CN102977244A - Bio-based polyester synthetic oil and preparation method thereof - Google Patents
Bio-based polyester synthetic oil and preparation method thereof Download PDFInfo
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- CN102977244A CN102977244A CN2012104865213A CN201210486521A CN102977244A CN 102977244 A CN102977244 A CN 102977244A CN 2012104865213 A CN2012104865213 A CN 2012104865213A CN 201210486521 A CN201210486521 A CN 201210486521A CN 102977244 A CN102977244 A CN 102977244A
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- fumaric acid
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Abstract
The invention relates to bio-based polyester synthetic oil and a preparation method thereof. The molecular structure of the bio-based polyester synthetic oil is R=CmH2[m+1] (m>=1), n=2-20, and the molecular mass is 700-7000. The preparation method comprises the steps of: hydrolyzing by taking agricultural and forestry waste as a raw material to obtain furfural; carrying out catalytic oxidation on the furfural to prepare fumaric acid; carrying out ZSM-5 catalytic esterification on furfuryl alcohol prepared by hydrogenation of the furfural and fumaric acid to prepare 2-furan methyl ester fumarate; and carrying out polymerization on the 2-furan methyl ester fumarate and a-olefin to prepare 2-furan methyl ester polyfumarate synthetic oil. The bio-based polyester synthetic oil and the preparation method thereof have the advantages that the prepared polyester synthetic oil can be used as lubricant base oil, a lubricant viscosity index modifier, an environment-friendly anti-wear extreme-pressure reagent and a high-cleanliness fuel lubricating additive, so that the range of application is wide.
Description
Technical field
The invention belongs to bio-based synthetic oil field, be specifically related to a kind of agriculture and forestry organic waste material that utilizes and be the technology of raw material synthesizing polyester oil.
Background technology
Polyester oil is relatively new gang's synthetic lubricant base oil, it is the multipolymer of alpha-olefin and unsaturated diester, its molecular structure characteristics are: being connected on the hydrocarbon skeleton is the hydrocarbon side chain that substitutes and paired ester pendant groups, so have the excellent characteristics such as oilness, viscosity-temperature characteristics, stability and sealing material consistency.The field that is mainly used in requiring high lubricity, viscosity-temperature characteristics and can shows the high performance-price ratio advantage is such as I. C. engine oil, gear oil and the heavy loading metalworking fluid of all automobiles.
Summary of the invention
The purpose of this invention is to provide a kind of synthetic lubricant base oil that can be used as, also can be used as lubricating oil viscosity index properties-correcting agent, environment-friendly type extreme pressure anti-wear additives, bio-based polyester synthetic oil of fuel with high cleanness oiliness additive and preparation method thereof.
Bio-based polyester synthetic oil of the present invention, its molecular structure is:
R=C
mH
2m+1?(m≥1)
N=2-20, molecular mass is 700-7000
The preparation method of bio-based polyester synthetic oil of the present invention is as follows:
1) take furfural as raw material, hydrogen peroxide is oxygenant, and its mol ratio is: H
2O
2/ furfural=1.5-4/1 is at V
2O
5Under condition of normal pressure, react on the catalyzer and make fumaric acid; V
2O
5Catalyst levels is the 1-5wt% of furfural, 50 ~ 120 ℃ of temperature of reaction, and equation is as follows:
2) take furfuryl alcohol and fumaric acid as raw material, its mol ratio is: furfuryl alcohol/fumaric acid=1-4/1, under the catalyzer condition of normal pressure, carry out esterification take ZSM-5 molecular sieve, and make fumaric acid two furfuryl esters; Catalyst levels is the 2-10 wt % of fumaric acid, 200 ~ 300 ℃ of temperature of reaction, and equation is as follows:
3) take fumaric acid two furfuryl esters and a-alkene as raw material, its mol ratio is: fumaric acid two furfuryls ester/a-alkene=1/1-10, initiator peroxidation di-isopropyl two carbonic ethers that add fumaric acid two furfuryl ester quality 1 ~ 2%, 70 ~ 150 ℃ of temperature of reaction, under pressure 0 ~ 10MPa condition, carry out polyreaction, make poly-fumaric acid two furfuryl ester synthetic oils.
The indices of polyester ucon oil of the present invention such as following table:
Described furfural is to be hydrolyzed take agriculture and forestry organic waste material as raw material to make;
Described furfuryl alcohol is take agriculture and forestry organic waste material as raw material, makes through hydrolysis, hydrogenation.
Described a-alkene is the two keys of a kind of C=C at 1 alkene, comprises the a-normal olefine: such as ethene, propylene, 1-butylene, 1-amylene, 1-hexene etc.; The a-branched-chain alkene, such as 3-methyl-1-butene, 2,3-methyl-1-butene etc.
Described ZSM-5 molecular sieve is outsourcing, its production unit: Tianjin southization catalyzer company limited.
Advantage of the present invention is: take agriculture and forestry organic waste material as raw material, cost is low, raw material sources are abundant, environmental protection, the polyester synthetic oil that makes, can be used as synthetic lubricant base oil, also can be used as lubricating oil viscosity index properties-correcting agent, environment-friendly type extreme pressure anti-wear additives, the fuel with high cleanness oiliness additive, of many uses.
Embodiment
The present invention obtains furfural take agriculture and forestry organic waste materials such as agricultural crop straw, corn cob, scrub growth stump things as the raw water solution.Furfural is through catalyzed oxidation fumaric acid processed; The furfuryl alcohol that fumaric acid and furfural hydrogenation make makes fumaric acid two furfuryl esters through the ZSM-5 catalytic esterification; Fumaric acid two furfuryl esters and a-olefinic polymerization system are gathered fumaric acid two furfuryl ester synthetic oils.If pressure does not refer in particular in the embodiments of the invention, be relative pressure.
Embodiment 1
1, the preparation of fumaric acid:
Take the furfural of agriculture and forestry organic waste material production as raw material, (mol ratio is H take hydrogen peroxide as oxygenant
2O
2/ furfural=2/1), at V
2O
5On the catalyzer (consumption is the 2wt% of furfural consumption), 95 ~ 100 ℃ of temperature of reaction, under the condition of normal pressure, reaction 30min makes fumaric acid, and yield is 75%.
Equation is as follows:
2, the preparation of fumaric acid two furfuryl esters:
Take the furfuryl alcohol of agriculture and forestry organic waste material production and fumaric acid as raw material (mol ratio: furfuryl alcohol/fumaric acid=2/1), take ZSM-5 molecular sieve as catalyzer (catalyst levels is the 4wt% of fumaric acid), 245 ~ 255 ℃ of temperature of reaction, under the condition of normal pressure, carry out esterification, make fumaric acid two furfuryl esters, yield is 47%.
Equation is as follows:
3, the preparation of poly-fumaric acid two furfuryl ester synthetic oils:
(the mol ratio: fumaric acid two furfuryls ester/a-alkene=1/4) take fumaric acid two furfuryl ester 1-butylene as raw material, initiator peroxidation di-isopropyl two carbonic ethers that add fumaric acid two furfuryl ester quality 2%, 110 ~ 115 ℃ of temperature of reaction, under the pressure 4-5MPa condition, carry out polyreaction, make poly-fumaric acid two furfuryl ester synthetic oils, yield is 63%.
The indices of polyester ucon oil of the present invention such as following table:
Embodiment 2
1, the preparation of fumaric acid:
Take the furfural of agriculture and forestry organic waste material production as raw material, (mol ratio is H take hydrogen peroxide as oxygenant
2O
2/ furfural=2/1), at V
2O
5On the catalyzer (consumption is the 2wt% of furfural consumption), 65 ~ 70 ℃ of temperature of reaction, under the condition of normal pressure, reaction 30min makes fumaric acid, and yield is 45%.
Equation is as follows:
2, the preparation of fumaric acid two furfuryl esters:
Take the furfuryl alcohol of agriculture and forestry organic waste material production and fumaric acid as raw material (mol ratio: furfuryl alcohol/fumaric acid=2/1), take ZSM-5 molecular sieve as catalyzer (catalyst levels is the 4wt% of fumaric acid), 210 ~ 215 ℃ of temperature of reaction, under the condition of normal pressure, carry out esterification, make fumaric acid two furfuryl esters, yield is 38%.
Equation is as follows:
3, the preparation of poly-fumaric acid two furfuryl ester synthetic oils:
(the mol ratio: fumaric acid two furfuryls ester/a-alkene=1/4) take fumaric acid two furfuryl ester 1-butylene as raw material, initiator peroxidation di-isopropyl two carbonic ethers that add fumaric acid two furfuryl ester quality 2%, 75 ~ 80 ℃ of temperature of reaction, under pressure 4 ~ 5MPa condition, carry out polyreaction, make poly-fumaric acid two furfuryl ester synthetic oils, yield is 39%.
The indices of polyester ucon oil of the present invention such as following table:
Embodiment 3
1, the preparation of fumaric acid:
Take the furfural of agriculture and forestry organic waste material production as raw material, (mol ratio is H take hydrogen peroxide as oxygenant
2O
2/ furfural=2/1), at V
2O
5On the catalyzer (consumption is the 2wt% of furfural consumption), 140 ~ 145 ℃ of temperature of reaction, under the condition of normal pressure, reaction 30min makes fumaric acid, and yield is 66%.
Equation is as follows:
2, the preparation of fumaric acid two furfuryl esters:
Take the furfuryl alcohol of agriculture and forestry organic waste material production and fumaric acid as raw material (mol ratio: furfuryl alcohol/fumaric acid=2/1), take ZSM-5 molecular sieve as catalyzer (catalyst levels is the 4wt% of fumaric acid), 280 ~ 285 ℃ of temperature of reaction, under the condition of normal pressure, carry out esterification, make fumaric acid two furfuryl esters, yield is 42%.
Equation is as follows:
3, the preparation of poly-fumaric acid two furfuryl ester synthetic oils:
(the mol ratio: fumaric acid two furfuryls ester/a-alkene=1/4) take fumaric acid two furfuryl ester 1-butylene as raw material, initiator peroxidation di-isopropyl two carbonic ethers that add fumaric acid two furfuryl ester quality 2%, 110 ~ 115 ℃ of temperature of reaction, under pressure 0.5 ~ 0.6MPa condition, carry out polyreaction, make poly-fumaric acid two furfuryl ester synthetic oils, yield is 58%.
The indices of polyester ucon oil of the present invention such as following table:
Claims (4)
1. bio-based polyester synthetic oil, it is characterized in that: its molecular structure is:
R=C
mH
2m+1?(m≥1)
N=2-20, molecular mass is 700-7000.
2. the preparation method of a bio-based polyester synthetic oil according to claim 1 is characterized in that:
1) take furfural as raw material, hydrogen peroxide is oxygenant, and its mol ratio is: H
2O
2/ furfural=1.5-4/1 is at V
2O
5Under condition of normal pressure, react on the catalyzer and make fumaric acid; V
2O
5Catalyst levels is the 1-5wt% of furfural, 50 ~ 120 ℃ of temperature of reaction;
2) take furfuryl alcohol and fumaric acid as raw material, its mol ratio is: furfuryl alcohol/fumaric acid=1-4/1, under the catalyzer condition of normal pressure, carry out esterification take ZSM-5 molecular sieve, and make fumaric acid two furfuryl esters; Catalyst levels is the 2-10 wt % of fumaric acid, 200 ~ 300 ℃ of temperature of reaction;
3) take fumaric acid two furfuryl esters and a-alkene (such as 1-butylene) as raw material, its mol ratio is: fumaric acid two furfuryls ester/a-alkene=1/1-10, initiator peroxidation di-isopropyl two carbonic ethers that add fumaric acid two furfuryl ester quality 1 ~ 2%, 70 ~ 150 ℃ of temperature of reaction, under pressure 0 ~ 10MPa condition, carry out polyreaction, make poly-fumaric acid two furfuryl ester synthetic oils.
3. the preparation method of bio-based polyester synthetic oil according to claim 2, it is characterized in that: described furfural is to be hydrolyzed take agriculture and forestry organic waste material as raw material to make.
4. the preparation method of bio-based polyester synthetic oil according to claim 2, it is characterized in that: described furfuryl alcohol is take agriculture and forestry organic waste material as raw material, hydrolysis, hydrogenation make.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9321714B1 (en) | 2014-12-05 | 2016-04-26 | Uop Llc | Processes and catalysts for conversion of 2,5-dimethylfuran derivatives to terephthalate |
| CN115124494A (en) * | 2021-03-26 | 2022-09-30 | 中国科学院宁波材料技术与工程研究所 | 2, 5-tetrahydrofuran dimethanol sulfate ester compound and preparation method and application thereof |
| US11912656B2 (en) | 2018-12-21 | 2024-02-27 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Oxidation of 5-hydroxy-2-furanone to maleates |
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|---|---|---|---|---|
| JPH04219283A (en) * | 1990-12-18 | 1992-08-10 | Asahi Denka Kogyo Kk | Thermal color developing material |
| CN101200522A (en) * | 2007-11-26 | 2008-06-18 | 内蒙古金骄特种新材料有限公司 | Polyester oil and preparation method thereof |
| CN101899145B (en) * | 2010-07-28 | 2012-07-11 | 江南大学 | Preparation method of 2, 5-furan diformyl polyester |
-
2012
- 2012-11-26 CN CN201210486521.3A patent/CN102977244B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04219283A (en) * | 1990-12-18 | 1992-08-10 | Asahi Denka Kogyo Kk | Thermal color developing material |
| CN101200522A (en) * | 2007-11-26 | 2008-06-18 | 内蒙古金骄特种新材料有限公司 | Polyester oil and preparation method thereof |
| CN101899145B (en) * | 2010-07-28 | 2012-07-11 | 江南大学 | Preparation method of 2, 5-furan diformyl polyester |
Non-Patent Citations (1)
| Title |
|---|
| W. R. EDWARDS ET AL.: "Furfuryl ester of some dicarboxylic acids", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9321714B1 (en) | 2014-12-05 | 2016-04-26 | Uop Llc | Processes and catalysts for conversion of 2,5-dimethylfuran derivatives to terephthalate |
| US11912656B2 (en) | 2018-12-21 | 2024-02-27 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Oxidation of 5-hydroxy-2-furanone to maleates |
| CN115124494A (en) * | 2021-03-26 | 2022-09-30 | 中国科学院宁波材料技术与工程研究所 | 2, 5-tetrahydrofuran dimethanol sulfate ester compound and preparation method and application thereof |
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|---|---|
| CN102977244B (en) | 2015-06-24 |
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Address after: 014060 Wanshuiquan, Rare Earth High-tech Zone, Baotou City, Inner Mongolia Autonomous Region Patentee after: Pretty Oriental Bio Fuel Group Limited Address before: 014030 Jinjiao Industrial Park, Binhe New Area, Baotou Rare Earth High-tech Zone, Inner Mongolia Autonomous Region Patentee before: Jinjiao Special New Materials (Group) Co., Ltd. |
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