GB832015A - Corrosion-inhibiting imidazolines - Google Patents
Corrosion-inhibiting imidazolinesInfo
- Publication number
- GB832015A GB832015A GB28047/57A GB2804757A GB832015A GB 832015 A GB832015 A GB 832015A GB 28047/57 A GB28047/57 A GB 28047/57A GB 2804757 A GB2804757 A GB 2804757A GB 832015 A GB832015 A GB 832015A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphur
- imidazoline
- reacting
- mols
- phosphorus
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/16—Radicals substituted by nitrogen 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
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
-
- 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
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
Liquid hydrocarbon compositions comprise, as a corrosion inhibitor, an imidazoline derivative obtainable either by reacting sulphur, a phosphorus sulphide or a mixture of sulphur and phosphorus with an imidazoline of the general formula <FORM:0832015/III/1> and reacting the product with an alkylene oxide, or by reacting sulphur, a phosphorus sulphide or a mixture of sulphur and phosphorus with the reaction product of an alkylene oxide and an imidazoline as above defined, R representing an aliphatic hydrocarbon radical containing 8-32 carbon atoms and R11 a divalent hydrocarbon radical containing 1-8 carbon atoms. Sulphur is believed to become attached to a CH2 group in the ring. The alkylene oxides may contain 2-6 carbon atoms. The preferred alkylene oxide-imidazoline reaction products contain the amino group hydroxyethylated with 1-9 mols. of ethylene oxide. The hydrocarbons may be petroleum crudes or fractions thereof and the compositions may contain from 1 part per million to 1% by weight of the inhibitor. The inhibitors are stated to reduce corrosion of metal especially ferrous metal, caused by hydrocarbons existing in admixture with water and an acid or oxygen. Specific inhibitors described are (1) the product obtained by reacting aminoethyl-1-heptadeca-2-imidazoline with 3 mols. of ethylene oxide and then with 2 mols. of sulphur and (2) the product obtained by reacting the imidazoline named in (1) with 1/4 mol. P2S5 and then with 3 mols. of ethylene oxide and corrosion tests are described with one or other of these inhibitors in a petrol-water emulsion or in distillation of a petroleum crude. A comparative inhibitor described is obtained by reacting the imidazoline named in (1) with 3 mols. of ethylene oxide.ALSO:The invention comprises imidazoline derivatives obtainable either by reacting sulphur, a phosphorus sulphide or a mixture of sulphur and phosphorus with an imidazoline of the general formula <FORM:0832015/IV (b)/1> and reacting the product with an alkylene oxide, or by reacting sulphur, a phosphorus sulphide or a mixture of sulphur and phosphorus with the reaction product of an imidazoline of the above general formula and an alkylene oxide, R representing a C8-32 monovalent aliphatic hydrocarbon radical and R11 a divalent hydrocarbon radical containing 1-8 carbon atoms. It is believed that the sulphur becomes attached to a CH2 group in the nucleus. The reaction with the sulphur containing reagent may be effected by heat; when sulphur itself is used an aromatic solvent may be present. Alkylene oxides employed may contain 2-6 carbon atoms. The preferred imidazoline-alkylene oxide product is one in which the amino-group has been hydroxyethylated with 1-9 mols. of ethylene oxide. The final sulphurized products are useful as inhibitors (see Group III). In examples: (1) aminoethyl - 1 - heptadeca - 2 - imidazoline is condensed with 3 mols. of ethylene oxide in the presence of BF3 at 220-250 DEG C. and the product is reacted with 2 mols. of sulphur in boiling benzene solution and thereafter the solvent is evaporated off; (2) the imidazoline of (1) is heated with 1/4 mol. of P2S5 at 200 DEG C. and the product is condensed with 3 mols. of ethylene oxide at 220-230 DEG C. in the presence of BF3. Imidazolines of the above general formula are prepared by condensing acids of the formula RCOOH with triamines of the formula H2N.CH2CH2NH-R11-NH2 at 250-300 DEG C. until 2 mols. of water are removed.ALSO:Corrosion of metals, particularly of ferrous metals by liquid hydrocarbons, such as crude petroleum of fractions thereof, in the presence of water and acids or oxygen, is reduced by means of an imidazoline derivative obtainable either by reacting sulphur, a phosphorus sulphide or mixture of phosphorus and sulphur with an imidazoline of the general formula: <FORM:0832015/II/1> and reacting the product with an alkylene oxide, or by reacting sulphur, a phosphorus sulphide or a mixture of phosphorus and sulphur with the reaction product of an imidazoline of the above formula and an alkylene oxide, R being a C8-32 aliphatic hydrocarbon radial and R11 a divalent hydrocarbon radical containing 1-8 carbon atoms. Sulphur is believed to become attached to a CH2 group in the ring. The alkylene oxides may contain 2-6 carbon atoms and the preferred imidazoline-alkylene oxide reaction product contains the amino group hydroxy ethylated with 1-9 moles of ethylene oxide. The inhibitors may be present in the hydrocarbon oils in amounts of from 1 part per million to 1% by weight. Specified inhibitors are those obtained by reacting amino ethyl-1-heptadeca-2 imidazoline either with 3 moles of ethylene oxide and then 2 moles of sulphur or with 1/4 mil P2S5 and then 3 moles of ethylene oxide; tests are described illustrating their use in reducing corrosion of steel by an aqueous acidic petrol emulsion or by distilling vapours of a crude petroleum. The product obtained by reacting the above-named imidazoline with 3 moles of ethylene oxide is described as a comparative corrosion inhibitor.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR832015X | 1956-09-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB832015A true GB832015A (en) | 1960-04-06 |
Family
ID=9295229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28047/57A Expired GB832015A (en) | 1956-09-19 | 1957-09-05 | Corrosion-inhibiting imidazolines |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1074944B (en) |
GB (1) | GB832015A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016180745A3 (en) * | 2015-05-11 | 2016-12-22 | Akzo Nobel Chemicals International B.V. | Nitrogen-containing anti-agglomerants for preserving the fluidity of fluids containing gas hydrates |
CN110424017A (en) * | 2019-08-27 | 2019-11-08 | 山东益丰生化环保股份有限公司 | A kind of molten corrosion inhibiter of oil and preparation method thereof |
-
0
- DE DENDAT1074944D patent/DE1074944B/en active Pending
-
1957
- 1957-09-05 GB GB28047/57A patent/GB832015A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016180745A3 (en) * | 2015-05-11 | 2016-12-22 | Akzo Nobel Chemicals International B.V. | Nitrogen-containing anti-agglomerants for preserving the fluidity of fluids containing gas hydrates |
US10876033B2 (en) | 2015-05-11 | 2020-12-29 | Nouryon Chemicals International B.V. | Nitrogen-containing anti-agglomerants for preserving the fluidity of fluids containing gas hydrates |
CN110424017A (en) * | 2019-08-27 | 2019-11-08 | 山东益丰生化环保股份有限公司 | A kind of molten corrosion inhibiter of oil and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
DE1074944B (en) | 1960-02-04 |
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