CA1231963A - Phosphonates - Google Patents
PhosphonatesInfo
- Publication number
- CA1231963A CA1231963A CA000450424A CA450424A CA1231963A CA 1231963 A CA1231963 A CA 1231963A CA 000450424 A CA000450424 A CA 000450424A CA 450424 A CA450424 A CA 450424A CA 1231963 A CA1231963 A CA 1231963A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- solution according
- solution
- weight
- phosphonic acid
- 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims description 23
- 239000002253 acid Substances 0.000 claims abstract description 47
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 ammonium ions Chemical class 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 71
- 239000002585 base Substances 0.000 claims description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 150000001768 cations Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 238000003860 storage Methods 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 230000003019 stabilising effect Effects 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000011149 active material Substances 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 3
- 239000011707 mineral Substances 0.000 abstract description 3
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012266 salt solution Substances 0.000 abstract description 2
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 150000003009 phosphonic acids Chemical class 0.000 description 13
- 239000013078 crystal Substances 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 7
- 238000006386 neutralization reaction Methods 0.000 description 6
- 125000004437 phosphorous atom Chemical group 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 101000837192 Drosophila melanogaster Teneurin-m Proteins 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940090960 diethylenetriamine pentamethylene phosphonic acid Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000002455 scale inhibitor Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 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
- C07F9/28—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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Hydrology & Water Resources (AREA)
- Molecular Biology (AREA)
- Detergent Compositions (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838308003A GB8308003D0 (en) | 1983-03-23 | 1983-03-23 | Phosphonates |
| GB8308003 | 1983-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1231963A true CA1231963A (en) | 1988-01-26 |
Family
ID=10540071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000450424A Expired CA1231963A (en) | 1983-03-23 | 1984-03-23 | Phosphonates |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0125766B1 (enExample) |
| JP (1) | JPS59181288A (enExample) |
| AT (1) | ATE46515T1 (enExample) |
| AU (1) | AU577281B2 (enExample) |
| CA (1) | CA1231963A (enExample) |
| DE (1) | DE3479804D1 (enExample) |
| ES (1) | ES530963A0 (enExample) |
| FI (1) | FI84270C (enExample) |
| GB (2) | GB8308003D0 (enExample) |
| NO (1) | NO841111L (enExample) |
| ZA (1) | ZA842073B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8405573D0 (en) * | 1984-03-02 | 1984-04-04 | Procter & Gamble | Aqueous aminomethylenephosphonic acid solutions |
| GB8529409D0 (en) * | 1985-11-29 | 1986-01-08 | Monsanto Europe Sa | Aminomethylenephosphonate compositions |
| GB8825589D0 (en) * | 1988-11-02 | 1988-12-07 | Albright & Wilson | Purification |
| US5034556A (en) * | 1989-04-03 | 1991-07-23 | Ppg Industries, Inc. | Reaction products of alpha-aminomethylene phosphonic acids and epoxy compounds and their use in coating compositions |
| IL101539A (en) | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Non-hygroscopic mono-ammonium salts of n-phosphonomethyl glycine derivatives their preparation and pesticidal compositons containing them |
| US5306526A (en) * | 1992-04-02 | 1994-04-26 | Ppg Industries, Inc. | Method of treating nonferrous metal surfaces by means of an acid activating agent and an organophosphate or organophosphonate and substrates treated by such method |
| US5294265A (en) * | 1992-04-02 | 1994-03-15 | Ppg Industries, Inc. | Non-chrome passivation for metal substrates |
| US5346009A (en) * | 1993-02-08 | 1994-09-13 | Shell Oil Company | Precipitation of scale inhibitors |
| DE69427348T2 (de) * | 1994-09-01 | 2002-06-13 | Solutia Europe N.V./S.A., Bruessel/Bruxelles | Hexamethylene Phosphonatkonzentrat |
| DE19849379A1 (de) * | 1998-10-27 | 2000-05-04 | Cht R Beitlich Gmbh | Wäßrige Lösungen von Phosphonsäuren |
| EP1681294A1 (en) * | 2005-01-17 | 2006-07-19 | Solutia Europe N.V./S.A. | Process for the manufacture of aminopolyalkylene-phosphonic acid compounds |
| EP2112156A1 (en) | 2008-04-25 | 2009-10-28 | Thermphos International B.V. | Method for the Manufacture of Aminoalkylene Phosphonic Acid |
| MX2011012592A (es) | 2009-05-28 | 2012-04-19 | Metodo para la fabricacion de acidos aminoalquilenfosfonicos. | |
| CN106661062A (zh) * | 2014-06-02 | 2017-05-10 | 奇默和施瓦茨莫斯多夫有限及两合公司 | 用于制备结晶dtpmp的方法 |
| CN110804071B (zh) * | 2019-11-08 | 2021-09-17 | 山东泰和水处理科技股份有限公司 | 一种二乙烯三胺五亚甲基膦酸的生产方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3434969A (en) * | 1967-08-11 | 1969-03-25 | Calgon Corp | Scale inhibiting |
| US3738937A (en) * | 1970-05-08 | 1973-06-12 | Textilana Corp | Polyalkylene polyamino polykis methylene phosphonic acids and salts thereof and methods for producing same |
| US4164574A (en) * | 1972-03-24 | 1979-08-14 | Petrolite Corporation | Use of polyquaternary ammonium methylene phosphonates as microbiocides |
| GB1563521A (en) * | 1977-01-10 | 1980-03-26 | Monsanto Europe Sa | Organophosphorus scale inhibitor compositions and their use in aqueous alkaline cleaning solutions |
| NO150445C (no) * | 1979-04-06 | 1984-10-17 | Unilever Nv | Bleke- og vaskepreparat |
| US4459241A (en) * | 1983-04-28 | 1984-07-10 | The Dow Chemical Company | Compounds containing quaternary ammonium and methylenephosphonic acid groups |
-
1983
- 1983-03-23 GB GB838308003A patent/GB8308003D0/en active Pending
-
1984
- 1984-03-20 ZA ZA842073A patent/ZA842073B/xx unknown
- 1984-03-20 FI FI841109A patent/FI84270C/fi not_active IP Right Cessation
- 1984-03-21 NO NO841111A patent/NO841111L/no unknown
- 1984-03-22 AU AU26023/84A patent/AU577281B2/en not_active Expired
- 1984-03-23 CA CA000450424A patent/CA1231963A/en not_active Expired
- 1984-03-23 ES ES530963A patent/ES530963A0/es active Granted
- 1984-03-23 AT AT84301975T patent/ATE46515T1/de not_active IP Right Cessation
- 1984-03-23 GB GB08407607A patent/GB2138424B/en not_active Expired
- 1984-03-23 EP EP84301975A patent/EP0125766B1/en not_active Expired
- 1984-03-23 DE DE8484301975T patent/DE3479804D1/de not_active Expired
- 1984-03-23 JP JP59054615A patent/JPS59181288A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8506320A1 (es) | 1985-07-01 |
| FI84270B (fi) | 1991-07-31 |
| GB8308003D0 (en) | 1983-04-27 |
| JPS59181288A (ja) | 1984-10-15 |
| FI841109L (fi) | 1984-09-24 |
| GB8407607D0 (en) | 1984-05-02 |
| AU577281B2 (en) | 1988-09-22 |
| GB2138424A (en) | 1984-10-24 |
| ES530963A0 (es) | 1985-07-01 |
| GB2138424B (en) | 1987-04-15 |
| FI84270C (fi) | 1991-11-11 |
| ZA842073B (en) | 1984-10-31 |
| ATE46515T1 (de) | 1989-10-15 |
| FI841109A0 (fi) | 1984-03-20 |
| AU2602384A (en) | 1984-09-27 |
| JPH0466240B2 (enExample) | 1992-10-22 |
| EP0125766B1 (en) | 1989-09-20 |
| NO841111L (no) | 1984-09-24 |
| DE3479804D1 (en) | 1989-10-26 |
| EP0125766A1 (en) | 1984-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |