GB763992A - Dicarboxyphenylphosphonic acid - Google Patents
Dicarboxyphenylphosphonic acidInfo
- Publication number
- GB763992A GB763992A GB12005/54A GB1200554A GB763992A GB 763992 A GB763992 A GB 763992A GB 12005/54 A GB12005/54 A GB 12005/54A GB 1200554 A GB1200554 A GB 1200554A GB 763992 A GB763992 A GB 763992A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- potassium
- salts
- acid
- sodium
- 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
- GCVZZYGDTUQTSF-UHFFFAOYSA-N 3-phosphonophthalic acid Chemical compound OC(=O)C1=CC=CC(P(O)(O)=O)=C1C(O)=O GCVZZYGDTUQTSF-UHFFFAOYSA-N 0.000 title 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000011575 calcium Substances 0.000 abstract 2
- 229910052791 calcium Inorganic materials 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229940078552 o-xylene Drugs 0.000 abstract 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- YWMZBCLSKMHYEO-UHFFFAOYSA-N 1-phosphonocyclohexa-3,5-diene-1,2-dicarboxylic acid Chemical compound OC(=O)C1C=CC=CC1(C(O)=O)P(O)(O)=O YWMZBCLSKMHYEO-UHFFFAOYSA-N 0.000 abstract 1
- WUEAMTVQNGYLRI-UHFFFAOYSA-N 2-dichlorophosphoryl-1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=C(P(Cl)(Cl)=O)C(C(C)C)=C1 WUEAMTVQNGYLRI-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000003112 potassium compounds Chemical class 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 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
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
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)
- Catalysts (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
o-Dicarboxyphenylphosphonic acid and salts thereof are prepared in two stages; (1) polychloro derivatives of a compound of formula <FORM:0763992/IV(b)/1> are prepared by chlorination with elemental chlorine at 100-200 DEG C. until at least one atom of chlorine is introduced into each methyl group, and (2) the product of the first step is simultaneously hydrolysed and oxidized by treatment with an alkaline solution of a watersoluble permanganate to give a compound of formula <FORM:0763992/IV(b)/2> wherein M1-M4 are the same or different cations. The chlorination is conducted, preferably in the presence of ultra-violet light, until 4 or 5 chlorine atoms have been introduced into the methyl groups. For the oxidation and hydrolysis step, potassium, sodium or calcium permanganates and potassium or sodium hydroxides are specified. The potassium compounds are preferred, and give a solution of the tetra-potassium salt, from which manganese dioxide is separated by filtration. The monopotassium salt is precipitated from the solution by addition of mineral acid. The free acid and other salts may be prepared by normal methods. The salts may be derived from sodium, magnesium, calcium, barium, aluminium, iron, zinc, ammonia, amines or quaternary bases. The compounds are used as intermediates in the preparation of organic colouring matters. An example illustrates the invention. Phosphonic dichloride of o-xylene is prepared by reacting o-xylene with hexagonal phosphoric anhydride, the product being either hydrolysed to the phosphonic acid and chlorinated with phosphorus pentachloride or treated directly with phosphorus pentachloride. Specification 737,036 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US763992XA | 1953-05-25 | 1953-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB763992A true GB763992A (en) | 1956-12-19 |
Family
ID=22131768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12005/54A Expired GB763992A (en) | 1953-05-25 | 1954-04-26 | Dicarboxyphenylphosphonic acid |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE962526C (en) |
| GB (1) | GB763992A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0855400A1 (en) * | 1997-01-28 | 1998-07-29 | Nissan Chemical Industries Ltd. | Phenylphosphonic acid derivative and production process therefor |
-
1954
- 1954-04-26 GB GB12005/54A patent/GB763992A/en not_active Expired
- 1954-05-26 DE DEA20401A patent/DE962526C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0855400A1 (en) * | 1997-01-28 | 1998-07-29 | Nissan Chemical Industries Ltd. | Phenylphosphonic acid derivative and production process therefor |
| US5880309A (en) * | 1997-01-28 | 1999-03-09 | Nissan Chemical Industries, Ltd. | Phenylphosphonic acid derivative and production process therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE962526C (en) | 1957-04-25 |
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