CN105368537A - Ester lubricant base oil and synthesis method thereof - Google Patents
Ester lubricant base oil and synthesis method thereof Download PDFInfo
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- CN105368537A CN105368537A CN201510768094.1A CN201510768094A CN105368537A CN 105368537 A CN105368537 A CN 105368537A CN 201510768094 A CN201510768094 A CN 201510768094A CN 105368537 A CN105368537 A CN 105368537A
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Abstract
The invention relates to ester lubricant base oil and a synthesis method thereof. The synthesis method comprises that acidic solid as a catalyst is added into an organic acid and an organic alcohol in a reactor, the raw materials undergo a reaction at a temperature of 150-180 DEG C for 2-6h to produce a crude ester, the excess organic acid or organic alcohol is separated by a reduced pressure distillation or molecular distillation method, the acid is further removed by an anion exchange resin so that an acid value is reduced to 0.1mg KOH/g or less and the high-quality ester lubricating base oil is obtained, and the separated organic acid or organic alcohol can be recycled and be used as raw materials for the next same reaction system so that a cost is effectively reduced.
Description
Technical field
The invention belongs to the synthesis technical field of ester compound in organic chemistry, particularly relate to polyol ester class lubricating oil base oil and synthetic method thereof.
Background technology
Lubricating oil in esters is good owing to having viscosity-temperature characteristics, resistance of oxidation is strong, superior oilness and biodegradable performance and be widely used in aviation, intermetallic composite coating, the fields such as weaving and food-processing, along with improving constantly of environmental requirement, esters syntholube will constantly replace existing mineral oil, especially refrigerator oil field, there are good development prospect and potentiality, but, lubricating oil in esters industrial scale domestic is at present relatively little, production technique defect is obvious, make production cost higher, quality product is undesirable, be mainly manifested in the following aspects:
1, adopt liquid acidic catalyst, especially have the sulfuric acid of severe corrosive, phosphoric acid, not only reaction controlling difficulty, and transformation efficiency is lower, by product is many, serious to equipment corrosion, and product needed, through subsequent disposal such as neutralization, washings, produces a large amount of waste water.
2, the excess organic acid added in production process, is not well separated and recycle, is increased production cost.
3, the product acid number produced is bigger than normal (being greater than 0.5mgKOH/g), and oxidation stability is undesirable, cannot use on a large scale as lubricant base.
In addition, the catalyzer that prior art adopts is likely also tosic acid, tributyl phosphate etc., and these catalyzer are all difficult to reclaim after a procedure, substantially all stay in the product, reduce the capability and performance of product.
Summary of the invention
Technical problem to be solved by this invention overcomes the deficiencies in the prior art, a kind of polyol ester class lubricating oil base oil and synthetic method thereof are provided, the method uses acidic solid catalyst, utilize underpressure distillation and molecular distillation to reclaim excessive acid, adopt the depickling of the negative ion exchange resin degree of depth, catalyzer can repeatedly use, the excess acid reclaimed can recycle, product yield and purity high, production cost significantly reduces, and produces without waste water.
In order to overcome the deficiencies in the prior art, present invention employs following technical scheme:
A synthetic method for lubricating oil in esters base oil, comprising with acid solid is catalyzer, under described catalyst action, esterification occurs with organic acid, Organic Alcohol for raw material; Described acidic solid catalyst utilizes ZrO
2or TiO
2with SiO
2or Al
2o
3the composite oxides formed.
Acidic solid catalyst of the present invention has certain specific surface area and certain pore size structure.
Preferably, described acidic solid catalyst has following feature: specific surface area is 200-600m
2/ g, aperture is 2-10nm; Further preferably, specific surface area is 300-550m
2/ g, aperture is 4-8nm.
Preferably, described acidic solid catalyst, its add-on be organic acid, Organic Alcohol gross weight 0.05% ~ 0.1%.
Preferably, described acidic solid catalyst can repeatedly use.
Described acidic solid catalyst can be prepared by prior art.
Preferably, the preparation method of described acidic solid catalyst comprises: alkoxide hydrolysis, coprecipitation method etc.
The acidic solid catalyst that the present invention obtains has the certain pore structure of high-ratio surface sum, and appendix metal oxide, after acidified, can provide active centre for reaction, speed of response is accelerated, and selectivity improves.
Particularly, the synthetic method of above-mentioned lubricating oil in esters base oil, comprises the following steps:
1) take acid solid as catalyzer, under above-mentioned catalyst action, esterification occurs for raw material with organic acid, Organic Alcohol, generate thick ester;
2) thick for gained ester is filtered, reclaim described acidic solid catalyst;
3) the thick ester underpressure distillation of gained after filtering, removes excess organic acid; Carry out molecular distillation again, remove the intermediate product of non-complete reaction further, obtain the ester of primary purification;
4) adopt anionite-exchange resin to carry out the degree of depth depickling ester of gained primary purification, reduce product acid number to below 0.1mgKOH/g, then dehydrated by underpressure distillation, obtain (high-quality lubricating oil in esters base oil).
The synthetic method of above-mentioned lubricating oil in esters base oil, wherein:
Step 1) described esterification reaction temperature is preferably 120-180 DEG C, and the reaction times is preferably 2 ~ 6 hours.
Step 2) reclaim the acidic solid catalyst that obtains and can recycle.
Step 3) described underpressure distillation condition optimization is temperature 150 ~ 250 DEG C, 10 ~ 1kPa residual voltage; Described molecular distillation condition optimization is temperature 250 ~ 300 DEG C, pressure 0.1 ~ 0.01kPa.Preferably, isolated organic acid can carry out recycle.
Step 4) described anionite-exchange resin is preferably macroporous resin, such as D301R, D392 etc., and it is weakly alkaline, is polystyrene grid structure; Described underpressure distillation dehydration conditions is preferably pressure 2.5-3Kpa, and temperature is generally normal temperature.
The present invention also comprises the lubricating oil in esters base oil prepared as stated above.
Lubricating oil in esters base oil of the present invention, its pour point is not higher than-30 DEG C, and flash-point is not less than 250 DEG C, and when usual 40 DEG C, kinematic viscosity is 10-100mm
2/ s, viscosity index is not less than 150, and between variant production, mutual solubility is good, can meet the service requirements under most high temperature or cold condition as lubricant base.
Lubricating oil in esters base oil of the present invention can be used as aviation engine lubricating oil, air-compressor lubricating oil, turbine oil, automobile engine lubricating oil, heavy load gear oil or very low temperature engine wet goods.
Owing to adopting above technical scheme, the present invention compared with prior art has the following advantages:
1, adopt acid solid to be catalyzer, new technology, by regulating the performance of catalyzer to improve selectivity, significantly reduce by product, product color is good, and yield improves obviously, and catalyzer, after simple separation, can be reused, reduce raw materials cost
2, compared with common liquid acidic catalyst, acidic solid catalyst can not etching apparatus, saves the investment of equipment, and removing catalyzer only needs simple filtration, and without the need to operations such as neutralization, washings, decreases the discharge of sewage, environmentally friendly.
3, employing underpressure distillation depickling, molecular distillation take off the array mode of intermediate product, both are not overlapping, excessive acid and intermediate product are separated, ensure there is no intermediate product in the organic acid deviate from, prevent intermediate product from reducing speed and the selectivity of reaction, and excessive organic acid can be reused, reduce raw materials cost.
4, adopt anionite-exchange resin to the further degree of depth depickling of the product after underpressure distillation and molecular distillation, the acid number of product can be made to be reduced to below 0.1mgKOH/g, improve the oxidation stability of product.
The acid alcohol esterification process that the present invention relates to prepares the technique that the synthesis of ester class has base oil, there is the features such as selectivity is good, yield is high, cost is low, without sewage discharge, the product purity obtained is high, acid number is low, oxidation stability and viscosity temperature characteristic excellent, suitable with same kind of products at abroad performance, there is the extremely strong market competitiveness.
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.
A synthetic method for lubricating oil in esters base oil, comprises the steps:
1) taking acid solid as catalyzer, is that raw material esterification under 120-180 DEG C of condition, after 2 ~ 6 hours, generates thick ester with organic acid, Organic Alcohol;
2) thick for gained ester is filtered, reclaim described acidic solid catalyst recycling;
3) the thick ester underpressure distillation of gained after filtering, removes excess organic acid; Described underpressure distillation condition is 150 ~ 250 DEG C, 10 ~ 1kPa residual voltage; Carry out molecular distillation again, remove the intermediate product of non-complete reaction further, obtain the ester of primary purification; Described molecular distillation condition is 250 ~ 300 DEG C, 0.1 ~ 0.01kPa; Isolated organic acid can carry out recycle;
4) adopt anionite-exchange resin to carry out the degree of depth depickling ester of gained primary purification, reduce product acid number to below 0.1mgKOH/g, then dehydrated by underpressure distillation, obtain high-quality lubricating oil in esters base oil; Described underpressure distillation dehydration conditions normal temperature, 2.5-3Kpa.
The synthesis of embodiment 1 TriMethylolPropane(TMP) capronate
TriMethylolPropane(TMP) and caproic acid are dropped in reactor in molar ratio at 1: 3.2, add appropriate solvent, the acidic solid catalyst of acid alcohol gross weight 0.1% is added under stirring, be warming up to 120 ~ 130 DEG C of reaction 3h, raised temperature is to 140-150 DEG C afterwards, sustained reaction 3h, synthesis obtains thick ester, filtered and recycled acidic solid catalyst, at 150 ~ 200 DEG C, the excessive caproic acid of underpressure distillation under 5kPa residual voltage, the caproic acid reclaimed can reuse as raw material, at 250 ~ 300 DEG C, molecular distillation intermediate product under 0.1KPa, the ester of primary purification enters in weakly alkaline macroporous anion exchange resin (D301R) post, carry out further degree of depth depickling, until acid number is reduced to below 0.1mgKOH/g, finally drying under reduced pressure under normal temperature 2.5-3KPa, obtaining yield is 95%, acid number is 0.08mgKOH/g, the TriMethylolPropane(TMP) capronate that outward appearance is yellowish.
The present embodiment acidic solid catalyst used utilizes ZrO
2with SiO
2by the composite oxides that alkoxide hydrolysis is formed; Its specific surface area is 530m
2/ g, aperture is 4.0-6.5nm.
The synthesis of embodiment 2 tetramethylolmethane capronate
Tetramethylolmethane and caproic acid (part reclaims from embodiment 1) are dropped in reactor in molar ratio at 1: 4.2, add appropriate solvent, the acidic solid catalyst (reclaiming from embodiment 1) of acid alcohol gross weight 0.1% is added under stirring, be warming up to 130 ~ 140 DEG C of reaction 3h, raised temperature is to 150-160 DEG C afterwards, sustained reaction 3h, synthesis obtains thick ester, filtered and recycled acidic solid catalyst, at 150 ~ 200 DEG C, the excessive caproic acid of underpressure distillation under 5kPa residual voltage, the caproic acid reclaimed can reuse as raw material, at 250 ~ 300 DEG C, molecular distillation intermediate product under 0.1KPa, the ester of primary purification enters in weakly alkaline macroporous anion exchange resin (D301R) post, further degree of depth depickling, until acid number is reduced to below 0.1mgKOH/g, finally drying under reduced pressure under normal temperature 2.5-3KPa, obtaining yield is 95%, acid number is 0.08mgKOH/g, the tetramethylolmethane capronate that outward appearance is yellowish.
The present embodiment acidic solid catalyst used is identical with embodiment 1.
Embodiment 3
By TriMethylolPropane(TMP) and mixed acid (mol
n-caproic acid: mol
isocaprylic acid=3:1) drop in reactor at 1: 3.2 in molar ratio, add appropriate solvent, the acidic solid catalyst of acid alcohol gross weight 0.1% is added under stirring, be warming up to 120 ~ 130 DEG C of reaction 3h, raised temperature is to 130-140 DEG C afterwards, sustained reaction 3h again, synthesis obtains thick ester, filtered and recycled acidic solid catalyst, at 150 ~ 200 DEG C, underpressure distillation excess acid under 5kPa residual voltage, restored acid can reuse as raw material, at 250 ~ 300 DEG C, molecular distillation intermediate product under 0.1KPa, the ester of primary purification enters in weakly alkaline macroporous anion exchange resin (D392) post, carry out further degree of depth depickling, until acid number is reduced to below 0.1mgKOH/g, finally drying under reduced pressure under normal temperature 2.5-3KPa, obtaining yield is 95%, acid number is 0.08mgKOH/g, the TriMethylolPropane(TMP) nitration mixture ester that outward appearance is yellowish.
The present embodiment acidic solid catalyst used utilizes TiO
2with Al
2o
3by the composite oxides that coprecipitation method is formed; Its specific surface area is 550m
2/ g, aperture is 4.5-6.8nm.
Embodiment 4
By tetramethylolmethane and mixing acid (mol
n-caproic acid: mol
isocaprylic acid=3:1, part reclaims from embodiment 3) drop in reactor at 1: 4.2 in molar ratio, add appropriate solvent, the acidic solid catalyst (reclaiming from embodiment 3) of acid alcohol gross weight 0.1% is added under stirring, be warming up to 130 ~ 140 DEG C of reaction 3h, raised temperature is to 130-140 DEG C afterwards, sustained reaction 3h again, synthesis obtains thick ester, filtered and recycled acidic solid catalyst, at 150 ~ 200 DEG C, the excessive caproic acid of underpressure distillation under 5kPa residual voltage, restored acid can reuse as raw material, at 250 ~ 300 DEG C, molecular distillation intermediate product under 0.1KPa, the ester of primary purification enters in weakly alkaline macroporous anion exchange resin (D301R) post and carries out further degree of depth depickling, until acid number is reduced to below 0.1mgKOH/g, finally drying under reduced pressure under normal temperature 2.5-3KPa, obtaining yield is 95%, acid number is 0.08mgKOH/g, the tetramethylolmethane nitration mixture ester that outward appearance is yellowish.
The present embodiment acidic solid catalyst used is identical with embodiment 3.
Comparative example 1
TriMethylolPropane(TMP) and caproic acid are dropped in reactor in molar ratio at 1: 3.2, add appropriate solvent, under stirring, add the tosic acid of acid alcohol gross weight 0.1%, be warming up to 120 ~ 130 DEG C of reaction 3h, raised temperature is to 140-150 DEG C afterwards, sustained reaction 3h, synthesis obtains thick ester, at 150 ~ 200 DEG C, the excessive caproic acid of underpressure distillation and tosic acid under 5kPa residual voltage, at 250 ~ 300 DEG C, molecular distillation intermediate product under 0.1KPa, the ester of primary purification enters weak base (NaHCO
3solution) wash, then carry out being washed to neutrality, finally drying under reduced pressure under normal temperature 2.5-3KPa, obtaining yield is 92%, the TriMethylolPropane(TMP) capronate that acid number is 0.5mgKOH/g, outward appearance is yellowish.
Comparative example 2
By tetramethylolmethane and mixing acid (mol
n-caproic acid: mol
isocaprylic acid=3:1) drop in reactor at 1: 4.2 in molar ratio, add appropriate solvent, under stirring, add the tosic acid of acid alcohol gross weight 0.1%, be warming up to 120 ~ 130 DEG C of reaction 3h, raised temperature is to 140-150 DEG C afterwards, sustained reaction 3h, synthesis obtains thick ester, at 150 ~ 200 DEG C, the excessive nitration mixture of underpressure distillation and tosic acid under 5kPa residual voltage, at 250 ~ 300 DEG C, molecular distillation intermediate product under 0.1KPa, the ester of primary purification enters weak base (NaHCO
3solution) wash, then carry out being washed to neutrality, finally drying under reduced pressure under normal temperature 2.5-3KPa, obtaining yield is 93%, the tetramethylolmethane nitration mixture ester that acid number is 0.6mgKOH/g, outward appearance is yellowish.
Obviously, comparative example 1, the liquid catalyst tosic acid used in 2, after completion of the reaction, cannot realize and being effectively separated of excess organic acid, and cannot realize reusing of catalyzer and excess organic acid, also just cannot reach the requirement of reduction production cost; Simultaneously, tosic acid is strong acid, a small amount of remaining just has a significant impact product property in the product, especially acid number, adopt traditional alkali cleaning-washing process, the yield of product declines also clearly, cannot reach the effect of degree of depth depickling, the range of application of oil based on the Esters oil of so just restriction.
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (9)
1. a synthetic method for lubricating oil in esters base oil, is characterized in that, comprising with acid solid is catalyzer, under described catalyst action, esterification occurs with organic acid, Organic Alcohol for raw material; Described acidic solid catalyst utilizes ZrO
2or TiO
2with SiO
2or Al
2o
3the composite oxides formed.
2. synthetic method according to claim 1, is characterized in that, described acidic solid catalyst has following feature: specific surface area is 200-600m
2/ g, aperture is 2-10nm; Preferably, specific surface area is 300-550nm, and aperture is 4-8nm.
3. synthetic method according to claim 1 and 2, is characterized in that, the add-on of described acidic solid catalyst be organic acid, Organic Alcohol gross weight 0.05% ~ 0.1%.
4. synthetic method according to claim 1 and 2, is characterized in that, the preparation method of described acidic solid catalyst comprises: alkoxide hydrolysis, coprecipitation method.
5. the synthetic method according to any one of claim 1-4, is characterized in that, comprises the following steps:
1) take acid solid as catalyzer, under described catalyst action, esterification occurs for raw material with organic acid, Organic Alcohol, generate thick ester;
2) thick for gained ester is filtered, reclaim described acidic solid catalyst;
3) the thick ester underpressure distillation of gained after filtering, removes excess organic acid; Carry out molecular distillation again, remove the intermediate product of non-complete reaction further, obtain the ester of primary purification;
4) adopt anionite-exchange resin to carry out the degree of depth depickling ester of gained primary purification, reduce product acid number to below 0.1mgKOH/g, then dehydrated by underpressure distillation, to obtain final product.
6. synthetic method according to claim 5, is characterized in that,
Step 1) described esterification reaction temperature is preferably 120-180 DEG C, and the reaction times is preferably 2 ~ 6 hours;
Step 3) described underpressure distillation condition optimization is temperature 150 ~ 250 DEG C, 10 ~ 1kPa residual voltage; Described molecular distillation condition optimization is temperature 250 ~ 300 DEG C, pressure 0.1 ~ 0.01kPa;
Step 4) described anionite-exchange resin is preferably macroporous resin; Described underpressure distillation dehydration conditions is preferably pressure 2.5-3Kpa.
7. the lubricating oil in esters base oil for preparing of method described in any one of claim 1-6.
8. lubricating oil in esters base oil according to claim 7, its pour point is not higher than-30 DEG C, and flash-point is not less than 250 DEG C, and when 40 DEG C, kinematic viscosity is 10-100mm
2/ s, viscosity index is not less than 150, and between variant production, mutual solubility is good.
9. the purposes of the lubricating oil in esters base oil for preparing of method described in any one of claim 1-6 or the lubricating oil in esters base oil described in any one of claim 7-8; Preferably, described purposes is as aviation engine lubricating oil, air-compressor lubricating oil, turbine oil, automobile engine lubricating oil, heavy load gear oil or very low temperature engine oil.
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Cited By (7)
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| CN109652213A (en) * | 2019-01-18 | 2019-04-19 | 重庆大学 | A kind of esters insulating oil and preparation method thereof |
| CN109880666A (en) * | 2019-03-13 | 2019-06-14 | 上海鸣起能源科技有限公司 | A kind of preparation method and its refining methd of synthetic ester lubricant |
| CN109913290A (en) * | 2019-03-22 | 2019-06-21 | 合肥学院 | A kind of synthetic method of ester lubricating oil utilizing molybdenum disulfide nanoparticles as catalysis and lubrication |
| CN112500906A (en) * | 2020-12-14 | 2021-03-16 | 蓝德环保科技集团股份有限公司 | Method for producing high-viscosity-index biological lubricating oil base oil by using waste oil |
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| CN115403472A (en) * | 2022-08-31 | 2022-11-29 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109652213A (en) * | 2019-01-18 | 2019-04-19 | 重庆大学 | A kind of esters insulating oil and preparation method thereof |
| CN109880666A (en) * | 2019-03-13 | 2019-06-14 | 上海鸣起能源科技有限公司 | A kind of preparation method and its refining methd of synthetic ester lubricant |
| CN109913290A (en) * | 2019-03-22 | 2019-06-21 | 合肥学院 | A kind of synthetic method of ester lubricating oil utilizing molybdenum disulfide nanoparticles as catalysis and lubrication |
| CN109913290B (en) * | 2019-03-22 | 2022-01-18 | 合肥学院 | Synthetic method of ester lubricating oil with catalysis and lubrication effects of molybdenum disulfide nanoparticles |
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| CN112500906A (en) * | 2020-12-14 | 2021-03-16 | 蓝德环保科技集团股份有限公司 | Method for producing high-viscosity-index biological lubricating oil base oil by using waste oil |
| CN114426484A (en) * | 2022-01-21 | 2022-05-03 | 中国石油化工股份有限公司 | Synthetic method of pentaerythritol ester |
| CN115403472A (en) * | 2022-08-31 | 2022-11-29 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
| CN115403472B (en) * | 2022-08-31 | 2024-04-05 | 中国石油化工股份有限公司 | Synthetic high-carbon-number fatty acid triol ester, preparation method thereof and modified mineral oil |
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