GB938108A - Phosphono esters of organic acids - Google Patents
Phosphono esters of organic acidsInfo
- Publication number
- GB938108A GB938108A GB13152/61A GB1315261A GB938108A GB 938108 A GB938108 A GB 938108A GB 13152/61 A GB13152/61 A GB 13152/61A GB 1315261 A GB1315261 A GB 1315261A GB 938108 A GB938108 A GB 938108A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- esters
- substituted
- methyl
- 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
- 150000007524 organic acids Chemical class 0.000 title 1
- 235000005985 organic acids Nutrition 0.000 title 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 title 1
- -1 2-ethyl hexyl Chemical group 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 4
- 239000003999 initiator Substances 0.000 abstract 3
- 150000003254 radicals Chemical class 0.000 abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000003879 lubricant additive Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000002978 peroxides Chemical group 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 abstract 1
- 238000007725 thermal activation Methods 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic 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
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A polyvinyl chloride composition contains as plasticizer an ester or esters having the formula:- <FORM:0938108/IV(a)/1> in which Q is a methylene chain of 2 or 3 methlene groups which may be substituted by a methyl group, n is an integer from 0 to 12 and R is an alkyl, substituted alkyl, or aryl group (see Group IV(b)). Specified R groups are methyl, ethyl, butyl and 2-ethyl hexyl and specified values for n are 0, 2, 4, 7, 8 and 12.ALSO:The invention comprises esters of the formula:- <FORM:0938108/IV(a)/1> wherein Q is a methylene chain of 2 or 3 methylene groups which may be substituted by a methyl group, n is an integer from 0 to 12 and R is an alkyl, substituted alkyl, or aryl group. They may be obtained by reacting a dialkyl, di(substituted alkyl) or diaryl phosphite (RO)2.P(H)-->O with a diester of the formula X-O-C(O).(CH2)nC(O).-O-X wherein X is an alkyl radical of 2 to 4 carbon atoms and n is an integer from 0 to 12 with the aid of a free radical initiator. The free radical initiator is preferably a peroxide such as tertiary butyl perbenzoate, benzoyl peroxide or azobisisobutyronitrile but other free radical initiators such as ultraviolet light or thermal activation may also be used. The reaction is conveniently carried out under a layer of inert gas, e.g. nitrogen and suitable reaction temperatures are from about 100 DEG to 110 DEG C. Examples are given for the production of esters of the above formula in which n is 0, 1, 2, 4, 7, or 8 and each R is methyl, ethyl, butyl, and 2-ethylhexyl respectively and also of the ester in which n is 12 and R is 2-ethylhexyl. The products are useful as plasticisers for polyvinyl chloride resins (see Group IV(a)) and as functional fluids and lubricant additives.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23105A US2989562A (en) | 1960-04-18 | 1960-04-18 | Method of preparing bis (3-dialkylphosphonopropyl) esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB938108A true GB938108A (en) | 1963-09-25 |
Family
ID=21813155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13152/61A Expired GB938108A (en) | 1960-04-18 | 1961-04-12 | Phosphono esters of organic acids |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2989562A (en) |
| DE (1) | DE1145171B (en) |
| GB (1) | GB938108A (en) |
| NL (1) | NL263689A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110451599A (en) * | 2019-08-30 | 2019-11-15 | 东南大学 | A method of nitrate nitrogen in water body is removed by UV activation formic acid |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2312090A1 (en) * | 1973-03-10 | 1974-09-12 | Basf Ag | POLY-DIALKYLPHOSPHONOALKYLCARBONATES AND THEIR USE FOR FLAME PROTECTION EQUIPMENT OF CELLULOSIC TEXTILES |
| DE2402174A1 (en) * | 1974-01-17 | 1975-07-31 | Bayer Ag | Phosphorus-containing dicarbamic acid diesters |
| FR2277093A1 (en) * | 1974-07-04 | 1976-01-30 | Poudres & Explosifs Ste Nale | DIETHYL HYDROXYMETHYLPHOSPHONATE ESTERS, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS FLAME-RESISTANT AGENTS |
| US5023312A (en) * | 1988-07-19 | 1991-06-11 | Erickson Frank L | Meadowfoam oil and meadowfoam oil derivatives as lubricant additives |
| US5302305A (en) * | 1989-02-09 | 1994-04-12 | The Lubrizol Corporation | Carboxylic esters, liquid compositions containing said carboxylic esters and methods of lubricating metal parts |
| DE102007010160A1 (en) | 2007-03-02 | 2008-09-04 | Lanxess Deutschland Gmbh | Halogen-free, flame-retardant polyurethane foams |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL145897B (en) * | 1948-04-12 | Union Carbide Corp | PROCEDURE FOR PREPARING GRAINED DETERGENTS. | |
| US2492994A (en) * | 1948-05-11 | 1950-01-03 | Shell Dev | Bituminous compositions |
| US2753368A (en) * | 1950-11-13 | 1956-07-03 | Shell Dev | Higher alkyl esters of phosphonic acids |
| US2725359A (en) * | 1951-03-07 | 1955-11-29 | Shell Dev | Lubricating oil composition |
| US2710301A (en) * | 1952-09-30 | 1955-06-07 | Shell Dev | Phosphorus esters and a process for the preparation of the same |
| US2770610A (en) * | 1952-10-30 | 1956-11-13 | Monsanto Chemicals | Esters of epoxidized phosphonic acids and halogenated organic materials stabilized therewith |
| US2837481A (en) * | 1955-03-31 | 1958-06-03 | California Research Corp | Metal alkyl phosphonate thickened lubricating oils |
| US2875231A (en) * | 1956-02-14 | 1959-02-24 | Eastman Kodak Co | Catalytic process of reacting a phosphite and lactone |
-
0
- NL NL263689D patent/NL263689A/xx unknown
-
1960
- 1960-04-18 US US23105A patent/US2989562A/en not_active Expired - Lifetime
-
1961
- 1961-04-12 DE DEA37180A patent/DE1145171B/en active Pending
- 1961-04-12 GB GB13152/61A patent/GB938108A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110451599A (en) * | 2019-08-30 | 2019-11-15 | 东南大学 | A method of nitrate nitrogen in water body is removed by UV activation formic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| NL263689A (en) | |
| US2989562A (en) | 1961-06-20 |
| DE1145171B (en) | 1963-03-14 |
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