CN106281509A - A kind of novel PIBA as gasoline cleaning agent and synthetic method thereof - Google Patents
A kind of novel PIBA as gasoline cleaning agent and synthetic method thereof Download PDFInfo
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- CN106281509A CN106281509A CN201610761445.0A CN201610761445A CN106281509A CN 106281509 A CN106281509 A CN 106281509A CN 201610761445 A CN201610761445 A CN 201610761445A CN 106281509 A CN106281509 A CN 106281509A
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- piba
- novel
- cleaning agent
- synthetic method
- gasoline cleaning
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/04—Liquid carbonaceous fuels essentially based on blends of hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/22—Function and purpose of a components of a fuel or the composition as a whole for improving fuel economy or fuel efficiency
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2270/00—Specifically adapted fuels
- C10L2270/02—Specifically adapted fuels for internal combustion engines
- C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines
Abstract
The present invention relates to a kind of novel PIBA as gasoline cleaning agent and synthetic method thereof, described PIBA can be represented by following formula: in formula, and n is the number of repeat unit of polyisobutylene segment；X is the organic group of amino-contained.PIBA of the present invention is prepared through Friedel Crafts alkylated reaction one step with amido benzene by high-activity polyisobutene, synthesis technique is simple, production cost is low, product yield is high, avoid tradition PIBA production technology high pressure and the use of noble metal catalyst, have a good application prospect.
Description
Technical field
The present invention relates to a kind of novel PIBA as gasoline cleaning agent and synthetic method thereof, belong to petrochemical industry neck
Territory.
Background technology
At present, in China's motor petrol, olefin(e) centent higher (olefin(e) centent is 30～50%), sends out far above American-European-Japanese grade
Reach country's motor petrol standard.Owing to engine nozzle, air inlet valve position operating temperature are higher, the alkene (especially two in gasoline
Alkene) etc. unstable component easily there is oxidation and condensation reaction, and under the common effect of other impurity in the oil, finally with
The form of carbon distribution is deposited on electromotor key position.The existence of carbon distribution can cause gasoline combustion process to deteriorate, oil consumption increases, starts
Acc power and hydraulic performance decline, exhaust pollutant discharge increase, be a major reason of Present Domestic haze weather generation.Prevent
The effective ways of carbon distribution are to add detersive in the oil.
Gasoline cleaning agent is the surfactant of a kind of pbz polymer organic amine compound, can be aoxidizing shape in gasoline
Become potential deposit breakup or be solubilized in gasoline, stop them to be deposited on petrolic fuel nozzle, intake valve etc.
Key position.The deposit that these positions have been formed, they can be stripped down by detersive from metal surface, point
Dissipate, peptization in gasoline, improve automobile engine combustion system situation, reduce the hydro carbons in motor vehicle exhaust emission, carbon monoxide
Deng harmful substance, thus play minimizing discharge, save maintenance cost and the positive role of fuel-economizing.
PIBA is one of gasoline cleaning agent of developing in recent years, and this kind of detersive adds in gasoline not only can be controlled
The generation of gasoline engine low-temperature components deposit processed, and to removing and suppressing the high temperature site deposition things such as intake valve highly effective.
Joining in gasoline, fuel system can be suppressed to be internally generated deposit, that can remove rapidly again that fuel system generated is heavy
Long-pending thing, so that it is guaranteed that engine power performance normally plays, extends the defects liability period of fuel system.
More to the study on the synthesis of PIBA, United States Patent (USP) US4832702 high-activity polyisobutene is big at 280
Carrying out catalytic carboxylation reaction under air pressure conditions and generate polyisobutylene alcohol, under 120 atmospheric pressure, ammonolysis generates polyisobutylene
Amine.The method technique is simple, and product yield is high, but need to use high pressure reactor, invests bigger.
The Dong Limei of United States Patent (USP) US5346965, US5508356 and China uses chloridising to produce PIBA.First
First polyisobutylene leads to chlorine and carries out substitution reaction generation chlorination polyisobutylene, and then amine solution generates PIBA.Use chlorination
It is simple that method prepares PIBA technique, but remains a small amount of chlorine the most in the product, easily causes to environment two
Secondary pollution.
United States Patent (USP) US5567845, US5124484 utilize hydrogen formyl reaction to prepare PIBA, production process
In do not use the Cl that toxicity is bigger2, the most chloride in product, but reaction needs noble metal to make catalyst and must be the highest
Pressure under just can carry out, reaction system viscosity is the biggest, it is difficult to realize the regeneration of catalyst.
Summary of the invention
It is an object of the invention to overcome the deficiencies in the prior art, it is provided that a kind of production technology is simple, low cost, pollution
The novel PIBA gasoline cleaning agent that little, using effect is good.
PIBA of the present invention can be represented by logical formula (II),
In formula (II), n=10～40；X is the one in following groups:
—NH(CH2CH2NH)mH, m=0～2 or
—O(CH2CH2NH)m’H, m '=0～2 or
—N(CH2CH2NH2)2Or
—NHCH2CH2OH or
—N(CH2CH2OH)2Or
—NHCH(CH3) OH or
—NHCH(CH3)NH2Or
PIBA of the present invention by high-activity polyisobutene and amido benzene through Friedel-Crafts alkylated reaction one
Step synthesis, step is as follows:
Amido benzene, high-activity polyisobutene and catalyst are added by the mol ratio of 0.8～1.2:0.8～1.2:0.1～0.3
Enter in enamel reaction still, then add aromatic solvent, then with the air in nitrogen replacement reaction kettle, be warming up to 150～170 DEG C instead
Answer 5～10 hours；It is cooled to room temperature after having reacted, adds demulsifier, then neutralize with excess NaOH or KOH and be washed to pH=
8～10, anhydrous Na2SO4Being dried, filter, filtrate i.e. obtains PIBA through decompression distillation desolvation and other low-boiling-point substances.
Reaction equation is as follows:
Described high-activity polyisobutene end amount vinyl content >=70%, molecular weight is 800～2000.
Described amido benzene represents by logical formula (I):
In formula, X is the one in following groups:
—NH(CH2CH2NH)mH, m=0～2 or
—O(CH2CH2NH)m’H, m '=0～2 or
—N(CH2CH2NH2)2Or
—NHCH2CH2OH or
—N(CH2CH2OH)2Or
—NHCH(CH3) OH or
—NHCH(CH3)NH2Or
Further, preferred reactant mol ratio is amido benzene: high-activity polyisobutene: catalyst=1:1:0.2.
Further, described catalyst is lewis acid or organic acid, preferably boron trifluoride diethyl etherate or trifluoromethanesulfonic acid.
Further, described aromatic solvent is mixed trimethylbenzene or heavy aromatics, and its consumption is the 2 of reactant amido benzene weight
～4 times.
Further, described reaction temperature is 150～170 DEG C, preferably 160 DEG C.
Further, described demulsifier is polyoxyethylene polyoxypropylene polyethers or butanol, and consumption is reactant gross weight
0.2～1.0%.
Further, described decompression distillation condition is vacuum 0.1MPa, temperature 80～120 DEG C.
The present invention compared with prior art has following prominent substantive distinguishing features and a marked improvement:
PIBA of the present invention by high-activity polyisobutene and amido benzene through Friedel-Crafts alkylated reaction one
Step synthesis, synthesis technique is simple, production cost is low, product yield is high, and it is high to avoid tradition PIBA production technology
Pressure and the use of precious metal catalyst, be advantageously implemented large-scale production, reduces production cost, has good economic effect
Benefit.
PIBA of the present invention is added in commercially available gasoline, can not only suppress and clean automobile engine fuel oil and enter
The atomizer of gas system, the carbon distribution of intake valve, and deposit when can also significantly reduce burning, reduce gasoline consumption, extends
Service life of aeroengine, reduces motor vehicle exhaust emission, has important using value.Continuous increasing along with China's automobile pollution
Length, the enhancing of people's awareness of saving energy and the attention to environmental protection, product of the present invention will have the wide market demand.
Detailed description of the invention
The present invention is described in further detail by following example, but the technology contents described in the present embodiment is illustrative, and
It not determinate, should not limit to protection scope of the present invention according to this.
Example 1
By 93 grams of aniline, 1000 grams of high-activity polyisobutenes (molecular weight 1000), 30 grams of boron trifluoride diethyl etherate and 300 milliliters
Mixed trimethylbenzene joins in enamel reaction still, with the air in nitrogen replacement reaction kettle, is warming up to 150 DEG C and stirs 8 hours.Reaction
It is cooled to room temperature after completing, adds 8 grams of butanol, neutralize and be washed to pH=8～10, anhydrous Na with excess NaOH2SO4It is dried, mistake
Filter, filtrate decompression distillation desolvation and other low-boiling-point substances obtain product 1028 grams.
Example 2
By 137 grams of N-phenylethanol amines, 1000 grams of high-activity polyisobutenes (molecular weight 1000), 40 grams of boron trifluoride diethyl etherate
Join in enamel reaction still with 450 milliliters of heavy aromatics, with the air in nitrogen replacement reaction kettle, be warming up to 170 DEG C of stirrings 10
Hour.It is cooled to room temperature after having reacted, adds 15 grams of polyoxyethylene polyoxypropylene polyethers, neutralize with excess NaOH and be washed to
PH=8～10, anhydrous Na2SO4Being dried, filter, filtrate decompression distillation desolvation and other low-boiling-point substances obtain product 1095 grams.
Example 3
By 137 grams of N-phenylethylenediamines, 1000 grams of high-activity polyisobutenes (molecular weight 1000), 30 grams of boron trifluoride diethyl etherate
Join in enamel reaction still with 350 milliliters of mixed trimethylbenzenes, with the air in nitrogen replacement reaction kettle, be warming up to 160 DEG C of stirrings 8
Hour.It is cooled to room temperature after having reacted, adds 10 grams of butanol, neutralize and be washed to pH=8～10 with excess KOH, anhydrous
Na2SO4Being dried, filter, filtrate decompression distillation desolvation and other low-boiling-point substances obtain product 1082 grams.
Example 4
93 grams of aniline, 2000 grams of high-activity polyisobutenes (molecular weight 2000), 25 grams of trifluoromethanesulfonic acid and 500 milliliters are mixed
Trimethylbenzene joins in enamel reaction still, with the air in nitrogen replacement reaction kettle, is warming up to 160 DEG C and stirs 6 hours.React
It is cooled to room temperature after one-tenth, adds 10 grams of polyoxyethylene polyoxypropylene polyethers, neutralize and be washed to pH=8～10 with excess NaOH,
Anhydrous Na2SO4Being dried, filter, filtrate decompression distillation desolvation and other low-boiling-point substances obtain product 2034 grams.
Example 5
By 162 grams of N-phenyldiethanol-amines, 2000 grams of high-activity polyisobutenes (molecular weight 2000), 30 grams of trifluoromethanesulfonic acid
Join in enamel reaction still with 500 milliliters of mixed trimethylbenzenes, with the air in nitrogen replacement reaction kettle, be warming up to 160 DEG C of stirrings 8
Hour.It is cooled to room temperature after having reacted, adds 6 grams of butanol, neutralize and be washed to pH=8～10 with excess NaOH, anhydrous
Na2SO4Being dried, filter, filtrate decompression distillation desolvation and other low-boiling-point substances obtain product 2087 grams.
Example 6
By 180 grams of N-phenylpiperazines, 1000 grams of high-activity polyisobutenes (molecular weight 1000), 40 grams of trifluoromethanesulfonic acid and
500 milliliters of mixed trimethylbenzenes join in enamel reaction still, with the air in nitrogen replacement reaction kettle, are warming up to 150 DEG C of stirrings 5 little
Time.It is cooled to room temperature after having reacted, adds 9 grams of polyoxyethylene polyoxypropylene polyethers, neutralize with excess NaOH and be washed to pH
=8～10, anhydrous Na2SO4Being dried, filter, filtrate decompression distillation desolvation and other low-boiling-point substances obtain product 1057 grams.
Example 7 performance test
By 300ppm, examples detailed above 1～6 products obtained therefrom is added dosage add in commercially available 92# gasoline, carry out gasoline clear
Clean performance test, result is as follows:
PIBA of the present invention can be by endoscopic visualisation to the cleaning effect of electromotor: first by the unused mistake of endoscopic observation
The carbon deposit situation of the inlet valve of automobile engine of detersive, atomizer and piston face, then fills and has added the poly-isobutyl of the present invention
The gasoline of alkene, carries out splanchnoscopy after gasoline is run through again.Found that inlet valve, atomizer and piston face previously covered
Carbon deposit come off the most in a large number, and have obvious metallic luster, show detersive of the present invention to inlet valve of automobile engine, atomizer and
Piston has good cleaning and clean-keeping function.
Saving energy test uses MA-2018 fuel oil consumption test instrument, by GB/T12545 " automotive fuel wastage test method "
Carry out, the results are shown in Table 1.In table, data display rate of economizing gasoline is 1～3%, shows that adding PIBA of the present invention in the oil has
Certain oil-saving effect.
Exhaust emission testing is carried out by GB18352.3-2005 " light-duty vehicle pollutant emission limit and measuring method ", knot
Fruit is shown in Table 1.In table, data display adds after PIBA of the present invention, and vehicle exhaust major pollutants index HC, CO, NOx are equal
It is decreased obviously, illustrates that PIBA of the present invention can effectively control the discharge of automobile exhaust pollution thing.
Table 1 PIBA gasoline detergent measure of merit
Table 1 data display that detersive of the present invention reaches the using effect of the most presently commercially available gasoline cleaning agent.
Claims (10)
1. the synthetic method of the novel PIBA being used as gasoline cleaning agent, it is characterised in that step is as follows:
Amido benzene, high-activity polyisobutene and catalyst are joined by the mol ratio of 0.8～1.2:0.8～1.2:0.1～0.3
In reactor, then add aromatic solvent, then with the air in nitrogen replacement reaction kettle, be warming up to 150～170 DEG C of stirrings 5～10
Hour；It is then cooled to room temperature, adds demulsifier, then neutralize and be washed to pH=8～10, anhydrous Na with NaOH or KOH2SO4Dry
Dry, to filter, filtrate obtains PIBA through decompression distillation desolvation and other low-boiling-point substances.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Described amido benzene represents by logical formula (I):
In formula, X is the one in following groups:
—NH(CH2CH2NH)mH, m=0～2 or
—O(CH2CH2NH)m’H, m '=0～2 or
—N(CH2CH2NH2)2Or
—NHCH2CH2OH or
—N(CH2CH2OH)2Or
—NHCH(CH3) OH or
—NHCH(CH3)NH2Or
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
End amount vinyl content >=70% of described high-activity polyisobutene, molecular weight is 800～2000.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Described catalyst is lewis acid or organic acid.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Described catalyst is boron trifluoride diethyl etherate or trifluoromethanesulfonic acid.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Reactant molar ratio is amido benzene: high-activity polyisobutene: catalyst=1:1:0.2.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Described aromatic solvent is mixed trimethylbenzene or heavy aromatics, and its consumption is 2～4 times of amido benzene weight.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Described demulsifier is polyoxyethylene polyoxypropylene polyethers or butanol, and consumption is the 0.2～1.0% of reactant gross weight.
The synthetic method of the novel PIBA as gasoline cleaning agent the most according to claim 1, it is characterised in that
Described decompression distillation condition is vacuum 0.1MPa, and temperature is 80～120 DEG C.
10., according to the novel PIBA as gasoline cleaning agent described in claim 1～9 any claim, it is special
Levying and be, described PIBA can be represented by logical formula (II),
In formula (I), between n value 10～40；X is the one in following groups:
—NH(CH2CH2NH)mH, m=0～2 or
—O(CH2CH2NH)m’H, m '=0～2 or
—N(CH2CH2NH2)2Or
—NHCH2CH2OH or
—N(CH2CH2OH)2Or
—NHCH(CH3) OH or
—NHCH(CH3)NH2Or
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|---|---|---|---|
| CN201610761445.0A CN106281509B (en) | 2016-08-30 | 2016-08-30 | A kind of novel polyisobutylene amine and its synthetic method as gasoline cleaning agent |
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|---|---|---|---|
| CN201610761445.0A CN106281509B (en) | 2016-08-30 | 2016-08-30 | A kind of novel polyisobutylene amine and its synthetic method as gasoline cleaning agent |
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| CN106281509B CN106281509B (en) | 2018-10-12 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1646575A (en) * | 2002-04-05 | 2005-07-27 | 巴斯福股份公司 | Polyisobutenamines |
| CN1768109A (en) * | 2003-04-01 | 2006-05-03 | 巴斯福股份公司 | Polyalkene amines with improved applicational properties. |
| CN101260329A (en) * | 2008-04-18 | 2008-09-10 | 东南大学 | Special-purpose polyisobutene amine for gasoline and diesel oil clean dispersing agent and preparation method thereof |
| CN101659717A (en) * | 2009-09-18 | 2010-03-03 | 济南开发区星火科学技术研究院 | Benzoyl polyisobutene amine for gasoline detergent and preparation method |
-
2016
- 2016-08-30 CN CN201610761445.0A patent/CN106281509B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1646575A (en) * | 2002-04-05 | 2005-07-27 | 巴斯福股份公司 | Polyisobutenamines |
| CN1768109A (en) * | 2003-04-01 | 2006-05-03 | 巴斯福股份公司 | Polyalkene amines with improved applicational properties. |
| CN101260329A (en) * | 2008-04-18 | 2008-09-10 | 东南大学 | Special-purpose polyisobutene amine for gasoline and diesel oil clean dispersing agent and preparation method thereof |
| CN101659717A (en) * | 2009-09-18 | 2010-03-03 | 济南开发区星火科学技术研究院 | Benzoyl polyisobutene amine for gasoline detergent and preparation method |
Non-Patent Citations (1)
| Title |
|---|
| 张成龙: "异丁烯控制阳离子聚合及制备芳胺端基官能化聚异丁烯的研究", 《全国博士学位论文全文数据库（电子期刊） 工程科技Ⅰ辑》 * |
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