CN102965175B - Method for preparing alkyl naphthalene type lubrication base oil - Google Patents
Method for preparing alkyl naphthalene type lubrication base oil Download PDFInfo
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- CN102965175B CN102965175B CN201210525041.3A CN201210525041A CN102965175B CN 102965175 B CN102965175 B CN 102965175B CN 201210525041 A CN201210525041 A CN 201210525041A CN 102965175 B CN102965175 B CN 102965175B
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- naphthalene
- octene
- alkyl naphthalene
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Abstract
The invention relates to a method for preparing alkyl naphthalene type lubrication base oil. The method comprises the following steps of: performing Friedel-Crafts alkylation reaction on naphthalene and 1-octylene by using methanesulfonic acid as a catalyst; respectively performing alkali wash, washing, reduced pressure distilling and suction-filtering on the alkylated product to finally obtain the alkyl naphthalene type lubrication base oil. The alkyl naphthalene type lubrication base oil synthesized by the method is low in viscosity, low in inclination point, high in oxidization stability, good in heat stability and hydrolytic stability, and high in dissolvability and dispersing power. The method is easy to operate and high in yield, and overcomes the defects that the traditional alkylate catalyst (such as aluminum trichloride and boron trifluoride diethyl etherate) is difficult to separate and pollutes environment; and methanesulfonic acid serving as the catalyst is easily separated and can be degradable.
Description
Technical field
The present invention relates to a kind of preparation method of alkylnaphthalene type lubricating base oil.
Background technology
Along with industrialized development, a lot of machinery is more and more harsher to the requirement of lubricant, under the condition of some continuous high temperatures, low temperature, the lubricant take mineral oil as base oil can not meet the demands, and the application using chemical feedstocks synthetic product as lubricant just progressively increases.The characteristic of synthetic oil is better than mineral oil, obtains using more widely in special lubricated field.Oil supply present situation in short supply in the world's also impels synthetic oil technology and the additive synthetic technology in lubricated field to develop rapidly simultaneously.In various synthetic oils, alkylated aromatic hydrocarbons, due to its unique molecular structure and interatomic bonding strength, has the not available performance of other synthetic class oil, as high in oxidation stability, thermostability and stability to hydrolysis preferably, good solvability and dispersive ability etc.Long chain alkyl naphthalene generally refers to the alkylnaphthalene of alkyl carbon atoms number more than 8, as a kind of important organic intermediate or processed oil, be widely used in the fields such as weaving, printing and dyeing, food product pack, heat conduction matter, solvent, transformer oil, liquid crystal, oil recovery, lubricant.In alkylnaphthalene structure, the naphthalene nucleus of electron rich can capture the oxidisability group that alkyl oxidation produces, and make whole oxidative chain be difficult to form, thereby stoped oxidising process, thereby alkylnaphthalene has good thermal oxidation stability as base oil.
Long chain alkyl naphthalene is mainly by the alkylated reaction preparation of naphthalene, and wherein alkene, alcohol and halohydrocarbon etc. all can be used as the alkylating reagent of naphthalene.Tradition alkylation catalyst mainly comprises the mineral acid such as hydrofluoric acid, the vitriol oil and some Lewis acid, as A1C1
3all exist and be difficult for reclaiming Deng, these catalyzer, corrodibility is strong, strong toxicity and the shortcoming such as seriously polluted.
The present invention, take easily separated recovery, degradable methylsulfonic acid as catalyzer, by the alkylated reaction of naphthalene, 1-octene, synthesizes and has compared with low viscosity, compared with low pour point, and the better alkylnaphthalene type lubricating base oil of oxidation stability and thermostability.
Summary of the invention
The object of the invention is, a kind of preparation method of alkylnaphthalene type lubricating base oil is provided, the method is take methylsulfonic acid as catalyzer, be there is to Fu-Ke alkylated reaction in naphthalene and 1-octene, again alkylate is carried out respectively to alkali cleaning, washing, underpressure distillation and suction filtration, finally obtain alkylnaphthalene type lubricating base oil.The alkylnaphthalene type lubricating base oil synthetic by the method for the invention has compared with low-viscosity, compared with low pour point, higher oxygen stability, better thermostability and stability to hydrolysis, good solvability and dispersive ability, the method is easy and simple to handle, and yield is high, used catalyst methylsulfonic acid is easily separated, degradable, has overcome traditional alkylation catalyst (as aluminum chloride, boron trifluoride diethyl etherate etc.) and has separated shortcoming difficult, contaminate environment.
The preparation method of a kind of alkylnaphthalene type lubricating base oil of the present invention, carries out according to the following steps:
A, naphthalene and catalyzer methylsulfonic acid, stopper 2.6-DI-tert-butylphenol compounds are mixed, oil bath is heated to naphthalene fusing, slowly drips 1-octene, rapid stirring, 80 ℃ of temperature of reaction, reaction times 5-8h;
B, reaction finish rear leaving standstill, and remove the bottom containing catalyzer after obvious layering, upper organic phase is carried out to sodium hydroxide or potassium hydroxide alkali cleaning, then wash, until washing lotion is neutrality;
C, to through alkali cleaning, be washed to neutral upper organic phase and carry out underpressure distillation, remove unreacted naphthalene and 1-octene, obtain crude product;
D, crude product is removed to slag with suction filtration after activated decoloration, can obtain alkylnaphthalene type lubricant base.
In step a, the mol ratio of naphthalene, 1-octene, methylsulfonic acid and 2.6-DI-tert-butylphenol compounds is 1.1-1.5:1:0.5-1:0.001-0.005.
The preparation method of a kind of alkylnaphthalene type lubricating base oil of the present invention, the method alpha-olefin used is 1-octene, adopt the mode and the naphthalene that slowly drip, the mixture reaction that methylsulfonic acid and 2.6-DI-tert-butylphenol compounds form, method of the present invention is easy and simple to handle, yield is high, used catalyst methylsulfonic acid is easily separated, degradable, overcome traditional alkylation catalyst not easily separated, the shortcoming of not environmental protection, the alkylnaphthalene type lubricating base oil that adopts the method for the invention to prepare has compared with low viscosity, compared with low pour point, higher oxygen stability, better thermostability and stability to hydrolysis, good solvability and dispersive ability, voltage breakdown is higher, medium consumption factor is lower, can be used as transformer oil uses.
Embodiment
Example is below to further illustrate of the present invention, rather than limits the invention.
Embodiment 1
In the there-necked flask of being furnished with agitator, prolong, dropping funnel, add naphthalene 16.6g, methylsulfonic acid 6.5mL and 2.6-DI-tert-butylphenol compounds 0.06g, stir, oil bath is heated to 80 ℃ of temperature, from dropping funnel, add 1-octene 15.6mL, in the time that naphthalene melts, start slow dropping, 5-7s/d, rapid stirring continues reaction 5h after octene drips;
After reaction finishes, there-necked flask reaction product is transferred to separating funnel and leaves standstill, after obvious layering, remove the bottom containing catalyzer, upper organic phase is carried out to sodium hydroxide alkali cleaning, then wash, until washing lotion is neutrality;
To carrying out underpressure distillation through the upper organic phase of alkali cleaning, washing, remove unreacted naphthalene and 1-octene, obtain crude product;
Crude product is removed to slag with suction filtration after mass ratio 5% activated decoloration, can obtain the golden yellow transparent alkylnaphthalene type lubricating base oil of color, quality is 19.35g, and yield is 69.5%, and iodine number is 8.2.
Embodiment 2
In the there-necked flask of being furnished with agitator, prolong, dropping funnel, add naphthalene 19.2g, methylsulfonic acid 6.5mL and 2.6-DI-tert-butylphenol compounds 0.06g, stir, oil bath is heated to 80 ℃ of temperature, from dropping funnel, add 1-octene 15.6mL, in the time that naphthalene melts, start slow dropping, 5-7s/d, rapid stirring continues reaction 6h after octene drips;
After reaction finishes, there-necked flask reaction product is transferred to separating funnel and leaves standstill, after obvious layering, remove the bottom containing catalyzer, upper organic phase is carried out to potassium hydroxide alkali cleaning, then wash, until washing lotion is neutrality;
To carrying out underpressure distillation through the upper organic phase of alkali cleaning, washing, remove unreacted naphthalene and 1-octene, obtain crude product;
Crude product is removed to slag with suction filtration after mass ratio 5% activated decoloration, can obtain the golden yellow transparent alkylnaphthalene type lubricating base oil of color, quality is 19.57g, and yield is 64.4%, and iodine number is 9.4.
Embodiment 3
In the there-necked flask of being furnished with agitator, prolong, dropping funnel, add naphthalene 16.6g, methylsulfonic acid 3.3mL and 2.6-DI-tert-butylphenol compounds 0.04g, stir, oil bath is heated to 80 ℃ of temperature, from dropping funnel, add 1-octene 15.6mL, in the time that naphthalene melts, start slow dropping, 5-7s/d, rapid stirring continues reaction 7h after octene drips;
After reaction finishes, there-necked flask reaction product is transferred to separating funnel and leaves standstill, after obvious layering, remove the bottom containing catalyzer, upper organic phase is carried out to sodium hydroxide alkali cleaning, then wash, until washing lotion is neutrality;
To carrying out underpressure distillation through the upper organic phase of alkali cleaning, washing, remove unreacted a small amount of naphthalene and 1-octene, obtain crude product;
Crude product is removed to slag with suction filtration after mass ratio 5% activated decoloration, can obtain the golden yellow transparent alkylnaphthalene type lubricating base oil of color, quality is 20.02g, and yield is 71.9%, and iodine number is 8.9.
Embodiment 4
In the there-necked flask of being furnished with agitator, prolong, dropping funnel, add naphthalene 116.5g, methylsulfonic acid 45.5mL and 2.6-DI-tert-butylphenol compounds 0.57g, stir, oil bath is heated to 80 ℃ of temperature, from dropping funnel, add 1-octene 109mL, in the time that naphthalene melts, start slow dropping, 2-3s/d, rapid stirring continues reaction 8h after octene drips;
After reaction finishes, there-necked flask reaction product is transferred to separating funnel and leaves standstill, after obvious layering, remove the bottom containing catalyzer, upper organic phase is carried out to potassium hydroxide alkali cleaning, then wash, until washing lotion is neutrality;
To carrying out underpressure distillation through the upper organic phase of alkali cleaning, washing, remove unreacted naphthalene and 1-octene, obtain crude product;
Crude product is removed to slag with suction filtration after mass ratio 5% activated decoloration, can obtain the golden yellow transparent alkylnaphthalene type lubricating base oil of color, quality is 136.07g, and yield is 69.8%, and iodine number is 6.7.
Embodiment 5
The alkylnaphthalene type lubricating base oil obtaining by embodiment 4 is after testing: 40 ℃ of kinematic viscosity of temperature are 12.099 mm
2s
-1, 100 ℃ of kinematic viscosity of temperature are 2.421 mm
2s
-1, viscosity index is 17.9, pour point-48 ℃, and 172 ℃ of flash-points, 186 ℃ of burning-points, the oxidation stability test duration is 32.5h, and voltage breakdown is 61.9kV, and medium consumption factor is 0.004, can be used as transformer oil and uses.
Claims (1)
1. a preparation method for alkylnaphthalene type lubricating base oil, is characterized in that carrying out according to the following steps:
A, naphthalene and catalyzer methylsulfonic acid, stopper 2.6-DI-tert-butylphenol compounds are mixed, oil bath is heated to naphthalene fusing, slowly drip 1-octene, rapid stirring, 80 ℃ of temperature of reaction, reaction times 5-8h, wherein the mol ratio of naphthalene, 1-octene, methylsulfonic acid and 2.6-DI-tert-butylphenol compounds is 1.1-1.5:1:0.5-1:0.001-0.005;
B, reaction finish rear leaving standstill, and remove the bottom containing catalyzer after obvious layering, upper organic phase is carried out to sodium hydroxide or potassium hydroxide alkali cleaning, then wash, until washing lotion is neutrality;
C, to through alkali cleaning, be washed to neutral upper organic phase and carry out underpressure distillation, remove unreacted naphthalene and 1-octene, obtain crude product;
D, crude product is removed to slag with suction filtration after activated decoloration, can obtain alkylnaphthalene type lubricating base oil.
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| CN201210525041.3A CN102965175B (en) | 2012-12-10 | 2012-12-10 | Method for preparing alkyl naphthalene type lubrication base oil |
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| CN201210525041.3A CN102965175B (en) | 2012-12-10 | 2012-12-10 | Method for preparing alkyl naphthalene type lubrication base oil |
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| CN102965175B true CN102965175B (en) | 2014-05-21 |
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| CN105001939A (en) * | 2015-04-21 | 2015-10-28 | 常州科乐催化剂有限公司 | Method for preparing alkyl-naphthalene-type lubricating oil with solid-state protonic acid as catalysts |
| CN114507110A (en) * | 2022-01-11 | 2022-05-17 | 中国石油大学(华东) | Production method of alkyl naphthalene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4604491A (en) * | 1984-11-26 | 1986-08-05 | Koppers Company, Inc. | Synthetic oils |
| CN101205161A (en) * | 2006-12-22 | 2008-06-25 | 中国石油化工股份有限公司 | Method for preparing long chain alkyl naphthalene |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4604491A (en) * | 1984-11-26 | 1986-08-05 | Koppers Company, Inc. | Synthetic oils |
| CN101205161A (en) * | 2006-12-22 | 2008-06-25 | 中国石油化工股份有限公司 | Method for preparing long chain alkyl naphthalene |
Non-Patent Citations (2)
| Title |
|---|
| 柳影等.长链烷基萘基础油的合成及润滑性能研究.《润滑与密封》.2011,第36卷(第12期), |
| 长链烷基萘基础油的合成及润滑性能研究;柳影等;《润滑与密封》;20111231;第36卷(第12期);第23-25，49页 * |
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Granted publication date: 20140521 Termination date: 20191210 |