CN1245207A - Composition as improver for improving flowability of diesel oil - Google Patents
Composition as improver for improving flowability of diesel oil Download PDFInfo
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- CN1245207A CN1245207A CN 98103578 CN98103578A CN1245207A CN 1245207 A CN1245207 A CN 1245207A CN 98103578 CN98103578 CN 98103578 CN 98103578 A CN98103578 A CN 98103578A CN 1245207 A CN1245207 A CN 1245207A
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Abstract
A composition of flow improver additive diesel oil contains polyethylene-ethyl acetate whose number-average molecular weight is 1000-2500, and C6-C22 alkylmonoester or biester derivatives chosen from C6-C22 alkyl ester and maleic anhydride copolymer or their mixture, whose number-average molecular weight is 500-10000, in weight ratio of 1 : (0.1-10). Said composition has obvious coagulation depressing effect and filtering effect to high-wax narrow-fraction diesel oil.
Description
The present invention relates to be used for compositions of additives diesel oil, that contain nitrogen, two kinds of elements of oxygen, exactly relate to a kind of composition as improver for improving flowability of diesel oil.
The alkane that contains various different carbon numbers in the diesel oil, wherein what of long-chain n-praaffin have a significant impact the low temperature flowability of oil product.When temperature reduced, normal paraffin came out with the isolated in form of plate crystal, and interact to form tridimensional network liquid oils is wrapped up, and made that the viscosity of oil product increases, flowing property descends.This phenomenon can cause the oil circuit filter screen to stop up, and influences vehicle and normally uses, and also can influence the accumulating and the loading and unloading of diesel oil.
As everyone knows, these problems can be alleviated by add FLOW IMPROVERS in diesel oil.Diesel flow improver not only can improve the low temperature flowability of diesel oil, make diesel oil in low temperature environment, be able to normal use, and to improve refinery's production handiness, save tempered oil, aspects such as volume increase solar oil are all significant, therefore are subjected to extensive attention industrial.
Diesel flow improver generally all is the polymkeric substance that contains the ethylenical unsaturated double bonds compound, as ethene, propylene, alpha-olefin, vinyl acetate, (methyl) acrylate, α, the polymkeric substance of β-unsaturated dicarboxylic acid or acid anhydrides, vinylbenzene etc., and the composition of the polar derivative of polymkeric substance and various polymkeric substance.The carbon number distribution that has been found that in the diesel oil positive structure hydrocarbon content and positive structure hydrocarbon is to the pour point depression of diesel flow improver and fall the filter effect and have a significant impact.In general, positive structure hydrocarbon content is few in the diesel oil, and cut is wide, and then diesel oil is good to the susceptibility of FLOW IMPROVERS, and present most of FLOW IMPROVERS all only are applicable to above-mentioned diesel oil, are positive structure hydrocarbon content height, the narrow diesel oil of cut and be not suitable for wax content.
The multipolymer of ethene and unsaturated ester, as US3,048,479 disclosed polyethylene vinyl acetate ester (EVA) is to use at present more a kind of diesel flow improver, but it is to 0 of the narrow diesel oil of wax content height, cut such as China
#Diesel oil can only reduce condensation point, can not reduce cold filter clogging temperature.
US4,663,491, the disclosed alkyl acrylate-copolymer-maleic anhydride of CN1102416A has certain filter effect of falling, but inoperative to condensation point.
" maleic anhydride copolymer reduces the research of cold filter point of diesel oil " literary composition that " petroleum journal (refining of petroleum) " the 12nd volume the 4th periodical is stepped on reported the amide derivatives of alkyl acrylate-copolymer-maleic anhydride synthetic and pour point depression, the filter effect is fallen.Claim in the literary composition that this agent is good to the wide diesel oil susceptibility of cut, and do not mention effect the narrow diesel oil of cut.
US5,178,641 disclose polyethylene vinyl acetate ester (EVA) and the acid amides of alkyl acrylate-copolymer-maleic anhydride or the composition of ammonium salt (AMA), and wherein the number-average molecular weight of AMA is 5000 ~ 25000.Because the AMA molecular weight is higher, EVA and AMA do not dissolve each other, thereby AMA need be grafted on the EVA, have increased operation steps.Simultaneously, nitrogenous additive can cause certain pollution to environment.
The objective of the invention is to based on prior art, overcome its defective, provide a kind of and can reduce cold filter clogging temperature, can reduce the composition as improver for improving flowability of diesel oil of condensation point again.
Composition as improver for improving flowability of diesel oil provided by the invention comprises following component:
(A) number-average molecular weight is polyethylene-vinyl acetate ester of 1000 ~ 2500;
(B) number-average molecular weight be 500 ~ 10000 be selected from vinylformic acid C
6~ C
22The C of alkyl ester and copolymer-maleic anhydride
6~ C
22A kind of or its mixture in alkyl monoester or the diester derivatives.
Wherein (A) and weight ratio (B) are 1: 0.1 ~ 10.
Said component (A) is present widely used polyethylene vinyl acetate ester diesel flow improver, can buy from market, also can be according to US3, and 048,479 or other pertinent literature disclosed method self-control.The number-average molecular weight of polyethylene vinyl acetate ester can be 1000 ~ 2500, preferred 1500 ~ 2000.
Said component (B) is the monoesters of alkyl acrylate and copolymer-maleic anhydride or the derivative of dibasic acid esters, also can be their mixture.Wherein, the alkyl in the alkyl acrylate can be C
6~ C
22, preferred C
10~ C
20, C preferably
12~ C
18Alkyl, and straight chain linear alkyl preferably.Dodecylacrylate for example, tetradecyl ester, cetyl ester, stearyl or its mixture.The ester group that links to each other with maleic anhydride in the monoesters of said multipolymer or the diester derivatives can be C
6~ C
22, preferred C
8～C
20, C preferably
10~ C
18Straight chained alkyl monoesters or dibasic acid esters.The molecular weight of multipolymer can be 500 ~ 10000, preferred 1000 ~ 8000.
The preparation of alkyl acrylate and copolymer-maleic anhydride can be with reference to US 4,663, and 491, CN1102416A and US 5,187,641 documents such as grade.Generally be under the initiator effect that can produce free radical, alkyl acrylate and maleic anhydride to be carried out the free radical solution polymerization reaction.Used initiator can be superoxide or azo compound, as ditertiary butyl peroxide, Diisopropyl azodicarboxylate etc.The consumption of initiator generally is 0.5 ~ 2% of alkyl acrylate and a maleic anhydride gross weight.Said solvent can be that toluene, dimethylbenzene, ethylbenzene, normal hexane, hexanaphthene etc. also can be the aromatic hydrocarbons thinning oils as the described solvent of CN1102416A, and boiling range is 159 ~ 185 ℃, and the latter is preferred.Solvent load generally is 30 ~ 150% of a monomer material gross weight.The mol ratio of alkyl acrylate and maleic anhydride can be 1: 0.25 ~ 2 in the reactant, preferred 1: 0.5 ~ 1.The feed way of reactant can be once all to add, also can be that the alkyl acrylate that reactive behavior is high adds in batches, specific practice is to contain the mixed solution of solvent of alkyl acrylate, initiator and 20 ~ 70% per hour to add 40 ~ 100% of total amount, preferred 50 ~ 80% feed rate joins in the reaction system that contains maleic anhydride and 30 ~ 80% solvents, and then back flow reaction 2～7 hours.
Reaction can not treatedly directly be carried out esterification after finishing.
The monoester derivates of multipolymer can synthesize as follows, in solvent, alkyl acrylate-copolymer-maleic anhydride and at least a positive structure alkanol pressed the mixed in molar ratio of maleic anhydride and positive structure alkanol 1: 0.5 ~ 1, be heated to 100 ~ 200 ℃, reacted 4 ~ 5 hours.
The diester derivatives of multipolymer can synthesize as follows: the mixed in molar ratio of alkyl acrylate-copolymer-maleic anhydride and at least a positive structure alkanol being pressed maleic anhydride and positive structure alkanol 1: 1 ~ 2 in solvent, the tosic acid that adds weight again and be multipolymer and positive structure alkanol gross weight 1.5% is as catalyzer, be heated to 100 ~ 200 ℃, reacted 4 ~ 5 hours.After reaction finishes, be the calcium oxide neutralization of 1.5 times of tosic acid, use the diatomite suction filtration while hot with weight.
In above-mentioned copolymer derivative synthetic, the solvent that said solvent uses when being selected from synthetic copolymer, as toluene, dimethylbenzene, ethylbenzene etc., the preferred aromatic hydrocarbons thinning oil, said positive structure alkanol is C
6~ C
22Positive structure alkanol, preferred C
8～C
20, C preferably
10~ C
18Positive structure alkanol.For the ease of postorder operation with store, can in derivative, add solvent and be made into 50% the liquid of releasing.
Component in the composition provided by the invention (A) can be 1: 0.1 ~ 10 with the weight ratio of ratio of component, preferred 1: 0.25 ~ 8, preferably 1: 0.5 ~ 6.
The addition of composition provided by the invention in diesel oil generally is 100 ~ 2000ppm, preferred 300 ~ 1000ppm.
According to using needs, can also add other additive in the composition provided by the invention, as detergent-dispersant additive, sanitas etc.
Composition as improver for improving flowability of diesel oil provided by the invention makes it paraffinic base diesel oil owing to adopted special formula, and particularly wax content height, the narrow diesel oil of fraction not only have good pour point depression effect, also have and significantly fall the filter effect.For example for the Yanshan Mountain 0
#Tempered oil, condensation point can reduce by 15 ~ 25 ℃, and cold filter clogging temperature can reduce by 2 ~ 4 ℃; To the Yanshan Mountain-10
#Mixed oil, condensation point can reduce by 20～30 ℃, and cold filter clogging temperature can reduce by 4～6 ℃
The invention will be further described below by embodiment.
Example 1
This example is the preparation of multipolymer in the component (B).
Place one electric mixer is housed 9.8g (0.1mol) maleic anhydride and 25g aromatic hydrocarbons thinning oil solvent, thermometer, reflux condensing tube, in the reactor of dropping funnel and nitrogen ingress pipe, fed nitrogen 5 ~ 10 minutes, and in reaction process, keep faint nitrogen gas stream, heated and stirred is warming up to 140 ~ 150 ℃, with the 32.4g octadecyl acrylate, 0.8g ditertiary butyl peroxide and 30g aromatic hydrocarbons thinning oil mixture splash into reactor (mol ratio of octadecyl acrylate and maleic anhydride 1: 1) from dropping funnel, 1.5 drip off in hour, keep 140 ~ 150 ℃ of temperature, back flow reaction 3 hours, cool to room temperature is waited until the preparation derivative.The sample that takes a morsel records number-average molecular weight Mn=1304 with gel permeation chromatography.
Example 2
This example is the preparation of multipolymer in the component (B).
Place one electric mixer is housed 9.8g (0.1mol) maleic anhydride and 30g aromatic hydrocarbons thinning oil solvent, thermometer, reflux condensing tube, in the reactor of dropping funnel and nitrogen ingress pipe, fed nitrogen 5 ~ 10 minutes, and in reaction process, keep faint nitrogen gas stream, heated and stirred is warming up to 140 ~ 150 ℃, with the 59.2g Process Conditions of Cetane Acrylate, 0.7g ditertiary butyl peroxide and 40g aromatic hydrocarbons thinning oil mixture splash into reactor (mol ratio of octadecyl acrylate and maleic anhydride 2: 1) from dropping funnel, drip off in 2 hours, keep 140 ~ 150 ℃ of temperature, back flow reaction 5 hours, cool to room temperature is waited until the preparation derivative.The sample that takes a morsel records number-average molecular weight Mn=2606 with gel permeation chromatography.
Example 3
This example is the preparation of multipolymer in the component (B).
Place one electric mixer is housed 9.8g (0.1mol) maleic anhydride and 10g aromatic hydrocarbons thinning oil solvent, thermometer, reflux condensing tube, in the reactor of dropping funnel and nitrogen ingress pipe, fed nitrogen 5 ~ 10 minutes, and in reaction process, keep faint nitrogen gas stream, heated and stirred is warming up to 140 ~ 150 ℃, with the 26.8g tetradecyl acrylate, 0.4g ditertiary butyl peroxide and 20g aromatic hydrocarbons thinning oil mixture splash into reactor (mol ratio of tetradecyl acrylate and maleic anhydride 1: 1) from dropping funnel, 1.5 drip off in hour, keep 140 ~ 150 ℃ of temperature, back flow reaction 5 hours, cool to room temperature is waited until the preparation derivative.The sample that takes a morsel records number-average molecular weight Mn=6439 with gel permeation chromatography.
Example 4
This example is the preparation of component (B) monoester derivates.
In the multipolymer that example 1 makes, add the positive tetradecyl alcohol of 21.4 grams, 5 gram aromatic hydrocarbons thinning oils under 140 ~ 150 ℃, reacted 4 hours, after reaction finishes, add 5 gram aromatic hydrocarbons thinning oils again and be made into 50% diluent.
Example 5
This example is the preparation of component (B) monoester derivates.
In the multipolymer that example 1 makes, add 18.6 gram n-dodecanols, 5 gram aromatic hydrocarbons thinning oils under 140 ~ 150 ℃, reacted 4 hours, after reaction finishes, add 5 gram aromatic hydrocarbons thinning oils again and be made into 50% diluent.
Example 6
This example is the preparation of component (B) diester derivatives.
In the multipolymer that example 2 makes, add the positive stearyl alcohol of 27.0 grams, 17 gram aromatic hydrocarbons thinning oils and 1.4 gram tosic acid, under 140 ~ 150 ℃, reacted 5 hours, after reaction finishes, add 10 gram solvents, be made into 50% diluent, add 2.1 gram calcium oxide neutralizations, and use the diatomite suction filtration, filtrate is diester derivatives.
Example 7
This example is the preparation of component (B) diester derivatives.
In the multipolymer that example 3 makes, add the positive tetradecyl alcohol of 24.2 grams, 20.8 gram aromatic hydrocarbons thinning oils and 0.9 gram tosic acid, under 140 ~ 150 ℃, reacted 5 hours, after reaction finishes, add the gram solvent, be made into 50% diluent, add 1.3 gram calcium oxide neutralizations, and use the diatomite suction filtration, filtrate is diester derivatives.
Example 8 ~ 11
This example is the preparation of the composition as improver for improving flowability of diesel oil of the present invention's raising.Plastic of poly vinyl acetate (EVA with different molecular weight, Beijing Organic Chemical Plant produces) with the diluent (concentration is 50%) of the derivative of component (B) acrylate-copolymer-maleic anhydride that is selected from one of example 4 ~ 7, mix according to the weight ratio shown in the table 1, obtain different compositions.
Table 1
| Example | ????8 | ????9 | ????10 | ????11 |
| Component A (Mn) | ????1500 | ????2000 | ????1800 | ????1800 |
| B component | Example 4 | Example 6 | Example 5 | Example 7 |
| A∶B | ????2∶1 | ????1∶1 | ????1∶2 | ????1∶4 |
Example 12
This example is the result of use of composition in diesel oil that example 8 ~ 11 makes.
Select for use two kinds of diesel oil as test oil, be respectively (a) Yanshan Mountain 0
#Mixed oil and (b) Yanshan Mountain-10
#Mixed oil.The physicochemical property of two kinds of diesel oil sees Table 2, add agent after, pour point depression and fall the filter effect see Table 3.
By table 3 as can be seen, composition as improver for improving flowability of diesel oil provided by the invention is to paraffinic base diesel oil, and particularly wax content height, the narrow diesel oil of fraction not only have good pour point depression effect, also have and significantly fall the filter effect.
Table 2
| Physicochemical property | Diesel oil | |
| ????(a) | ????(b) | |
| CFPP/ ℃ of SP/ ℃ of initial boiling point/℃ 20% heats up in a steamer a little/℃ 50% heat up in a steamer a little/℃ 90% heat up in a steamer a little/℃ do/℃ positive structure hydrocarbon of positive structure hydrocarbon content/% carbon number C≥17Positive structure hydrocarbon content/% | ????-2 ????-6 ????193 ????234 ????275 ????358 ????345 ????24.7 ????C 5~C 23????9.59 | ????-7 ????-14 ????180 ????214 ????229 ????320 ????343 ????30.6 ????C 5~C 23????6.07 |
Table 3
| The additive source | Diesel oil | Dosage, ppm | Cold filter clogging temperature, ℃ | Condensation point, ℃ |
| Example 8 | ??(a) ??(b) | 500 600 | -5 -12 | ??＜30 ??＜30 |
| Example 9 | ??(a) ??(b) | 500 800 | -4 -11 | ??＜30 ??＜30 |
| Example 10 | ??(a) ??(b) | 600 500 | -5 -12 | ??＜25 ??＜30 |
| Example 11 | ??(a) ??(b) | 600 1000 | -6 -13 | ??＜25 ??＜30 |
Claims (8)
1. composition as improver for improving flowability of diesel oil comprises following component:
(A) number-average molecular weight is 1000 ~ 2500 polyethylene vinyl acetate ester;
(B) number-average molecular weight be 500 ~ 10000 be selected from vinylformic acid C
6~ C
22The C of alkyl ester and copolymer-maleic anhydride
6~ C
22Alkyl monoester or diester derivatives or its mixture, wherein, component (A) is 1: 0.1 ~ 10 with the weight ratio of component (B).
2. according to the described composition of claim 1, the number-average molecular weight that it is characterized in that component (A) is 1500 ~ 2000.
3. according to the described composition of claim 1, the number-average molecular weight that it is characterized in that said multipolymer in the component (B) is 1000 ~ 8000.
4. according to the described composition of claim 1, it is characterized in that said alkyl acrylate is C
10~ C
20Alkyl ester.
5. according to claim 1 or 4 described compositions, it is characterized in that said alkyl acrylate is C
12~ C
18Alkyl ester.
6. according to the described composition of claim 1, the derivative that it is characterized in that said multipolymer is C
8~ C
20Alkyl monoester or diester derivatives or its mixture.
7. according to claim 1 or 6 described compositions, the derivative that it is characterized in that said multipolymer is C
10~ C
18Alkyl monoester or diester derivatives or its mixture.
8. according to the described composition of claim 1, it is characterized in that the component (A) and the weight ratio of component (B) are 1: 0.25 ~ 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98103578A CN1067712C (en) | 1998-08-13 | 1998-08-13 | Composition as improver for improving flowability of diesel oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98103578A CN1067712C (en) | 1998-08-13 | 1998-08-13 | Composition as improver for improving flowability of diesel oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1245207A true CN1245207A (en) | 2000-02-23 |
| CN1067712C CN1067712C (en) | 2001-06-27 |
Family
ID=5218005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98103578A Expired - Lifetime CN1067712C (en) | 1998-08-13 | 1998-08-13 | Composition as improver for improving flowability of diesel oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1067712C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102191093A (en) * | 2010-03-10 | 2011-09-21 | 中国石油天然气股份有限公司 | Preparation method of diesel oil low temperature flow properties improver |
| CN102510878A (en) * | 2009-09-25 | 2012-06-20 | 赢创罗曼克斯添加剂有限公司 | Composition to improve cold flow properties of fuel oils |
| CN102918106A (en) * | 2010-05-28 | 2013-02-06 | 住友电木株式会社 | Semiconductor-sealing epoxy resin composition and semiconductor device using same |
| CN103045312A (en) * | 2013-01-16 | 2013-04-17 | 深圳市三岠科技有限公司 | Diesel oil pour point depressant and preparation method thereof |
| CN109114426A (en) * | 2017-06-26 | 2019-01-01 | 中国石油天然气集团公司 | Composition, pour point depressant for crude oil, preparation method and application for pour point depressant for crude oil |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3031900C2 (en) * | 1980-08-23 | 1983-06-09 | Chemische Fabriek Servo B.V., 7491 Delden | Copolymers of n-alkyl acrylates and maleic anhydride and their use as crystallization inhibitors for crude oils containing paraffin |
| DE4036225A1 (en) * | 1990-11-14 | 1992-05-21 | Basf Ag | Petroleum distillates with improved cold flow - contg. ethylene-based flow improver and copolymer of alkyl acrylate] and unsatd. di:carboxylic acid in amide form |
| AU680915B2 (en) * | 1993-07-27 | 1997-08-14 | Shell Internationale Research Maatschappij B.V. | Polymeric flow improver additives |
-
1998
- 1998-08-13 CN CN98103578A patent/CN1067712C/en not_active Expired - Lifetime
Cited By (10)
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|---|---|---|---|---|
| CN102510878A (en) * | 2009-09-25 | 2012-06-20 | 赢创罗曼克斯添加剂有限公司 | Composition to improve cold flow properties of fuel oils |
| CN102510878B (en) * | 2009-09-25 | 2015-08-05 | 赢创罗曼克斯添加剂有限公司 | Improve the composition of oil fuel cold flow properties |
| TWI510609B (en) * | 2009-09-25 | 2015-12-01 | Evonik Rohmax Additives Gmbh | A composition to improve cold flow properties of fuel oils |
| US10131776B2 (en) | 2009-09-25 | 2018-11-20 | Evonik Oil Additives Gmbh | Composition to improve cold flow properties of fuel oils |
| CN102191093A (en) * | 2010-03-10 | 2011-09-21 | 中国石油天然气股份有限公司 | Preparation method of diesel oil low temperature flow properties improver |
| CN102918106A (en) * | 2010-05-28 | 2013-02-06 | 住友电木株式会社 | Semiconductor-sealing epoxy resin composition and semiconductor device using same |
| CN102918106B (en) * | 2010-05-28 | 2015-09-16 | 住友电木株式会社 | Epoxy resin composition for semiconductor encapsulation and its semiconductor device of use |
| CN103045312A (en) * | 2013-01-16 | 2013-04-17 | 深圳市三岠科技有限公司 | Diesel oil pour point depressant and preparation method thereof |
| CN109114426A (en) * | 2017-06-26 | 2019-01-01 | 中国石油天然气集团公司 | Composition, pour point depressant for crude oil, preparation method and application for pour point depressant for crude oil |
| CN109114426B (en) * | 2017-06-26 | 2020-09-04 | 中国石油天然气集团公司 | Composition for crude oil pour point depressant, preparation method and application |
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|---|---|
| CN1067712C (en) | 2001-06-27 |
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