants with Dodecyl Dimethyl Amine.Two-step method synthesis target product is the method achieve, has the advantages that with low cost and its surface is active high.This product can be applied in aviation alloyed aluminium inhibition system, and experiment proves that corrosion inhibition is better than using isopropylamine as the corrosion inhibition of corrosion inhibiter merely.
Description
Technical field
The invention belongs to technical field of fine, more particularly to a kind of 2- chlorinations, the poly- hydroxypropyl isopropylamine quaternary ammoniums of 3-
The synthetic method of salt surfactant and application.
Technical background
Gemini surface active be using two traditional surfactant molecules, by special linking group, with
The class novel surfactant that chemical bond mode is connected into.In recent years, the development with Chemical Engineering Technology and economic demand, are passed
The surfactant of system can not meet the demand of people due to many limitations present in self structure.With traditional table
Face activating agent is compared, and Gemini surface active is shown more excellent due to two hydrophilic groups and two lipophilic groups
Point, specifically include it is following some：(1) surface tension efficiency high is reduced；(2) CMC value is low, strong into micella ability；(3) it is water-soluble
It is good；(4) Kraft points are low；(5) it is good with other surfaces active ingredient.Therefore, raw material is easy to get, structure is novel, excellent performance
The research of Gemini surface active already turns into focus.
As the important fine chemicals of a class, Quaternary ammonium gemini surfactants have been widely used in metal and delayed
Erosion, synthetic detergent, food industry, textile industry, agricultural, mining industry, oil exploration and exploitation, paper industry, traffic, building
Construction industry, environmental protection, medicine etc. are produced and the every field such as life, and it is improved in production technology, energy-conservation, product quality carries
Great function has been played in terms of high, productivity ratio raising, cost reduction, added value increase.But at present, quaternary ammonium salt Gemini
Surfactant price is relatively expensive, it is difficult to a large amount of productions, still has a segment distance away from industrialization.Therefore, if reducing its production
After cost, it will can replace traditional single-stranded surfactant in many fields.
The content of the invention
For deficiencies of the prior art, it is an object of the invention to provide a kind of with low cost and its surface
The high 2- chlorinations of activity, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-.
In order to achieve the above object, the 2- chlorinations that the present invention is provided, the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-
Synthetic method include the following steps for carrying out in order：
1) prepared by intermediate：Isopropylamine is dissolved in the ethanol that isopropylamine is made as in the absolute ethyl alcohol of solvent molten
Liquid；Epoxychloropropane is added dropwise into the solution in ice bath and stirs, continues that reaction 10h- is stirred at room temperature after completion of dropping
14h；Then in vacuum rotary steam 1h-2h at 40 DEG C, to remove absolute ethyl alcohol and unreacted epoxychloropropane, water white transparency is obtained
Viscous liquid shape intermediate, i.e. N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine；Reaction equation is as follows：
2) Quaternary ammonium gemini surfactants are synthesized：By step 1) obtained N, N- bis- (2- hydroxyl -3- chloropropyls) is different
Propylamine is dissolved in ethanol/deionized water mixture as mixed solvent with Dodecyl Dimethyl Amine, is stirred at room temperature
10h-14h and carry out quaterisation；The vacuum rotary steam 1h-2h at 60 DEG C again, to remove solvent and the complete dodecane of unreacted
Base dimethyl tertiary amine, obtains wax；Then the wax is washed with n-hexane, then the wax after washing is utilized into acetone weight
Crystallization three times, spontaneously dries to constant weight after taking-up, obtains the final product of white solid, be i.e. 2- chlorinations, the poly- hydroxypropyls of 3- are different
Propylamine quaternary surfactant.
During above-mentioned intermediate and Dodecyl Dimethyl Amine react, the N atom attacks in long chain tertiary amine
Cl atoms in intermediate, and replace, and then Quaternary ammonium gemini surfactants are generated, reaction equation is as follows：
In step 1) in, described isopropylamine and the mol ratio of epoxychloropropane are 1:2-1:3.
In step 2) in, described is with double intermediates of chlorine substituent and the mol ratio of Dodecyl Dimethyl Amine
1:2-1:3。
In step 2) in, described in the mixed solvent ethanol and the volume ratio of deionized water are 1:1-2:1.
The 2- chlorinations that the present invention is provided, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3- is first with different
Propylamine carries out intermediate of the reaction synthesis with double chlorine substituents with epoxychloropropane, recycles the intermediate and dodecyl two
Methyl reactive tertiary amine synthesizes the final product for obtaining belonging to Quaternary ammonium gemini surfactants.It the method achieve two-step method conjunction
Into target product, have the advantages that with low cost and its surface is active high.This product can be applied to aviation alloyed aluminium inhibition
In system, experiment proves that corrosion inhibition is better than using isopropylamine as the corrosion inhibition of corrosion inhibiter merely.
Brief description of the drawings
Fig. 1 is N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine1H NMR hydrogen spectrograms；
Fig. 2 is 2- chlorinations, the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-1H NMR hydrogen spectrograms；
Embodiment
The present invention is described in further detail with reference to specific embodiment.
Embodiment 1：
The 2- chlorinations that this implementation is provided, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3- is included by suitable
The following steps that sequence is carried out：
1) prepared by intermediate：20mL is added in beaker as the absolute ethyl alcohol of solvent, 5mL isopropylamines are accurately weighed and slow
It is slow to instill in beaker, then the epoxychloropropane that 9.3mL purity is 99% is taken, with the speed of 10 seconds/drop under ice bath and stirring condition
Degree is slowly instilled in the solution in beaker, until epoxychloropropane completion of dropping；Continue that reaction 10h is stirred at room temperature；Reaction
After stopping, rotary evaporator water bath temperature is set as 40 DEG C, and vacuum distillation 1h removes solvent and the complete epoxychloropropane of unreacted,
Obtain 13.6g water white transparency viscous liquid shape intermediate, i.e. N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine.
2) Quaternary ammonium gemini surfactants are synthesized：By step 1) obtained N, N- bis- (2- hydroxyl -3- chloropropyls) is different
Propylamine 12.2g (0.05mol) is with 27mL (0.1mol) Dodecyl Dimethyl Amines in ethanol/deionized water solvent at room temperature
Middle progress quaterisation 10h.Stop after reaction, set rotary evaporator water bath temperature as 60 DEG C, above-mentioned reaction liquid is subtracted
Pressure distillation 1h, removes solvent and the complete Dodecyl Dimethyl Amine of unreacted, obtains wax.It is wax-like that this is washed with n-hexane
Thing, recycles acetone recrystallization three times, is spontaneously dried after taking-up to constant weight, obtains the final product of 32.6g white solids, i.e.,
2- chlorinations, the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-.
Embodiment 2：
The 2- chlorinations that this implementation is provided, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3- is included by suitable
The following steps that sequence is carried out：
1) prepared by intermediate：20mL is added in beaker as the absolute ethyl alcohol of solvent, 5mL isopropylamines are accurately weighed and slow
It is slow to instill in beaker, then the epoxychloropropane that 11.7mL purity is 99% is taken, with the speed of 10 seconds/drop under ice bath and stirring condition
Degree is slowly instilled in the solution in beaker, until epoxychloropropane completion of dropping；Continue that reaction 12h is stirred at room temperature；Reaction
After stopping, rotary evaporator water bath temperature is set as 40 DEG C, and vacuum distillation 1.5h removes solvent and the complete epoxy chloropropionate of unreacted
Alkane, obtains 14.0g water white transparency viscous liquid shape intermediate, i.e. N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine.
2) Quaternary ammonium gemini surfactants are synthesized：By step 1) obtained N, N- bis- (2- hydroxyl -3- chloropropyls) is different
Propylamine 12.2g (0.05mol) is with 33.8mL (0.125mol) Dodecyl Dimethyl Amines in ethanol/deionized water at room temperature
Quaterisation 12h is carried out in solvent.Stop after reaction, rotary evaporator water bath temperature is set as 60 DEG C, by above-mentioned reaction solution
Body vacuum distillation 1.5h, removes solvent and the complete Dodecyl Dimethyl Amine of unreacted, obtains wax.Washed with n-hexane
The wax, recycles acetone recrystallization three times, is spontaneously dried after taking-up to constant weight, obtains the final of 33.0g white solids
Product, i.e. 2- chlorinations, the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-.
Embodiment 3：
The 2- chlorinations that this implementation is provided, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3- is included by suitable
The following steps that sequence is carried out：
1) prepared by intermediate：20mL is added in beaker as the absolute ethyl alcohol of solvent, 5mL isopropylamines are accurately weighed and slow
It is slow to instill in beaker, then the epoxychloropropane that 14.0mL purity is 99% is taken, with the speed of 10 seconds/drop under ice bath and stirring condition
Degree is slowly instilled in the solution in beaker, until epoxychloropropane completion of dropping；Continue that reaction 14h is stirred at room temperature；Reaction
After stopping, rotary evaporator water bath temperature is set as 40 DEG C, and vacuum distillation 2h removes solvent and the complete epoxychloropropane of unreacted,
Obtain 13.8g water white transparency viscous liquid shape intermediate, i.e. N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine.
2) Quaternary ammonium gemini surfactants are synthesized：By step 1) obtained N, N- bis- (2- hydroxyl -3- chloropropyls) is different
Propylamine 12.2g (0.05mol) is with 40.7mL (0.15mol) Dodecyl Dimethyl Amines in ethanol/deionized water at room temperature
Quaterisation 14h is carried out in solvent.Stop after reaction, rotary evaporator water bath temperature is set as 60 DEG C, by above-mentioned reaction solution
Body vacuum distillation 2h, removes solvent and the complete Dodecyl Dimethyl Amine of unreacted, obtains wax.This is washed with n-hexane
Wax, recycles acetone recrystallization three times, is spontaneously dried after taking-up to constant weight, obtains the final production of 33.2g white solids
Thing, i.e. 2- chlorinations, the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-.
The present inventor is by step 1) made from water white transparency viscous liquid shape intermediate examined using NMR
Survey, Fig. 1 is the intermediate1H NMR hydrogen spectrograms, as can be seen from Figure,1H NMR(CDCl3)δ1.019-1.109(m,6H,
CH3(CH)CH3), 2.522-2.615 (m, 4H, CH2NCH2), 2.636-3.044 (m, 1H, CH3(CH)CH3), 3.572-3.585
(m,4H,(CH2CH)2), 3.685-3.698 (m, 2H, (CH2CH)2), 3.878-3.922 (m, 2H, (OH)2), it is possible thereby to prove
The structure of the intermediate is N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine.
The present inventor is by step 2) made from the final product of white solid detected using NMR, scheme
2 be the final product1H NMR hydrogen spectrograms, as can be seen from Figure,1H NMR(CDCl3)δ0.806-0.824(t,6H,
(CH3)2), 0.840-1.017 (m, 6H, CH3(CH)CH3), 1.033-1.289 (m, 36H, (CH3(CH2)9)2), 1.687 (s, 4H,
(CH3(CH2)9CH2)2), 2.686-2.745 (m, 1H, CH3(CH)CH3), 2.956-3.056 (m, 4H, (CH2CH)2), 3.252-
3.312(m,12H,(N+(CH3)2)2), 3.542-3.554 (m, 8H, (N+(CH2)2)2), 3.870-3.901 (m, 2H,
(CH2CH)2), 4.293-4.309 (m, 2H, (OH)2), it is possible thereby to which the structure for proving the final product is 2- chlorinations, the poly- hydroxyls of 3-
Propyl group isopropylamine quaternary surfactant, belongs to Quaternary ammonium gemini surfactants.
Claims (4)
1. a kind of 2- chlorinations, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-, it is characterised in that：Described
Synthetic method includes the following steps carried out in order：
1) prepared by intermediate：Isopropylamine is dissolved in as in the absolute ethyl alcohol of solvent and is made the ethanol solution of isopropylamine；
Epoxychloropropane is added dropwise into the solution in ice bath and stirs, continues that reaction 10h-14h is stirred at room temperature after completion of dropping；So
After vacuum rotary steam 1h-2h at 40 DEG C, to remove absolute ethyl alcohol and unreacted epoxychloropropane, water white transparency stickiness liquid is obtained
Body shape intermediate, i.e. N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine；Reaction equation is as follows：
2) Quaternary ammonium gemini surfactants are synthesized：By step 1) obtained N, N- bis- (2- hydroxyl -3- chloropropyls) isopropylamine
It is dissolved in Dodecyl Dimethyl Amine in ethanol/deionized water mixture as mixed solvent, 10h- is stirred at room temperature
14h and carry out quaterisation；The vacuum rotary steam 1h-2h at 60 DEG C again, to remove solvent and the complete dodecyl two of unreacted
Methyl tertiary amine, obtains wax；Then the wax is washed with n-hexane, then the wax after washing is utilized into acetone recrystallization
Three times, spontaneously dried after taking-up to constant weight, obtain the final product of white solid, i.e. 2- chlorinations, the poly- hydroxypropyl isopropylamines of 3-
Quaternary surfactant；Reaction equation is as follows：
2. 2- chlorinations according to claim 1, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-, its
It is characterised by：In step 1) in, described isopropylamine and the mol ratio of epoxychloropropane are 1:2-1:3.
3. 2- chlorinations according to claim 1, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-, its
It is characterised by：In step 2) in, the described intermediate and the mol ratio of Dodecyl Dimethyl Amine that carry double chlorine substituents
For 1:2-1:3.
4. 2- chlorinations according to claim 1, the synthetic method of the poly- hydroxypropyl isopropylamine quaternary surfactants of 3-, its
It is characterised by：In step 2) in, described in the mixed solvent ethanol and the volume ratio of deionized water are 1:1-2:1.
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| CN201710321262.1A CN107162918A (en) | 2017-05-09 | 2017-05-09 | 2 chlorinations, the synthetic method of 3 poly- hydroxypropyl isopropylamine quaternary surfactants |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108823577A (en) * | 2018-07-02 | 2018-11-16 | 中国民航大学 | The corrosion inhibiter of amide containing type gemini surfactant |
| CN108854840A (en) * | 2018-05-03 | 2018-11-23 | 沈阳化工大学 | A kind of poly quaternary surfactant preparation method of amide containing coupling link |
| CN109174465A (en) * | 2018-09-14 | 2019-01-11 | 武汉工程大学 | A kind of quaternary ammonium salt suitable for flotation |
| WO2019119293A1 (en) * | 2017-12-20 | 2019-06-27 | Rhodia Operations | New cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture |
| CN110105226A (en) * | 2019-04-15 | 2019-08-09 | 西南石油大学 | A kind of preparation method and applications of the acidified corrosion inhibiter of polycationic quaternary ammonium |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516093A (en) * | 2011-12-08 | 2012-06-27 | 江苏博特新材料有限公司 | Gemini type asphalt emulsifier and preparation method thereof |
-
2017
- 2017-05-09 CN CN201710321262.1A patent/CN107162918A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102516093A (en) * | 2011-12-08 | 2012-06-27 | 江苏博特新材料有限公司 | Gemini type asphalt emulsifier and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| JAN CHLEBICKIA等: "Preparation, Surface-Active Properties,and Antimicrobial Activities of Bis-quaternary Ammonium Salts from Amines and Epichlorohydrin", 《JOURNAL OF SURFACTANTS AND DETERGENTS》 * |
| JOANNA WEGRZYNSKA等: "Preparation, Surface-Active and Antielectrostatic Properties of Multiple Quaternary Ammonium Salts", 《JOURNAL OF SURFACTANTS AND DETERGENTS》 * |
| 李杰等: "季铵盐型Gemini 表面活性剂的合成及性能研究", 《季铵盐型GEMINI 表面活性剂的合成及性能研究》 * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019119293A1 (en) * | 2017-12-20 | 2019-06-27 | Rhodia Operations | New cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture |
| CN111491914A (en) * | 2017-12-20 | 2020-08-04 | 罗地亚经营管理公司 | Novel cationic quaternary ammonium compounds and compositions containing the same and methods of making the same |
| US20200392070A1 (en) * | 2017-12-20 | 2020-12-17 | Rhodia Operations | New cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture |
| EP3728181A4 (en) * | 2017-12-20 | 2021-07-14 | Rhodia Operations | New cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture |
| US11773053B2 (en) * | 2017-12-20 | 2023-10-03 | Rhodia Operations | Cationic quaternary ammonium compounds and compositions comprising same and processes for their manufacture |
| CN111491914B (en) * | 2017-12-20 | 2024-04-26 | 罗地亚经营管理公司 | Novel cationic quaternary ammonium compound, composition comprising the same and process for producing the same |
| CN108854840A (en) * | 2018-05-03 | 2018-11-23 | 沈阳化工大学 | A kind of poly quaternary surfactant preparation method of amide containing coupling link |
| CN108854840B (en) * | 2018-05-03 | 2020-07-21 | 沈阳化工大学 | Preparation method of polyquaternium surfactant containing amide connecting chain |
| CN108823577A (en) * | 2018-07-02 | 2018-11-16 | 中国民航大学 | The corrosion inhibiter of amide containing type gemini surfactant |
| CN109174465A (en) * | 2018-09-14 | 2019-01-11 | 武汉工程大学 | A kind of quaternary ammonium salt suitable for flotation |
| CN110105226A (en) * | 2019-04-15 | 2019-08-09 | 西南石油大学 | A kind of preparation method and applications of the acidified corrosion inhibiter of polycationic quaternary ammonium |
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Application publication date: 20170915 |