GB859218A - Terephthaldiamide derivatives and their use in lubricating oil compositions - Google Patents
Terephthaldiamide derivatives and their use in lubricating oil compositionsInfo
- Publication number
- GB859218A GB859218A GB27301/57A GB2730157A GB859218A GB 859218 A GB859218 A GB 859218A GB 27301/57 A GB27301/57 A GB 27301/57A GB 2730157 A GB2730157 A GB 2730157A GB 859218 A GB859218 A GB 859218A
- Authority
- GB
- United Kingdom
- Prior art keywords
- terephthaldiamide
- oil
- compounds
- lubricating
- substituted
- 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 abstract 5
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical class NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 title abstract 5
- 239000010687 lubricating oil Substances 0.000 title abstract 3
- 239000003921 oil Substances 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001555 benzenes Chemical class 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 238000013329 compounding Methods 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000004519 grease Substances 0.000 abstract 2
- 230000001050 lubricating effect Effects 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000004760 silicates Chemical class 0.000 abstract 2
- 239000002562 thickening agent Substances 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000002199 base oil Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003245 coal Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- PQPVPZTVJLXQAS-UHFFFAOYSA-N hydroxy-methyl-phenylsilicon Chemical compound C[Si](O)C1=CC=CC=C1 PQPVPZTVJLXQAS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- JOYVYZUJCNLBRL-UHFFFAOYSA-N methyl 4-[(2-methylphenyl)carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NC1=CC=CC=C1C JOYVYZUJCNLBRL-UHFFFAOYSA-N 0.000 abstract 1
- 239000010688 mineral lubricating oil Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000010689 synthetic lubricating oil Substances 0.000 abstract 1
- -1 terephthaldiamide compound Chemical class 0.000 abstract 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
-
- 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
- C10M2203/06—Well-defined aromatic 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
- C10M2207/282—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
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
-
- 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
- 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
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Lubricating greases are prepared by compounding a polymeric oil with a thickener comprising a terephthaldiamide compound having the formula: <FORM:0859218/IV(a)/1> in which R1 and R2 are each a hydrocarbon radical, and the benzene nucleus may be substituted by one or more alkyl p radicals having up to 8 carbon atoms. In an example, a poly (phenylmethyl siloxane) oil (3 parts) is heated, with stirring, to 600 DEG F. with 1 part of a mixture of N, N1-di-p-tolylterephthaldiamide and methylN-tolylterephthalamate. The cooled product is then milled at 4000 psi to give a smooth, soft grease with a high-speed (10,000 RPM) bearinglife of 300 hours at 500 DEG F. The Specification also mentions that various specified tetraalkyl silicates, polysiloxyglycols and alkyleneoxide polymers, e.g. from propylene oxide and water or alkyl alcohol, acetylated propylene oxide polymers, polyethers made e.g. from ethylene glycol, polyoxyalkylene diols and polyalkylene glycol ethers or esters may be used as oils. For the preparation of the terephthaladiamide compounds-see Group IV(b).ALSO:The invention comprises terephthaldiamide compounds of the general formula: <FORM:0859218/IV(b)/1> in which R1 and R2 are each a hydrocarbon radical, and the benzene nucleus may be substituted by one or more alkyl radicals having up to 8 carbon atoms. The compounds may be used to thicken lubricating oils to make greases (Group III). In Example 1, terephthaloyl dichloride is reacted with a mixture of aniline and n-dodecyl amine in toluene solution using triethylamine as HCl-acceptor. The product is a mixture of N, N1-didodecyl terephthaldiamide, N1, N - diphenyl terephthaldiamide, and N1-dodecyl-N-phenyl terephthaldiamide, predominating in the latter. In Example 2, dimethyl terephthalate and p-toluidine are heated together at 170-210 DEG C. for 6 hours. The product consisted of the ditoluidide of terephthalic acid mixed with methyl-N-tolyl terephthalamate.ALSO:Lubricating greases are prepared by compounding a mineral or synthetic lubricating oil with a thickener comprising a derivative of terephthal-diamide having the formula: <FORM:0859218/III/1> in which R1 and R2 are each a hydrocarbon radical, and the benzene nucleus may be substituted by one or more alkyl radicals having up to 8 carbon atoms. The lubricating oil may be a petroleum oil, or an oil produced by polymerization of an olefine or an alkylene oxide, or by synthesis from coal or carbon monoxide. Organic silicates, silicones, phosphates and esters of dicarboxylic acids may also be employed. In Example 3, a California naphthenic base oil is stirred, and heated to 490 DEG F., with about 18% by weight of N - dodecyl - N1 - phenyl - terephthaldiamide (admixed with the corresponding N,N1-didocyl and the N,N1-diphenyl compounds); the composition is milled at 425 DEG -450 DEG F., and pancooled to give a grease having an ASTM Dropping Point of 502 DEG F. For the preparation of the terephthaldiamide compounds (see Group IV(b)).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US859218XA | 1956-08-30 | 1956-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB859218A true GB859218A (en) | 1961-01-18 |
Family
ID=22194866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27301/57A Expired GB859218A (en) | 1956-08-30 | 1957-08-29 | Terephthaldiamide derivatives and their use in lubricating oil compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB859218A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2007116642A1 (en) * | 2006-03-24 | 2009-08-20 | 株式会社ジャパンエナジー | Semi-solid lubricant composition for transmission element and mechanical system provided with the same |
| EP1803792A4 (en) * | 2004-10-20 | 2010-07-28 | Porite Corp | THERMOREVERSIBLE GEL LUBRICATING COMPOSITION, METHOD FOR MANUFACTURING SAME, AND BEARING LUBRICANT AND BEARING SYSTEM USING SAME |
-
1957
- 1957-08-29 GB GB27301/57A patent/GB859218A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1803792A4 (en) * | 2004-10-20 | 2010-07-28 | Porite Corp | THERMOREVERSIBLE GEL LUBRICATING COMPOSITION, METHOD FOR MANUFACTURING SAME, AND BEARING LUBRICANT AND BEARING SYSTEM USING SAME |
| JPWO2007116642A1 (en) * | 2006-03-24 | 2009-08-20 | 株式会社ジャパンエナジー | Semi-solid lubricant composition for transmission element and mechanical system provided with the same |
| EP2000524A4 (en) * | 2006-03-24 | 2010-09-15 | Japan Energy Corp | SEMI-SOLID LUBRICANT COMPOSITION FOR TRANSMISSION ELEMENT AND MECHANICAL SYSTEM HAVING THE SAME |
| US7973000B2 (en) * | 2006-03-24 | 2011-07-05 | Japan Energy Corporation | Semi-solid lubricant composition for transmission element and mechanical system provided with the same |
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