CN107162905A - Ester type diesel antiwear additive and preparation method thereof - Google Patents
Ester type diesel antiwear additive and preparation method thereof Download PDFInfo
- Publication number
- CN107162905A CN107162905A CN201710427539.9A CN201710427539A CN107162905A CN 107162905 A CN107162905 A CN 107162905A CN 201710427539 A CN201710427539 A CN 201710427539A CN 107162905 A CN107162905 A CN 107162905A
- Authority
- CN
- China
- Prior art keywords
- ester type
- antiwear additive
- epoxides
- preparation
- type diesel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000007866 anti-wear additive Substances 0.000 title claims abstract description 27
- 150000002148 esters Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000010792 warming Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 9
- 238000006073 displacement reaction Methods 0.000 claims abstract description 8
- 150000002924 oxiranes Chemical class 0.000 claims description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 8
- 239000005642 Oleic acid Substances 0.000 claims description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 5
- 150000002118 epoxides Chemical class 0.000 abstract 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002283 diesel fuel Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- -1 fatty acid ester Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/76—Esters containing free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to ester type diesel antiwear additive and preparation method thereof, step includes：Fatty acid mixed is added in autoclave；Vacuum is opened, nitrogen displacement three times is warming up to 80 DEG C ~ 120 DEG C；Epoxides is slowly introducing, reaction temperature is controlled at 100 ~ 150 DEG C, and Stress control is in 0.3 ~ 0.6MPa；The mol ratio of fatty acid mixed and epoxides is 1:（1~5）；After the completion of epoxides charging, continue to react 1 ~ 3 hour at 130 ~ 180 DEG C, treat that pressure is down to 0.02 ~ 0.03MPa, stop reaction.The present invention is prepared in ester type antiwear additive, production process with epoxides addition and is not added with catalyst, it is to avoid later stage refinement treatment caused by the introducing of foreign ion, technique is simple, economic and environment-friendly.
Description
Technical field
The present invention relates to a kind of diesel antiwear additive, and in particular to a kind of ester type diesel antiwear additive and preparation method thereof.
Background technology
With the raising of environmental requirement, sulphur, nitrogen content are further reduced in derv fuel, and refinery passes through desulfurization removing nitric skill
Art so that the sulphur of diesel oil, nitrogen content reduction, but the content of the wherein natural polar compound with lubricity are also decreased,
So as to substantially reduce the greasy property of diesel oil, engine scuffing is caused.The diesel antiwear additive of current commercialization mainly has aliphatic acid
Type antiwear additive and fatty acid ester type antiwear additive.Fatty acid ester type antiwear additive is generally aliphatic acid and made with alcohol under catalyst action
It is standby, need to add catalyst in esterification process, on the one hand post processing removes the complex process of catalyst, on the one hand may cause product
Middle metal ion residual, influences product quality.
The content of the invention
It is an object of the invention to provide a kind of ester type diesel antiwear additive and preparation method thereof, after overcoming existing esterification technique to need
The deficiency of continuous processing catalyst, preparation technology is simpler, and anti-wear effect is more preferable.
The technical solution adopted in the present invention is：
The preparation method of ester type diesel antiwear additive, it is characterised in that：
Comprise the following steps：
Step one：Fatty acid mixed is added in autoclave；
Step 2：Vacuum is opened, nitrogen displacement three times is warming up to 80 DEG C ~ 120 DEG C；
Step 3：Epoxides is slowly introducing, reaction temperature is controlled at 100 ~ 150 DEG C, and Stress control is in 0.3 ~ 0.6MPa；Mixing
The mol ratio of aliphatic acid and epoxides is 1:（1~5）；
Step 4：After the completion of epoxides charging, continue to react 1 ~ 3 hour at 130 ~ 180 DEG C, treat pressure be down to 0.02 ~
0.03MPa, stops reaction.
Described epoxides is oxirane or expoxy propane.
The fatty acid mixed is oleic acid.
Ester type diesel antiwear additive made from the preparation method of ester type diesel antiwear additive as mentioned.
The present invention has advantages below：
1st, the introducing of foreign ion is avoided：The present invention is highly polar using fatty acid mixed, straight under conditions of catalyst is not added with
Connect and occur addition reaction with epoxides, generate ester type antiwear additive, traditional handicraft is oleic acid and polyalcohol in strong acid, strong base catalyst
The lower esterification of agent effect forms ester type antiwear additive, and relative to the latter, the former can avoid introducing foreign ion, impurity using catalyst
On the one hand ion can influence diesel oil inorganic ions index of correlation, while will also result in cylinder interior equipment corrosion etc..
2nd, technique is simple：The present invention uses direct single step reaction, it is to avoid later separation refined unit, economic and environment-friendly.
Embodiment
With reference to embodiment, the present invention will be described in detail.
The preparation method of ester type diesel antiwear additive of the present invention, comprises the following steps：
Step one：Fatty acid mixed is added in autoclave；
Step 2：Vacuum is opened, nitrogen displacement three times is warming up to 80 DEG C ~ 120 DEG C；
Step 3：Epoxides is slowly introducing, reaction temperature is controlled at 100 ~ 150 DEG C, and Stress control is in 0.3 ~ 0.6MPa；Mixing
The mol ratio of aliphatic acid and epoxides is 1:（1~5）；
Step 4：After the completion of epoxides charging, continue to react 1 ~ 3 hour at 130 ~ 180 DEG C, treat pressure be down to 0.02 ~
0.03MPa, stops reaction.
Described epoxides is oxirane or expoxy propane.
The fatty acid mixed is oleic acid.
Embodiment 1
Oleic acid 282g（1mol）It is pumped into autoclave, is warming up to 80 DEG C, vacuumizes, then with nitrogen displacement three times, is warming up to 120
DEG C, it is passed through expoxy propane 58g（1mol）, control pressure is warming up to 150 DEG C after the completion of 0.6MPa, charging, reacts 1 hour, kettle
Pressure drop is cooled to less than 80 DEG C, products therefrom is ester type antiwear additive to 0.02MPa.
Embodiment 2
By oleic acid 282g（1mol）It is pumped into autoclave, is warming up to 80 DEG C, vacuumizes, then with nitrogen displacement three times, is warming up to
120 DEG C, it is passed through expoxy propane 145g（2.5mol）, control pressure is warming up to 150 DEG C after the completion of 0.5MPa, charging, reaction 1.5
Hour, then it is passed through expoxy propane 145g（2.5mol）, control pressure is in 0.6MPa, and 160 DEG C are continued to react 1.5 hours, kettle pressure drop
To 0.02MPa, less than 80 DEG C are cooled to, products therefrom is ester type antiwear additive.
Embodiment 3
By oleic acid 282g（1mol）It is pumped into autoclave, is warming up to 80 DEG C, vacuumizes, then with nitrogen displacement three times, is warming up to
120 DEG C, it is passed through oxirane 44g（1mol）, control pressure in 0.6MPa, be warming up to 150 DEG C continue react 1 hour, kettle pressure drop
To 0.03MPa, less than 80 DEG C are cooled to, products therefrom is ester type antiwear additive.
Embodiment 4
By oleic acid 282g（1mol）It is pumped into autoclave, is warming up to 80 DEG C, vacuumizes, then with nitrogen displacement three times, is warming up to
120 DEG C, it is passed through oxirane 110g（2.5mol）, control pressure is warming up to 150 DEG C after the completion of 0.5MPa, charging, reaction 1.5
Hour, then it is passed through oxirane 110g（2.5mol）Control pressure is in 0.6MPa, and 160 DEG C are continued to react 1.5 hours, and kettle pressure drop is extremely
0.02MPa, is cooled to less than 80 DEG C, products therefrom is ester type antiwear additive.
Tested according to Q/SHCG 57-2014 preparing ester type antiwear additive lubricity, its effect is as follows：（Standard
Regulation plus agent diesel oil WS1.4/um≤420.）
Present disclosure is not limited to cited by embodiment, and those of ordinary skill in the art are right by reading description of the invention
Any equivalent conversion that technical solution of the present invention is taken, is that claim of the invention is covered.
Claims (4)
1. the preparation method of ester type diesel antiwear additive, it is characterised in that：
Comprise the following steps：
Step one：Fatty acid mixed is added in autoclave；
Step 2：Vacuum is opened, nitrogen displacement three times is warming up to 80 DEG C ~ 120 DEG C；
Step 3：Epoxides is slowly introducing, reaction temperature is controlled at 100 ~ 150 DEG C, and Stress control is in 0.3 ~ 0.6MPa；Mixing
The mol ratio of aliphatic acid and epoxides is 1:（1~5）；
Step 4：After the completion of epoxides charging, continue to react 1 ~ 3 hour at 130 ~ 180 DEG C, treat pressure be down to 0.02 ~
0.03MPa, stops reaction.
2. the preparation method of ester type diesel antiwear additive according to claim 1, it is characterised in that：
Described epoxides is oxirane or expoxy propane.
3. the preparation method of ester type diesel antiwear additive according to claim 1, it is characterised in that：
The fatty acid mixed is oleic acid.
4. ester type diesel antiwear additive made from the preparation method of ester type diesel antiwear additive as claimed in claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710427539.9A CN107162905A (en) | 2017-06-08 | 2017-06-08 | Ester type diesel antiwear additive and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710427539.9A CN107162905A (en) | 2017-06-08 | 2017-06-08 | Ester type diesel antiwear additive and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107162905A true CN107162905A (en) | 2017-09-15 |
Family
ID=59825994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710427539.9A Pending CN107162905A (en) | 2017-06-08 | 2017-06-08 | Ester type diesel antiwear additive and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107162905A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108277051A (en) * | 2017-12-28 | 2018-07-13 | 宁夏宝塔化工中心实验室(有限公司) | A kind of preparation method of ester type diesel oil antiwear agent |
| CN110240956A (en) * | 2019-05-20 | 2019-09-17 | 中海油天津化工研究设计院有限公司 | A kind of preparation method of fatty acid ester type diesel antiwear additive |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999015607A1 (en) * | 1997-09-22 | 1999-04-01 | Infineum Usa L.P. | Lubricity additives for fuel oil compositions |
| CN102753662A (en) * | 2009-08-18 | 2012-10-24 | 卢布里佐尔公司 | Lubricating composition containing an antiwear agent |
| CN104974340A (en) * | 2015-06-25 | 2015-10-14 | 淄博德信联邦化学工业有限公司 | Preparation method of highly active polyether polyol containing ester bonds in main chain |
-
2017
- 2017-06-08 CN CN201710427539.9A patent/CN107162905A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999015607A1 (en) * | 1997-09-22 | 1999-04-01 | Infineum Usa L.P. | Lubricity additives for fuel oil compositions |
| CN102753662A (en) * | 2009-08-18 | 2012-10-24 | 卢布里佐尔公司 | Lubricating composition containing an antiwear agent |
| CN104974340A (en) * | 2015-06-25 | 2015-10-14 | 淄博德信联邦化学工业有限公司 | Preparation method of highly active polyether polyol containing ester bonds in main chain |
Non-Patent Citations (2)
| Title |
|---|
| 李彦等: "《柴油抗磨剂对柴油质量影响研究》", 《当代化工》 * |
| 蔺建民等: "《脂肪酸衍生物低硫柴油抗磨剂的研究》", 《精细石油化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108277051A (en) * | 2017-12-28 | 2018-07-13 | 宁夏宝塔化工中心实验室(有限公司) | A kind of preparation method of ester type diesel oil antiwear agent |
| CN110240956A (en) * | 2019-05-20 | 2019-09-17 | 中海油天津化工研究设计院有限公司 | A kind of preparation method of fatty acid ester type diesel antiwear additive |
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|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170915 |
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| RJ01 | Rejection of invention patent application after publication |