DE3047378A1 - Verfahren zur herstellung von phosphorsaeure-monoester - Google Patents
Verfahren zur herstellung von phosphorsaeure-monoesterInfo
- Publication number
- DE3047378A1 DE3047378A1 DE19803047378 DE3047378A DE3047378A1 DE 3047378 A1 DE3047378 A1 DE 3047378A1 DE 19803047378 DE19803047378 DE 19803047378 DE 3047378 A DE3047378 A DE 3047378A DE 3047378 A1 DE3047378 A1 DE 3047378A1
- Authority
- DE
- Germany
- Prior art keywords
- phosphoric acid
- reaction
- mol
- mixture
- hydroxyl compound
- 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.)
- Granted
Links
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 71
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 17
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- -1 hydroxyl compound Chemical class 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 230000000865 phosphorylative effect Effects 0.000 claims description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 10
- 150000005690 diesters Chemical class 0.000 description 8
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- JTXUVYOABGUBMX-UHFFFAOYSA-N didodecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCC JTXUVYOABGUBMX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000005187 foaming Methods 0.000 description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 1
- 229940093541 dicetylphosphate Drugs 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- ZUVCYFMOHFTGDM-UHFFFAOYSA-N hexadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(O)=O ZUVCYFMOHFTGDM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16379179A JPS5686191A (en) | 1979-12-17 | 1979-12-17 | Preparation of phosphoric monoester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3047378A1 true DE3047378A1 (de) | 1981-09-10 |
| DE3047378C2 DE3047378C2 (https=) | 1988-08-11 |
Family
ID=15780766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803047378 Granted DE3047378A1 (de) | 1979-12-17 | 1980-12-16 | Verfahren zur herstellung von phosphorsaeure-monoester |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4350645A (https=) |
| JP (1) | JPS5686191A (https=) |
| DE (1) | DE3047378A1 (https=) |
| ES (1) | ES8200699A1 (https=) |
| MX (1) | MX152149A (https=) |
| PH (1) | PH16133A (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4493782A (en) * | 1983-07-07 | 1985-01-15 | Amchem Products, Inc. | Cleansing compositions comprising ethoxylated alcohol monoesters of phosphoric acid |
| JPS62104802A (ja) * | 1985-07-24 | 1987-05-15 | Asahi Denka Kogyo Kk | 乳化重合用乳化剤 |
| DE3622440A1 (de) * | 1986-07-04 | 1988-01-07 | Henkel Kgaa | Alkyl-hydroxyalkyl-phosphorsaeureester |
| DE3643763A1 (de) * | 1986-12-20 | 1988-06-30 | Henkel Kgaa | Direktveresterung mit o-phosphorsaeure |
| US5260051A (en) * | 1990-12-17 | 1993-11-09 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising phosphate ester compounds containing a beneficial reagent component |
| US5451401A (en) * | 1993-09-29 | 1995-09-19 | The Procter & Gamble Company | Diphosphonic acid esters as tartar control agents |
| US5554781A (en) * | 1994-03-30 | 1996-09-10 | Reierson; Robert L. | Monoalkyl phosphonic acid ester production process |
| US5550274A (en) * | 1994-03-30 | 1996-08-27 | Reierson; Robert L. | In-situ phosphation reagent process |
| EP1207135B1 (en) * | 1994-03-30 | 2008-03-05 | Rhodia Inc. | Phosphation reagent, process and use |
| JP3115489B2 (ja) * | 1994-09-20 | 2000-12-04 | 花王株式会社 | リン酸モノエステルの製造方法 |
| US5463101A (en) * | 1994-12-01 | 1995-10-31 | Rhone-Poulenc Inc. | Process of making low dioxane alkoxylate phosphate esters |
| DE69532295T2 (de) * | 1994-12-09 | 2004-09-23 | Kao Corp. | Verfahren zur herstellung von phosphorsäuremonoestern |
| US6765041B1 (en) * | 2000-11-27 | 2004-07-20 | Millenium Inorganic Chemicals, Inc. | Organo-acid phosphate treated pigments |
| EP1433790B1 (en) * | 2002-12-26 | 2007-04-25 | Kao Corporation | Processes for producing and stabilizing phosphates |
| US20050239921A1 (en) | 2004-04-27 | 2005-10-27 | Birmingham John N | Preparation of organic additive-treated, pyrogenic silica-encapsulated titanium dioxide particles |
| JP4583895B2 (ja) * | 2004-11-22 | 2010-11-17 | 花王株式会社 | リン酸エステルの製造方法 |
| EP1869118A4 (en) * | 2005-03-16 | 2010-08-18 | Du Pont | INORGANIC PIGMENTS AND POLYMERIC FILMS EASILY CLEANED, CONTAINING THE SAME PIGMENTS |
| US7601212B2 (en) | 2005-08-29 | 2009-10-13 | E.I. Du Pont De Nemours And Company | Pigment particles coated with polysaccharides and having improved properties |
| CN101831514A (zh) * | 2010-05-15 | 2010-09-15 | 甘肃宏良皮业股份有限公司 | 一种磷酸酯皮革加脂剂的制备方法 |
| HUE026774T2 (en) | 2013-02-22 | 2016-08-29 | Omya Int Ag | New surface treatment of white minerals for use in plastics |
| ES2660425T3 (es) | 2014-12-02 | 2018-03-22 | Omya International Ag | Proceso para la producción de un material compactado, material así producido y uso del mismo |
| EP3072687A1 (en) | 2015-03-24 | 2016-09-28 | Omya International AG | Easy to disperse calcium carbonate to improve hot tack strength |
| KR101724272B1 (ko) | 2015-05-11 | 2017-04-07 | 재단법인 한국화학융합시험연구원 | 모노 함량이 높은 알킬 포스페이트의 제조방법 |
| EP3176204A1 (en) | 2015-12-02 | 2017-06-07 | Omya International AG | Surface-treated fillers for ultrathin breathable films |
| CN109414389B (zh) * | 2016-06-27 | 2022-05-24 | 帝斯曼知识产权资产管理有限公司 | 局部用组合物 |
| CN109310609B (zh) * | 2016-06-27 | 2022-06-28 | 帝斯曼知识产权资产管理有限公司 | 包含微颜料的组合物 |
| EP3272524A1 (en) | 2016-07-21 | 2018-01-24 | Omya International AG | Calcium carbonate as cavitation agent for biaxially oriented polypropylene films |
| WO2018095515A1 (en) | 2016-11-22 | 2018-05-31 | Omya International Ag | Surface-treated fillers for biaxially oriented polyester films |
| ES2764676T3 (es) | 2016-12-21 | 2020-06-04 | Omya Int Ag | Rellenos tratados en la superficie para películas de poliéster |
| EP3572456A1 (en) | 2018-05-23 | 2019-11-27 | Omya International AG | Surface-treated fillers for polyester films |
| EP3623428A1 (en) | 2018-09-17 | 2020-03-18 | Omya International AG | Compacted polymer-based filler material for plastic rotomoulding |
| EP3628705A1 (en) | 2018-09-28 | 2020-04-01 | Omya International AG | Process for preparing a coarse surface treated filler material product |
| US20220177403A1 (en) | 2019-03-08 | 2022-06-09 | Stepan Company | Reactive surfactants |
| CN116157454A (zh) | 2020-07-16 | 2023-05-23 | Omya国际股份公司 | 由包含碳酸钙或碳酸镁的材料和包含至少一种可交联化合物的表面处理组合物形成的组合物 |
| EP4182393A1 (en) | 2020-07-16 | 2023-05-24 | Omya International AG | A composition formed from a calcium carbonate-comprising material and a grafted polymer |
| EP4182388A1 (en) | 2020-07-16 | 2023-05-24 | Omya International AG | Use of a porous filler for reducing the gas permeability of an elastomer composition |
| CA3178667A1 (en) | 2020-07-16 | 2022-01-20 | Tobias Keller | Alkaline earth metal minerals as carriers for surfactants in drilling fluids |
| CN116194525A (zh) | 2020-07-16 | 2023-05-30 | Omya国际股份公司 | 增强的弹性体组合物 |
| EP3974385A1 (en) | 2020-09-24 | 2022-03-30 | Omya International AG | A moisture-curing one-component polymer composition comprising a natural ground calcium carbonate (gcc) |
| WO2022073934A1 (en) | 2020-10-05 | 2022-04-14 | Omya International Ag | Kit comprising surface-treated calcium carbonate and a peroxide agent for improving the mechanical properties of polyethylene/polypropylene compositions |
| US20230357035A1 (en) | 2020-11-02 | 2023-11-09 | Omya International Ag | Process for producing precipitated calcium carbonate in the presence of natural ground calcium carbonate |
| CN118414387A (zh) | 2021-12-22 | 2024-07-30 | Omya国际股份公司 | 用于聚合物配制剂的具有高生物基碳含量的沉淀碳酸钙 |
| CN118414307A (zh) | 2021-12-22 | 2024-07-30 | Omya国际股份公司 | 用于聚合物配制剂的具有高生物基碳含量的含碳酸钙材料 |
| WO2025149508A1 (en) | 2024-01-10 | 2025-07-17 | Omya International Ag | Removal of the unpleasant smell in calcium carbonate filled polymer compositions |
| WO2026062128A1 (en) | 2024-09-19 | 2026-03-26 | Omya International Ag | Polystyrene polymer formulation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3331896A (en) * | 1964-09-15 | 1967-07-18 | Gen Aniline & Film Corp | Method of preparing alkali soluble phosphate esters of hydroxylic organic compounds |
-
1979
- 1979-12-17 JP JP16379179A patent/JPS5686191A/ja active Granted
-
1980
- 1980-11-25 US US06/210,352 patent/US4350645A/en not_active Expired - Lifetime
- 1980-12-16 DE DE19803047378 patent/DE3047378A1/de active Granted
- 1980-12-16 ES ES497824A patent/ES8200699A1/es not_active Expired
- 1980-12-16 PH PH24987A patent/PH16133A/en unknown
- 1980-12-17 MX MX185306A patent/MX152149A/es unknown
Non-Patent Citations (2)
| Title |
|---|
| CHRISTEN: Grundlagen der organischen Chemie, S.269 * |
| Ind. eng. Chem. 34, 20-25 (1942) * |
Also Published As
| Publication number | Publication date |
|---|---|
| US4350645A (en) | 1982-09-21 |
| ES497824A0 (es) | 1981-11-16 |
| JPS5761358B2 (https=) | 1982-12-23 |
| MX152149A (es) | 1985-05-31 |
| JPS5686191A (en) | 1981-07-13 |
| PH16133A (en) | 1983-07-08 |
| DE3047378C2 (https=) | 1988-08-11 |
| ES8200699A1 (es) | 1981-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |