GB1032378A - Improvements in or relating to the production of phosphonic acids and their salts - Google Patents
Improvements in or relating to the production of phosphonic acids and their saltsInfo
- Publication number
- GB1032378A GB1032378A GB4390164A GB4390164A GB1032378A GB 1032378 A GB1032378 A GB 1032378A GB 4390164 A GB4390164 A GB 4390164A GB 4390164 A GB4390164 A GB 4390164A GB 1032378 A GB1032378 A GB 1032378A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reaction
- oxide
- water
- gas
- 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
- 150000003009 phosphonic acids Chemical class 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 239000007789 gas Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- -1 Fe3+ ions Chemical class 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000004437 phosphorous atom Chemical group 0.000 abstract 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 2
- 238000001556 precipitation Methods 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 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 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 abstract 1
- 235000021314 Palmitic acid Nutrition 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 235000010216 calcium carbonate Nutrition 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000005485 electric heating Methods 0.000 abstract 1
- 229960004887 ferric hydroxide Drugs 0.000 abstract 1
- 239000008233 hard water Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000725 suspension 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
- C07F9/28—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
- C07F9/3839—Polyphosphonic acids
- C07F9/386—Polyphosphonic acids containing hydroxy substituents in the hydrocarbon radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Water is softened by the addition of phosphonic acids or phosphonates containing at least 2 P atoms in the molecule, e.g. of the formula <FORM:1032378/C1/1> where R is alkyl or aryl prepared in specified manner (see Division C2). In an example a compound of the above formula where R is methyl was found to inhibit the precipitation of CaCO3 when a soda solution is added to hard water. Also, precipitation of Fe3+ ions as ferric hydroxide from water containing Fe3+ ions is chlorinated hydrocarbon, but particularly nitrogen, introduced to the system via conduits 8 may serve (a) to convey the oxide, e.g. silica, introduced from separators or storage bins 12 to the reaction vessel 1 via conduit 11, (b) as carrier for A via conduit 11, (c) as carrier for and to dilute, the steam, preferably 100 g./m.3 gas, via 10 to conduit 11, and (d) after prior heating in 9, as source of part of the heat for the reaction. These may advantageously be combined by heating the gas by burning an oxyhydrogen flame, and using this heated gas to convey the reactants, or, in the absence of inert gas steam alone may serve this purpose. The reaction vessel is a vertical tubular furnace 1, heated internally by electric heating elements 6. The reactants, heated to 200-800 DEG C., ascend in suspension and the treated oxide passes from settling zone 2 to outlet 3, contact with oxygen being avoided before cooling below 200 DEG C. Gases and untreated oxide are continuously removed via 4 to separators 12 for recycling of the oxide.ALSO:Phosphonic acids or salts thereof containing 2 P atoms in the molecule are obtained from mixtures formed by reaction of carboxy type acylating agents with phosphorous acid or by reaction of PCl3 with carboxylic acids, by treating the mixture with C1-C5 alkanols and (a) distilling off the volatile substances formed and, if desired, converting the acids into the salts, or (b) separating the alcoholic layer after addition of aqueous base. The preferred alkanols are methanol and ethanol. Examples are given in which acetic acid, caproic acid, capric acid, palmitic acid, stearic acid and benzoic acid is reacted with PCl3 and in which acetic anhydride or acetyl chloride is reacted with phosphorous acid. The products may be used in water-softening processes (see Division C1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH50724A DE1194852B (en) | 1963-11-02 | 1963-11-02 | Process for the production of phosphonic acids or their salts with at least two phosphorus atoms in the molecule |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1032378A true GB1032378A (en) | 1966-06-08 |
Family
ID=7157463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4390164A Expired GB1032378A (en) | 1963-11-02 | 1964-10-28 | Improvements in or relating to the production of phosphonic acids and their salts |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE655066A (en) |
| CH (1) | CH441307A (en) |
| DE (1) | DE1194852B (en) |
| GB (1) | GB1032378A (en) |
| NL (1) | NL141203B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855284A (en) * | 1963-11-02 | 1974-12-17 | Henkel & Cie Gmbh | Process for the manufacture of phosphonic acids and phosphonates having at least two phosphorus atoms |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3400148A (en) * | 1965-09-23 | 1968-09-03 | Procter & Gamble | Phosphonate compounds |
| US3400176A (en) * | 1965-11-15 | 1968-09-03 | Procter & Gamble | Propanepolyphosphonate compounds |
| US3959360A (en) * | 1975-07-31 | 1976-05-25 | Monsanto Company | Process for preparing 1-hydroxy, ethylidene-1,1-diphosphonic acid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL124638C (en) * | 1961-07-03 |
-
1963
- 1963-11-02 DE DEH50724A patent/DE1194852B/en active Pending
-
1964
- 1964-09-02 NL NL6410204A patent/NL141203B/en not_active IP Right Cessation
- 1964-10-28 GB GB4390164A patent/GB1032378A/en not_active Expired
- 1964-10-30 BE BE655066D patent/BE655066A/xx unknown
- 1964-10-30 CH CH1404464A patent/CH441307A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855284A (en) * | 1963-11-02 | 1974-12-17 | Henkel & Cie Gmbh | Process for the manufacture of phosphonic acids and phosphonates having at least two phosphorus atoms |
Also Published As
| Publication number | Publication date |
|---|---|
| NL141203B (en) | 1974-02-15 |
| DE1194852B (en) | 1965-06-16 |
| BE655066A (en) | 1965-04-30 |
| NL6410204A (en) | 1965-05-03 |
| CH441307A (en) | 1967-08-15 |
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