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US3973910A Expired / Lapsed US ⏱️ 0.0 years remaining

Method of measuring the N-nitrosoamine content of a sample

Assignee: Thermo Fisher Scientific Inc
•
Filing: 1973-02-05
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Granted: 1976-08-10
•
Expires: 1993-02-05
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Abstract

Abstract The N-nitrosoamine content of a sample is measured by breaking the N--NO bond in the N-nitrosoamine molecule so as to liberate nitric oxide and thereafter measuring the amount of nitric oxide liberated.

Inventors

  • 👤 David H. Fine

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 21:42
CPC Classifications
G; G01; G01N; G01N31/00; Y; Y10; Y10T; Y10T436/00; Y10T436/17; Y10T436/170769; Y10T436/171538; Y10T436/173845

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 128 words
A method of measuring the content in a sample of compounds having the general formula: ##EQU1## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. heating the sample to provide an amount of thermal energy effective to break the N--NO bond and ineffective to break other molecular bonds in any substantial number for selectively liberating nitric oxide (NO), said heating step being the sole energization step for breaking molecular bonds; and b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said heating step.
Claim 2
Independent Claim 128 words
A method of measuring the content in a sample of compounds having the general formula: ##EQU1## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. heating the sample to provide an amount of thermal energy effective to break the N--NO bond and ineffective to break other molecular bonds in any substantial number for selectively liberating nitric oxide (NO), said heating step being the sole energization step for breaking molecular bonds; and b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said heating step.
Claim 3
Dependent Claim 38 words
A method according to claim 1 wherein the amount of nitric oxide (NO) liberated is measured by: a. reacting the nitric oxide (NO) with ozone (O 3 ); and b. measuring the intensity of the resultant chemiluminescent emission.
Claim 4
Dependent Claim 31 words
A method according to claim 1 wherein the amount of nitric oxide (NO) liberated is determined by measuring the intensity of the infrared absorption spectrum of the liberated nitric oxide (NO).
Claim 5
Dependent Claim 17 words
The method of claim 1 wherein said heating step comprises the step of flash vaporizing the sample.
Claim 6
Dependent Claim 40 words
A method according to claim 1 wherein the amount of nitric oxide (NO) liberated is determined by: a. oxidizing the nitric oxide (NO) to produce nitrogen dioxide (NO 2 ); and b. measuring the nitrogen dioxide (NO 2 ) concentration.
Claim 7
Dependent Claim 35 words
The method according to claim 5 wherein the concentration of said nitrogen dioxide (NO 2 ) is determined by measuring the intensity of the ultra violet absorption spectrum of the nitric dioxide (NO 2 ).
Claim 8
Independent Claim 138 words
A method of measuring the content in a sample of compounds having the general formula: ##STR4## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. heating said sample to a temperature from 100°C to about 300°C to provide an amount of thermal energy sufficient to break the N--NO bond and insufficient to break other molecular bonds in any substantial number, said heating step being the sole energization step for breaking molecular bonds, thereby to selectively liberate nitric oxide (NO) gas; and b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said heating step.
Claim 9
Independent Claim 138 words
A method of measuring the content in a sample of compounds having the general formula: ##STR4## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. heating said sample to a temperature from 100°C to about 300°C to provide an amount of thermal energy sufficient to break the N--NO bond and insufficient to break other molecular bonds in any substantial number, said heating step being the sole energization step for breaking molecular bonds, thereby to selectively liberate nitric oxide (NO) gas; and b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said heating step.
Claim 10
Dependent Claim 28 words
A method according to claim 7 in which said N--NO bond is broken by passing the sample through a heated conduit forming a reaction chamber for said sample.
Claim 11
Dependent Claim 30 words
A method according to claim 8 wherein said heating step comprises the step of injecting the sample into said reaction chamber heated to a temperature from 200°C to about 300°C.
Claim 12
Dependent Claim 44 words
A method according to claim 7 wherein said sample is non-gaseous, further comprising the steps of dissolving said sample in a liquid in which compounds having the general formula: ##STR5## are soluble and thereafter subjecting the resulting compound containing liquid to said heating step.
Claim 13
Dependent Claim 23 words
A method according to claim 9 in which the residence time of the sample in said reaction chamber is less than 10 seconds.
Claim 14
Independent Claim 166 words
A method of measuring the content in a sample, wherein said sample is in a gaseous form, of compounds having the general formula: ##STR6## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. breaking the N--NO bond by heating said sample in a reaction chamber heated to a temperature from 200°C to about 300°C to cause said sample to liberate nitric oxide (NO) gas; and b. measuring in the gaseous phase the amount of said nitric oxide (NO) gas liberated by said breaking step by reacting said nitric oxide (NO) gas with ozone (O 3 ) gas and by measuring the intensity of the chemiluminescent emission resulting from said reaction to provide a direct and immediate measurement of the content of said compounds in said sample.
Claim 15
Independent Claim 166 words
A method of measuring the content in a sample, wherein said sample is in a gaseous form, of compounds having the general formula: ##STR6## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. breaking the N--NO bond by heating said sample in a reaction chamber heated to a temperature from 200°C to about 300°C to cause said sample to liberate nitric oxide (NO) gas; and b. measuring in the gaseous phase the amount of said nitric oxide (NO) gas liberated by said breaking step by reacting said nitric oxide (NO) gas with ozone (O 3 ) gas and by measuring the intensity of the chemiluminescent emission resulting from said reaction to provide a direct and immediate measurement of the content of said compounds in said sample.
Claim 16
Independent Claim 125 words
A method of measuring the content in a sample of compounds having the general formula: ##STR7## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitue with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. flash vaporizing the sample at a temperature from 200°C to about 300°C for approximately instantaneously breaking the N--NO bond while providing a level of thermal energy to the sample insufficient to break other molecular bonds thereby selectively liberating nitric oxide (NO) gas; and b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said breaking step.
Claim 17
Independent Claim 125 words
A method of measuring the content in a sample of compounds having the general formula: ##STR7## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitue with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. flash vaporizing the sample at a temperature from 200°C to about 300°C for approximately instantaneously breaking the N--NO bond while providing a level of thermal energy to the sample insufficient to break other molecular bonds thereby selectively liberating nitric oxide (NO) gas; and b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said breaking step.
Claim 18
Dependent Claim 34 words
The method according to claim 13 wherein said measuring step comprises reacting said nitric oxide (NO) with ozone (O 3 ) and measuring the intensity of the chemiluminescent emission resulting from said reacting step.
Claim 19
Independent Claim 110 words
A method of measuring in a sample the content of compounds selected from the group consisting of: N-nitrosodimethylamine N-nitrosopiperidine N-nitrosodiamylamine N-nitrosomethylurea N-nitroso-N-methylurethane N-nitrosoethylurea Ethyl-N-nitrososarcosinate Diphenylnitrosoamine Phenylnitrosourea N-nitrosodibutylamine N-nitroso-N-ethylaniline N-nitrosodiacetylamine N-nitrosodibenzylamine and mixtures thereof comprising the steps of: a. heating the sample at a temperature from 100°C to about 300°C for providing an amount of thermal energy sufficient to break the N--NO bond and insufficient to break other molecular bonds in any substantial number, said heating step being the sole energization step for breaking molecular bonds, thereby to selectively liberate nitric oxide (NO) gas; b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said heating step.
Claim 20
Independent Claim 110 words
A method of measuring in a sample the content of compounds selected from the group consisting of: N-nitrosodimethylamine N-nitrosopiperidine N-nitrosodiamylamine N-nitrosomethylurea N-nitroso-N-methylurethane N-nitrosoethylurea Ethyl-N-nitrososarcosinate Diphenylnitrosoamine Phenylnitrosourea N-nitrosodibutylamine N-nitroso-N-ethylaniline N-nitrosodiacetylamine N-nitrosodibenzylamine and mixtures thereof comprising the steps of: a. heating the sample at a temperature from 100°C to about 300°C for providing an amount of thermal energy sufficient to break the N--NO bond and insufficient to break other molecular bonds in any substantial number, said heating step being the sole energization step for breaking molecular bonds, thereby to selectively liberate nitric oxide (NO) gas; b. measuring in the gaseous phase the amount of nitric oxide (NO) liberated by said heating step.
Claim 21
Dependent Claim 18 words
The method according to claim 15 wherein said heating step comprises the step of flash vaporizing the sample.
Claim 22
Dependent Claim 49 words
The method according to claim 15 wherein said measuring step comprises reacting said nitric oxide (NO) with ozone (O 3 ) and measuring the intensity of the chemiluminescent emission resulting from said reacting to provide a direct and immediate measurement of the content of said compositions and said sample.
Claim 23
Dependent Claim 40 words
The method according to claim 17 wherein said heating step comprises the step of passing the sample through a heated conduit, further comprising the step of admitting the output from said heated conduit directly into a reaction chamber containing ozone.
Claim 24
Independent Claim 122 words
A method of measuring in a sample the content of compounds selected from the group consisting of: N-nitrosodimethylamine N-nitrosopiperidine N-nitrosodiamylamine N-nitrosomethylurea N-nitroso-N-methylurethane N-nitrosoethylurea Ethyl-N-nitrososarcosinate Diphenylnitrosoamine Phenylnitrosourea N-nitrosodibutylamine N-nitroso-N-ethylaniline N-nitrosodiacetylamine N-nitrosodibenzylamine and mixtures thereof, comprising the steps of: a. breaking the N--NO bond in said compounds by heating said sample to a temperature from 200°C to about 300°C for selectively liberating nitric oxide (NO); and b. measuring in the gaseous phase the amount of said nitric oxide (NO) liberated by said breaking step by reacting said nitric oxide (NO) with ozone (O 3 ) and by measuring the intensity of the chemiluminescent emission resulting from said reaction to provide a direct and immediate measurement of the content of said compounds in said sample.
Claim 25
Independent Claim 122 words
A method of measuring in a sample the content of compounds selected from the group consisting of: N-nitrosodimethylamine N-nitrosopiperidine N-nitrosodiamylamine N-nitrosomethylurea N-nitroso-N-methylurethane N-nitrosoethylurea Ethyl-N-nitrososarcosinate Diphenylnitrosoamine Phenylnitrosourea N-nitrosodibutylamine N-nitroso-N-ethylaniline N-nitrosodiacetylamine N-nitrosodibenzylamine and mixtures thereof, comprising the steps of: a. breaking the N--NO bond in said compounds by heating said sample to a temperature from 200°C to about 300°C for selectively liberating nitric oxide (NO); and b. measuring in the gaseous phase the amount of said nitric oxide (NO) liberated by said breaking step by reacting said nitric oxide (NO) with ozone (O 3 ) and by measuring the intensity of the chemiluminescent emission resulting from said reaction to provide a direct and immediate measurement of the content of said compounds in said sample.
Claim 26
Dependent Claim 22 words
A method according to claim 19 in which said N--NO bond is broken by passing said sample through a heated reaction chamber.
Claim 27
Dependent Claim 23 words
A method according to claim 20 in which the residence time of the sample in said reaction chamber is less than 10 seconds.
Claim 28
Dependent Claim 33 words
A method according to claim 19 wherein said sample is non-gaseous, further comprising the step of converting said non-gaseous sample to a gaseous form prior to the measurement of said nitric oxide (NO).
Claim 29
Dependent Claim 50 words
A method according to claim 22 wherein said converting step comprises the steps of dissolving said sample in a liquid in which said compounds are soluble and injecting the resulting compound containing liquid into said heated tube to cause said sample to vaporize and to liberate said nitric oxide (NO).
Claim 30
Independent Claim 112 words
A method of measuring the N-nitrosoamine content of a sample, wherein the N-nitrosoamines have the general formula: ##STR8## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. breaking the N--NO bond by exposing the N-nitrosoamine molecule to a high intensity electrical field for adding to the N-nitrosoamine molecule an amount of energy sufficient to liberate the nitric oxide (NO); and b. measuring the amount of nitric oxide liberated by said breaking step.
Claim 31
Independent Claim 112 words
A method of measuring the N-nitrosoamine content of a sample, wherein the N-nitrosoamines have the general formula: ##STR8## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. breaking the N--NO bond by exposing the N-nitrosoamine molecule to a high intensity electrical field for adding to the N-nitrosoamine molecule an amount of energy sufficient to liberate the nitric oxide (NO); and b. measuring the amount of nitric oxide liberated by said breaking step.
Claim 32
Independent Claim 110 words
A method of measuring the N-nitrosoamine content of a sample, wherein the N-nitrosoamines have the general formula: ##STR9## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. breaking the N-NO bond by exposing the N-nitrosoamine molecule to microwave energy for adding to the N-nitrosoamine molecule an amount of energy sufficient to liberate the nitric oxide (NO); and b. measuring the amount of nitric oxide (NO) liberated by said breaking step.
Claim 33
Independent Claim 110 words
A method of measuring the N-nitrosoamine content of a sample, wherein the N-nitrosoamines have the general formula: ##STR9## wherein R 1 and R 2 are the same or different organic radicals, including those radicals which together constitute with the non-nitroso N of the depicted N--NO bond a nitrogen heterocyclic radical, and wherein the N--NO bond is the weakest bond in the molecule, comprising the steps of: a. breaking the N-NO bond by exposing the N-nitrosoamine molecule to microwave energy for adding to the N-nitrosoamine molecule an amount of energy sufficient to liberate the nitric oxide (NO); and b. measuring the amount of nitric oxide (NO) liberated by said breaking step.

References Cited (Backward Citations)

US2395489A Cited
US3647387A Cited
US3718429A Cited
US3746513A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-10 1980-02-09 1980-08-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-10 1984-02-09 1984-08-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-10 1988-02-09 1988-08-10 $7700.00 Window Closed / Lapsed

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