DE832313C - Verfahren zur Herstellung von Schmiermitteln bzw. Schmiermittelzusaetzen - Google Patents
Verfahren zur Herstellung von Schmiermitteln bzw. SchmiermittelzusaetzenInfo
- Publication number
- DE832313C DE832313C DEP25364D DEP0025364D DE832313C DE 832313 C DE832313 C DE 832313C DE P25364 D DEP25364 D DE P25364D DE P0025364 D DEP0025364 D DE P0025364D DE 832313 C DE832313 C DE 832313C
- Authority
- DE
- Germany
- Prior art keywords
- lubricants
- production
- lubricant additives
- compounds
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000314 lubricant Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003879 lubricant additive Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002485 combustion reaction Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 5
- 159000000007 calcium salts Chemical class 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 229960004889 salicylic acid Drugs 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 acrolein Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- FJMYNXGWSXFTMF-UHFFFAOYSA-L calcium;6-carboxy-2,3-di(propan-2-yl)phenolate Chemical compound [Ca+2].CC(C)C1=CC=C(C(O)=O)C([O-])=C1C(C)C.CC(C)C1=CC=C(C(O)=O)C([O-])=C1C(C)C FJMYNXGWSXFTMF-UHFFFAOYSA-L 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- RJKGJBPXVHTNJL-UHFFFAOYSA-N 1-nitronaphthalene Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=CC2=C1 RJKGJBPXVHTNJL-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- HXISMZRZHNLOHG-UHFFFAOYSA-N 2-hydroxy-3,4-di(propan-2-yl)benzoic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C(O)=C1C(C)C HXISMZRZHNLOHG-UHFFFAOYSA-N 0.000 description 1
- WWPLDSOFBMZGIJ-UHFFFAOYSA-N 2-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=CC=C1C(O)=O WWPLDSOFBMZGIJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/02—Alkylation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F240/00—Copolymers of hydrocarbons and mineral oils, e.g. petroleum resins
-
- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
- C10M2209/062—Vinyl esters of saturated carboxylic or carbonic acids, e.g. vinyl acetate
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/082—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type monocarboxylic
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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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
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
-
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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- C10N2010/02—Groups 1 or 11
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- C10N2010/12—Groups 6 or 16
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- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von Schmiermitteln bzw. Schmiermittelzusätzen.
Das Verfahren ist dadurch gekennzeichnet,· daß aromatische Verbindungen, die eine oder mehrere
polare Gruppen, wie die O H- oder COO H-Gruppe, enthalten, zusammen mit einem Überschuß von Verbindungen
mit einer aliphatischen Doppelbindung, die mehr als vier Kohlenstoffatome im Molekül enthalten,
gleichzeitig einem Alkylierungs- und Polymerisationsprozeß unterworfen werden.
Beispielsweise kommen gemäß der Erfindung folgende aromatische Verbindungen in Betracht: Benzylalkohol,
Benzoesäure, Mandelsäure, Phenol, Salicylsäure, Aminophenol, Nitronaphthalin, Naph- j
thalinsulfonsäure oder Mischungen von diesen oder ähnliche Substanzen.
Beispiele von Verbindungen mit einer aliphatischen Doppelbindung, die mehr als etwa vier
Kohlenstoffatome im Molekül enthalten, sind: Olefine, wie Hexen, Decen und Ceten, Cycloolefine,
wie Cyclohexen, Mischungen, die Olefine enthalten, wie z. B. Destillate, erzeugt durch Cracker! von
Paraffinwachs im dampfförmigen oder flüssigen Zustand, ungesättigte Alkohole, wie Allyl- und
Oleinalkohol, ungesättigte Carbonsäuren, wie öl- und Linolsäure, ungesättigte Aldehyde, wie Acrolein, ungesättigte Ester, wie sie im Rübsamenöl
oder Sojabohnenöl usw. enthalten sind.
Die Alkylierungs- und Polymerisationsprozesse werden in Gegenwart von Katalysatoren, wie z. B.
von Aluminiumchlorid, Borfluorid und Flußsäure, durchgeführt, und zwar in der Regel bei einer Temperatur
von über etwa 500.
Obwohl die durch den Alkylierungs- und Polymerisationsprozeß erhaltenen Produkte als Schmieröle
oder als Zusätze zu diesen geeignet sind, kommen sie noch mehr als Ausgangsmaterial für die
Herstellung von Metallsalze enthaltenden Schmiermitteln oder von Metallsalzzusätzen zu an sich bekannten
Schmiermitteln in Betracht, um diesen Spezialeigenschaften zu verleihen.
So fördern die Salze der Metalle der zweiten und
ίο dritten Gruppe des periodischen Systems, von Metallen
der sechsten Gruppe und von denen der Fe-Gruppe, wenn sie in Schmiermitteln beispielsweise
für Zylinder von Verbrennungskraftmaschinen verwendet werden, das Reinhalten der Zylinder, verhindern
die Bildung von kohlenstoffartigen Ablagerungen auf den Kolben und in den Kolbenringnuten,
beugen dem Kleben der Kolbenringe in ihren Nuten vor und schrärfken die Abnutzung und das
Reißen infolge Korrosion ein.
Im allgemeinen verbessern die Zusätze gemäß der Erfindung die Beständigkeit der Schmiermittel
gegen Oxydation und Zersetzung bei hohen Temperaturen.
Diese Wirkungen sind an sich bekannt, und es ist, um sie zu erzielen, bereits vorgeschlagen worden,
den Schmiermitteln Salze mehrwertiger Metalle aromatischer Carbonsäuren, die im Kern substituiert
sein können, z. B. das Calciumsalz der Di isopropy!salicylsäure, zuzusetzen.
Jedoch es ist ein Nachteil der bekannten Zusätze, daß ihre Herstellung nicht einfach ist und daß es
schwierig ist, sie dem Schmiermittel einzuverleiben-Die Produkte gemäß der Erfindung und die daraus
erhaltenen Metallsalze können auf einfachere Weise hergestellt und darüber hinaus ohne Schwierigkeiten
mit dem Schmiermittel gemischt werden, dem sie beizufügen sind. Überdies haben sie den
bedeutenden Vorteil, daß sie ausgezeichnete Erfolge ergeben, wenn sie in Schmiermitteln mit einem
hohen Viskositätsindex verwendet werden, was auf die erwähnten, bereits bekannten Zusätze nicht zutrifft,
die am besten in ölen mit einem niedrigen Viskositätsindex wirken. Jedoch ist es ein wesentlicher
Punkt für ein in jeder Hinsicht überlegenes Schmieröl, z. B. für Dieselmotoren, daß es einen
hohen Viskositätsindex aufweist, um einerseits die Schwierigkeiten beim Ingangsetzen bei kaltem
Wetter zu vermeiden und andererseits eine ausreichend hohe Viskosität bei der Arbeitstemperatur
der Maschine zu haben.
Die Überlegenheit der die Metallsalze enthaltenden Produkte gemäß der Erfindung kann nicht erklärt
werden durch die Anwesenheit der durch Polymerisation der ungesättigten aliphatischen Verbindüngen
gebildeten Komponente, denn ein durch Mischen erhaltenes Produkt, z. B. durch Mischen
des Calciumsalzes der Diisopropylsalicylsäure mit einem Produkt, das durch Polymerisation eines
durch Cracken von Paraffinwachs im dampfförmigen Zustand erzeugten Destillats (Siedepunkte etwa
zwischen 30 und 3400) erhalten wurde, war im praktischen Gebrauch dem Calciumsalz eines gemäß
der Erfindung hergestellten Produktes weit unterlegen, nämlich dadurch, daß man eine Mischung
von Salicylsäure und eines Überschusses des gleichen Crackdestillats gleichzeitig einem Alkylierungs-
und Polymerisationsprozeß unterwarf.
Die Erfindung wird an dem nachstehenden Beispiel erläutert.
Eine Mischung von Salicylsäure mit einem zwischen 30 und 3400 siedenden, durch Spalten
von Paraffin in dampfförmigem Zustand erhaltenen Destillat in dem Gewichtsverhältnis von 1 : 8 wurde
auf etwa ioo° erhitzt, während gasförmiges Borfluorid
eingeführt wurde. Nach annähernd 2 Stunden wurde festgestellt, daß etwa 70% der Salicylsäure
und 75% der Olefine sich umgesetzt hatten. Nach Vornahme einer Wasserdampfdestillation und
Waschen mit Wasser, um unveränderte Olefine und nicht umgesetzte Salicylsäure zu entfernen, blieb
ein ziemlich viskoses öl mit einer Säurezahl 55 übrig.
Durch Erhitzen unter gleichzeitigem Verrühren mit der für die Neutralisation erforderlichen Menge
von gelöschtem Kalk erhielt man ein Calciumsalz enthaltendes ölartiges Produkt.
Eine Menge von 4% von diesem Produkt wurde in gereinigtem Venezuela-Schmieröl-Destillat ge- go
löst. Bei dem Ausprobieren dieses Öls in einem Benzinmotor wurde gefunden, daß die Kolben
sauberer blieben und daß die Ablagerung auf dem Kolben geringer war als in dem Falle, in dem das
gleiche Schmieröl bei einem Zusatz von 1 Gewichtsprozent von Calcium-Diisopropylsalicylat ausprobiert
wurde (beide Schmieröle hatten den gleichen Calciumgehalt).
Auch bei Verwendung in einer Dieselmaschine ergab das das Calciumsalz enthaltende Produkt ein
besseres Resultat hinsichtlich der Ablagerung von verunreinigenden Stoffen auf dem Kolben und Zylinder
im Vergleich mit dem Calciumdiisopropylsalicylat.
Claims (1)
- PATENTANSPRUCH:Verfahren zur Herstellung von Schmiermitteln bzw. Schmiermittelzusätzen, insbesondere für Verbrennungskraftmaschinen, dadurch gekennzeichnet, daß aromatische Verbindungen, die eine oder mehrere polare Gruppen, wie die OH- oder COOH-Gruppe, enthalten, zusammen mit einem Überschuß von Verbindungen mit einer aliphatischen Doppelbindung, die mehr als vier Kohlenstoffatome im Molekül enthalten, gleichzeitig einer Alkylierungs- und Polymerisationsbehandlung unterworfen und gegebenenfalls anschließend in ihre Metallsalze übergeführt werden.© 3234 2.52
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP23366A DE1091669B (de) | 1948-12-18 | 1959-08-14 | Hochdruckentladungslampe |
| US48888A US3090883A (en) | 1948-12-18 | 1960-08-11 | Electric high pressure discharge lamps |
| GB27999/60A GB963700A (en) | 1948-12-18 | 1960-08-12 | Improvements in high pressure discharge lamps |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL120645A NL65636C (de) | 1945-07-31 | 1945-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE832313C true DE832313C (de) | 1952-02-21 |
Family
ID=19788534
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP25364D Expired DE832313C (de) | 1945-07-31 | 1948-12-18 | Verfahren zur Herstellung von Schmiermitteln bzw. Schmiermittelzusaetzen |
| DEN1764A Expired DE865927C (de) | 1945-07-31 | 1950-09-04 | Verfahren zur Herstellung von Schmiermitteln bzw. Schmiermittelzusaetzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN1764A Expired DE865927C (de) | 1945-07-31 | 1950-09-04 | Verfahren zur Herstellung von Schmiermitteln bzw. Schmiermittelzusaetzen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2483859A (de) |
| DE (2) | DE832313C (de) |
| FR (1) | FR929275A (de) |
| GB (2) | GB625104A (de) |
| NL (1) | NL65636C (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4320021A (en) | 1975-10-14 | 1982-03-16 | The Lubrizol Corporation | Amino phenols useful as additives for fuels and lubricants |
| US5207940A (en) * | 1990-09-12 | 1993-05-04 | Ethyl Corporation | α-olefin oligomer-phenol lubricant oil adducts |
| US5225588A (en) * | 1992-02-03 | 1993-07-06 | Ethyl Corporation | Process for alkylating salicylates with polyalphaolefin |
| CN108264892A (zh) * | 2017-12-21 | 2018-07-10 | 东北农业大学 | 一种用于释放地下油质材料的表面活性剂的组合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2197837A (en) * | 1936-08-29 | 1940-04-23 | Socony Vacuum Oil Co Inc | Mineral oil composition |
| US2228671A (en) * | 1938-10-04 | 1941-01-14 | Standard Oil Co | Compounded mineral oil |
| US2228661A (en) * | 1938-10-08 | 1941-01-14 | Standard Oil Co | Compounded oil |
| NL50248C (de) * | 1938-12-05 | 1941-04-15 | ||
| US2347546A (en) * | 1940-12-07 | 1944-04-25 | Sinclair Refining Co | Lubricating oil composition |
| US2324784A (en) * | 1941-01-02 | 1943-07-20 | Standard Oil Dev Co | Condensation product and method of preparing and using same |
| US2347547A (en) * | 1941-08-15 | 1944-04-25 | Sinclair Refining Co | Lubricating oil composition |
| US2356685A (en) * | 1943-06-14 | 1944-08-22 | Standard Oil Co California | Compounded oils |
-
1945
- 1945-07-31 NL NL120645A patent/NL65636C/xx active
-
1946
- 1946-02-11 GB GB4251/46A patent/GB625104A/en not_active Expired
- 1946-04-12 GB GB11339/46A patent/GB632990A/en not_active Expired
- 1946-06-18 FR FR929275D patent/FR929275A/fr not_active Expired
- 1946-07-23 US US685779A patent/US2483859A/en not_active Expired - Lifetime
-
1948
- 1948-12-18 DE DEP25364D patent/DE832313C/de not_active Expired
-
1950
- 1950-09-04 DE DEN1764A patent/DE865927C/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR929275A (fr) | 1947-12-22 |
| GB625104A (en) | 1949-06-22 |
| DE865927C (de) | 1953-02-05 |
| NL65636C (de) | 1950-05-15 |
| US2483859A (en) | 1949-10-04 |
| GB632990A (en) | 1949-12-05 |
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