GB803199A - Aminophenol-aldehyde condensation products, their metal compounds and process for the preparation thereof - Google Patents
Aminophenol-aldehyde condensation products, their metal compounds and process for the preparation thereofInfo
- Publication number
- GB803199A GB803199A GB38245/56A GB3824556A GB803199A GB 803199 A GB803199 A GB 803199A GB 38245/56 A GB38245/56 A GB 38245/56A GB 3824556 A GB3824556 A GB 3824556A GB 803199 A GB803199 A GB 803199A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glyoxal
- amino
- resin
- aminophenol
- acetate
- 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
- 239000007859 condensation product Substances 0.000 title abstract 2
- 150000002736 metal compounds Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 15
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 10
- 239000011347 resin Substances 0.000 abstract 9
- 229920005989 resin Polymers 0.000 abstract 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 8
- 239000000243 solution Substances 0.000 abstract 8
- 150000003839 salts Chemical class 0.000 abstract 7
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical group CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 abstract 6
- 229910052770 Uranium Inorganic materials 0.000 abstract 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 5
- 229910052759 nickel Inorganic materials 0.000 abstract 5
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 239000007864 aqueous solution Substances 0.000 abstract 4
- 229910001385 heavy metal Inorganic materials 0.000 abstract 4
- 239000011261 inert gas Substances 0.000 abstract 4
- 239000002798 polar solvent Substances 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 229910052788 barium Inorganic materials 0.000 abstract 3
- 229910052802 copper Inorganic materials 0.000 abstract 3
- 229940015043 glyoxal Drugs 0.000 abstract 3
- SUYLOMATYCPVFT-UHFFFAOYSA-N 2,4,6-triaminophenol Chemical compound NC1=CC(N)=C(O)C(N)=C1 SUYLOMATYCPVFT-UHFFFAOYSA-N 0.000 abstract 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910021645 metal ion Inorganic materials 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- KIAWNCIDEJNMPR-UHFFFAOYSA-N 2,6-diamino-4-methylphenol Chemical compound CC1=CC(N)=C(O)C(N)=C1 KIAWNCIDEJNMPR-UHFFFAOYSA-N 0.000 abstract 1
- NDROQXDNEVYURW-UHFFFAOYSA-N 2,6-diamino-4-methylphenol;dihydrochloride Chemical compound Cl.Cl.CC1=CC(N)=C(O)C(N)=C1 NDROQXDNEVYURW-UHFFFAOYSA-N 0.000 abstract 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 1
- 108091005950 Azurite Proteins 0.000 abstract 1
- 150000001224 Uranium Chemical group 0.000 abstract 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 abstract 1
- MFFPRTBZCWRKHT-UHFFFAOYSA-N [U+6].NC1=C(C=CC=C1)O.NC1=C(C=CC=C1)O.O=C(C(C=O)=O)C=O Chemical compound [U+6].NC1=C(C=CC=C1)O.NC1=C(C=CC=C1)O.O=C(C(C=O)=O)C=O MFFPRTBZCWRKHT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910052793 cadmium Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 abstract 1
- GWBUNZLLLLDXMD-UHFFFAOYSA-H tricopper;dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[O-]C([O-])=O.[O-]C([O-])=O GWBUNZLLLLDXMD-UHFFFAOYSA-H 0.000 abstract 1
- -1 uranyl ions Chemical class 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/19—Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Selective ion-exchange resins are prepared from aminophenols or aminothiophenols and aliphatic dialdehydes. The resins are prepared from phenols containing at least two amino groups (for mono-aminophenols see Group IV (b)) by heating with the dialdehyde in the presence of a polar solvent, preferably at a temperature below the boiling-point of the solvent, and in the case of thiophenols in the absence of oxygen, e.g. in the presence of an inert gas. The products may be treated at room or moderately elevated temperatures with aqueous or alcoholic solutions of heavy metals to produce salts or complexes, preferably at a pH higher than 1.8; the heavy metals may be eluted by strong acids. Amino-phenols specified are o-amino-, o-amino-thio-, 2,4,6,-triamino-phenols and 2 : 6-diamino-p-cresol. Dialdehydes specified are glyoxal, methyl glyoxal and succindialdehyde. Polar solvents: water and methyl alcohol. Inert gas: nitrogen. Metal ions taken up include U, Cu, Ni and Ba. In examples: (5) 0.1 mol. 2,6-diamino-p-cresol dihydrochloride is dissolved in 700 c.c. of 80 per cent methanol, 200 c.c. 1 N NaOH solution are added followed by 0.12 mol. glyoxal; the mixture is boiled for 4 hours, cooled, filtered and dried. The product is shaken with Cu acetate at pH 3-6 for several hours to give a Cu resin complex of 20 parts Cu to 100 parts resin; (6) as (5) but from 2,4,6-triaminophenol; and a Cu tetramine complex buffered at pH 7; (7) the resin of (5) is shaken with uraryl acetate, the uranium atom being subsequently eluted; (8) the resin of (5) takes up Cu from an aqueous solution of Na, Ba and Cu salts; (9) the resin of (5) takes up U from a solution of U, Mg and K salts; (10) the resin of (6) takes up Cu from a treated azurite; (11) the resin of (6) takes up U from a solution of U, Zn, Co and Ni salts; (12) the resin of 5 takes up Ni from an aqueous solution of Co and Ni salts.ALSO:Selective ion-exchange compounds are prepared from aminophenols or aminothiophenols and aliphatic dialdehydes. The aminophenols contain one amino group (for two or more amino groups see Group IV (a)) and are heated with the dialdehyde in the presence of a polar solvent, preferably at a temperature below the boiling-point of the solvent, and in the case of thiophenols in the absence of oxygen, e.g. in the presence of an inert gas. Schiff's bases are formed. The products may be treated at room or moderately elevated temperatures with aqueous or alcoholic solutions of heavy metals to produce salts or complexes, preferably at a pH higher than 1.8; the heavy metals may be eluted by strong acids. Aminophenols specified are o-amino-, o-amino-thio-, 2,4,6-triaminophenols and 2,6-di-amino-p-cresol. Dialdehydes specified are glyoxal, methyl glyoxal and succindialdehyde. Polar solvents: water and methyl alcohol. Inert gas: nitrogen. Metal ions taken up include U, Cu, Ni and Ba. In examples: (1) glyoxal di(aminophenol) is prepared from o-aminophenol and glyoxal. Ni acetate is boiled with a methanol solution thereof to give red needles of glyoxal-di-(aminophenol)-nickel (II) containing 2.H2O at 5th and 6th positions which are removable by diphosphoric pentoxides. (2) As (1) but using Ba(OH)2 in place of Ni acetate to give the Ba salt. (3) Dioxosuccinaldehyde-di(o-aminophenol)-uranium (VI) is prepared by boiling an aqueous solution of o-aminophenol, succindialdehyde and uranyl acetate to give dark violet needles. (4) Methyl glyoxaldi(o-aminothiophenol) is prepared from o-aminothiophenol and methyl glyoxal in a nitrogenated atmosphere and aqueous solution: a methanol solution of the product is boiled with Cu acetate to give glyoxal-di-(o-aminothiophenol)-Cu (II). (13) The condensation product of (1) takes up uranyl ions from a solution of Co, Ni, Zn, Cd and U acetates.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE803199X | 1955-12-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB803199A true GB803199A (en) | 1958-10-22 |
Family
ID=6721032
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38245/56A Expired GB803199A (en) | 1955-12-15 | 1956-12-14 | Aminophenol-aldehyde condensation products, their metal compounds and process for the preparation thereof |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE553361A (en) |
FR (1) | FR1162817A (en) |
GB (1) | GB803199A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4394521A (en) * | 1980-04-30 | 1983-07-19 | Lonza-Werke G.M.B.H. | Process for the production of the Schiff's bases of 2,6-dichloro-5-hydroxy-aniline |
-
0
- BE BE553361D patent/BE553361A/xx unknown
-
1956
- 1956-12-14 GB GB38245/56A patent/GB803199A/en not_active Expired
- 1956-12-15 FR FR1162817D patent/FR1162817A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4394521A (en) * | 1980-04-30 | 1983-07-19 | Lonza-Werke G.M.B.H. | Process for the production of the Schiff's bases of 2,6-dichloro-5-hydroxy-aniline |
Also Published As
Publication number | Publication date |
---|---|
BE553361A (en) | 1900-01-01 |
FR1162817A (en) | 1958-09-17 |
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