CN110804476B - Preparation method of biomass-based low-viscosity fully-synthetic lubricating oil - Google Patents
Preparation method of biomass-based low-viscosity fully-synthetic lubricating oil Download PDFInfo
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- CN110804476B CN110804476B CN201911063255.1A CN201911063255A CN110804476B CN 110804476 B CN110804476 B CN 110804476B CN 201911063255 A CN201911063255 A CN 201911063255A CN 110804476 B CN110804476 B CN 110804476B
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- 239000010689 synthetic lubricating oil Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000002028 Biomass Substances 0.000 title abstract description 17
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims abstract description 52
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims abstract description 40
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims abstract description 28
- RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 claims abstract description 25
- DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000010687 lubricating oil Substances 0.000 claims abstract description 25
- VVWPSAPZUZXYCM-UHFFFAOYSA-N 9-methoxy-9-oxononanoic acid Chemical compound COC(=O)CCCCCCCC(O)=O VVWPSAPZUZXYCM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002243 precursor Substances 0.000 claims abstract description 21
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005642 Oleic acid Substances 0.000 claims abstract description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000003509 tertiary alcohols Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 15
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 15
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims abstract description 11
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims abstract description 11
- 229940073769 methyl oleate Drugs 0.000 claims abstract description 11
- -1 bromo Grignard reagent Chemical class 0.000 claims abstract description 10
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 239000003054 catalyst Substances 0.000 claims description 27
- 238000005984 hydrogenation reaction Methods 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000005643 Pelargonic acid Substances 0.000 claims description 12
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 239000002199 base oil Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 239000011777 magnesium Substances 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000007789 sealing Methods 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052681 coesite Inorganic materials 0.000 claims description 6
- 229910052906 cristobalite Inorganic materials 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052682 stishovite Inorganic materials 0.000 claims description 6
- 229910052905 tridymite Inorganic materials 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- 150000004795 grignard reagents Chemical class 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 238000007248 oxidative elimination reaction Methods 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- 229910020667 PBr3 Inorganic materials 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 5
- 238000003747 Grignard reaction Methods 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- 229910005887 NiSn Inorganic materials 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
Classifications
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- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/04—Well-defined hydrocarbons aliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
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- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/0206—Well-defined aliphatic compounds used as base material
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- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
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- Oil, Petroleum & Natural Gas (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application discloses a preparation method of biomass-based low-viscosity fully-synthetic lubricating oil, which comprises the following steps: the method comprises the following steps of carrying out oxidative fracture on oleic acid or methyl oleate, selectively hydrogenating nonanoic acid to obtain nonanol, preparing brominated alkane by brominating nonanol, preparing dimethyl azelate by brominating azelaic acid or monomethyl azelate, reacting a bromo Grignard reagent and the dimethyl azelate to synthesize a crotch-type tertiary alcohol precursor, and further hydrogenating to obtain the low-viscosity lubricating oil with the crotch-type structure. Its advantages are: the method adopts green and renewable biomass oleic acid or methyl oleate as a raw material, realizes carbon chain growth by constructing brominated alkanes and dimethyl nonanoate through a Grignard reaction to obtain long-chain crotch-type tertiary alcohol as a precursor, and further dehydrates and hydrogenates the precursor to obtain the high-quality low-viscosity fully-synthesized biomass-based lubricating oil. The use of fossil energy is avoided, and the concept of green sustainable development is met; the cheap and easily obtained oleic acid compound is selected, so that the raw material cost and the high-end total synthetic lubricating oil cost are greatly reduced.
Description
Technical Field
The application relates to the technical field of biomass-based fully synthetic lubricating oil, in particular to a preparation method of biomass-based low-viscosity fully synthetic lubricating oil.
Background
The lubricating oil market, especially the fully synthetic lubricating oil, greatly expands the application range of the lubricating oil under the conditions of high load, high rotating speed, high vacuum, high-energy radiation and strong oxidation medium, and provides excellent oxidation stability, viscosity-temperature property, wear resistance and lubricity, thereby greatly prolonging the oil change period and the service life of equipment, slowing down the abrasion and corrosion of the equipment and reducing the maintenance period of the equipment. At present, the fully synthetic lubricating oil is mainly prepared by adopting an olefin oligomerization method, and Chinese patent (CN 108559012A) reports that metallocene polymerization alpha-olefin is adopted to prepare fully synthetic lubricating oil base oil. However, at present, the alpha-olefin is mainly from non-renewable energy petrochemical industry or coal chemical industry, the carbon number distribution of the prepared alpha-olefin is wide, the separation cost is high, and the cost is increased.
Renewable biomass-based fully synthetic lubricating oil is concerned about, is easy to biodegrade, and has wide, cheap and easily available biomass sources. Chinese patent (CN 107384556A) reports that a bio-based lubricating oil prepared by mixing base oil such as soybean oil, pentaerythritol ester and castor oil with additives is not suitable for precision machinery due to low viscosity index and poor oxidation resistance caused by high oxygen content in the prepared lubricating oil. In order to improve the quality of the biomass lubricating oil, chinese patent (CN 103905306a) reports that rapeseed oil is used as a raw material and an ion exchange resin is used as a catalyst to perform epoxidation on the rapeseed oil, but the problem of high oxygen content in the biomass lubricating oil is not solved. The bio-based lubricating oil is required to synthesize the biomass lubricating oil with higher quality and controllable performance (viscosity, pour point, oxidation resistance and the like).
Disclosure of Invention
The method aims to prepare the fully synthetic lubricating oil by utilizing renewable biomass oleic acid, the raw materials are green, environment-friendly, cheap and easy to obtain, the process is simple and flexible, the yield of the lubricating oil is high, and the oleic acid or methyl oleate can be efficiently converted into the fully synthetic lubricating oil.
The synthetic route is as follows:
route for converting oleic acid into crotch-type low-viscosity fully-synthetic lubricating oil
Oxidizing oleic acid or methyl oleate (step 1), selectively hydrogenating nonanoic acid into nonanol (step 2), brominating nonanol to prepare brominated alkanes (step 3), preparing dimethyl azelate (step 4) from monomethyl azelate or azelaic acid, reacting a bromo-Grignard reagent with dimethyl azelate to prepare a crotch-type tertiary alcohol precursor (step 5), and finally hydrogenating the crotch-type tertiary alcohol precursor into the crotch-type low-viscosity fully-synthesized lubricating oil (step 6).
The following technical scheme is adopted in the application:
a method of making a lubricating oil, comprising the steps of:
step 1, oxidative cleavage of oleic acid or methyl oleate
Oleic acid or methyl oleate, an oxidant and a solvent react for 12 hours at the temperature of 40-80 ℃, and pelargonic acid, azelaic acid or monomethyl azelate are obtained after the reaction is finished and separated;
step 2, selective hydrogenation of nonanoic acid to nonanol
Adding pelargonic acid, hydrogenation catalyst and solvent into a reaction kettle, wherein the active center of the hydrogenation catalyst is Ru, Pt or Ni, sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle, and introducing 1.0-4.0MPa H into the reaction kettle2Obtaining reaction solution, cooling after the reaction is finished, and releasing H2And distilling to separate nonanol;
step 3, preparing bromoalkane by brominating nonanol
Placing the three-necked bottle in ice bath, adding solvent, introducing nitrogen as shielding gas, and dropwise adding nonanol and catalyst HgO + Br2、PBr3Or O3+Br2After the dropwise addition is finished, reacting for 1-3h, extracting and separating to obtain bromononane;
step 4, preparing dimethyl azelate from azelaic acid or monomethyl azelate
Reacting azelaic acid or monomethyl azelate, methanol and a catalyst at the temperature of 100 ℃ and 110 ℃ for 3h, wherein the catalyst is concentrated sulfuric acid, ion exchange resin and ZrOSO4After the reaction is finished, separating to obtain dimethyl azelate;
step 5, the bromo Grignard reagent reacts with dimethyl azelate to synthesize the crotch type tertiary alcohol precursor
Placing magnesium chips and anhydrous ether subjected to anhydrous treatment in a three-necked bottle, introducing nitrogen as protective gas, slowly dropwise adding bromononane until the magnesium chips are completely dissolved, slowly dropwise adding dimethyl azelate, after the reaction is finished, carrying out quenching reaction, and separating to obtain a crotch-type tertiary alcohol precursor;
step 6, further hydrogenating the crotch type tertiary alcohol precursor to obtain the synthetic lubricating oil base oil
Adding a crotch type tertiary alcohol precursor, a hydrogenation catalyst and a solvent into a reaction kettle, wherein the active center of the hydrogenation catalyst is Pd, Ru or Ni, sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle, and introducing 1.0-6.0MPa H into the reaction kettle2Heating the temperature of the reaction kettle to 200-350 ℃, reacting for 2-6H, and releasing H after the reaction is finished2And distilling to obtain the synthetic lubricant base oil.
Wherein, the oxidant in the step 1 is one or a combination of more of potassium permanganate, sodium hypochlorite and hydrogen peroxide.
Wherein, the solvent in the step 1 is water or ethanol.
Wherein the solvent in the step 2 is C6-C16Or a combination of one or more of linear alkanes or cyclic alkanes.
Wherein the hydrogenation catalyst in the step 2 comprises an active metal, an auxiliary agent and a carrier, the auxiliary agent is Re, Sn, Ir or Ce, and the carrier is mesoporous SiO2One or more of molecular sieve and activated carbon.
In the step 2, the mass of the active metal accounts for 0.1-10% of the mass of the carrier, and the volume ratio of the nonanoic acid to the solvent is 5:1-1: 1.
Wherein, the solvent in the step 3 is one or a combination of more of diethyl ether, methanol, ethanol, acetonitrile and tetrahydrofuran.
Wherein, in the step 3, the volume ratio of the nonanol to the solvent is 1: 1-5.
Wherein, the hydrogenation catalyst in the step 6 is a supported catalyst, and the cocatalyst is one or more of the simple substances or oxides of Re, Sn and Ir.
Wherein the loading amount of the active center of the hydrogenation catalyst in the step 6 is 0.1-10 wt.%, and the addition amount of the cocatalyst is 0.1-5.0 wt.%.
The above-mentioned at least one technical scheme that this application adopted can reach following beneficial effect:
the method takes biomass-based methyl oleate or oleic acid as a raw material, and prepares the high-quality low-viscosity crotch-type fully-synthetic bio-based lubricating oil by skillfully designing reaction steps and regulating and controlling the structure of the lubricating oil. The biomass-based fully synthetic lubricating oil has a controllable structure, has the quality comparable to that of commercial fully synthetic lubricating oil such as Mofu I, and has a wide commercial application prospect.
The method adopts green and renewable biomass oleic acid or methyl oleate as a raw material, realizes carbon chain growth by constructing brominated alkanes and dimethyl nonanoate through a Grignard reaction to obtain long-chain crotch-type tertiary alcohol as a precursor, and further dehydrates and hydrogenates the precursor to obtain the high-quality low-viscosity fully-synthesized biomass-based lubricating oil.
The application avoids the use of fossil energy and conforms to the concept of green sustainable development; meanwhile, the oleic acid compound which is cheap and easy to obtain is selected, so that the raw material cost and the high-end total synthetic lubricating oil cost are greatly reduced, and the product has market competitiveness.
Detailed Description
In order to make the objects, technical solutions and advantages of the present application more apparent, the technical solutions of the present application will be described in detail and completely with reference to the specific embodiments of the present application. It should be apparent that the described embodiments are only some of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
Example 1
(1) Oxidative cleavage of oleic acid to pelargonic and azelaic acid
20mL of oleic acid, 1.0g of potassium permanganate, 0.5g of sodium hydroxide and 50mL of H2O is added into a three-neck flask, stirred in an oil bath at the temperature of 80 ℃ and reacted overnight, and pelargonic acid and azelaic acid are separated.
The chromatographic analysis showed yields of pelargonic and azelaic acid of 47.4% and 45.8%, respectively.
(2) Selective hydrogenation of pelargonic acid to nonanol
0.05g of Ni (NO) was weighed3)2And 0.1g SnCl4Adding into 40mL of aqueous solution, stirring at 25 deg.C for 3h, adding carrier 2g SiO2Stirring for 3H, rotary evaporating at 60 deg.C until water is completely volatilized, drying the obtained precursor in an oven at 100 deg.C overnight, calcining at 450 deg.C in air for 4H, and adding high-purity H2Reducing at 450 deg.C for 4h, cooling completely, and adding N at 5:1 ratio2And air aged for future use.
0.2g of the prepared NiSn catalyst was added to the reaction vessel, and 2g of pelargonic acid and 80mL of n-hexane were added. Sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle; introducing 4MPa of H into the reaction kettle2And raising the temperature of the reaction kettle to 300 ℃ for reaction for 3 hours. After the reaction is finished, cooling is carried out to release H2Distilling to obtain nonanol.
The chromatographic analysis result shows that the yield of the nonanol is 100 percent.
(3) Preparation of bromoalkane by bromination of nonanol
After anhydrous treatment of a 100mL three-necked flask, the flask was placed in an ice bath, 25mL of anhydrous ether was added, and nitrogen was introduced as a shielding gas. After the temperature is constant, 25mL of nonanol and phosphorus tribromide are prepared by dropping 25mL of the mixture into a three-necked flask through a constant-pressure dropping funnel at the same time, wherein the molar ratio of the nonanol to the phosphorus tribromide is 3: 1. And after the dropwise addition is finished, stirring for 3 hours, extracting and separating to obtain the bromononane.
The chromatographic analysis result shows that the yield of the bromononane is 85 percent.
(4) Preparation of dimethyl azelate by reacting azelaic acid with methanol
Adding 20mL of azelaic acid, 50mL of methanol and 1mL of concentrated sulfuric acid into a three-neck flask, stirring for 3h in an oil bath at 110 ℃, and separating to obtain dimethyl azelate.
The chromatographic analysis result shows that the yield of the dimethyl azelate is 92 percent.
(5) Reacting excessive bromo Grignard reagent with dimethyl azelate to obtain crotch type tertiary alcohol
A100 mL three-necked flask was treated with water-free water and placed in an ice bath. 25mL of anhydrous ether was added and nitrogen was introduced as a blanket gas. After the temperature was constant, 2g of magnesium chips were added, the prepared bromononane was added dropwise to the three-necked flask through a constant pressure funnel until the magnesium chips were completely dissolved, and then dimethyl azelate was added dropwise to the three-necked flask through a constant pressure dropping funnel. The molar ratio of grignard reagent to dimethyl azelate is 5.5: 1. after the reaction was completed, quenching was performed with diluted hydrochloric acid.
The chromatographic analysis result shows that the yield of the precursor of the lubricating oil with the crotch structure is 80 percent.
(6) Dehydration and hydrogenation of crotch type tertiary alcohol into synthetic lubricating oil
0.05g of PdCl are weighed out2Adding into 40mL of aqueous solution, stirring at 25 deg.C for 3h, adding 1g of SiO2Stirring for 3 h. Heating to 60 deg.C, stirring until water is completely evaporated, drying in 100 deg.C oven overnight, calcining in air at 450 deg.C for 4 hr, and adding high-purity H2Reducing at 450 deg.C for 4h, cooling completely, and adding N at 5:1 ratio2And air aged for future use.
0.1g of hydrogenation catalyst was added to the reaction vessel, and 10g of the prepared lubricant precursor and 80mL of n-hexane were added. Sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle; introducing 4MPa of H into the reaction kettle2And raising the temperature of the reaction kettle to 300 ℃ for reaction for 3 hours. After the reaction is finished, cooling is carried out to release H2Distilling to obtain the fully synthetic crotch-type lubricating oil base oil.
The chromatographic analysis result shows that the yield of the crotch-type structural lubricating oil is 100 percent.
(7) The properties of the lubricating oil prepared were determined using the national standard method, as follows:
example 2
(1) Oxidation of methyl oleate to pelargonic acid and monomethyl azelate
20mL of oleic acid, 1g of sodium hypochlorite, 5mL of hydrogen peroxide and 50mL of H2O is added into a three-neck flask, stirred in an oil bath at 60 ℃ and reacted overnight, and pelargonic acid and monomethyl azelate are separated.
The chromatographic analysis showed yields of 48% and 49% for pelargonic acid and monomethyl azelate, respectively.
(2) Selective hydrogenation of pelargonic acid to nonanol
0.05g of RuCl was weighed3And 0.1g IrCl3Adding into 40mL of aqueous solution, stirring at 25 deg.C for 3h, adding carrier 2g SiO2Stirring for 3H, rotary evaporating at 60 deg.C until water is completely volatilized, drying the obtained precursor in an oven at 100 deg.C overnight, calcining at 450 deg.C in air for 4H, and adding high-purity H2Reducing at 450 deg.C for 4h, cooling completely, and adding N at 5:1 ratio2And air aged for future use.
0.2g of the prepared RuIr catalyst was added to the reaction vessel, 2g of pelargonic acid and 80mL of n-hexane were added. Sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle; introducing 4MPa of H into the reaction kettle2And raising the temperature of the reaction kettle to 300 ℃ for 6 hours. After the reaction is finished, cooling is carried out to release H2Distilling to obtain nonanol.
The chromatographic analysis result shows that the yield of the nonanol is 100 percent.
(3) Preparation of bromoalkane by bromination of nonanol
After anhydrous treatment is carried out on a 100mL three-necked flask, the three-necked flask is placed in an ice bath, 25mL of anhydrous ether is added, nitrogen is introduced to be used as protective gas, 25mL of nonanol and phosphorus tribromide are simultaneously dropwise added into the three-necked flask through a constant pressure dropping funnel after the temperature is constant, and the molar ratio of the nonanol to the phosphorus tribromide is 3: 1. And after the dropwise addition is finished, stirring for 3 hours, extracting and separating to obtain the bromononane.
The chromatographic analysis result shows that the yield of the bromononane is 85 percent.
(4) Preparation of dimethyl azelate from monomethyl azelate
Adding 20mL of azelaic acid, 50mL of methanol and 1mL of concentrated sulfuric acid into a three-neck flask, stirring for 3h in an oil bath at 110 ℃, and separating to obtain dimethyl azelate.
The chromatographic analysis showed 93% yield of dimethyl azelate.
(5) Reacting excessive bromo Grignard reagent with dimethyl azelate to obtain crotch type tertiary alcohol
After carrying out anhydrous treatment on a 100mL three-neck flask, putting the three-neck flask into an ice bath, adding 25mL anhydrous ether, introducing nitrogen as a protective gas, adding 2g magnesium chips after the temperature is constant, dropwise adding the prepared bromononane into the three-neck flask through a constant pressure funnel until the magnesium chips are completely dissolved, dropwise adding dimethyl azelate into the three-neck flask through a constant pressure dropping funnel, wherein the molar ratio of a Grignard reagent to the dimethyl azelate is 5.5: 1. after the reaction was completed, quenching was performed with diluted hydrochloric acid.
The chromatographic analysis result shows that the yield of the precursor of the lubricating oil with the crotch structure is 80 percent.
(6) Dehydration and hydrogenation of crotch type tertiary alcohol into synthetic lubricating oil
Weigh 0.05gNi (NO)3)2Adding into 40mL of aqueous solution, stirring at 25 deg.C for 3h, adding 1g of SiO2Stirring for 3H, heating to 60 deg.C, stirring until water is completely evaporated, drying in oven at 100 deg.C overnight, calcining in air at 450 deg.C for 4H, and adding high purity H2Reducing at 450 deg.C for 4h, cooling completely, and adding N at 5:1 ratio2And air aged for future use.
0.1g of hydrogenation catalyst was added to the reaction vessel, and 10g of the prepared lubricant precursor and 80mL of n-hexane were added. Sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle; introducing 4MPa of H into the reaction kettle2And raising the temperature of the reaction kettle to 300 ℃ for reaction for 3 hours. Inverse directionCooling after reaction, releasing H2Distilling to obtain the fully synthetic crotch-type lubricating oil base oil.
The chromatographic analysis result shows that the yield of the crotch-type structural lubricating oil is 100 percent.
(7) The properties of the lubricating oil prepared were determined using the national standard method, as follows:
the above description is only an example of the present application and is not intended to limit the present application. Various modifications and changes may occur to those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present application should be included in the scope of the claims of the present application.
Claims (10)
1. A preparation method of lubricating oil is characterized by comprising the following steps:
step 1, oxidative cleavage of oleic acid or methyl oleate
Oleic acid or methyl oleate, an oxidant and a solvent react for 12 hours at the temperature of 40-80 ℃, and pelargonic acid, azelaic acid or monomethyl azelate are obtained after the reaction is finished and separated;
step 2, selective hydrogenation of nonanoic acid to nonanol
Adding pelargonic acid, hydrogenation catalyst and solvent into a reaction kettle, wherein the active center of the hydrogenation catalyst is Ru, Pt or Ni, sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle, and introducing 1.0-4.0MPa H into the reaction kettle2Obtaining reaction solution, cooling after the reaction is finished, and releasing H2And distilling to separate nonanol;
step 3, preparing bromoalkane by brominating nonanol
Placing the three-necked bottle in ice bath, adding solvent, introducing nitrogen as shielding gas, and dropwise adding nonanol and catalyst HgO + Br2、PBr3Or O3+Br2After the dripping is finished, reacting for 1-3h,extracting and separating to obtain bromononane;
step 4, preparing dimethyl azelate from azelaic acid or monomethyl azelate
Reacting azelaic acid or monomethyl azelate, methanol and a catalyst at the temperature of 100 ℃ and 110 ℃ for 3h, wherein the catalyst is concentrated sulfuric acid, ion exchange resin and ZrOSO4After the reaction is finished, separating to obtain dimethyl azelate;
step 5, the bromo Grignard reagent reacts with dimethyl azelate to synthesize the crotch type tertiary alcohol precursor
Placing magnesium chips and anhydrous ether subjected to anhydrous treatment in a three-necked bottle, introducing nitrogen as protective gas, slowly dropwise adding bromononane until the magnesium chips are completely dissolved, slowly dropwise adding dimethyl azelate, after the reaction is finished, carrying out quenching reaction, and separating to obtain a crotch-type tertiary alcohol precursor, wherein the molar ratio of the Grignard reagent to the dimethyl azelate is 5.5: 1;
step 6, further hydrogenating the crotch type tertiary alcohol precursor to obtain the synthetic lubricating oil base oil
Adding a crotch type tertiary alcohol precursor, a hydrogenation catalyst and a solvent into a reaction kettle, wherein the active center of the hydrogenation catalyst is Pd, Ru or Ni, sealing the reaction kettle, and introducing H2Replacing air in the reaction kettle, and introducing 1.0-6.0MPa H into the reaction kettle2Heating the temperature of the reaction kettle to 200-350 ℃, reacting for 2-6H, and releasing H after the reaction is finished2And distilling to obtain the synthetic lubricant base oil.
2. The method of claim 1, wherein the oxidant in step 1 is one or more of potassium permanganate, sodium hypochlorite and hydrogen peroxide.
3. The method according to claim 1, wherein the solvent used in step 1 is water or ethanol.
4. The method according to claim 1, wherein the solvent used in the step 2 is C6-C16One or more of linear or cyclic alkanes ofAnd (4) combination.
5. The preparation method of claim 1, wherein in the step 2, the hydrogenation catalyst comprises an active metal, an auxiliary agent and a carrier, wherein the auxiliary agent is Re, Sn, Ir or Ce, and the carrier is mesoporous SiO2One or more of molecular sieve and activated carbon.
6. The method of claim 5, wherein in step 2, the active metal accounts for 0.1-10% of the carrier by mass, and the ratio of the nonanoic acid to the solvent is 5:1-1:1 by volume.
7. The method of claim 1, wherein the solvent in step 3 is one or more selected from the group consisting of diethyl ether, methanol, ethanol, acetonitrile, and tetrahydrofuran.
8. The method of claim 1, wherein in step 3, the ratio of nonanol to solvent is 1:1 to 5 by volume.
9. The method according to claim 1, wherein the hydrogenation catalyst in step 6 is a supported catalyst, and the promoter is one or more of the elements or oxides of Re, Sn and Ir.
10. The process of claim 1 wherein the hydrogenation catalyst in step 6 has an active site loading of 0.1 to 10 wt.% and the promoter is added in an amount of 0.1 to 5.0 wt.%.
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