GB993741A - Aminoalkane phosphonates - Google Patents
Aminoalkane phosphonatesInfo
- Publication number
- GB993741A GB993741A GB40745/61A GB4074561A GB993741A GB 993741 A GB993741 A GB 993741A GB 40745/61 A GB40745/61 A GB 40745/61A GB 4074561 A GB4074561 A GB 4074561A GB 993741 A GB993741 A GB 993741A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phenyl
- benzyl
- prepared
- c13h27n
- 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 239000000446 fuel Substances 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000314 lubricant Substances 0.000 abstract 2
- -1 2-ethylhexyl Chemical group 0.000 abstract 1
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 abstract 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000013556 antirust agent Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000002283 diesel fuel Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000002816 fuel additive Substances 0.000 abstract 1
- 239000000295 fuel oil Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003879 lubricant additive Substances 0.000 abstract 1
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 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
- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention comprises compounds of formula <FORM:0993741/C2/1> where R is C12- 24 t-alkyl, R1 and R2 are C1- 8 alkyl or monochloroalkyl, phenyl, benzyl, or phenyl or benzyl substituted in the ring with one chlorine atom and/or one C1- 4 alkyl group, and R3 is hydrogen or C1- 3 alkyl. The invention also comprises mixtures of such compounds in which the components differ only in that they contain different t-alkyl groups, e.g. mixtures in which the t-alkyl groups contain from 12-15 with an average of 13 carbon atoms, or 18-24 carbon atoms. They are prepared by reacting at about 25-100 DEG C. an azomethine RN = CHR3 (or a mixture thereof) with a phosphite (R1O)(R2O)P(O)H. A solvent may be used. The azomethine may be prepared in situ by the reaction of an appropriate aldehyde and a appropriate amine or amines. The products are used as lubricant and fuel additives (see Division C5). Starting materials prepared in examples are azomethines of average structures t-C13H27N = CH2 and t-C13H27N = CH-CH3 from a mixture of C12- 15 t-alkylamines and formaldehyde and acetaldehyde respectively.ALSO:Lubricating and liquid fuel compositions comprise as anti-rust agent one or more amino-alkanephosphonates of formula <FORM:0993741/C4-C5/1> where R is C12- 24 t-alkyl, R1 and R2 are C1- 8 alkyl or monochloroalkyl, phenyl, benzyl, or phenyl or benzyl substituted in the ring with one chlorine atom and/or one C1- 4 alkyl group, and R3 is hydrogen or C1- 3 alkyl. Fuels include distillate fuels boiling from 75-750 DEG F., e.g. gasolines, jet and diesel fuels and furnace oils, and lubricants include mineral oils and synthetic lubricants such as bis (2-ethylhexyl) sebecate. 0.001 to 10.0 wt. per cent of additive may be used.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6980460A | 1960-11-17 | 1960-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB993741A true GB993741A (en) | 1965-06-02 |
Family
ID=22091320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB40745/61A Expired GB993741A (en) | 1960-11-17 | 1961-11-14 | Aminoalkane phosphonates |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1168427B (en) |
| GB (1) | GB993741A (en) |
| NL (1) | NL271182A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4331546A (en) * | 1979-01-31 | 1982-05-25 | Mobil Oil Corporation | Lubricant composition containing phosphite-diarylamine-carbonyl compound reaction product |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA480212A (en) * | 1952-01-15 | R. Turner William | Lubricant | |
| BE589601A (en) * | ||||
| US2914478A (en) * | 1953-09-28 | 1959-11-24 | Union Oil Co | Antirust composition |
| GB782058A (en) * | 1954-02-15 | 1957-08-28 | Lubrizol Corp | Organic metal compositions and methods of preparing same |
| US2881202A (en) * | 1955-10-07 | 1959-04-07 | Fmc Corp | Gasoline ignition control additives |
| BE566824A (en) * | 1957-04-18 | |||
| BE580173A (en) * | 1958-07-01 |
-
0
- NL NL271182D patent/NL271182A/xx unknown
-
1961
- 1961-11-03 DE DER31399A patent/DE1168427B/en active Pending
- 1961-11-14 GB GB40745/61A patent/GB993741A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1168427B (en) | 1964-04-23 |
| NL271182A (en) |
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