GB1053193A - - Google Patents
Info
- Publication number
- GB1053193A GB1053193A GB2524365A GB2524365A GB1053193A GB 1053193 A GB1053193 A GB 1053193A GB 2524365 A GB2524365 A GB 2524365A GB 2524365 A GB2524365 A GB 2524365A GB 1053193 A GB1053193 A GB 1053193A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- amine
- carbon atoms
- esters
- prepared
- 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
- -1 amine salts Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical class 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 150000001412 amines Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 201000006747 infectious mononucleosis Diseases 0.000 abstract 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
Classifications
-
- 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
- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
- C10L1/2658—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) amine salts
-
- 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
-
- 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
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- 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
- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
- C10L1/2641—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) oxygen bonds only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Lubricants (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,053,193. Alkanol amine salts of alkyl acid orthophosphate esters. E. I. DU PONT DE NEMOURS & CO. June 15, 1965 [June 15, 1964; Jan. 13, 1965], No. 25243/65. Heading C2C. [Also in Division C5] The invention comprises a salt of a primary mono- or di-alkyl orthophosphate ester in which each alkyl group contains from 8 to 16 carbon atoms and an alkanol amine having the formula wherein R and R<SP>1</SP> are hydrogen or alkyl, cycloalkyl, phenyl or alkyl phenyl groups, R and R<SP>1</SP> together containing a total of from 8 to 24 carbon atoms, R<SP>11</SP> is an alkyl, cycloalkyl, phenyl or aralkyl group containing 6 to 25 carbon atoms and R<SP>111</SP> is hydroxyethyl or a hydroxypropyl radical. The salt may be prepared by neutralizing the alkyl orthophosphate ester with the appropriate alkanol amine, the reactants normally being in equimolar proportions. The orphosphate esters may be obtained by reacting an alcohol (3 moles) with phosphorus pentoxide (1 mole) to give an approximately equimolar mixture of the corresponding mono- and di-alkyl esters of phosphoric acid. This mixture may be used as such to prepare a mixture of amine salts or the separate esters may be isolated from it and used to prepare individual amine salts. The alcohols used may be branched- or straight-chain primary alkanols having 8 to 16 carbon atoms or mixtures thereof. The branched-chain alkanols may be those prepared by the Oxo-process using a branchedchain olefin such as C 7 -C 15 mono-olefinic polymers and interpolymers of propylene and butylene, or they may be prepared by the aldolisation of appropriate aldehydes followed by hydrogenation or by the alkaline condensation of primary alcohols of the type RCH 2 CH 2 OH where R is an alkyl group of from 2 to 6 carbon atoms. The alkanol-amines of type A above may be obtained by the reaction of the appropriate amine RR<SP>1</SP>NH with 3-chloropropanediol-1,2 and those of type B may be prepared by reading the appropriate amine R<SP>11</SP>NH 2 with ethylene oxide or propylene oxide or, when R<SP>111</SP> is hydroxyethyl, by reacting the alkyl or aralkyl chloride R<SP>11</SP>Cl with diethanolamine. The amine phosphate salts are useful as anti-stalling additives for hydrocarbon distillate fuels (see Division C5).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37535764A | 1964-06-15 | 1964-06-15 | |
| US425329A US3428713A (en) | 1964-06-15 | 1965-01-13 | Alkanol amine salts of phosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1053193A true GB1053193A (en) | 1966-12-30 |
Family
ID=27007028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2524365A Expired GB1053193A (en) | 1964-06-15 | 1965-06-15 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US3428713A (en) |
| DE (1) | DE1545502C3 (en) |
| FR (1) | FR1451313A (en) |
| GB (1) | GB1053193A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3962338A (en) * | 1968-05-22 | 1976-06-08 | Merck & Co., Inc. | Novel methods and compounds employed therein |
| US4031125A (en) * | 1973-11-19 | 1977-06-21 | Merck & Co., Inc. | 3-Sulfonate ester of 2,3-dihydroxypropylamine |
| EP0597806A1 (en) * | 1992-11-11 | 1994-05-18 | Ciba-Geigy Ag | Novel cyclohexyl substituted glycidylethers |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3852288A (en) * | 1970-08-27 | 1974-12-03 | Du Pont | Process for color stable alkyl and alkenyl acid phosphate compositions |
| US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
| US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
| US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
| US4435186A (en) | 1982-05-03 | 1984-03-06 | Texaco Inc. | Alcohol fuels containing wear-inhibiting amounts of reaction products of amines and phosphate esters of phosphonic acids |
| US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
| US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
| US4522629A (en) * | 1983-09-23 | 1985-06-11 | Mobil Oil Corporation | Borated phosphonates as lubricant and fuel additives |
| US4555353A (en) * | 1983-09-23 | 1985-11-26 | Mobil Oil Corporation | Borated phosphonates as lubricant and fuel additives |
| US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
| JPS61146872A (en) * | 1984-12-20 | 1986-07-04 | 三菱レイヨン株式会社 | Weft yarn treating agent for air jet loom |
| US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
| US5453275A (en) * | 1988-05-05 | 1995-09-26 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
| DE19740069A1 (en) * | 1997-09-12 | 1999-03-18 | Clariant Gmbh | Mixtures of long-chain phosphoric acid alkyl esters |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656372A (en) * | 1948-06-22 | 1953-10-20 | Textilana Inc | Mixtures of orthophosphates |
| US2988434A (en) * | 1957-01-14 | 1961-06-13 | Gulf Oil Corp | Auxiliary fuels |
| US3115400A (en) * | 1960-08-01 | 1963-12-24 | Armour & Co | Motor fuel composition |
| US3012056A (en) * | 1960-08-11 | 1961-12-05 | Universal Oil Prod Co | Alkyl acid phosphate salt of the reaction product of epihalohydrin and amine |
| US3136809A (en) * | 1962-05-18 | 1964-06-09 | Du Pont | Stabilization of alpha, beta-unsaturated nitriles |
| US3247134A (en) * | 1962-07-09 | 1966-04-19 | Owens Corning Fiberglass Corp | Fire retardant cellular polyurethane compositions containing an organic phosphate amine salt |
| US3325565A (en) * | 1963-10-01 | 1967-06-13 | Exxon Research Engineering Co | Mixed monoalkyl and dialkyl esters of phosphoric acid partially neutralized with a primary alkyl amine |
-
1965
- 1965-01-13 US US425329A patent/US3428713A/en not_active Expired - Lifetime
- 1965-06-12 DE DE1545502A patent/DE1545502C3/en not_active Expired
- 1965-06-14 FR FR20682A patent/FR1451313A/en not_active Expired
- 1965-06-15 GB GB2524365A patent/GB1053193A/en not_active Expired
-
1967
- 1967-10-19 US US676619A patent/US3505044A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3962338A (en) * | 1968-05-22 | 1976-06-08 | Merck & Co., Inc. | Novel methods and compounds employed therein |
| US4031125A (en) * | 1973-11-19 | 1977-06-21 | Merck & Co., Inc. | 3-Sulfonate ester of 2,3-dihydroxypropylamine |
| EP0597806A1 (en) * | 1992-11-11 | 1994-05-18 | Ciba-Geigy Ag | Novel cyclohexyl substituted glycidylethers |
| US5668227A (en) * | 1992-11-11 | 1997-09-16 | Ciba-Geigy Corporation | Cyclohexyl-group-containing glycidyl ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| US3505044A (en) | 1970-04-07 |
| FR1451313A (en) | 1966-01-07 |
| DE1545502C3 (en) | 1974-06-06 |
| DE1545502B2 (en) | 1973-10-31 |
| US3428713A (en) | 1969-02-18 |
| DE1545502A1 (en) | 1970-04-30 |
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