CN110144248A - A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring - Google Patents
A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring Download PDFInfo
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- CN110144248A CN110144248A CN201910526061.4A CN201910526061A CN110144248A CN 110144248 A CN110144248 A CN 110144248A CN 201910526061 A CN201910526061 A CN 201910526061A CN 110144248 A CN110144248 A CN 110144248A
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- depressant
- alcoholysis
- diesel fuel
- phenyl ring
- fuel containing
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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
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
-
- 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
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
-
- 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
- C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of preparation methods of alcoholysis depressant for diesel fuel containing phenyl ring, it is characterized in that, include: step 1: after benzyl methacrylate and maleic anhydride are mixed, initiator progress polymerization reaction is added and obtains benzyl methacrylate-maleic anhydride binary polymer；Step 2: after benzyl methacrylate-maleic anhydride binary polymer and higher alcohols are mixed, catalyst is added and carries out esterification, after reaction, boil off solvent, methanol is added thereto again, precipitating is generated, by gained washing of precipitate, vacuum drying, obtains alcoholysis depressant for diesel fuel containing phenyl ring.Preparation method of the present invention is simple, raw material is cheap and easily-available；It can be effectively improved the low temperature flow of diesel oil, add dosage few, depression effeCt is good.
Description
Technical field
The invention belongs to diesel fuel additives technical field, specially a kind of diesel pour inhibitor and preparation method thereof.
Background technique
With the fast development of Chinese economy, domestic higher and higher to the demand and quality requirement of diesel oil.Petrifaction diesel
Have many advantages, such as combustion powered foot and of reduced contamination, has been widely used in the diesel engine of national transport vehicle.But
It is, since temperature is very low, to result in diesel engine in northern China and some cold districts and often stop working and can not normally transport
Row, greatly affected the efficiency of transport and the life of the people.
Pour-point depressant is called cold flow improver, is a kind of seldom by additional amount but can be effectively improved diesel oil crystallization
The additive of behavior.Currently, the pour-point depressant stability and dispersibility that have been developed that both at home and abroad are poor, depression effeCt also people not to the utmost
Meaning.Therefore, developing a kind of novel pour-point depressant seems particularly necessary.
Summary of the invention
It is an object of the present invention to provide a kind of simple processes, the preparation method of the good diesel pour inhibitor of depression effeCt.
In order to achieve the above object, the present invention provides a kind of preparation method of alcoholysis depressant for diesel fuel containing phenyl ring,
It is characterized in that, comprising:
Step 1: after benzyl methacrylate and maleic anhydride are mixed, initiator progress polymerization reaction is added and obtains methyl
Benzyl acrylate-maleic anhydride binary polymer；
Step 2: after benzyl methacrylate-maleic anhydride binary polymer and higher alcohols are mixed, be added catalyst into
Row esterification boils off solvent, then methanol is added thereto after reaction, generates precipitating, and gained precipitating is washed
It washs, be dried in vacuo, obtain alcoholysis depressant for diesel fuel containing phenyl ring.
Preferably, in the step 1, the molar ratio of benzyl methacrylate and maleic anhydride is 1:0.9-1.1, preferably
1:1.
Preferably, the initiator in the step 1 is benzoyl peroxide, and dosage is maleic anhydride and metering system
The 0.9~1.2% of acid benzyl ester gross mass.
Preferably, the polymerization reaction in the step 1 carries out in solvent toluene.
Preferably, the polymerization reaction in the step 1 is 85~95 DEG C, and the reaction time is 7~9h.
Preferably, the higher alcohols in the step 2 are tetradecyl alchohol, hexadecanol or octadecyl alcolol.
Preferably, the catalyst in the step 2 is p-methyl benzenesulfonic acid；Its dosage is benzyl methacrylate-Malaysia
The 1~2% of acid anhydrides binary polymer and higher alcohols gross mass.
Preferably, the molar ratio of the higher alcohols in the step 2 and maleic anhydride is 1.8-2.2:1.
Preferably, the esterification in the step 2 carries out in solvent xylene.
Preferably, the esterification reaction temperature be 150~160 DEG C, the reaction time be 20~for 24 hours.
Preferably, the vacuum drying temperature in the step 2 is 60 DEG C.
Compared with prior art, the beneficial effects of the present invention are:
(1) the designed diesel fuel additives (alcoholysis type binary pour-point depressant) synthesized of the present invention is binary polymer, required original
Expect that type is less, cheap, simple production process；Preparation method of the present invention is simple, raw material is cheap and easily-available；Obtaining pour-point depressant can
It is effectively improved the low temperature flow of diesel oil, adds dosage few, depression effeCt is good.
(2) the designed diesel fuel additives synthesized can preferably improve the low temperature flow of diesel oil, especially can substantially drop
The condensation point and cold filter plugging point of low diesel oil；
(3) the designed diesel fuel additives dosage synthesized is few, and a small amount of addition can reach optimum efficiency.
Detailed description of the invention
Fig. 1 is the nucleus magnetic hydrogen spectrum of the alcoholysis depressant for diesel fuel containing phenyl ring obtained in embodiment 1；
Fig. 2 is the nucleus magnetic hydrogen spectrum of the alcoholysis depressant for diesel fuel containing phenyl ring obtained in embodiment 2；
Fig. 3 is the nucleus magnetic hydrogen spectrum of the alcoholysis depressant for diesel fuel containing phenyl ring obtained in embodiment 3.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Used each raw material is commercial product in following embodiment.
The measurement method of condensation point and cold filter plugging point is respectively according to " GB/T510-83 petroleum products questionable points measurement in the present invention
Method " and " SH/T0248-2006 diesel oil and domestic heating oil cold filter plugging point measuring method " progress.
Embodiment 1
A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring, specific steps are as follows:
(1) 17.62g benzyl methacrylate and 9.81g maleic anhydride are added to after being mixed in three-necked flask, are added
0.28g benzoyl peroxide is added in 35ml toluene under nitrogen atmosphere.System is warming up to 90 DEG C, carries out polymerization reaction 8h；Decompression
Solvent is boiled off, then methanol is added thereto, generates precipitating, filtering washs the precipitating with excessive methanol, 60 DEG C of vacuum
It is dry, obtain benzyl methacrylate-maleic anhydride binary polymer；
(2) 10g benzyl methacrylate-maleic anhydride binary polymer and 15.63 tetradecyl alchohols is taken to be added to three-necked flask
After middle mixing, 35ml dimethylbenzene is added, 0.38g catalyst p-methyl benzenesulfonic acid is added, is warming up to 150 DEG C of progress esterification 20h.
After reaction, solvent is boiled off, then methanol is added thereto, generates precipitating, filtering, by the excessive first of the precipitating
Alcohol washing, 60 DEG C of vacuum drying, obtain alcoholysis depressant for diesel fuel containing phenyl ring, nucleus magnetic hydrogen spectrum is shown in that Fig. 1, molecular weight are shown in Table 1.
Table 1: the gel chromatography analysis of additive
Embodiment 2
A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring, specific steps are as follows:
(1) 17.62g benzyl methacrylate and 9.81g maleic anhydride are added to after being mixed in three-necked flask, are added
0.28g benzoyl peroxide is added in 35ml toluene under nitrogen atmosphere.System is warming up to 90 DEG C, carries out polymerization reaction 8h；Decompression
Solvent is boiled off, then methanol is added thereto, generates precipitating, filtering washs the precipitating with excessive methanol, 60 DEG C of vacuum
It is dry, obtain benzyl methacrylate-maleic anhydride binary polymer；
(2) 10g benzyl methacrylate-maleic anhydride binary polymer and 17.68g hexadecanol is taken to be added to three-necked flask
After middle mixing, 35ml dimethylbenzene is added, 0.41g catalyst p-methyl benzenesulfonic acid is added, is warming up to 150 DEG C of progress esterification 22h.
After reaction, solvent is boiled off, then methanol is added thereto, generates precipitating, filtering, by the excessive first of the precipitating
Alcohol washing, 60 DEG C of vacuum drying, obtain alcoholysis depressant for diesel fuel containing phenyl ring, nucleus magnetic hydrogen spectrum is shown in that Fig. 2, molecular weight are shown in Table 2.
Table 2: the gel chromatography analysis of additive
Embodiment 3
A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring, specific steps are as follows:
(1) 17.62g benzyl methacrylate and 9.81g maleic anhydride are added to after being mixed in three-necked flask, are added
0.28g benzoyl peroxide is added in 35ml toluene under nitrogen atmosphere.System is warming up to 90 DEG C, carries out polymerization reaction 8h；Decompression
Solvent is boiled off, then methanol is added thereto, generates precipitating, filtering washs the precipitating with excessive methanol, 60 DEG C of vacuum
It is dry, obtain benzyl methacrylate-maleic anhydride binary polymer；
(2) 10g benzyl methacrylate-maleic anhydride binary polymer and 19.73g octadecyl alcolol is taken to be added to three-necked flask
After middle mixing, 35ml dimethylbenzene is added, 0.45g catalyst p-methyl benzenesulfonic acid is added, is warming up to 150 DEG C of progress esterification 23h.
After reaction, solvent is boiled off, then methanol is added thereto, generates precipitating, filtering, by the excessive first of the precipitating
Alcohol washing, 60 DEG C of vacuum drying, obtain alcoholysis depressant for diesel fuel containing phenyl ring, nucleus magnetic hydrogen spectrum is shown in that Fig. 3, molecular weight are shown in Table 3.
Table 3: the gel chromatography analysis of additive
Embodiment 4
Application of one of above-described embodiment 1-3 diesel fuel additives in diesel oil pour point depression, diesel fuel additives is in diesel oil
Additive amount be preferably 500ppm/kg, diesel fuel additives is added to after being mixed evenly at 40-50 DEG C in diesel oil, ultrasound
Disperse 15-20min to get the diesel oil containing the additive.
The cold filter plugging point of the resulting diesel oil containing above-mentioned diesel fuel additives of above-described embodiment and condensation point variation are shown in after tested
Following table.
| Embodiment 1 | Embodiment 2 | Embodiment 3 | |
| △SP(℃) | 18 | 16 | 11 |
| △CFPP(℃) | 7 | 5 | 3 |
Note: SP: condensation point, CFPP: cold filter plugging point
Above content is only the basic explanation under present inventive concept, and that technical solution according to the present invention is done is any etc.
Effect transformation, is within the scope of protection of the invention.
Claims (10)
1. a kind of preparation method of alcoholysis depressant for diesel fuel containing phenyl ring characterized by comprising
Step 1: after benzyl methacrylate and maleic anhydride are mixed, initiator progress polymerization reaction is added and obtains metering system
Acid benzyl ester-maleic anhydride binary polymer；
Step 2: after benzyl methacrylate-maleic anhydride binary polymer and higher alcohols are mixed, catalyst is added and carries out ester
Change reaction, after reaction, boil off solvent, then methanol is added thereto, generate precipitate, by gained washing of precipitate,
Vacuum drying, obtains alcoholysis depressant for diesel fuel containing phenyl ring.
2. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
In 1, the molar ratio of benzyl methacrylate and maleic anhydride is 1:0.9-1.1.
3. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
Initiator in 1 is benzoyl peroxide, and dosage is the 0.9~1.2% of maleic anhydride and benzyl methacrylate gross mass.
4. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
Polymerization reaction in 1 carries out in solvent toluene.
5. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
Polymerization reaction in 1 is 85~95 DEG C, and the reaction time is 7~9h.
6. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
Higher alcohols in 2 are tetradecyl alchohol, hexadecanol or octadecyl alcolol.
7. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
Catalyst in 2 is p-methyl benzenesulfonic acid；Its dosage is benzyl methacrylate-maleic anhydride binary polymer and the total matter of higher alcohols
The 1~2% of amount.
8. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
The molar ratio of higher alcohols and maleic anhydride in 2 is 1.8-2.2:1.
9. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the step
Esterification in 2 carries out in solvent xylene.
10. the preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring as described in claim 1, which is characterized in that the ester
Change reaction temperature be 150~160 DEG C, the reaction time be 20~for 24 hours.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910526061.4A CN110144248A (en) | 2019-06-18 | 2019-06-18 | A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring |
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| CN201910526061.4A CN110144248A (en) | 2019-06-18 | 2019-06-18 | A kind of preparation method of the alcoholysis depressant for diesel fuel containing phenyl ring |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530305A (en) * | 2014-12-01 | 2015-04-22 | 上海应用技术学院 | Diesel oil pour-point depressant and preparation method and application thereof |
| CN106279514A (en) * | 2016-08-15 | 2017-01-04 | 上海应用技术学院 | A kind of preparation method of diesel pour inhibitor |
| CN107189000A (en) * | 2017-06-21 | 2017-09-22 | 上海应用技术大学 | A kind of polyaryl alcoholysis type ter-polymers diesel pour inhibitor and preparation method thereof |
-
2019
- 2019-06-18 CN CN201910526061.4A patent/CN110144248A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530305A (en) * | 2014-12-01 | 2015-04-22 | 上海应用技术学院 | Diesel oil pour-point depressant and preparation method and application thereof |
| CN106279514A (en) * | 2016-08-15 | 2017-01-04 | 上海应用技术学院 | A kind of preparation method of diesel pour inhibitor |
| CN107189000A (en) * | 2017-06-21 | 2017-09-22 | 上海应用技术大学 | A kind of polyaryl alcoholysis type ter-polymers diesel pour inhibitor and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| HEMANT P. SONI, ET AL: "Performance-based designing of wax crystal growth inhibitors", 《ENERGY & FUELS》 * |
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