US3864378A
Expired / Lapsed
US
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Process for preparing 2-hydroxyethyliminodiacetonitrile
Assignee: Bethlehem Steel Corp
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Filing: 1973-02-05
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Granted: 1975-02-04
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Expires: 1993-02-05
Abstract
Abstract 2-Hydroxyethyliminodiacetonitrile is prepared from monoethanolamine, formaldehyde and hydrogen cyanide at pH 7-9. Hydrolysis of the nitrile in an aqueous solution, after removal of any excess cyanide and formaldehyde, results in the formation of 2-hydroxyethyliminodiacetic acid, or corresponding salt, free from contamination. 2-hydroxyethyliminodiacetates are useful as detergent builders.
Inventors
- 👤 Otto A Homberg
- 👤 Jr Carl E Fries
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 16:07
CPC Classifications
C; C07; C07C; C07C255/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
81 words
A PROCESS FOR THE SYNTHESIS OF 2HYDROXYETHYLIMINODIACETONITRILE COMPRISING: REACTING MONOETHANOLAMINE, FORMALDEHYDE AND HYDROGEN CYANIDE AT FROM ABOUT PH 7 TO ABOUT PH 9, SAID REACTION BEING CARRIED OUT IN THE ABSENCE OF ANY ALKALI OR ALKALINE EARTH METAL HYDROXIDE AND WHEREIN SAID REACTION IS CARRIED OUT IN AQUEOUS MEDIUM, THE FORMALDEHYDE AND HYDROGEN CYANIDE ARE INITIALLY PRESENT IN ABOUT 30 TO 50 PERCENT STOICHIOMETRIC EXCESS, AND SAID REACTION IS CARRIED OUT AT A TEMPERATURE OF FROM ABOUT 40*-70*C TO FORM 2-HYDROXYETHYLIMINODIACETONITRILE.
Claim 2
Dependent Claim
81 words
A PROCESS FOR THE SYNTHESIS OF 2HYDROXYETHYLIMINODIACETONITRILE COMPRISING: REACTING MONOETHANOLAMINE, FORMALDEHYDE AND HYDROGEN CYANIDE AT FROM ABOUT PH 7 TO ABOUT PH 9, SAID REACTION BEING CARRIED OUT IN THE ABSENCE OF ANY ALKALI OR ALKALINE EARTH METAL HYDROXIDE AND WHEREIN SAID REACTION IS CARRIED OUT IN AQUEOUS MEDIUM, THE FORMALDEHYDE AND HYDROGEN CYANIDE ARE INITIALLY PRESENT IN ABOUT 30 TO 50 PERCENT STOICHIOMETRIC EXCESS, AND SAID REACTION IS CARRIED OUT AT A TEMPERATURE OF FROM ABOUT 40*-70*C TO FORM 2-HYDROXYETHYLIMINODIACETONITRILE.
Claim 3
Dependent Claim
27 words
A process as defined in claim 1 wherein said pH is established and maintained during the course of the reaction solely through the use of said reactants.
Claim 4
Dependent Claim
20 words
A process as defined in claim 1 in which said reaction is carried out at a pH of about 8.
Claim 5
Dependent Claim
39 words
A process as defined in claim 1 in which said reaction is carried out by mixing the monoethanolamine and formaldehyde together to form a first mixture and mixing this first mixture with hydrogen cyanide to form a second mixture.
Claim 6
Dependent Claim
18 words
The process as defined in claim 1 in which the formaldehyde and hydrogen cyanide are utilized as glycolonitrile.
Claim 7
Dependent Claim
22 words
A process as defined in claim 4 in which the temperature at which said first mixture is formed is about 40*-70* C.
Claim 8
Dependent Claim
22 words
A process as defined in claim 4 in which the temperature at which said first mixture is formed is about 15*-85* C.
Claim 9
Dependent Claim
106 words
A process for the synthesis of 2-hydroxyethyliminodiacetonitrile comprising: reacting monoethanolamine, formaldehyde and hydrogen cyanide at from about pH 7 to about pH 9, said reaction is carried out in aqueous medium, the formaldehyde and hydrogen cyanide are initially present in about a 30 to 50 percent stoichiometric excess, and said reaction is carried out by mixing the monoethanolamine and formaldehyde at a temperature of about 40*-70* C. to form a first mixture and mixing this first mixture with hydrogen cyanide at a temperature of about 38*-42* C. to form 2-hydroxyethyliminodiacetonitrile, said reaction being carried out in the absence of any alkali or alkaline earth metal hydroxide.
Claim 10
Dependent Claim
106 words
A process for the synthesis of 2-hydroxyethyliminodiacetonitrile comprising: reacting monoethanolamine, formaldehyde and hydrogen cyanide at from about pH 7 to about pH 9, said reaction is carried out in aqueous medium, the formaldehyde and hydrogen cyanide are initially present in about a 30 to 50 percent stoichiometric excess, and said reaction is carried out by mixing the monoethanolamine and formaldehyde at a temperature of about 40*-70* C. to form a first mixture and mixing this first mixture with hydrogen cyanide at a temperature of about 38*-42* C. to form 2-hydroxyethyliminodiacetonitrile, said reaction being carried out in the absence of any alkali or alkaline earth metal hydroxide.
Claim 11
Dependent Claim
86 words
A process for the synthesis of 2-hydroxyethyliminodiacetonitrile comprising: reacting monoethanolamine, formaldehyde and hydrogen cyanide at from about pH 7 to about pH 9, said reaction is carried out in aqueous medium, and said reaction is carried out by mixing the monoethanolamine and formaldehyde at a temperature of about 15*-85* C and mixing this first mixture with hydrogen cyanide at a temperature of about 30* - 65* C to form 2-hydroxyethylaminodiacetonitrile, said reaction being carried out in the absence of any alkali or alkaline earth metal hydroxide.
Claim 12
Dependent Claim
86 words
A process for the synthesis of 2-hydroxyethyliminodiacetonitrile comprising: reacting monoethanolamine, formaldehyde and hydrogen cyanide at from about pH 7 to about pH 9, said reaction is carried out in aqueous medium, and said reaction is carried out by mixing the monoethanolamine and formaldehyde at a temperature of about 15*-85* C and mixing this first mixture with hydrogen cyanide at a temperature of about 30* - 65* C to form 2-hydroxyethylaminodiacetonitrile, said reaction being carried out in the absence of any alkali or alkaline earth metal hydroxide.
Claim 13
Dependent Claim
24 words
A process as defined in claim 9 wherein the formaldehyde and hydrogen cyanide are initially present in about 30 to 50 percent stoichiometric excess.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-02-03 | 1978-08-05 | 1979-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-02-03 | 1982-08-05 | 1983-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-02-03 | 1986-08-05 | 1987-02-04 | $7700.00 | Window Closed / Lapsed |