GB660110A - Improvements in or relating to the preparation of lubricants and compositions containing the same - Google Patents
Improvements in or relating to the preparation of lubricants and compositions containing the sameInfo
- Publication number
- GB660110A GB660110A GB28545/47A GB2854547A GB660110A GB 660110 A GB660110 A GB 660110A GB 28545/47 A GB28545/47 A GB 28545/47A GB 2854547 A GB2854547 A GB 2854547A GB 660110 A GB660110 A GB 660110A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ether
- product
- under
- hydrogen sulphide
- pressure
- 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 abstract 8
- 239000000203 mixture Substances 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 22
- 239000000047 product Substances 0.000 abstract 18
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 13
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 5
- 229960000834 vinyl ether Drugs 0.000 abstract 5
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 4
- 238000004821 distillation Methods 0.000 abstract 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- 229940052303 ethers for general anesthesia Drugs 0.000 abstract 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 3
- 229910052753 mercury Inorganic materials 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
- 150000000475 acetylene derivatives Chemical class 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000007689 inspection Methods 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- -1 polymethylene Polymers 0.000 abstract 2
- 239000000344 soap Substances 0.000 abstract 2
- 150000003568 thioethers Chemical class 0.000 abstract 2
- XYFNXHGRCIZMQQ-UHFFFAOYSA-N 1-but-3-en-2-yloxybut-2-ene Chemical compound CC=CCOC(C)C=C XYFNXHGRCIZMQQ-UHFFFAOYSA-N 0.000 abstract 1
- DUKJZYZDOKKAMU-UHFFFAOYSA-N 1-chloronaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=O)C=CC2=C1 DUKJZYZDOKKAMU-UHFFFAOYSA-N 0.000 abstract 1
- KRNGNWGELWHIOU-UHFFFAOYSA-N 1-hex-1-enoxyhex-1-ene Chemical compound CCCCC=COC=CCCCC KRNGNWGELWHIOU-UHFFFAOYSA-N 0.000 abstract 1
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QRQVZZMTKYXEKC-UHFFFAOYSA-N 3-(3-hydroxypropylsulfanyl)propan-1-ol Chemical compound OCCCSCCCO QRQVZZMTKYXEKC-UHFFFAOYSA-N 0.000 abstract 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005069 Extreme pressure additive Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 230000002159 abnormal effect Effects 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 239000010730 cutting oil Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003349 gelling agent Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 238000005461 lubrication Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical class CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005049 silicon tetrachloride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
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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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/043—Polyoxyalkylene ethers with a thioether group
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- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/241—Manufacturing joint-less pipes
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/242—Hot working
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/243—Cold working
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
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- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
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- 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—Semi-solids; greasy
Abstract
Synthetic lubricants are prepared by reacting an aliphatic ether having two olefinic radicals attached to the ether oxygen atom with hydrogen sulphide or a mercaptan and thereafter removing volatile components from the product by distillation under reduced pressure until the remaining product has a boiling-point equivalent to at least 160 DEG C. under 0.2 cm. mercury pressure. This distillation may be effected under any reduced pressure providing that it is continued until the boiling-point of the remaining product has risen to the equivalent of 160 DEG C. under 0.2 cm. mercury pressure. The interaction of the olefinic and sulphur compounds may be effected in presence of ultra-violet light, peroxides, air or oxygen resulting in adducts formed by abnormal addition, or in presence of aluminium chloride, silicon tetrachloride or basic catalysts, e.g. alkali metal or alkaline earth metal hydroxides, primary, secondary or tertiary amines, pyridine or piperidine. Reaction temperatures of up to 150 DEG C. may be used. The reactants are preferably employed in the ratio of between 0.5 to 2 mols. of olefinic ether per mol. hydrogen sulphide or mercaptan. Diluents such as saturated hydrocarbons may be present. Olefinic ethers mentioned are divinyl ether, diisopropyl ether, diallyl ether, dicrotyl ether, dimethallyl ether, di-(a -methyl allyl) ether, (1 - butene - 3 - yl) - (2 - butene - 4 - yl) ether, dihexenyl ether, allyl-(2-methyl-4-pentene-2-yl) ether, allyl linalyl ether and halogenated derivatives of the type of hexachlor-divinyl ether. The mercaptans used may be aliphatic, and are preferably the normal or iso-alkyl chain mercaptans of primary, secondary or tertiary character; methyl, ethyl, butyl, amyl, hexyl, heptyl and octyl mercaptans and polymethylene dimercaptans are mentioned. In examples: (1) Hydrogen sulphide and diallyl ether in equimolar amounts are subjected to ultra-violet light in a sealed evacuated quartz bomb and in liquid state and the product distilled to 235 DEG C. under 2.3 cms. pressure; (2) hydrogen sulphide and dimethyallyl ether are similarly reacted and the product distilled to 240 DEG C. at about 2 cms. pressure; (3) di-(b -mercapto ethyl) ether and diallyl ether are similarly reacted, the product being distilled up to 240 DEG C. under 8 mms. pressure; (4) hydrogen sulphide (0.28 mol.) is bubbled into 180 ccs. divinyl ether in an irradiated flask at 0 DEG C. and the product distilled up to 240 DEG C. under 1 cm. pressure; (5) hydrogen sulphide and diallyl ether in equimolar amounts are heated in presence of di-t.-butyl peroxide in an autoclave at 100 DEG C. and the product distilled up to 240 DEG C. under 0.2 cm. pressure. Specification 558,790 is referred to. The Specification as open to inspection under Sect. 91 relates to the production of lubricants by reacting an organic compound having at least one unsaturated linkage between two carbon atoms of aliphatic nature with hydrogen sulphide or a mercaptan and separating from the product the material volatilizing at relatively low temperatures. The unsaturated reagents mentioned include olefines, dienes, acetylenes, ethers and thioethers; some may contain such substituents as alkoxy, aryloxy and aralkoxy groups or chlorine and other halogen atoms. Numerous examples are given. Products containing terminal hydroxy groups may be etherified or esterified and many agents for this purpose are given, including hydroxy-and carboxy-alkylating agents. In a further example, allyl alcohol and hydrogen sulphide are heated in an autoclave in presence of di-n-butylamine and the product distilled up to 134 DEG C. at 0.3 cm. pressure, the lubricating portion being bis-(b -hydroxy-a -methyl-ethyl) sulphide; a by-product is b -hydroxy-a -methyl-ethyl mercaptan. This subject-matter does not appear in the Specification as accepted.ALSO:Synthetic lubricants comprise the products obtained by reacting an aliphatic ether having two olefinic radicals attached to the ether oxygen atom with hydrogen sulphide or a mercaptan and thereafter removing volatile components from the priduct by distillation under reduced pressure until the remaining product has a boiling point equivalent to at least 160 DEG C. under 0.2 cm. mercury (see Group IVb). Distillation may be effected under any convenient reduced pressure providing that it is continued until the boiling point of the remaining product has risen to the equivalent of 160 DEG C. under 0.2 cm. pressure. They may be used compounded with minor amounts of metallic soaps or other gelling agents, corrosion inhibitors such as organic acids capable of forming water-insoluble metallic soaps, anti-oxidants such as 1, 2-dihydroxy benzene, extreme pressure additives and other lubricants such as alkylene oxide or glycol polymers. They may be used for low temperature and extreme pressure lubrication; their use in hypoid gear lubricants, cutting oil compositions and metal drawing compounds is mentioned. Examples describe products derived from (1) diallyl ether, dimethallyl and divinyl ether respectively and hydrogen sulphide and (2) diallyl ether and di-(b -mercapto ethyl) ether. Other starting materials, are mentioned including hexachlor-divinyl ether. The Specification as open to inspection under Sect. 91 relates to synthetic lubricants obtained by reacting any organic compound having at least one unsaturated linkage between two carbon atoms of aliphatic nature with hydrogen sulphide or a mercaptan and removing from the product the material which volatilizes at relatively low temperatures. The unsaturated reagents are stated to include olefines, dienes, acetylenes, ethers and thioethers and many examples are given. The synthetic lubricants include those products having terminal hydroxyl groups which have been etherified or esterified by organic or inorganic acids; many etherifying and esterifying agents are mentioned. An additional example describes a product derived from allyl alcohol and hydrogen sulphide and said to be bis (b -hydroxy a methyl ethyl) sulphide; the wear characteristics of the di-2-ethyl hexoate of bis (gammahydroxy propyl) sulphide are given. This subject-matter does not appear in the Specification as accepted.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28545/47A GB660110A (en) | 1947-10-24 | 1947-10-24 | Improvements in or relating to the preparation of lubricants and compositions containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28545/47A GB660110A (en) | 1947-10-24 | 1947-10-24 | Improvements in or relating to the preparation of lubricants and compositions containing the same |
Publications (1)
Publication Number | Publication Date |
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GB660110A true GB660110A (en) | 1951-10-31 |
Family
ID=10277321
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28545/47A Expired GB660110A (en) | 1947-10-24 | 1947-10-24 | Improvements in or relating to the preparation of lubricants and compositions containing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB660110A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2706177A (en) * | 1952-07-24 | 1955-04-12 | Exxon Research Engineering Co | Stabilization of organic sulfurcontaining compounds |
US2948669A (en) * | 1960-08-09 | Production of superior neutral oils |
-
1947
- 1947-10-24 GB GB28545/47A patent/GB660110A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2948669A (en) * | 1960-08-09 | Production of superior neutral oils | ||
US2706177A (en) * | 1952-07-24 | 1955-04-12 | Exxon Research Engineering Co | Stabilization of organic sulfurcontaining compounds |
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