GB743752A - Improvements in or relating to mono-acid phosphoric ester products - Google Patents
Improvements in or relating to mono-acid phosphoric ester productsInfo
- Publication number
- GB743752A GB743752A GB22419/53A GB2241953A GB743752A GB 743752 A GB743752 A GB 743752A GB 22419/53 A GB22419/53 A GB 22419/53A GB 2241953 A GB2241953 A GB 2241953A GB 743752 A GB743752 A GB 743752A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- product
- alkyl
- ester
- mono
- 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
- 150000002148 esters Chemical class 0.000 title abstract 6
- 239000002253 acid Substances 0.000 title abstract 3
- -1 dodecyl phenyl Chemical group 0.000 abstract 6
- 239000003921 oil Substances 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 3
- 230000029936 alkylation Effects 0.000 abstract 3
- 238000005804 alkylation reaction Methods 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FQEMSHFIWLKFST-UHFFFAOYSA-N (2-dodecylphenyl) methyl hydrogen phosphate Chemical compound P(=O)(OC)(OC1=C(C=CC=C1)CCCCCCCCCCCC)O FQEMSHFIWLKFST-UHFFFAOYSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- HPJPZYNKWDXYJK-UHFFFAOYSA-N [chloro(dodecyl)phosphoryl]oxybenzene Chemical compound C(CCCCCCCCCCC)P(=O)(OC1=CC=CC=C1)Cl HPJPZYNKWDXYJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 235000004426 flaxseed Nutrition 0.000 abstract 1
- 125000005456 glyceride group Chemical group 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 229940057995 liquid paraffin Drugs 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 125000001477 organic nitrogen group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
-
- 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
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- 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
- C10M2223/043—Ammonium or amine 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
- 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
-
- 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)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Lubricants (AREA)
Abstract
The invention comprises a mono acid phosphoric ester product consisting mainly of <FORM:0743752/IV(a)/1> in which R is alkyl up to 4 C, and R1 is a branched dodecyl phenyl radical derived from the alkyl phenol formed by alkylation of phenol with propylene tetramer and salts derived from the ester; also a method for the production of the ester by the reaction between an aliphatic alcohol containing up to 4 C atoms with a product containing mainly dodecylphenoxy phosphoryl chloride, so that the alcohol does not accumulate during the reaction. An example is given of the preparation of a product from the dodecyl phenol obtained by treating phenol with propylene tetramer of 181-218 DEG C. boiling range in presence of an alkylation catalyst in reaction with phosphorus oxychloride, giving an alkyl phenoxy phosphoryl dichloride, which is treated with methyl alcohol to give the methyl dodecylphenyl monohydrogen phosphate. The product is suitable for making oil/water emulsions, which can be used to protect ferrous metals from rusting. The salts of the products with alkali and other metals and with organic nitrogen bases, e.g. cyclohexylamine, have similar properties. Specification 699,080 is referred to.ALSO:The invention comprises a mono-acid phosphoric ester product consisting mainly of a compound of the formula <FORM:0743752/III/1> in which R is alkyl up to 4C and R1 is a branched dodecyl phenyl radical derived from the alkyl phenol formed by alkylation of phenol with propylene tetramer, and salts derived from the ester (see Group IV(b)). The product is miscible with lubricating oils, kerosene, liquid paraffin, diesel oils, gasoline, and glyceride oils such as linseed, and may be used to prepare oil-in-water emulsions by mixing with the oil, e.g. mineral oil, adding to its own volume of water, stirring and diluting as required. Specification 699,080 is referred to.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB326550X | 1953-08-14 | ||
| GB30554X | 1954-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB743752A true GB743752A (en) | 1956-01-25 |
Family
ID=26237985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22419/53A Expired GB743752A (en) | 1953-08-14 | 1953-08-14 | Improvements in or relating to mono-acid phosphoric ester products |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE531106A (en) |
| CH (1) | CH326550A (en) |
| DE (1) | DE1024520B (en) |
| FR (1) | FR1103205A (en) |
| GB (1) | GB743752A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19910463B4 (en) * | 1998-03-18 | 2007-05-10 | Lanxess Deutschland Gmbh | Dialkylphosphoric acids by the methanol method |
-
0
- BE BE531106D patent/BE531106A/xx unknown
-
1953
- 1953-08-14 GB GB22419/53A patent/GB743752A/en not_active Expired
-
1954
- 1954-06-12 CH CH326550D patent/CH326550A/en unknown
- 1954-06-26 FR FR1103205D patent/FR1103205A/en not_active Expired
- 1954-07-17 DE DEI8916A patent/DE1024520B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR1103205A (en) | 1955-10-31 |
| DE1024520B (en) | 1958-02-20 |
| CH326550A (en) | 1957-12-31 |
| BE531106A (en) |
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