DE2520459C3 - Verwendung von Carbonsäureestergemischen als Schmiermittel - Google Patents
Verwendung von Carbonsäureestergemischen als SchmiermittelInfo
- Publication number
- DE2520459C3 DE2520459C3 DE2520459A DE2520459A DE2520459C3 DE 2520459 C3 DE2520459 C3 DE 2520459C3 DE 2520459 A DE2520459 A DE 2520459A DE 2520459 A DE2520459 A DE 2520459A DE 2520459 C3 DE2520459 C3 DE 2520459C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acids
- viscosity
- mol
- mixture
- 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
- 239000000203 mixture Substances 0.000 title claims description 19
- 239000000314 lubricant Substances 0.000 title claims description 10
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 23
- 150000007513 acids Chemical class 0.000 claims description 18
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 14
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 13
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
- 239000003879 lubricant additive Substances 0.000 claims description 3
- 238000002485 combustion reaction Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002826 coolant Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 21
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 10
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 10
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- -1 trimethylolpropane ester Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 description 1
- HYLPNBCGXPCTSC-UHFFFAOYSA-N [N].[Sr] Chemical compound [N].[Sr] HYLPNBCGXPCTSC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- 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
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
-
- 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
- C10M2207/28—Esters
- C10M2207/287—Partial esters
-
- 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
- C10M2209/10—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
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22398/74A IT1010487B (it) | 1974-05-08 | 1974-05-08 | Esteri come componenti di lubrifi canti |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2520459A1 DE2520459A1 (de) | 1975-11-13 |
| DE2520459B2 DE2520459B2 (de) | 1979-06-21 |
| DE2520459C3 true DE2520459C3 (de) | 1989-05-18 |
Family
ID=11195746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2520459A Expired DE2520459C3 (de) | 1974-05-08 | 1975-05-07 | Verwendung von Carbonsäureestergemischen als Schmiermittel |
Country Status (22)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144183A (en) * | 1973-01-22 | 1979-03-13 | Henkel Kommanditgesellschaft Auf Aktien | Mixed branched and straight chain ester oils |
| IT1050335B (it) * | 1975-12-11 | 1981-03-10 | Snam Progetti | Esteri organici da impiegare in composizioni lubrificanti |
| US4290337A (en) * | 1977-01-03 | 1981-09-22 | Nittetsu Bolten Kabushiki Kaisha | Fastener set |
| US4477383A (en) * | 1982-05-05 | 1984-10-16 | National Distillers And Chemical Corporation | Di- and tripentaerythritol esters of isostearic acid |
| JPS5963105U (ja) * | 1982-10-22 | 1984-04-25 | ワイケイケイ株式会社 | 簡易構造物 |
| JPS5965101U (ja) * | 1982-10-25 | 1984-05-01 | ワイケイケイ株式会社 | 建物の躯体への取付装置 |
| JPS5965103U (ja) * | 1982-10-26 | 1984-05-01 | ワイケイケイ株式会社 | 簡易構造物 |
| JPH0730345B2 (ja) * | 1986-09-08 | 1995-04-05 | 出光興産株式会社 | 潤滑油組成物 |
| DE3712133A1 (de) * | 1987-04-10 | 1988-10-20 | Siwa Gmbh | Schmiermittel bzw. schmiermittelkonzentrat |
| DE3712132A1 (de) * | 1987-04-10 | 1988-10-20 | Grill Max Gmbh | Schmiermittel bzw. schmiermittelkonzentrat |
| US5665683A (en) * | 1987-04-10 | 1997-09-09 | Bremer & Leguil Gmbh | Lubricant and lubricant concentrate |
| DE3927155A1 (de) * | 1989-08-17 | 1991-02-21 | Henkel Kgaa | Umweltfreundliches grundoel fuer die formulierung von hydraulikoelen |
| DE4214653A1 (de) * | 1992-05-02 | 1993-11-04 | Henkel Kgaa | Motorengrundoele mit verbesserter dichtungsvertraeglichkeit |
| US6693064B2 (en) † | 1996-04-16 | 2004-02-17 | Unichema Chemie B.V. | Hydraulic fluids |
| US20040075079A1 (en) * | 1998-10-13 | 2004-04-22 | Unichema Chemie Bv | Hydraulic fluids |
| CA2729919A1 (en) * | 2008-07-18 | 2010-01-21 | Huntsman Petrochemical Corporation | Natural oil based autocatalytic polyols |
| EP3307857B1 (en) | 2015-06-12 | 2019-10-09 | Novamont S.p.A. | Low pour point trimethylolpropane esters |
| WO2019087351A1 (ja) * | 2017-11-02 | 2019-05-09 | 花王株式会社 | 潤滑油基油、および該潤滑油基油を含有する潤滑油組成物 |
| RU2704978C1 (ru) * | 2018-12-26 | 2019-11-01 | федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный технический университет" | Основа смазочного масла |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048608A (en) * | 1959-03-18 | 1962-08-07 | Heyden Newport Chemical Corp | Neopentyl glycol esters |
| US3309318A (en) * | 1965-04-30 | 1967-03-14 | Emery Industries Inc | Blends of ester lubricants |
| US3673226A (en) * | 1968-04-10 | 1972-06-27 | Ethyl Corp | Synthetic lubricants |
| GB1301003A (en) * | 1969-07-10 | 1972-12-29 | Ethyl Corp | Lubricant materials |
| US3670013A (en) * | 1969-10-16 | 1972-06-13 | Hercules Inc | Synthesis of partial esters of certain poly(neopentyl polyols) and aliphatic monocarboxylic acids |
-
1974
- 1974-05-08 IT IT22398/74A patent/IT1010487B/it active
-
1975
- 1975-04-21 GB GB1648075A patent/GB1462027A/en not_active Expired
- 1975-04-24 YU YU1047/75A patent/YU36191B/xx unknown
- 1975-04-28 CH CH541175A patent/CH617419A5/it not_active IP Right Cessation
- 1975-04-29 US US05/572,651 patent/US4025447A/en not_active Expired - Lifetime
- 1975-05-02 LU LU72396A patent/LU72396A1/xx unknown
- 1975-05-05 HU HUSA2787A patent/HU170743B/hu not_active IP Right Cessation
- 1975-05-05 RO RO7582141A patent/RO70591A/ro unknown
- 1975-05-06 NO NO751627A patent/NO143529C/no unknown
- 1975-05-06 SE SE7505291A patent/SE426389B/xx not_active IP Right Cessation
- 1975-05-06 NL NLAANVRAGE7505342,A patent/NL181105B/xx not_active Application Discontinuation
- 1975-05-06 FR FR7514127A patent/FR2270230B1/fr not_active Expired
- 1975-05-06 PL PL1975180186A patent/PL102226B1/pl unknown
- 1975-05-07 BE BE156123A patent/BE828807A/xx not_active IP Right Cessation
- 1975-05-07 ZA ZA00752955A patent/ZA752955B/xx unknown
- 1975-05-07 SU SU752129353A patent/SU743579A3/ru active
- 1975-05-07 CS CS753212A patent/CS187321B2/cs unknown
- 1975-05-07 DE DE2520459A patent/DE2520459C3/de not_active Expired
- 1975-05-07 DK DK203475A patent/DK147978C/da active
- 1975-05-07 CA CA226,495A patent/CA1060040A/en not_active Expired
- 1975-05-08 JP JP5432575A patent/JPS5726554B2/ja not_active Expired
- 1975-05-08 DD DD185930A patent/DD119204A5/xx unknown
- 1975-05-08 DD DD193315A patent/DD124389A5/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |