GB994136A - Method for the preparation of phosphate esters of surface active agents - Google Patents
Method for the preparation of phosphate esters of surface active agentsInfo
- Publication number
- GB994136A GB994136A GB48718/63A GB4871863A GB994136A GB 994136 A GB994136 A GB 994136A GB 48718/63 A GB48718/63 A GB 48718/63A GB 4871863 A GB4871863 A GB 4871863A GB 994136 A GB994136 A GB 994136A
- Authority
- GB
- United Kingdom
- Prior art keywords
- surfactant
- oxide
- carbon atoms
- water
- surfactants
- 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
- 239000004094 surface-active agent Substances 0.000 title abstract 13
- 238000000034 method Methods 0.000 title abstract 3
- 150000003014 phosphoric acid esters Chemical class 0.000 title abstract 3
- -1 aliphatic alcohols Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 150000001412 amines Chemical class 0.000 abstract 4
- 229940117927 ethylene oxide Drugs 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000002736 nonionic surfactant Substances 0.000 abstract 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 2
- 150000002989 phenols Chemical class 0.000 abstract 2
- 150000003456 sulfonamides Chemical class 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 2
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 abstract 1
- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 abstract 1
- 229920001281 polyalkylene Polymers 0.000 abstract 1
- 229940005657 pyrophosphoric acid Drugs 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Classifications
-
- 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
- C07F9/098—Esters of polyphosphoric acids or anhydrides
-
- 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
- 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
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Phosphate esters, of non-ionic surface-active agents that are condensation products of at least one mole. of alkylene oxide with one mole. of a compound having at least 6 carbon atoms and a reactive hydrogen, are prepared by reacting P2O5 with the surfactant in the presence of 0.1% to 3% by weight based on the weight of non-ionic surfactant of water or suitable mineral acid. Preferred surfactants are polyalkylene derivatives of alkylated or polyalkylated phenols, multi-branched chain aliphatic alcohols of at least 7 carbon atoms, straight chain aliphatic alcohols of at least 10 carbon atoms and also include fatty amines or amides, rosin amines; long chain unsubstituted or aryl-substituted sulphonamides, and high molecular weight mercaptans. Alkylene oxides are propylene-, butylene-, or preferably ethylene-oxide. Acids used are phosphoric, sulphuric, hydrochloric, boric, bromic, hydrobromic, hypobromous, hypophosphoric, metaphosphoric, and pyrophosphoric acids, or water, at 0.1% to 3%, preferably 0.1-0.8%, by weight of the surfactant. P2O5 is used at 1-3 mols. to 1-2 mols. of surfactant, and reaction is performed at up to 200 DEG C. Examples are given for phosphation of a nonyl phenol condensed with 15 mols. ethylene oxide, under anhydrous conditions as a comparative example, and in the presence of water, and phosphoric, hydrochloric and sulphuric acids. The process is used to prepare phosphates of higher homologues of the surfactants, and highly phosphated surfactants.ALSO:Non-ionic surface-active agents that are the condensation products of at least one mole of alkylene oxide with 1 mole of a compound having at least 6 carbon atoms and an active hydrogen, are esterified to ortho- or pyrophosphate esters by reaction with P2O5, in the presence of 0.1 to 3% by weight based on the weight of non-ionic surfactant of water or mineral acid. Preferred surfactants are: polyalkylene oxide derivatives of alkylated or polyalkylated phenols, multi-branched chain alcohols of at least 7 carbon atoms, at least 10 C straight-chain aliphatic alcohols, and also include fatty amines or amides; rosin amines; long-chain unsubstituted or aryl substituted sulphonamides; and high molecular weight mercaptans. Alkylene oxides are butylene-, propylene-, or preferably, ethylene-oxide. Acids used are hypo-, meta-, or pyrophosphoric acid; or boric, bromic, hydrobromic, hydrochloric, sulphoric or hypobromous acid. P2O5 is reacted at 1-3 moles per 1-2 moles of surfactant. Examples are given for phosphation of nonyl phenol condensed with 15 moles of ethylene oxide, in the presence of water, or phosphoric, hydrochloric, or sulphuric acid. The process is used to prepare phosphate esters of higher homologues of surfactant (e.g. M.W. > 2000) and esters of surfactants of a high degree of phosphation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US243721A US3346670A (en) | 1962-12-11 | 1962-12-11 | Method for the preparation of phosphate esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994136A true GB994136A (en) | 1965-06-02 |
Family
ID=22919857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48718/63A Expired GB994136A (en) | 1962-12-11 | 1963-12-10 | Method for the preparation of phosphate esters of surface active agents |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3346670A (en) |
| BE (1) | BE641097A (en) |
| GB (1) | GB994136A (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496104A (en) * | 1965-10-18 | 1970-02-17 | Yawata Seitetsu Kk | Cold rolling agent |
| US3462365A (en) * | 1966-06-23 | 1969-08-19 | Nalco Chemical Co | Scale inhibiting compounds |
| US3488289A (en) * | 1966-06-24 | 1970-01-06 | Texaco Inc | Composition and method for treating scale |
| US3502587A (en) * | 1966-10-06 | 1970-03-24 | Nalco Chemical Co | Scale inhibiting compositions |
| US3692884A (en) * | 1969-02-07 | 1972-09-19 | Edwin R Gaskell | Phosphate esters |
| US3963628A (en) * | 1974-06-07 | 1976-06-15 | Union Carbide Corporation | Fiber lubricant composition |
| US4118327A (en) * | 1977-03-28 | 1978-10-03 | Colgate Palmolive Company | Fabric softener and anti-static compositions |
| US4154887A (en) * | 1978-03-31 | 1979-05-15 | Gaf Corporation | Surface treatment of rigid polyvinyl chloride |
| JPS5512164A (en) * | 1978-07-13 | 1980-01-28 | Kao Corp | Antibiotic soap |
| US4215002A (en) * | 1978-07-31 | 1980-07-29 | Texaco Inc. | Water-based phosphonate lubricants |
| US4346148A (en) * | 1979-05-04 | 1982-08-24 | The Lubrizol Corporation | Phosphorus-containing compositions, lubricants containing them and metal workpieces coated with same |
| US4358509A (en) * | 1979-05-04 | 1982-11-09 | The Lubrizol Corporation | Novel metal working additive compositions, lubricants containing them and metal workpieces coated with same |
| US4256594A (en) * | 1979-05-04 | 1981-03-17 | The Lubrizol Corporation | Hot melt metal working lubricants containing phosphorus-containing compositions |
| US4579672A (en) * | 1983-05-10 | 1986-04-01 | Exxon Research & Engineering Co. | Functional fluids and lubricants having improved water tolerance |
| US5286300A (en) * | 1991-02-13 | 1994-02-15 | Man-Gill Chemical Company | Rinse aid and lubricant |
| WO2020185513A1 (en) | 2019-03-08 | 2020-09-17 | Stepan Company | Reactive surfactants |
| EP4307891A1 (en) | 2021-03-19 | 2024-01-24 | Nouryon Chemicals International B.V. | Agrochemical composition |
| PL441023A1 (en) | 2022-04-26 | 2023-10-30 | Pcc Exol Spółka Akcyjna | Method for preparing monoesters and diesters of phosphoric acids from alcohols |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853471A (en) * | 1955-11-29 | 1958-09-23 | Gen Aniline & Film Corp | Making addition polymers and copolymers with phosphorus compound emulsifier |
| US3010903A (en) * | 1957-11-01 | 1961-11-28 | Exxon Research Engineering Co | Phosphate additives for hydrocarbon compositions |
| US3033889A (en) * | 1958-10-21 | 1962-05-08 | Gen Aniline & Film Corp | Phosphate esters of branched chain alcohols |
| BE596967A (en) * | 1959-11-12 | |||
| US3079419A (en) * | 1960-12-07 | 1963-02-26 | Stauffer Chemical Co | Process for the manufacture of trialkyl phosphates |
-
1962
- 1962-12-11 US US243721A patent/US3346670A/en not_active Expired - Lifetime
-
1963
- 1963-12-10 GB GB48718/63A patent/GB994136A/en not_active Expired
- 1963-12-11 BE BE641097D patent/BE641097A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3346670A (en) | 1967-10-10 |
| BE641097A (en) | 1964-04-01 |
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