GB812131A - Improvements in dinonylnaphthalene sulfonates and process of producing same - Google Patents
Improvements in dinonylnaphthalene sulfonates and process of producing sameInfo
- Publication number
- GB812131A GB812131A GB1423/56A GB142356A GB812131A GB 812131 A GB812131 A GB 812131A GB 1423/56 A GB1423/56 A GB 1423/56A GB 142356 A GB142356 A GB 142356A GB 812131 A GB812131 A GB 812131A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oils
- acid
- dinonylnaphthalene
- zinc
- calcium
- 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
- 238000000034 method Methods 0.000 title abstract 2
- WDNQRCVBPNOTNV-UHFFFAOYSA-M 2,3-di(nonyl)naphthalene-1-sulfonate Chemical class C1=CC=C2C(S([O-])(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 WDNQRCVBPNOTNV-UHFFFAOYSA-M 0.000 title 1
- 239000003921 oil Substances 0.000 abstract 16
- 239000003960 organic solvent Substances 0.000 abstract 8
- 239000000203 mixture Substances 0.000 abstract 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 5
- 239000011575 calcium Substances 0.000 abstract 5
- 229910052791 calcium Inorganic materials 0.000 abstract 5
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 5
- -1 naphtha Substances 0.000 abstract 5
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 239000000446 fuel Substances 0.000 abstract 4
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 4
- 239000011707 mineral Substances 0.000 abstract 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 4
- 239000011734 sodium Substances 0.000 abstract 4
- 229910052708 sodium Inorganic materials 0.000 abstract 4
- 239000011780 sodium chloride Substances 0.000 abstract 4
- RAADJDWNEAXLBL-UHFFFAOYSA-N 1,2-di(nonyl)naphthalene Chemical compound C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 RAADJDWNEAXLBL-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 3
- 229910052788 barium Inorganic materials 0.000 abstract 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 3
- 239000010410 layer Substances 0.000 abstract 3
- 239000010687 lubricating oil Substances 0.000 abstract 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 3
- 239000011777 magnesium Substances 0.000 abstract 3
- 229910052749 magnesium Inorganic materials 0.000 abstract 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 3
- 239000011591 potassium Substances 0.000 abstract 3
- 229910052700 potassium Inorganic materials 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 238000005406 washing Methods 0.000 abstract 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 3
- 239000011701 zinc Substances 0.000 abstract 3
- 229910052725 zinc Inorganic materials 0.000 abstract 3
- ANYJSVKEVRJWRW-UHFFFAOYSA-N 4,5-di(nonyl)naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(CCCCCCCCC)=C2C(CCCCCCCCC)=CC=CC2=C1 ANYJSVKEVRJWRW-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- WDNQRCVBPNOTNV-UHFFFAOYSA-N Dinonylnaphthylsulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 WDNQRCVBPNOTNV-UHFFFAOYSA-N 0.000 abstract 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000654 additive Substances 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 2
- 150000003751 zinc Chemical class 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 230000002152 alkylating Effects 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 230000000111 anti-oxidant Effects 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical class [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000994 depressed Effects 0.000 abstract 1
- 239000002283 diesel fuel Substances 0.000 abstract 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003502 gasoline Substances 0.000 abstract 1
- 239000008079 hexane Substances 0.000 abstract 1
- 239000010720 hydraulic oil Substances 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract 1
- 238000005461 lubrication Methods 0.000 abstract 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000012044 organic layer Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Chemical group 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 229940086542 triethylamine Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
- C07C309/34—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by two rings
- C07C309/35—Naphthalene sulfonic acids
- C07C309/36—Naphthalene sulfonic acids substituted by alkyl groups
- C07C309/37—Naphthalene sulfonic acids substituted by alkyl groups by alkyl groups containing at least three 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
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/25—Internal-combustion engines
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
Abstract
Compositions used as rust inhibitors in lubricating oils, including ester-type oils and hydrocarbon oils, mineral seal oils, rustproofing oils, hydraulic oils and motor fuels such as naphtha, gasoline and diesel fuel, and as additives giving better upper-cylinder and valve-stem lubrication in motor fuels, comprise solutions in organic solvents, oils and motor fuels of dinonylnaphthalene sulphonic acids the major portion of the nonyl radicals of which contain more than one tertiary carbon atom, or the sodium, potassium, calcium, magnesium, barium, zinc, ammonium and amine salts thereof. A composition may contain 0.01-10 per cent by weight of the salts or free acid in lubricating oils and may contain one or more antioxidants, pour point depressants and oiliness additives.ALSO:Plasticizers for rubber comprise dinonylnaphthalene sulphonic acids, the major portion of the nonyl groups of which contain more than one tertiary carbon atom, and their sodium, potassium, calcium, magnesium, barium, zinc, ammonium and amine salts and their solutions in mineral seal oil. A paste of the zinc salt and a mineral seal oil may be used to plasticize smoked sheet rubber.ALSO:Dinonylnaphthalene sulphonic acids the major portion of the nonyl radicals of which contain more than one tertiary carbon atom and solutions thereof in organic solvents and in oils are made by agitating a mixture of a diphonylnaphthalene sulphonic acid in the nonyl radicals of which contains more than one tertiary carbon atom, sulphuric acid or oleum, and an inert volatile organic solvent under sulphonating conditions, separating off the spent acid layer and repeatedly washing the organic layer, comprising a solution of the diphonylnaphthalene sulphonic acid in the solvent, with water. Any desired amount of the organic solvent may then be removed by distillation. After the separation of the spent acid and before, during or after the washing, an oil may be added to the dinonylnaphthalene sulphonic acid solution and the organic solvent removed. Solutions of the sodium, potassium, calcium, magnesium, barium, zinc, ammonium and amine salts of the dinonylnaphthalene sulphonic acid in oils are made by adding an appropriate base to the washed solution of the acid in oil or in a mixture of organic solvent and oil, the solvent being removed by distillation. Bases specified are sodium, calcium and barium hydroxides and carbonates, ammonium hydroxide, zinc oxide, and amines such as dimethylamine, ethylenediamine and mono-, di- and tri-ethylamine. Inert volatile organic solvents which may be used in the process are petroleum naphtha, hexane, heptane, octane and chlorinated alkanes. Oils which may be used are hydrocarbon oils or ester-type oils. During the washing of the organic solvent layer, isopropyl alcohol may be added to assist the separation of the layers. The dinonylnaphthalene is made by alkylating naphthalene with nonenes the major portion of which contains at least one tertiary carbon atoms such as tripropylene, in an anhydrous solvent such as naphtha, sulphur dioxide, nitrobenzene or a mixture of benzene and nitrobenzene and in the presence of hydrogen fluoride or anhydrous aluminium chloride. Detailed description is given for the preparation and sulphonation of the dinonylnaphthalene, and for the preparation of mineral seal oil solutions of the acid and its calcium and zinc salts. The compounds are used in compositions for lubricating oils and motor fuels (see Group III) and as plasticizers for rubber (see Group IV (a)).
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB812131A true GB812131A (en) | 1959-04-22 |
Family
ID=1626818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1423/56A Expired GB812131A (en) | 1956-01-16 | Improvements in dinonylnaphthalene sulfonates and process of producing same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB812131A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004046284A1 (en) * | 2002-11-14 | 2004-06-03 | The Lubrizol Corporation | Additive composition for industrial fluid |
| CN116355673A (en) * | 2021-12-28 | 2023-06-30 | 中国石油天然气股份有限公司 | Rust inhibitor and preparation method and application thereof |
-
1956
- 1956-01-16 GB GB1423/56A patent/GB812131A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004046284A1 (en) * | 2002-11-14 | 2004-06-03 | The Lubrizol Corporation | Additive composition for industrial fluid |
| CN116355673A (en) * | 2021-12-28 | 2023-06-30 | 中国石油天然气股份有限公司 | Rust inhibitor and preparation method and application thereof |
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