NL8602640A - METHOD FOR SELECTIVELY RECOVERY OF PHOSPHORIC ACID DI-ESTERS FROM A MIXTURE OF PHOSPHORIC ACID MONO AND DI ESTERS. - Google Patents
METHOD FOR SELECTIVELY RECOVERY OF PHOSPHORIC ACID DI-ESTERS FROM A MIXTURE OF PHOSPHORIC ACID MONO AND DI ESTERS. Download PDFInfo
- Publication number
- NL8602640A NL8602640A NL8602640A NL8602640A NL8602640A NL 8602640 A NL8602640 A NL 8602640A NL 8602640 A NL8602640 A NL 8602640A NL 8602640 A NL8602640 A NL 8602640A NL 8602640 A NL8602640 A NL 8602640A
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- Netherlands
- Prior art keywords
- phosphoric acid
- agents
- diesters
- mixture
- saponification
- Prior art date
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 37
- -1 PHOSPHORIC ACID DI-ESTERS Chemical class 0.000 title claims description 27
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 9
- 238000011084 recovery Methods 0.000 title claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 35
- 238000005260 corrosion Methods 0.000 claims description 16
- 230000007797 corrosion Effects 0.000 claims description 16
- 239000003112 inhibitor Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000007127 saponification reaction Methods 0.000 claims description 13
- 229920000151 polyglycol Polymers 0.000 claims description 10
- 239000010695 polyglycol Substances 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000004575 stone Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 2
- 239000002455 scale inhibitor Substances 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000005340 bisphosphate group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- VEVVRTWXUIWDAW-UHFFFAOYSA-N dodecan-1-amine;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCCCCCN VEVVRTWXUIWDAW-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/36—Organic compounds containing phosphorus
- C11D3/362—Phosphates or phosphites
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/167—Phosphorus-containing compounds
- C23F11/1673—Esters of phosphoric or thiophosphoric acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Hydrology & Water Resources (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
r NO 33902 '* ^r NO 33902 '* ^
Werkwijze voor het selectief winnen van fosforzuur-di-esters uit een mengsel van fosforzuur-mono- en -di-esters 5 De uitvinding heeft betrekking op een werkwijze voor het selectief winnen van fosforzuur-di-esters uit een mengsel van fosforzuur-mono- en -di-esters.The invention relates to a method for the selective recovery of phosphoric acid diesters from a mixture of phosphoric acid monoesters and diesters. and diesters.
Door omzetting van fosforoxychloride met alcoholen verkrijgt men een reactiemengsel dat naast andere produkten fosforzuur-monoalkyl-10 esterdichloride, fosforzuur-dialkylestermonochloride, fosforzuur-tri-alkylester en tetraalkylpyrofosfaat bevat (DE-AS 1.272.283). Door omzetting van fosfortrichloride net alcoholen verkrijgt men vergelijkbare estermengsels.By reaction of phosphorus oxychloride with alcohols, a reaction mixture is obtained which, in addition to other products, contains phosphoric acid monoalkyl ester dichloride, phosphoric dialkyl ester monochloride, phosphoric acid trialkyl ester and tetraalkyl pyrophosphate (DE-AS 1,272,283). Comparable ester mixtures are obtained by converting phosphorus trichloride with alcohols.
Bij de reactie van 1 mol fosforpentoxide met 3 mol alcohol ver-15 krijgt men een estermengsel, dat overwegend uit de fosforzuur-mono-ester en -di-ester bestaat.The reaction of 1 mole of phosphorus pentoxide with 3 moles of alcohol results in an ester mixture consisting predominantly of the phosphoric acid monoester and diester.
Van deze fosforzuuresters hebben de di-esters bijzonder gunstige eigenschappen. Zo zijn de oppervlaktespanning en de kritische micelcon-centratie ervan veel lager dan die van de monoesters. Het wasvermogen 20 en bevochtigend vermogen van de di-esters zijn daardoor veel beter dan die van de mono-esters met een vergelijkbare struktuur en/of vergelijkbare mol.massa. De di-esters hebben bovendien de eigenschap, in waterig milieu met metaalionen te reageren. Zo kunnen waardevolle metalen zoals uraan, thorium en beryllium via oplosmiddel extractie met dialkylfosfa-25 ten gewonnen worden.The diesters of these phosphoric acid esters have particularly favorable properties. For example, the surface tension and its critical micelle concentration are much lower than that of the monoesters. The washing power and wetting power of the diesters are therefore much better than that of the monoesters with a comparable structure and / or comparable molecular weight. The diesters also have the property of reacting with metal ions in an aqueous medium. For example, valuable metals such as uranium, thorium and beryllium can be recovered via solvent extraction with dialkyl phosphates.
De fosforzuur-mono-esters, in het bijzonder die van geëthoxy-leerde alcoholen en fenolen, zijn thermisch aanvankelijk instabieler dan de overeenkomstige fosforzuurdi-esters. Dit kan bij relatief hoge temperaturen tot grote problemen leiden, wanneer men mengsels van mono-30 en diesters als corrosie-inhibitoren bij het winnen van aardolie en aardgas toepast.The phosphoric acid monoesters, especially those of ethoxylated alcohols and phenols, are more thermally initially unstable than the corresponding phosphoric acid diesters. This can lead to major problems at relatively high temperatures when mixtures of mono-30 and diesters are used as corrosion inhibitors in the recovery of petroleum and natural gas.
Een scheiding van mono- en di-esters via destillatie leidt tot af-braakprodukten en daardoor tot moeilijkheden bij het winnen van zuivere di-ester.Separation of mono- and diesters via distillation leads to degradation products and therefore difficulties in recovering pure diester.
35 Derhalve lag aan de uitvinding het probleem ten grondslag een werkwijze voor het selectief winnen van fosforzuur-di-esters uit een mengsel van fosforzuurmono- en -di-esters te verschaffen, waarbij het isoleren van de zuivere di-esters zonder afbraak op eenvoudige wijze mogelijk is.Therefore, the problem underlying the invention was to provide a process for the selective recovery of phosphoric acid diesters from a mixture of phosphoric acid mono- and diesters, wherein the pure diesters are isolated without degradation in a simple manner is possible.
40 Dit probleem werd volgens de uitvinding, zoals aangegeven in de ©ÖÖ2640 i Φ\ ^ 2 conclusies, opgelost.This problem was solved according to the invention as stated in the claims.
Verrassenderwijs werd gevonden, dat bij de hydrolyse resp. bij de verzeping van het estermengsel met base bij een pH van 5-10, bij voorkeur van 6-8, de mono-esters nagenoeg kwantitatief verzepen, terwijl de 5 fosforzuur-di-esters niet verzepen. Bij de verzeping volgens de uitvinding moeten de basen tenminste 1 mol H2O per mol mono-ester bevatten, resp. moet deze hoeveelheid water geheel of gedeeltelijk aan het reak-tiemengsel worden toegevoegd, wanneer dit geen of minder dan 1 mol H2O per mol bevat.It has surprisingly been found that in the hydrolysis resp. in the saponification of the ester mixture with base at a pH of 5-10, preferably of 6-8, the mono-esters saponify substantially quantitatively, while the 5 phosphoric acid diesters do not saponify. In the saponification according to the invention, the bases must contain at least 1 mole H 2 O per mole monoester, resp. this amount of water must be added in whole or in part to the reaction mixture if it contains no or less than 1 mole H 2 O per mole.
10 Bij pH-waarden boven 10 worden noch de mono-ester noch de di-ester verzeept.At pH values above 10, neither the monoester nor the diester are saponified.
Fosforzuur-esters die de voorkeur genieten, zijn esters van alifa-tische alcoholen, zoals methanol, butanol, 2-ethyl hexyl alcohol, deca-nol, tridecanol, oleylalcohol en stearylalcohol, en aromatische alcoho-15 len zoals alkylfenolen, en in het bijzonder geëthoxyleerde alcoholen met 1 tot 20, bij voorkeur 2 tot 8 mol ethyleenoxyde (EO), zoals butanol, octanol, decanol met 1, 2, 3 of 4 mol EO, tridecanol met 3, 5 of 8,5 mol EO, alkylfenolethoxylaten met 1 tot 20 mol EO, zoals nonyl-fenol met 4 tot 10 mol EO alsmede mengsel daarvan.Preferred phosphoric acid esters are esters of aliphatic alcohols such as methanol, butanol, 2-ethyl hexyl alcohol, decanol, tridecanol, oleyl alcohol and stearyl alcohol, and aromatic alcohols such as alkyl phenols, and in particular ethoxylated alcohols with 1 to 20, preferably 2 to 8 moles of ethylene oxide (EO), such as butanol, octanol, decanol with 1, 2, 3 or 4 moles of EO, tridecanol with 3, 5 or 8.5 moles of EO, alkylphenol ethoxylates with 1 up to 20 moles EO, such as nonyl phenol with 4 to 10 moles EO and mixture thereof.
20 De verzeping vindt bij een temperatuur van 100 - 250°C, bij voorkeur van 120 - 180°C en in het bijzonder van 140 - 160°C en in het algemeen onder een druk van 1 tot 20 bar plaats. De hydrolyse is in het algemeen na ongeveer een half uur tot ongeveer 10 uur beëindigd.The saponification takes place at a temperature of 100 - 250 ° C, preferably of 120 - 180 ° C and in particular of 140 - 160 ° C and generally under a pressure of 1 to 20 bar. The hydrolysis generally ends after about half an hour to about 10 hours.
Als basen gebruikt men bij voorkeur NaOH, Κ0Η, NH3 en/of aminen, 25 bij voorkeur als waterige oplossingen, in concentraties van 10 - 50%.The bases preferably used are NaOH, Η0Η, NH3 and / or amines, preferably as aqueous solutions, in concentrations of 10 - 50%.
Eventueel voegt men bij de verzeping een oplosmiddel toe, bijvoorbeeld een aromatische koolwaterstof, zoals tolueen of xyleen.Optionally, a solvent is added to the saponification, for example an aromatic hydrocarbon, such as toluene or xylene.
De selectieve hydrolyse volgens de uitvinding, waarbij enkel de mono-ester verzeept wordt, was niet te verwachten, daar bij de zure hy-30 drolyse de di-ester op gelijke wijze gehydrolyseerd wordt.The selective hydrolysis according to the invention, in which only the monoester is saponified, was not to be expected, since in the acid hydrolysis the diester is hydrolysed in the same manner.
Na de verzeping van de mono-ester van het mengsel van mono- en di-ester blijven het zout van de di-ester, de vrije alcohol (van de mono-ester) alsook het gevormde bifosfaat en water, die men in fasen kan scheiden, in het reaktiemengsel aanwezig.After the saponification of the monoester of the mixture of mono and diester, the salt of the diester, the free alcohol (of the monoester) as well as the formed bisphosphate and water remain, which can be separated in phases present in the reaction mixture.
35 De zuivering van de di-ester kan bijvoorbeeld geschieden door aan zuren, waarbij de fosforzuur-di-ester in de zure vorm met of zonder toepassing van een organisch oplosmiddel van de waterige zoutfase kan worden gescheiden.The purification of the diester can be effected, for example, by acidification, whereby the phosphoric acid diester can be separated from the aqueous salt phase with or without the use of an organic solvent in the acid form.
De zuivering kan ook geschieden door ontwatering van het verkregen 40 reaktiemengsel, bij voorkeur door azeotrope destillatie, waarna het S e 0 2 6 4 0 3 achtergebleven zout door filtratie van de di-ester kan worden afgescheiden.The purification can also be effected by dewatering the reaction mixture obtained, preferably by azeotropic distillation, after which the salt remaining can be separated by filtration from the diester.
Bij di-esters op basis van bij lage temperatuur kokende alcoholen kan na de hydrolyse de vrije alcohol door destillatie uit het verkregen 5 mengsel worden teruggewonnen en desgewenst weer bij de fosfaatester-be-reiding worden gebruikt.In diesters based on low-boiling alcohols, after the hydrolysis, the free alcohol can be recovered by distillation from the resulting mixture and, if desired, be reused in the phosphate ester preparation.
Bij di-esters op basis van polyglycolethers blijven de bij relatief hoge temperatuur kokende alkylpolyglycolethers over, welke slechts moeilijk te destilleren zijn. Het is vaak niet noodzakelijk deze niet-10 ionogene tensiden te verwijderen, omdat ze geen storende invloed op de toepassingseigenschappen hebben. Vaak versterken deze niet-ionogene componenten zelfs de gewenste eigenschappen van de di-esters.Diesters based on polyglycol ethers leave the alkyl boiling alkyl polyglycol ethers at a relatively high temperature, which are only difficult to distill. It is often not necessary to remove these non-ionic surfactants because they do not interfere with the application properties. Often these non-ionic components even enhance the desired properties of the diesters.
De volgens deze uitvinding verkregen fosforzuur-di-esters hebben een onverwacht hoge thermische stabiliteit. Men kan ze als thermosta-15 biele corrosie-inhibitoren, antistatica, extractiemiddelen voor metalen, detergentia, emulgeermiddelen, dispergeermiddelen, alsmede middelen voor het verhinderen van afzettingen resp. steenvorming (scale-in-hibitoren) en complexvormers (chelaatvormers) toepassen.The phosphoric acid diesters obtained according to this invention have an unexpectedly high thermal stability. They can be used as thermostable corrosion inhibitors, antistatics, metal extractants, detergents, emulsifying agents, dispersing agents, as well as deposit inhibitors, respectively. apply stone formation (scale-in-hibitors) and complex formers (chelating agents).
Tegenover de toepassing van mengsels van mono- en di-esters vol-20 gens de stand van de techniek hebben de zuivere di-esters het onverwachte voordeel dat ze ook bij temperaturen ver boven 100°C toegepast kunnen worden. Bovendien geven ze een lage oppervlaktespanning en een lage kritische mice!concentratie.In contrast to the use of mixtures of mono- and diesters according to the prior art, the pure diesters have the unexpected advantage that they can also be used at temperatures far above 100 ° C. In addition, they give a low surface tension and a low critical mouse concentration.
De vele bekende toepassingsgebieden van anionogene fosfaattensiden 25 zoals textiel veredeling, chemisch reinigen, wasmiddelen, schuimmidde-len, emulsiepolymerisatie, concentraten voor vloerreiniging en andere speciale toepassingen gelden ook voor de volgens de uitvinding verkregen fosforzuur-di-esters.The many known fields of application of anionic phosphate tensides such as textile finishing, dry cleaning, detergents, foaming agents, emulsion polymerization, concentrates for floor cleaning and other special applications also apply to the phosphoric acid diesters obtained according to the invention.
Voorbeeld IExample I
30 In een autoclaaf van 5 liter voegt men bij ongeveer 20°C aan 932 g van een vetalcohol pol y glycoletherfosfaat (C12_CI5 vetalcohol met 8,5 mol EO), dat ongeveer 59 gew.% di-ester en ongeveer 34 gew.% mono- ester bevat (in totaal 1,5 zuurequival enten) onder roeren 118 g 50%'s kaliloog in verloop van een half uur toe. De temperatuur loopt 35 hierbij op tot 90°C. Men verhoogt de temperatuur tot 160°C (druk 4 bar) en houdt de temperatuur gedurende 1 uur bij 16ÖC. Vervolgens wordt na snel koelen tot 90°C 930 g tolueen en 665 g water toegevoegd. De waterfase wordt bij 9Ö°C afgescheiden.In a 5 liter autoclave, at about 20 ° C, 932 g of a fatty alcohol poly glycol ether phosphate (C12_CI5 fatty alcohol with 8.5 mol EO) is added, which contains about 59% by weight diester and about 34% by weight mono - Ester contains (a total of 1.5 acid equivalent grafts) with stirring 118 g of 50% potash in half an hour. The temperature hereby rises to 90 ° C. The temperature is raised to 160 ° C (pressure 4 bar) and the temperature is kept at 16 ° C for 1 hour. After rapid cooling to 90 ° C, 930 g of toluene and 665 g of water are then added. The water phase is separated at 90 ° C.
De organische bovenlaag wordt door azeotrope destillatie ontwaterd 40 en het overblijvende zout wordt door middel van filtratie van de 8 8 0 2 5 4 0 o» -*> 4 di-ester gescheiden. Men verkrijgt 1860 g van het ruwe di-vetalcohol-. polyglycoletherfosfaat (50% in tolueen). De ruwe di-ester bevat 31 gew.% di-ester als Na-zout, 19 gew.% polyglycolether en geen mono-ester. De opbrengst aan di-ester is nagenoeg 100%.The organic top layer is dewatered by azeotropic distillation and the residual salt is separated from the 8 8 0 2 5 4 0 4 -> 4 diester by filtration. 1860 g of the crude di-fatty alcohol are obtained. polyglycol ether phosphate (50% in toluene). The crude diester contains 31% by weight diester as Na salt, 19% by weight polyglycol ether and no monoester. The yield of diester is almost 100%.
5 Men verkrijgt dezelfde resultaten, wanneer men de verzeping gedurende 4 uur bij 140°C (druk 2,2 bar) uitvoert.The same results are obtained when the saponification is carried out for 4 hours at 140 ° C (pressure 2.2 bar).
Vergelijkbare resultaten verkrijgt men ook, wanneer men de verzeping met 71 g 25%'s waterige ammoniak-oplossing bij 140°C (2,2 bar) gedurende 8 uur uitvoert of met 84 g 50 %'s natronloog gedurende 1 uur 10 bij 160°C (4 bar).Similar results are also obtained when the saponification is carried out with 71 g of 25% aqueous ammonia solution at 140 ° C (2.2 bar) for 8 hours or with 84 g of 50% sodium hydroxide solution for 1 hour at 160 ° C (4 bar).
Voorbeeld IIExample II
Overeenkomend met de gegevens van voorbeeld I worden aan 728 g butylfosfaat, dat ongeveer 55 gew.% di-ester en ongeveer 45 gew.% mono-ester bevat (met in totaal 6 zuurequival enten), 336 g 50%'s natronloog 15 toegevoegd. De temperatuur loopt hierbij op tot 130°C. Men verhoogt de temperatuur tot 160°C (druk 7 bar) en houdt de temperatuur 1 uur op 160°C. Vervolgens koelt men snel af tot 90°C en voegt 216 g zwavelzuur (95%‘s) en 500 g water toe. Men mengt 30 minuten bij 85°C en scheidt bij 85°C de waterfase af. Uit de organische bovenlaag destilleert men 20 de butanol en het opgeloste water azeotroop af, het overblijvende zout filtreert men af. Het filtraat bevat meer dan 90 gew.% zure di-ester (400 g) en geen mono-ester. De opbrengst aan dibutyl fosfaat bedraagt meer dan 90%.Corresponding to the data of Example I, 336 g of 50% strength sodium hydroxide solution are added to 728 g of butyl phosphate, which contains about 55% by weight of diester and about 45% by weight of monoester (with a total of 6 acid equivalent grafts). . The temperature hereby rises to 130 ° C. The temperature is raised to 160 ° C (pressure 7 bar) and the temperature is kept at 160 ° C for 1 hour. It is then quickly cooled to 90 ° C and 216 g of sulfuric acid (95%) and 500 g of water are added. The mixture is mixed for 30 minutes at 85 ° C and the water phase is separated off at 85 ° C. The butanol and the dissolved water are distilled azeotropically from the organic top layer, the remaining salt is filtered off. The filtrate contains more than 90 wt.% Acid diester (400 g) and no monoester. The yield of dibutyl phosphate is more than 90%.
Voorbeeld IIIExample III
25 Volgens de gegevens van voorbeeld 1 voegt men aan 707 g nonyl-fenolpolyglycoletherfosfaat (met 10 mol EO), dat ongeveer 46 gew.% di-ester en 44 gew.% mono-ester bevat (met in totaal 1 zuurequival ent), 56 g 50%'s natronloog toe. De temperatuur loopt hierbij op tot 65°C.According to the data of Example 1, to 707 g of nonyl phenol polyglycol ether phosphate (with 10 moles of EO) containing about 46% by weight of diester and 44% by weight of monoester (with a total of 1 acid equivalent), 56 g 50% caustic soda. The temperature rises to 65 ° C.
Men verhoogt de temperatuur tot 160°C (druk 4 bar) en houdt de tempera-30· tuur 1 uur bij 160°C. Na snel koelen tot 90°C voegt men 725 g xyleen, 500 g water en 50 g dodecylamine toe en mengt 45 minuten bij 90°C. Bij 90°C scheidt men de waterfase af. De organische bovenlaag ontwatert men door azeotrope destillatie en men filtreert de zoutresten af. Het filtraat bevat (50% in xyleen) ongeveer 26 gew.% di-nonylfenolpolyglycol-35 etherfosfaatdodecylaminezout en ongeveer 23 gew.% nonylfenolpolyglycol-ether en geen mono-ester. Men verkrijgt 1400 g van het di-ester-amine-zout, hetgeen overeenkomt met een opbrengst van 96%.The temperature is raised to 160 ° C (pressure 4 bar) and the temperature is kept at 160 ° C for 1 hour. After rapid cooling to 90 ° C, 725 g of xylene, 500 g of water and 50 g of dodecylamine are added and the mixture is mixed at 90 ° C for 45 minutes. The water phase is separated at 90 ° C. The organic top layer is dewatered by azeotropic distillation and the salt residues are filtered off. The filtrate contains (50% in xylene) about 26% w / w di-nonylphenol polyglycol-ether phosphate dodecylamine salt and about 23% w / w nonylphenol polyglycol ether and no monoester. 1400 g of the diester amine salt are obtained, which corresponds to a yield of 96%.
Voert men de verzeping uit bij 190°C in plaats van bij 160°C, dan is de verzeping in een half uur voltooid.If the saponification is carried out at 190 ° C instead of 160 ° C, the saponification is completed in half an hour.
40 Voorbeeld IVExample IV
8602340 T -s ·· -»r 58602340 T -s ·· - »r 5
Volgens de gegevens van voorbeeld I voegt men aan 464 g alcohol-polyglycoletherfosfaat (2-ethylhexanoT met 3 mol EO), dat ongeveer 60 gew.% di-ester en ongeveer 40 gew.% mono-ester bevat (met in totaal 1,5 zuurequivalent), 210 g dodecylamine en 40 g water toe. De tempera-5 tuur loopt hierbij op tot 60°C.According to the data of Example I, 464 g of alcohol-polyglycol ether phosphate (2-ethylhexanoT with 3 mol EO) are added, which contains about 60% by weight of diester and about 40% by weight of monoester (with a total of 1.5 acid equivalent), 210 g of dodecylamine and 40 g of water. The temperature here rises to 60 ° C.
Men verhoogt de temperatuur tot 160°C en houdt de temperatuur 2 uur op 160°C (druk 3,2 bar). Men verkrijgt na snel afkoelen tot 90°C 714 gram produkt waarin zich 380 g van het di-esteramine-zout bevindt.The temperature is raised to 160 ° C and the temperature is kept at 160 ° C for 2 hours (pressure 3.2 bar). After rapid cooling to 90 [deg.] C., 714 grams of product are obtained, which contains 380 g of the diesteramine salt.
De opbrengst is nagenoeg 100%.The yield is almost 100%.
10 Voorbeeld 510 Example 5
Voor de toepassing van mengsels op basis van fosforzuur-di-esters met alkylpolyglycolether als corrosie-inhibitor in systemen met temperaturen tot 130°C is het noodzakelijk, dat de corrosie-inhibitor niet van samenstelling verandert door thermische invloeden. Om dit aspect te 15 controleren worden volgende proeven uitgevoerd:For the use of mixtures based on phosphoric acid diesters with alkyl polyglycol ether as a corrosion inhibitor in systems with temperatures up to 130 ° C, it is necessary that the corrosion inhibitor does not change composition due to thermal influences. The following tests are carried out to check this aspect:
In een drukcilinder van 100 ml wordt ca. 60 ml oplossing gebracht.About 60 ml of the solution is placed in a 100 ml pressure cylinder.
Deze oplossing bestaat voor 90 vol.% uit een organisch oplosmiddel, bijvoorbeeld wasbenzine en 10 vol.% corrosie-inhibitor. Als corrosie-inhibitor gebruikt men een produkt, dat overeenkomstig de gegevens van 20 voorbeeld I bereid wordt, maar 5 mol EO in plaats van 8,5 mol EO bevat. .90% by volume of this solution consists of an organic solvent, for example white spirit and 10% by volume of corrosion inhibitor. As a corrosion inhibitor, a product is prepared which is prepared according to the data of Example I, but contains 5 moles of EO instead of 8.5 moles of EO. .
Aan deze oplossing wordt ongveer 1 ml water toegevoegd.About 1 ml of water is added to this solution.
Daarna wordt de drukcilinder op een as bevestigd en met een snelheid van 30 omwentelingen per minuut geroteerd. Het geheel wordt in een stoof geplaatst en bij een konstante temperatuur van 150°C gehouden.The printing cylinder is then mounted on a shaft and rotated at a speed of 30 revolutions per minute. The whole is placed in an oven and kept at a constant temperature of 150 ° C.
25 Na bepaalde tijd wordt de rotatie beëindigd, de drukcilinder wordt afgekoeld en er wordt onderzocht of er veranderingen in de samenstelling van de corrosie-inhibitor zijn opgetreden.After a certain time, the rotation is stopped, the printing cylinder is cooled and it is investigated whether changes in the composition of the corrosion inhibitor have occurred.
Door de proeven wordt vastgesteld, dat de produkten op basis van fosforzuur-di-esters geen afbraakprodukten opleveren. De oplossing 30 blijft helder en uit het I.R. spectrum en chemische analyse blijkt, dat geen veranderingen opgetreden zijn. Vergelijkbare proeven met mengsels van fosforzuurmono- en -di-esters leveren troebele oplossingen op.The tests show that the products based on phosphoric acid diesters do not yield degradation products. The solution 30 remains clear and from the I.R. spectrum and chemical analysis show that no changes have occurred. Comparable tests with mixtures of phosphoric acid mono and diesters yield turbid solutions.
Voorbeeld VIExample VI
Produkten op basis van mengsels van fosforzuur-di-esters met 35 alkyl glycolethers worden als corrosie-inhibitoren beproefd. Hiervoor wordt de Wheeltest gebruikt.Products based on mixtures of phosphoric acid diesters with 35 alkyl glycol ethers are tested as corrosion inhibitors. The Wheel test is used for this.
Deze methode wordt vaak toegepast voor beproeven van corrosie-inhibitoren voor olie- en gasproduktiesystemen. De werking van de beproefde produkten wordt vastgesteld in een corrosief medium, dat be-40 staat uit een 120 cm3 NACE-oplossing (5% NaCl + 0,5% azijnzuur in wa- 8602340 -a« <- 6 ter), 30 cm3 wasbenzine en 50 ml C02-gas boven de vloeistof. De vloeistoffase is met CO2 verzadigd. In dit medium wordt een stalen strook geplaatst. De drukhouder wordt zo geroteerd, dat de stalen strook zowel door de waterfase als door de koolwaterstoffase reprodu-5 ceerbaar bevochtigd wordt. De proef duurt 24 uren en wordt bij een temperatuur van 50°C uitgevoerd.This method is often used for testing corrosion inhibitors for oil and gas production systems. The performance of the tested products is determined in a corrosive medium consisting of a 120 cm 3 NACE solution (5% NaCl + 0.5% acetic acid in water), 30 cm 3. white spirit and 50 ml of CO2 gas above the liquid. The liquid phase is saturated with CO2. A steel strip is placed in this medium. The pressure container is rotated so that the steel strip is reproducibly wetted by both the water phase and the hydrocarbon phase. The test lasts 24 hours and is carried out at a temperature of 50 ° C.
Na beëindiging van de corrosie-proef wordt de gewichtsafname van de stalen strook vastgesteld. Als corrosieinhibitor gebruikt men een produkt, dat overeenkomstig de gegevens van voorbeeld I bereid wordt, 10 echter met 3 mol EO in plaats van 8,5 mol EO.After the end of the corrosion test, the weight loss of the steel strip is determined. As a corrosion inhibitor, a product prepared according to the data of Example 1 is used, however with 3 moles of EO instead of 8.5 moles of EO.
De proef wordt met en zonder corrosie-inhibitor uitgevoerd en de werking van de inhibitie wordt als volgt uitgedrukt: gew.afn. zonder corr. inh. - gew.afn. met corr. inh.v iqo%= x % inhibitor 15 gew.afn. zonder corr. inh.The test is carried out with and without a corrosion inhibitor and the action of the inhibition is expressed as follows: parts by weight. without corr. cont. - weight afn. with corr. cont. iqo% = x% inhibitor 15 wt. without corr. cont.
In onderstaande tabel worden die op deze wijze verkregen resultaten samengevat.The results obtained in this way are summarized in the table below.
20 Tabel % corrosie-inhibitie 25 dpm 50 dpm 100 dpm corrosie-inhibitor 22% 65% 85% inhibitie 850264020 Table% corrosion inhibition 25 ppm 50 ppm 100 ppm corrosion inhibitor 22% 65% 85% inhibition 8502640
Claims (7)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3537696 | 1985-10-23 | ||
| DE19853537696 DE3537696A1 (en) | 1985-10-23 | 1985-10-23 | Process for selectively obtaining phosphoric diesters from a mixture of phosphoric monoester and diester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8602640A true NL8602640A (en) | 1987-05-18 |
Family
ID=6284263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8602640A NL8602640A (en) | 1985-10-23 | 1986-10-22 | METHOD FOR SELECTIVELY RECOVERY OF PHOSPHORIC ACID DI-ESTERS FROM A MIXTURE OF PHOSPHORIC ACID MONO AND DI ESTERS. |
Country Status (2)
| Country | Link |
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| DE (1) | DE3537696A1 (en) |
| NL (1) | NL8602640A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2689498B1 (en) * | 1992-04-07 | 1994-12-30 | Francais Prod Ind Cfpi | Agent inhibiting the corrosive properties of nitrogen fertilizing solutions, process using this agent and nitrogen fertilizing solutions containing it. |
| US5611991A (en) * | 1994-05-24 | 1997-03-18 | Champion Technologies, Inc. | Corrosion inhibitor containing phosphate groups |
| US5611992A (en) * | 1994-05-24 | 1997-03-18 | Champion Technologies Inc. | Corrosion inhibitor blends with phosphate esters |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3235627A (en) * | 1962-05-18 | 1966-02-15 | Rohm & Haas | Alkali soluble and alkali stable compositions comprised predominantly of phosphate monoesters |
-
1985
- 1985-10-23 DE DE19853537696 patent/DE3537696A1/en active Granted
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1986
- 1986-10-22 NL NL8602640A patent/NL8602640A/en not_active Application Discontinuation
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| Publication number | Publication date |
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| DE3537696C2 (en) | 1988-03-03 |
| DE3537696A1 (en) | 1987-04-23 |
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