US5023376A
Expired / Lapsed
US
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Reduction of nitrosamine formation
Assignee: Solvay Interox Inc
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Filing: 1989-07-17
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Granted: 1991-06-11
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Expires: 2009-07-17
Abstract
Abstract Reaction of amine-containing substrates with hydrogen peroxide can suffer from the problems of in situ generation of nitrosamines, which are allegedly carcinogens, as impurities and impaired product formation, especially in the presence of transition metals. The problems can be ameliorated by employing a selected range of alkyleneaminopoly(methylenephosphonic acid) compounds such as cyclohexane-1,2-diaminotetra(methylenephosphonic acid).
Inventors
- 👤 Noel S. Shehad
- 👤 Laurie L. Dussack
- 👤 Dirk van Hemelrijk
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:29
CPC Classifications
C; C07; C07C; C07C291/00; C07C291/02; C07C291/04
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
121 words
In a process for the reaction of a secondary or tertiary amine-containing substrate with an aqueous solution of hydrogen peroxide, the improvement comprising carrying out the reaction in the presence of an effective amount of an alkyleneaminopoly(methylenephosphonic acid) or water soluble salt thereof obeying either of the general formulae: ##STR2## in which X represents a group of formula --CH 2 --PO 3 My in which M represents H or a non-transition metal cation conferring water-solubility, Y represents 1 or 2, R° represents an aliphatic or alicyclic diradical of 2 or 3 carbon atoms length and containing from 2 to 6 carbon atoms, n represents an integer selected from 1 to 4 and m represents an integer selected from 4 to 6.
Claim 2
Dependent Claim
121 words
In a process for the reaction of a secondary or tertiary amine-containing substrate with an aqueous solution of hydrogen peroxide, the improvement comprising carrying out the reaction in the presence of an effective amount of an alkyleneaminopoly(methylenephosphonic acid) or water soluble salt thereof obeying either of the general formulae: ##STR2## in which X represents a group of formula --CH 2 --PO 3 My in which M represents H or a non-transition metal cation conferring water-solubility, Y represents 1 or 2, R° represents an aliphatic or alicyclic diradical of 2 or 3 carbon atoms length and containing from 2 to 6 carbon atoms, n represents an integer selected from 1 to 4 and m represents an integer selected from 4 to 6.
Claim 3
Dependent Claim
32 words
A process according to claim 1 in which the amount of alkyleneaminopoly(methylenephosphonic acid) or salt thereof is selected in the range of from 15 to 500 ppm w/w in the reaction mixture.
Claim 4
Dependent Claim
29 words
A process according to claim 1 in which the alkylene aminopoly(methylenephosphonic acid) or salt thereof is present in a mole ratio to the amine of from 1:20,000 to 1:1000.
Claim 5
Dependent Claim
42 words
A process according to claim 1 in which the alkyleneaminopoly(methylenephosphonic acid) or salt thereof is selected from formula 1 or 2 compounds in which R° represents a dimethylene diradical and respectively n is 1 or 2 or m is 4 or 6.
Claim 6
Dependent Claim
88 words
A process according to claim 1 in which the amine containing substrate is a secondary or tertiary amine of formula RR'R"N in which R and R' each represent an alkyl or cycloalkyl group and optionally at least one of which is substituted by an aromatic substituent or by an ethoxylate or propoxylate chain or in which R and R' combine with the N atom to form a heterocyclic nucleus and in which R" represents hydrogen, a functionality capable of reacting with hydrogen peroxide, an alkyl or cycloalkyl group.
Claim 7
Dependent Claim
34 words
A process according to claim 5 in which R in the amine containing substrate represents an alkyl group containing from 6 to 18 carbon atoms and R' and R" represent methyl or ethyl groups.
Claim 8
Dependent Claim
32 words
A process according to claim 5 in which the amine containing substrate is reacted with hydrogen peroxide in a mole ratio of the latter to the former of from 1.05:1 to 1.2:1.
Claim 9
Dependent Claim
17 words
A process according to claim 1 in which the amine-containing substance comprises a secondary or tertiary amine.
Claim 10
Dependent Claim
15 words
A process according to claim 1 in which the amine-containing substance comprises a tertiary amine.
Claim 11
Dependent Claim
31 words
A process according to claim 1, wherein said aqueous hydrogen peroxide solution contains at least 0.03 parts by weight of said alkyleneaminopoly(methylenephosphonic acid) per 100 parts by weight of hydrogen peroxide.
Claim 12
Dependent Claim
41 words
A process according to claim 10 in which the alkylene aminopoly(methylenephosphonic acid) or salt thereof is present in a weight ratio of from 0.3 to 3 parts w/w per 100 parts of hydrogen peroxide that is introduced into the reaction mixture.
References Cited (Backward Citations)
US2169976A
Cited
US2419283A
Cited
US2795611A
Cited
US3122417A
Cited
US3234140A
Cited
US4144272A
Cited
NL7401261A
Cited
US4247480A
Cited
US4304762A
Cited
EP0307184A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-06-10 | 1994-12-10 | 1995-06-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-06-10 | 1998-12-10 | 1999-06-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-06-10 | 2002-12-10 | 2003-06-11 | $7700.00 | Window Closed / Lapsed |