GB1184608A - Production of Nitrilotriacetic Acid and the Analogs Thereof. - Google Patents
Production of Nitrilotriacetic Acid and the Analogs Thereof.Info
- Publication number
- GB1184608A GB1184608A GB47928/67A GB4792867A GB1184608A GB 1184608 A GB1184608 A GB 1184608A GB 47928/67 A GB47928/67 A GB 47928/67A GB 4792867 A GB4792867 A GB 4792867A GB 1184608 A GB1184608 A GB 1184608A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- substituted
- unsubstituted
- formula
- carbon atoms
- 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
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 title abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 amine compound Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052796 boron Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 1
- 150000002830 nitrogen compounds Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/12—Formation of amino and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,184,608. Production of nitrilotriacetic acid and analogues thereof. HOOKER CHEMICAL CORP. 20 Oct., 1967 [20 Oct., 1966], No. 47928/67. Heading C2C. Compounds of the formula are obtained by premixing for from 0À1 to 100 seconds a carbonyl compound of the formula with a metal cyanide or ammonium cyanide, and reacting the premix with a nitrogen compound of the formula wherein a is 0 or 1, b is 0 or 1, c is an integer from 1 to 3 with the proviso that the sum of a, b and c is 3, each of R 1 , R 2 , R 3 and R 4 , which may be the same or different, represents hydrogen, a substituted or unsubstituted C 1-18 alkyl or alkenyl group, a substituted or unsubstituted C 3-18 alicyclic group, a substituted or unsubstituted C 6-20 aryl group, a substituted or unsubstituted C 7-20 aralkyl group, or an aminoalkyl group of 1-30 carbons wherein the alkyl group is substituted by 1 to 3 groups of the formula wherein each of R 6 and R 7 , which may be the same or different, is the same as defined for R 1-4 above, or R 3 and R 4 together form an alkylene group of 1 to 18 carbon atoms, or, when a, b and care each 1, R 1 and R 2 together form an alkylene group of 1 to 18 carbon atoms or a heteroalkylene radical of 1 to 18 carbon atoms containing at least one oxygen, nitrogen, sulphur, phosphorus, silicon or boron atom, and X is hydrogen, a nitrogen base or a metal. The reaction may be effected at a temperature of 0-110 C. for a period of 0À1 to 100 hours using a molar ratio of cyanide to carbonyl compound of from 0À5: 1 to 1À5: 1. The reaction may be effected continuously, e.g. by recovering the product from the reaction mixture and reacting the remaining solution with the premix. Specific examples are given in which the carbonyl compound employed is formalin and the amine compound is ammonia, morpholine, aniline, dimethylamine or ethylenediamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58797066A | 1966-10-20 | 1966-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1184608A true GB1184608A (en) | 1970-03-18 |
Family
ID=24351933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47928/67A Expired GB1184608A (en) | 1966-10-20 | 1967-10-20 | Production of Nitrilotriacetic Acid and the Analogs Thereof. |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE705255A (en) |
| CH (1) | CH530961A (en) |
| DE (1) | DE1643415A1 (en) |
| GB (1) | GB1184608A (en) |
| NL (1) | NL6713990A (en) |
| SE (1) | SE354651B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4319935A1 (en) * | 1993-06-16 | 1994-12-22 | Basf Ag | Use of glycine-N, N-diacetic acid derivatives as complexing agents for alkaline earth and heavy metal ions |
-
1967
- 1967-10-16 NL NL6713990A patent/NL6713990A/xx unknown
- 1967-10-17 BE BE705255D patent/BE705255A/xx unknown
- 1967-10-17 SE SE14211/67A patent/SE354651B/xx unknown
- 1967-10-19 CH CH1468367A patent/CH530961A/en not_active IP Right Cessation
- 1967-10-20 DE DE19671643415 patent/DE1643415A1/en active Pending
- 1967-10-20 GB GB47928/67A patent/GB1184608A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6713990A (en) | 1968-04-22 |
| CH530961A (en) | 1972-11-30 |
| BE705255A (en) | 1968-03-01 |
| SE354651B (en) | 1973-03-19 |
| DE1643415A1 (en) | 1971-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1138405A (en) | Morpholine derivatives | |
| US3131165A (en) | Amide stabilized formaldehyde polymers and process for preparing same | |
| GB1496033A (en) | Bituminous binder compositions | |
| GB1318645A (en) | 1,2,4-triazines | |
| GB1065658A (en) | A method for the preparation of amides | |
| GB1161801A (en) | 1,3,4-Oxadiazoles | |
| GB1184608A (en) | Production of Nitrilotriacetic Acid and the Analogs Thereof. | |
| ES347178A1 (en) | N-aromatic substituted acid amides | |
| US3733355A (en) | Production of nitrilotriacetic acid and the analogs therefor | |
| GB1436307A (en) | Diaromatic o-aminoalkyl-oximes | |
| GB1392551A (en) | Ergolene derivatives their preparation and use | |
| ES415021A1 (en) | Process for preparing herbicidal triazines | |
| ES332580A1 (en) | A procedure for the preparation of benzodiacepine derivatives. (Machine-translation by Google Translate, not legally binding) | |
| GB1462311A (en) | Amidoxime derivatives and process for preparing the same | |
| ES420697A1 (en) | Chlorinated mandelamidines | |
| GB1475513A (en) | Benzylamine derivatives process for science union et cie benzylamine derivatives process for their production and pharmaceutical compositions containing them | |
| GB1363415A (en) | Bis-pyridyl amine compounds | |
| GB1226797A (en) | ||
| GB1447023A (en) | N,n-dioxides | |
| GB1154275A (en) | Process for the Dimerization of Acrylonitrile | |
| GB1435332A (en) | Process for the production of 3-thiazolines | |
| GB1148102A (en) | Production of new hexahydropyrimidine derivatives | |
| ES348550A1 (en) | Substituted-2,3-dichloroquinoxalines and processes for preparing same | |
| GB1112210A (en) | Process for the production of thiocarboxylic acid amides | |
| GB1071815A (en) | Phenothiazine derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |