CN103333721B - Water-resistant hydrotrope agent for M15 methanol gasoline - Google Patents
Water-resistant hydrotrope agent for M15 methanol gasoline Download PDFInfo
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- CN103333721B CN103333721B CN201310296177.6A CN201310296177A CN103333721B CN 103333721 B CN103333721 B CN 103333721B CN 201310296177 A CN201310296177 A CN 201310296177A CN 103333721 B CN103333721 B CN 103333721B
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- methanol
- methanol gasoline
- water repellent
- hydrotropy
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Abstract
The invention discloses a water-resistant hydrotrope agent for M15 methanol gasoline. A structural formula of the agent is shown in a general formula (I). The agent is formed in a manner that alkyl glucosamine and normal polyhydroxyalkanoate are mixed and react in a methanol solution. The agent is a glycosyl surfactant, is mainly used for the M15 methanol gasoline, can improve the phase separation resistance and the water resistance of the M15 methanol gasoline, and has the advantages of good intermiscibility and less adding amount.
Description
Technical field
The invention belongs to methanol fuel for vehicles technical field, relate to a kind of methanol gasoline additive for vehicles, particularly a kind of additive that improves oil product resisting phase separation performance and improve water repelling property.
Background technology
Along with the economic fast development of China and living standards of the people improve constantly, consumption of petroleum is constantly soaring.When China's economic high speed development, be but faced with oil reserve and approach exhausted and petroleum-based energy serious waste, this reality impels us actively to utilize existing resource to find the clean energy products that some can replacing gasoline, and methanol gasoline attracts tremendous attention as most potential fuel substitute.
Methyl alcohol is a kind of water white volatile liquid, and octane value is high, and anti-knocking property are good, and oxygen level is high, and its combustionproperty is similar to gasoline, and after burning, HC, CO, NOx discharge lower than gasoline.From save energy, alleviate the angle of oil-fired dependence and protection of the environment considered, all prove that methyl alcohol is a kind of good alternative motor fuels, has very large exploitation value and application prospect.In gasoline, mix a certain proportion of methyl alcohol, just become methanol gasoline, conventional methanol gasoline has M15, M25 and M85.In methanol gasoline, need to add a certain amount of additive, to solve chance water and the low-temperature stratification of propellant combination, metallic corrosion performance, the problems such as swell rubber performance.
Can there is phenomenon of phase separation in methanol gasoline, this directly affects production and transport and the storage of methanol gasoline under the condition that has water to exist.In addition, methyl alcohol and gasoline mix uneven, can cause fuel feed insufficient, degradation under motor performance, so lamination problem is the matter of utmost importance that methanol gasoline must solve while applying in spark ignition engine.Investigator has carried out research in many ways with regard to these problems, as Hu Wenbin (the methanol gasoline performance impact research of dissolving each other. chemical engineering and equipment, 2012, (1): 7-9.) analyzed the impacts of factor on its mutual solubility such as water-content in Methanol-gasoline system, temperature, gasoline composition, and discussed the mechanism of action of solubility promoter and the selection of solubility promoter; Zhang Shuhua etc. (technical study of M15 Vehicular methanol petrol composite additive. chemical engineer, 2012, (9): 15-18.) by the research to compound additive for methanol gasoline, studied the layering situation of the M15 of composite additive mediation.
Summary of the invention
The object of this invention is to provide a kind of M15 methanol gasoline hydrotropy water repellent agent.Hydrotropy water repellent agent of the present invention can improve the resisting phase separation performance of M15 methanol gasoline and improve water repelling property, and intermiscibility is good, addition is few.
M15 methanol gasoline hydrotropy water repellent agent of the present invention is a kind of glycosyl surfactant active, and its structural formula can lead to as follows formula I and represent:
Wherein: the odd number that n is 11-17; M=1-5.
The alkyl glucose amine that the M15 methanol gasoline hydrotropy water repellent agent that above-mentioned logical formula I represents can be represented by following logical formula II:
The odd number that wherein n is 11-17;
The positive alkanoic acid representing with following logical formula III:
CH
3(CH
2)
mCOOH
(Ⅲ)
M=1-5 wherein;
According to the amount of substance of 1:1～1.5, than mixing, in methanol solution, hybrid reaction is removed solvent methanol after 18～20 hours and is obtained.
The concrete preparation method of M15 methanol gasoline hydrotropy water repellent agent of the present invention comprises the following steps:
1). glucose and alkylamine are dissolved in methanol solution according to the amount of substance ratio of 1:1.4～1.8, under room temperature, stir 8～10h, be warming up to 50～55 ℃ of reacting by heating 2～3h, suction filtration, acetone soln washing, dehydrated alcohol recrystallization obtains the alkyl glucose amine that logical formula II represents;
2). the alkyl glucose amine that logical formula II represents is dissolved in methanol solution according to the amount of substance ratio of 1:1～1.5 with the positive alkanoic acid that logical formula III represents, under room temperature, react 18～20h, rotary evaporation is removed solution methyl alcohol, add acetone to separate out insolubles, with washing with acetone, rotary evaporation obtains the M15 methanol gasoline hydrotropy water repellent agent that thick logical formula I represents.
M15 methanol gasoline hydrotropy water repellent agent provided by the invention is a class glycosyl surfactant active, be mainly used in M15 methanol gasoline, can be used as resisting phase separation agent and water repellent agent, be applied in M15 methanol gasoline, to improve the resisting phase separation performance of oil product and to improve water repelling property.
M15 methanol gasoline hydrotropy water repellent agent of the present invention has the advantages such as intermiscibility is good, toxicity is little, addition is few, environmental protection, low price.Under same experimental conditions, add 2% additive of the present invention, can make to take the water resisting property of the M15 methanol gasoline that 93# gasoline is formulation of base oil to improve 2 ‰ left and right, with conventional additive comparison, resisting phase separation is effective, large on the stratification temperature impact of system.
Embodiment
Embodiment 1
Get 5g glucose, 7.74g n-Laurylamine, add in 120ml methanol solution, magnetic agitation 8h, is warming up to 51 ℃ of heating and continues reaction 2h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 6.29g after dehydrated alcohol recrystallization.
Get 6.94g N-dodecyl glucosamine, 2.04g positive valeric acid, add in 150ml methanol solution, stirring at normal temperature reaction 18 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 30min after acetone is washed three times obtains thick positive valeric acid (N-dodecyl glucose) ammonium 4.49g.
To the positive valeric acid preparing (N-dodecyl glucose) ammonium (C
23h
47o
5nH
2o) carry out ultimate analysis, measured value is: C:63.10%; H:10.83%; N:3.34%, with calculated value: C:63.39%; H:11.36%; N:3.22% conforms to.
Nucleus magnetic hydrogen spectrum characterization data shows:
1h NMR (600 MHz, D
2o,
ppm): 0.71-0.90 (t, 6H, CH
3), 1.10-1.20 (m, 20H, CH
2), 1.28-1.38 (m, 4H, NH
2-CH
2-
cH 2 ,cO-CH
2-
cH 2 ), 2.10-2.23 (t, 2H, CO-
cH 2 ), 2.50 (m, 2H, NH
2-
cH 2 ), 2.67-2.81 (m, 2H, NH
2), 3.70-4.79 (m, 11H, sugar moieties), has further verified that product structure is positive valeric acid (N-dodecyl glucose) ammonium.
Embodiment 2
Get 5g glucose, 6.22g n-Laurylamine, add in 110ml methanol solution, magnetic agitation 9h, is warming up to 52 ℃ of heating and continues reaction 2.3h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 6.03g after dehydrated alcohol recrystallization.
Get 6.94g N-dodecyl glucosamine, 2.60g positive enanthic acid, add in 150ml methanol solution, stirring at normal temperature reaction 19 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 35min after acetone is washed three times obtains thick positive enanthic acid (N-dodecyl glucose) ammonium 4.77g.
Positive enanthic acid (N-dodecyl glucose) ammonium (C
25h
51o
5nH
2o) ultimate analysis data: calculated value: C:64.74%; H:11.54%; N:3.02%.Measured value: C:65.40%; H:12.60%; N:3.32%.Substantially conform to calculated value.
Nucleus magnetic hydrogen spectrum data:
1h NMR (600 MHz, D
2o,
ppm): 0.72-0.89 (t, 6H, CH
3), 1.10-1.25 (m, 24H, CH
2), 1.28-1.40 (m, 4H, NH
2-CH
2-
cH 2 ,cO-CH
2-
cH 2 ), 2.20-2.29 (t, 2H, CO-
cH 2 ), 2.55 (m, 2H, NH
2-
cH 2 ), 2.70-2.89 (m, 2H, NH
2), 3.90-4.58 (m, 11H, sugar moieties).
Embodiment 3
Get 5g glucose, 6.73g n-Laurylamine, add in 105ml methanol solution, magnetic agitation 8h, is warming up to 50 ℃ of heating and continues reaction 2.5h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 6.19g after dehydrated alcohol recrystallization.
Get 6.94g N-dodecyl glucosamine, 2.32g n-caproic acid, add in 150ml methanol solution, stirring at normal temperature reaction 19 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 35min after acetone is washed three times obtains thick n-caproic acid (N-dodecyl glucose) ammonium 4.63g.
Embodiment 4
Get 5g glucose, 7.25g n-Laurylamine, add in 110ml methanol solution, magnetic agitation 9h, is warming up to 51 ℃ of heating and continues reaction 2h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 6.23g after dehydrated alcohol recrystallization.
Get 6.94g N-dodecyl glucosamine, 1.76g butanic acid, add in 150ml methanol solution, stirring at normal temperature reaction 19 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 30min after acetone is washed three times obtains thick butanic acid (N-dodecyl glucose) ammonium 4.35g.
Embodiment 5
Get 5g glucose, 8.29g n-Laurylamine, add in 125ml methanol solution, magnetic agitation 10h, is warming up to 52 ℃ of heating and continues reaction 2.2h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 6.20g after dehydrated alcohol recrystallization.
Get 6.94g N-dodecyl glucosamine, 1.48g n Propanoic acid, add in 150ml methanol solution, stirring at normal temperature reaction 20 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 30min after acetone is washed three times obtains thick n Propanoic acid (N-dodecyl glucose) ammonium 4.21g.
Embodiment 6
Get 5g glucose, 9.45g cetylamine, add in 125ml methanol solution, magnetic agitation 8.5h, is warming up to 51 ℃ of heating and continues reaction 2.8h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.02g after dehydrated alcohol recrystallization.
Get 8.06g N-hexadecyl glucosamine, 2.04g positive valeric acid, add in 180ml methanol solution, stirring at normal temperature reaction 18.5 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 40min after acetone is washed three times obtains thick positive valeric acid (N-hexadecyl glucose) ammonium 4.85g.
Embodiment 7
Get 5g glucose, 10.12g cetylamine, add in 115ml methanol solution, magnetic agitation 9.5h, is warming up to 52 ℃ of heating and continues reaction 3h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.41g after dehydrated alcohol recrystallization.
Get 8.06g N-hexadecyl glucosamine, 2.60g positive enanthic acid, add in 180ml methanol solution, stirring at normal temperature reaction 19 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 35min after acetone is washed three times obtains thick positive enanthic acid (N-hexadecyl glucose) ammonium 5.12g.
Embodiment 8
Get 5g glucose, 10.79g cetylamine, add in 120ml methanol solution, magnetic agitation 8.5h, is warming up to 51 ℃ of heating and continues reaction 2.5h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.38g after dehydrated alcohol recrystallization.
Get 8.06g N-hexadecyl glucosamine, 1.76g butanic acid, add in 180ml methanol solution, stirring at normal temperature reaction 18.5 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 35min after acetone is washed three times obtains thick butanic acid (N-hexadecyl glucose) ammonium 4.71g.
Embodiment 9
Get 5g glucose, 11.47g cetylamine, add in 115ml methanol solution, magnetic agitation 10h, is warming up to 54 ℃ of heating and continues reaction 2.3h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.58g after dehydrated alcohol recrystallization.
Get 8.06gN-hexadecyl glucosamine, 1.48g n Propanoic acid, add in 180ml methanol solution, stirring at normal temperature reaction 20 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 45min after acetone is washed three times obtains thick n Propanoic acid (N-hexadecyl glucose) ammonium 4.77g.
Embodiment 10
Get 5g glucose, 10.54g octadecylamine, add in 120ml methanol solution, magnetic agitation 10h, is warming up to 53 ℃ of heating and continues reaction 2.5h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.65g after dehydrated alcohol recrystallization.
Get 8.62g N-octadecyl glucosamine, 2.32g n-caproic acid, add in 185ml methanol solution, stirring at normal temperature reaction 20 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 37min after acetone is washed three times obtains thick n-caproic acid (N-octadecyl glucose) ammonium 5.25g.
Embodiment 11
Get 5g glucose, 11.3g octadecylamine, add in 115ml methanol solution, magnetic agitation 9h, is warming up to 54 ℃ of heating and continues reaction 2h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.80g after dehydrated alcohol recrystallization.
Get 8.62g N-octadecyl glucosamine, 2.04g positive valeric acid, add in 185ml methanol solution, stirring at normal temperature reaction 19 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 35min after acetone is washed three times obtains thick positive valeric acid (N-octadecyl glucose) ammonium 4.80g.
Embodiment 12
Get 5g glucose, 12.05g octadecylamine, add in 120ml methanol solution, magnetic agitation 8.5h, is warming up to 53 ℃ of heating and continues reaction 2.6h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.76g after dehydrated alcohol recrystallization.
Get 8.62g N-octadecyl glucosamine, 1.76g butanic acid, add in 185ml methanol solution, stirring at normal temperature reaction 19.5 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 38min after acetone is washed three times obtains thick butanic acid (N-octadecyl glucose) ammonium 4.98g.
Embodiment 13
Get 5g glucose, 12.8g octadecylamine, add in 115ml methanol solution, magnetic agitation 8.5h, is warming up to 50 ℃ of heating and continues reaction 2.4h.Suction filtration, washes twice with acetone solution, obtains N-dodecyl glucosamine 9.89g after dehydrated alcohol recrystallization.
Get 8.62g N-octadecyl glucosamine, 1.48g n Propanoic acid, add in 185ml methanol solution, stirring at normal temperature reaction 18.3 hours, rotary evaporation falls after solution, acetone is separated out insolubles, and rotary evaporation 42min after acetone is washed three times obtains thick n Propanoic acid (N-octadecyl glucose) ammonium 4.85g.
Application examples 1
Glycosyl surfactant active prepared by above-described embodiment 1-13 adds to respectively in M15 methanol gasoline, the water repelling property of rear M15 methanol gasoline is added in test, and compare with blank M15 methanol gasoline and the M15 methanol gasoline that is added with higher alcohols, result is as shown in the table.
As can be seen from the above table, glycosyl surfactant active of the present invention is for the improvement of M15 methanol gasoline water repelling property, the more traditional higher alcohols additive of its water repelling property is effective, when addition is 2%, can make 93# gasoline is water resisting property raising 2 ‰ left and right of the M15 methanol gasoline of formulation of base oil, and Bc is good, and toxicity is little, and cost is low.
By upper table, be it can also be seen that, along with the increase of tensio-active agent carbochain, the water solubilization of its M15 methanol gasoline during as additive has a little to reduce gradually, and the hydrophobicity size of visible additive has certain associated with water solubilization.
Application examples 2
Using n Propanoic acid (the N-dodecyl glucose) ammonium of embodiment 5 and embodiment 1 preparation and positive two kinds of glycosyl surfactant actives of valeric acid (N-dodecyl glucose) ammonium as additive, test adds respectively the stratification temperature of mixed system after the additive of different ratios, investigates the impact of additive on Methanol-gasoline system mutual solubility.
From upper table data, under same experimental conditions, add 1～3% additive of the present invention, the stratification temperature of Methanol-gasoline mixed system significantly reduces with respect to traditional higher alcohols, and what the resisting phase separation Performance Ratio tradition higher alcohols of additive of the present invention will be good is many.
Claims (5)
1. a M15 methanol gasoline hydrotropy water repellent agent, is a kind of glycosyl surfactant active, and its structural formula represents as led to formula I:
Wherein: the odd number that n is 11-17; M=1-5.
2. the preparation method of M15 methanol gasoline hydrotropy water repellent agent described in claim 1, the M15 methanol gasoline hydrotropy water repellent agent that described logical formula I represents is by the alkyl glucose amine that leads to formula II and represent:
The odd number that wherein n is 11-17;
The positive alkanoic acid representing with logical formula III:
CH
3(CH
2)
mCOOH
(Ⅲ)
M=1-5 wherein;
According to 1:(1～1.5) amount of substance than mixing, in methanol solution, normal temperature hybrid reaction is removed solvent methanol after 18～20 hours and is obtained.
3. the preparation method of M15 methanol gasoline hydrotropy water repellent agent according to claim 2, comprises the following steps:
1). by glucose and alkylamine according to 1:(1.4～1.8) amount of substance ratio be dissolved in methanol solution, under room temperature, stir 8～10h, be warming up to 50～55 ℃ of reacting by heating 2～3h, suction filtration, acetone soln washing, dehydrated alcohol recrystallization obtains the alkyl glucose amine that logical formula II represents;
2). the positive alkanoic acid that the alkyl glucose amine that logical formula II represents and logical formula III represent is according to 1:(1～1.5) amount of substance ratio be dissolved in methanol solution, under room temperature, react 18～20h, rotary evaporation is removed solution methyl alcohol, add acetone to separate out insolubles, with washing with acetone, rotary evaporation obtains the M15 methanol gasoline hydrotropy water repellent agent that thick logical formula I represents.
Described in claim 1 M15 methanol gasoline hydrotropy water repellent agent as the application of M15 methanol gasoline resisting phase separation agent.
Described in claim 1 M15 methanol gasoline hydrotropy water repellent agent as the application of M15 methanol gasoline water repellent agent.
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| CN103333721B true CN103333721B (en) | 2014-10-29 |
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Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804389A (en) * | 1985-08-16 | 1989-02-14 | The Lubrizol Corporation | Fuel products |
| US4781730A (en) * | 1987-06-05 | 1988-11-01 | The Lubrizol Corporation | Fuel additive comprising a hydrocarbon soluble alkali or alkaline earth metal compound and a demulsifier |
| US5194639A (en) * | 1990-09-28 | 1993-03-16 | The Procter & Gamble Company | Preparation of polyhydroxy fatty acid amides in the presence of solvents |
| DE4235783A1 (en) * | 1992-10-23 | 1994-04-28 | Basf Ag | Process for the preparation of N-alkanoyl-polyhydroxyalkylamines |
| CN101948396B (en) * | 2010-08-23 | 2012-12-26 | 张延涵 | Polyether amine, production method thereof and application of polyether amine in methanol gasoline |
| CN102329665B (en) * | 2011-09-03 | 2013-06-12 | 陕西延长石油(集团)有限责任公司研究院 | Additive capable of improving water resistance of methanol gasoline |
| CN102344837B (en) * | 2011-09-03 | 2014-05-07 | 西安祺祥能源科技发展有限公司 | Additive for improving resisting phase separation performance and heat value of methanol gasoline |
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Effective date of registration: 20160705 Address after: 030006, Wharton building, 88 development road, 12 hi tech Development Zone, Shanxi, Taiyuan Patentee after: Shanxi alcohol ether cleaning fuel industry technology center (Co., Ltd.) Address before: 030006 Shanxi city of Taiyuan province Jinyang street saiding road high tech Zone Wharton building Patentee before: Shanxi Huadun Industry Co., Ltd. |
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Effective date of registration: 20190717 Address after: Room 410, Office Building, Venous Industry Park, Zhenjiang New District, Jiangsu Province Patentee after: CRPC Innovation Energy Co., Ltd. Address before: 030006, Wharton building, 88 development road, 12 hi tech Development Zone, Shanxi, Taiyuan Patentee before: Shanxi alcohol ether cleaning fuel industry technology center (Co., Ltd.) |