US4313004A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the reduction of dicyanoglycols
Assignee: Milliken Research Corp
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Filing: 1981-02-02
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Granted: 1982-01-26
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Expires: 2001-02-02
Abstract
Abstract A method for preparing a diaminoalkoxy compound of the formula: ##STR1## wherein m and n are both numbers from 0 to about 25 and m+n equals at least 1, R 1 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms; and R 2 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms; which comprises incrementally introducing a dicyanoglycol compound of the formula: ##STR2## wherein m, n, R 1 and R 2 have the values indicated above into a reaction medium at a rate sufficient to minimize cleavage reactions, at a temperature of from about 90° C. to about 160° C. in the presence of hydrogen at a pressure of from about 800 psi to about 2200 psi; ammonia in an amount of from about 10 to about 40 weight percent based on the weight of dicyanoglycol compound; and a nickel catalyst in an amount sufficient to catalyze said reaction, whereby said dicyanoglycol compound is reduced to said diaminoalkoxy compound.
Inventors
- 👤 Edward W. Kluger
- 👤 Andre M. Goineau
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 16:29
CPC Classifications
C; C07; C07C; C07C255/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
170 words
A method for preparing a diaminoalkoxy ##STR9## wherein m and n are both numbers from 0 to about 25 and m+n equals at least 1 R 1 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms; and R 2 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms; which comprises incrementally introducing a dicyanoglycol compound of the formula: ##STR10## wherein m, n, R 1 and R 2 have the values indicated above into a reaction medium at a rate sufficient to minimize cleavage reactions, at a temperature of from about 90° C. to about 160° C. in the presence of hydrogen at a pressure of from about 800 psi to about 2200 psi; ammonia in an amount of from about 10 to about 40 weight percent based on the weight of dicyanoglycol compound; and a nickel catalyst in an amount sufficient to catalyze said reaction, whereby said dicyanoglycol compound is reduced to said diaminoalkoxy compound.
Claim 2
Independent Claim
170 words
A method for preparing a diaminoalkoxy ##STR9## wherein m and n are both numbers from 0 to about 25 and m+n equals at least 1 R 1 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms; and R 2 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms; which comprises incrementally introducing a dicyanoglycol compound of the formula: ##STR10## wherein m, n, R 1 and R 2 have the values indicated above into a reaction medium at a rate sufficient to minimize cleavage reactions, at a temperature of from about 90° C. to about 160° C. in the presence of hydrogen at a pressure of from about 800 psi to about 2200 psi; ammonia in an amount of from about 10 to about 40 weight percent based on the weight of dicyanoglycol compound; and a nickel catalyst in an amount sufficient to catalyze said reaction, whereby said dicyanoglycol compound is reduced to said diaminoalkoxy compound.
Claim 3
Dependent Claim
27 words
The method of claim 1, wherein said rate of incremental introduction of said dicyanoglycol into said reaction medium is adjusted so that said reduction occurs substantially instantaneously.
Claim 4
Dependent Claim
31 words
The method of claim 2, wherein said rate of incremental introduction of said dicyanoglycol is adjusted so that said reaction medium does not contain more than about 5 percent reaction intermediates.
Claim 5
Dependent Claim
13 words
The method of claim 1, wherein said temperature is from about 120°-135° C.
Claim 6
Dependent Claim
13 words
The method of claim 1, wherein said pressure is from about 1000-2000 psi.
Claim 7
Dependent Claim
23 words
The method of claim 1, wherein the amount of ammonia used is from about 5 to about 30 moles per mole of dicyanoglycol.
Claim 8
Dependent Claim
22 words
The method of claim 6, wherein the amount of ammonia is from about 12 to about 20 moles per mole of dicyanoglycol.
Claim 9
Dependent Claim
44 words
The method of claim 1, wherein m and n are both at least 1 and not more than about 10; R 1 is H; and R 2 is selected from H and a lower alkyl group containing from 1 to about 4 carbon atoms.
Claim 10
Dependent Claim
17 words
The method of claim 1, wherein said dicyanoglycol is bis-(-2-cyanoethyl)diethylene glycol and said diaminoalkoxy compound is bis-(-3-aminopropyl)diethyleneglycol.
Claim 11
Dependent Claim
18 words
The method of claim 1, wherein said dicyanoglycol is bis-(-2-cyanoethyl)ethylene glycol and said diaminoalkoxy compound is bis-(-3-aminopropyl)ethylene glycol.
Claim 12
Dependent Claim
16 words
The method of claim 1, wherein said dicyanoglycol is bis-(-2-cyanoethyl)ether and said diaminoalkoxy compound is bis-(-3-aminopropyl)ether.
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) | 1985-01-25 | 1985-07-27 | 1986-01-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-25 | 1989-07-27 | 1990-01-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-25 | 1993-07-27 | 1994-01-26 | $7700.00 | Window Closed / Lapsed |