Method for the manufacture of halophthalic acids and anhydrides
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-209/48
C07D-493/02
C07C-051/16
C07C-051/255
출원번호
US-0063114
(2002-03-22)
발명자
/ 주소
Colborn, Robert Edgar
Hall, David Bruce
Koch, Peter
Oeckel, Gerald
출원인 / 주소
General Electric Company
인용정보
피인용 횟수 :
3인용 특허 :
180
초록
A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide.
대표청구항▼
A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide. N2O saturated aqueous solution with a 137Cs γ-ray source for a pe
A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide. N2O saturated aqueous solution with a 137Cs γ-ray source for a period of time sufficient to generate a total equivalent concentration of hydroxyl radical of at least 10 μM, the solution comprising at least 50 picomoles of the peptide or protein, a molar ratio of D2O to total solution of at least 0.1 percent, and at least 5 μM reduced dithiothreitol; (ii) adding an amount of reduced dithiothreitol to the solution to replace reduced dithiothreitol depleted in step (i); (iii) contacting the solution with N2O gas, having less than 3000 parts per million O2,for at least five minutes; and (iv) repeating steps (i) thru (iii) until a cumulative total equivalent concentration of hydroxyl radical of 10 μM to 10 mM is achieved in the N2O saturated aqueous solution thereby labeling said solvent-accessible, reduced carbon atom. 10. A method of labeling a solvent-accessible, reduced carbon atom in a peptide or protein with deuterium, the method comprising generating a total equivalent concentration of hydroxyl radical of at least 10 μM in an aqueous N2O saturated solution that includes at least 50 picomoles of the peptide or protein, a molar ratio of D2O to total solution of at least 0.1 percent, and at least 5 μM reduced dithiothreitol for a time and under conditions effective to label said solvent-accessible, reduced carbon atom; wherein the hydrogen atom abstractor reacts with the solvent-accessible, reduced carbon atom in the peptide or protein to form a corresponding carbon-centered radical of the solvent-accessible, reduced carbon atom and the reduced dithiothreitol donates the deuterium to the carbon-centered radical thereby labeling the solvent-accessible, reduced carbon atom in the peptide or protein with the deuterium; with the proviso that when the total equivalent concentration of hydroxyl radical is achieved, the solution has an O2concentration of less than 6 μM. 11. The method of claim 10 wherein the total equivalent concentration of hydroxyl radical is achieved by a method selected from the group consisting of exposing a light sensitive hydroperoxide in said solution to light, exposing said solution to γ-rays, exposing said solution to accelerated electrons, exposing said solution to β-radiation, exposing said solution to 137Cs radiolysis, exposing said solution to 60Co radiolysis, exposing said solution to 32PO4radiolysis, exposing said solution to Cu Kαradiation, exposing said solution to molybdenum Kαradiation, exposing said solution to synchrotron radiation, and exposing said solution to neutron radiation. 12. The method of claim 10 wherein the total equivalent concentration of hydroxyl radical is generated by 137Cs radiolysis. 13. The method of claim 10 wherein the total equivalent concentration of hydroxyl radical is achieved by a metal-catalyzed Fenton reaction. 14. The method of claim 10 wherein the total equivalent concentration of hydroxyl radical is achieved by radiation. 15. The method of claim 10 wherein the total equivalent concentration of hydroxyl radical is achieved by radiolysis or pulse radiolysis. 16. A method of determining the amount of deuterium which has been incorporated into an amino acid of a peptide or protein comprising: (a) labeling a solvent-accessible, reduced carbon atom in a peptide or protein with deuterium by generating a hydrogen atom abstractor in a solution comprising the peptide or protein, a heavy hydrogen source, and a heavy hydrogen donor, for a time and under conditions effective to label a solvent accessible, reduced carbon atom on said peptide or protein, wherein the solution is substantially oxygen free when the hydrogen atom abstractor is generated; (b) sequentially hydrolyzing the peptide or protein into a plurality of hydrolyzed amino acids after the hydrogen atom abstractor is generated; (c) optionally, derivatizing the plurality of hydrolyzed amino acids prior to purification; (d) purifying a sequentially hydrolyzed amino acid selected from the plurality of hydrolyzed amino acids; and (e) quantifying the amount of deuterium covalently bonded to a solvent-accessible, reduced carbon atom of the sequentially hydrolyzed amino acid. 17. The method of claim 16 wherein a labeled carbon atom in the peptide or protein is identified. 18. The method of claim 16 wherein an amount of heavy hydrogen associated with a carbon atom in an amino acid selected from the plurality of amino acids is determined by mass spectrometry. 19. A method of labeling a solvent-accessible, reduced carbon atom in a peptide or protein with a deuterium atom, the method comprising achieving a total equivalent concentration of hydroxyl radical of at least 10 μM in an aqueous N2O saturated solution comprising at least 50 picomoles of the peptide or protein, a molar ratio of D2O to total solution of at least 0.1 percent, and at least 5 μM reduced dithiothreitol for a time and under conditions effective to label said solvent-accessible, reduced carbon atom; wherein hydroxyl radical reacts with the solvent-accessible, reduced carbon atom in the peptide or protein to form a corresponding carbon-centered radical of the solvent-accessible, reduced carbon atom and the reduced dithiothreitol donates the deuterium to the carbon-centered radical thereby labeling the solvent-accessible, reduced carbon atom in the peptide or protein with the deuterium; with the proviso that when the total equivalent concentration of hydroxyl radical is achieved, the aqueous N2O saturated solution has an O2concentration of less than 6 μM. 20. A method of labeling a solvent-accessible, reduced carbon atom in a peptide or protein with deuterium, the method comprising: (i) irradiating an N2O saturated aqueous solution with a 137Cs γ-ray source for a period of time sufficient to generate a total equivalent concentration of hydroxyl radical of at least 10 μM, the solution comprising at least 50 picomoles of the peptide or protein, a molar ratio of D2O to total solution of at least 0.1 percent, and at least 5 μM reduced dithiothreitol; (ii) adding an amount of reduced dithiothreitol to the solution to replace reduced dithiothreitol depleted in step (i); (iii) contacting the solution with N2O gas, having less than 3000 parts per million O2,for at least five minutes; and (iv) repeating steps (i) thru (iii), under conditions effective to label said solvent accessible, reduced carbon atom, until a cumulative total equivalent concentration of hydroxyl radical of 10 μM to 10 mM is achieved in the N2O saturated aqueous-solution. 21. A method of labeling solvent-accessible, reduced carbon atoms in a peptide or protein, the method comprising: generating a hydrogen atom abstractor in a solution comprising the peptide or protein, a heavy hydrogen source, and a heavy hydrogen donor, for a time and under conditions effective to label said solvent-accessible, reduced carbon atoms; wherein (i) the solution is substantially oxygen free when the hydrogen atom abstractor is generated in the solution; (ii) the heavy hydrogen donor is selected from the group consisting of a reduced, water soluble thiol, H2S, L-ascorbic acid, (±)-α-tocopherol, a phenol, a water soluble phosphine, and a water soluble phosphite; and (iii) the hydrogen atom abstractor reacts, during said generating step, with said solvent-accessible, reduced carbon atoms to form corresponding carbon-centered radicals and the heavy hydrogen donor donates a heavy hydrogen to each said corresponding carbon-centered radical; with the proviso that when the heavy hydrogen donor is a water soluble phosphine or water soluble phosphite, the heavy hydrogen donor contains a bond select ed from the group consisting of P--H, P--D, and P--T. 22. The method of claim 21, wherein the solution is substantially oxygen free when at least one solvent-accessible, reduced carbon atom in the peptide or protein is labeled with heavy hydrogen. 23. The method of claim 21, wherein the solution is substantially oxygen free when at least five percent of the solvent-accessible, reduced carbon atoms in the peptide or protein are labeled with heavy hydrogen. 24. The method of claim 21, wherein the solution is made substantially oxygen free by contacting the solution with a gas, having less than 3000 parts per million O2,for at least an amount of time that is sufficient to make the concentration of O2dissolved in the solution 6 μM or less. 25. The method of claim 24, wherein the gas is selected from the group consisting of N2O, N2,argon, helium, and anoxic mixtures thereof. 26. The method of claim 24, wherein the solution is contacted with the gas by bubbling the gas into the solution. 27. The method of claim 21, wherein the solution is made substantially oxygen free by contacting the solution with a N2O gas, having less than 3000 parts per million O2,for a sufficient amount of time such that at least five percent of the carbon-centered radicals, which are formed by a reaction of the hydrogen atom abstractor with solvent-accessible, reduced carbon atoms in the peptide or protein, are repaired by donation of a hydrogen isotope by the heavy hydrogen donor. 28. The method of claim 21, wherein the hydrogen atom abstractor is selected from the group consisting of peroxonitrous acid, hydrogen atom, hydroperoxyl radical, alkoxyl radical, alkyl radical, singlet oxygen, metal oxo species, and hydroxyl radical. 29. The method of claim 21, wherein the hydrogen atom abstractor is a total equivalent concentration of hydroxyl radical, and the solution includes an electron scavenger source when the total equivalent concentration of hydroxyl radical is generated. 30. The method of claim 29, wherein the total equivalent concentration of hydroxyl radical is generated by a metal-catalyzed Fenton reaction. 31. The method of claim 29, wherein the total equivalent concentration of hydroxyl radical is generated by radiation. 32. The method of claim 29, wherein the electron scavenger source is selected from the group consisting of solvated N2O, ascorbate, tetranitromethane, nitrate, CCl4,a thiol, a disulfide, a fluorinated aromatic compound, and a nitro aromatic compound. 33. The method of claim 29, wherein the electron scavenger source is solvated N2O derived from N2O gas bubbled into the solution prior to the generation of the total equivalent concentration of hydroxyl radical. 34. The method of claim 29, wherein the total equivalent concentration of hydroxyl radical that is generated in the solution is at least 10 μM. 35. The method of claim 29, wherein the total equivalent concentration of hydroxyl radical is generated by a method selected from the group consisting of exposing a light sensitive hydroperoxide in said solution to light, exposing said solution to γ-rays, exposing said solution to accelerated electrons, exposing said solution to β-radiation, exposing said solution to 137Cs radiolysis, exposing said solution to 60Co radiolysis, exposing said solution to 32PO4radiolysis, exposing said solution to Cu Kαradiation, exposing said solution to molybdenum Kαradiation, exposing said solution to synchrotron radiation, and exposing said solution to neutron radiation. 36. The method of claim 29, wherein the electron scavenger source is oxidized dithiothreitol present in the solution. 37. The method of claim 36, wherein the oxidized dithiothreitol is present in the solution at a concentration of at least 0.05 μM. 38. The method of claim 21, wherein the solution is made substantially oxygen free by contacting the solution with a N2O gas, having less than 20 parts per million O2,until a concentration of O2dissolved in the solution when the hydrogen atom abstractor is generated is sufficiently low that a substantial number of the corresponding carbon-centered radicals, formed by the reaction of the hydrogen atom abstractor with solvent-accessible, reduced carbon atoms in the peptide or protein, are repaired by donation of a hydrogen isotope by the heavy hydrogen donor. 39. The method according to claim 21, wherein a positive pressure is maintained against the solution with a N2O gas, having less than 20 parts per million O2,when the hydrogen atom abstractor is generated. 40. The method of claim 21, wherein the solution is made substantially oxygen free by bubbling the solution with argon for five minutes or longer, and then bubbling the solution with N2O gas, having less than 500 parts per million O2,until a concentration of O2dissolved in the solution when the hydrogen atom abstractor is generated is sufficiently low that a substantial number of the corresponding carbon-centered radicals, formed by the reaction of the hydrogen atom abstractor with solvent-accessible, reduced carbon atoms in the peptide or protein, are repaired by donation of a hydrogen isotope by the heavy hydrogen donor. 41. The method of claim 21, wherein the heavy hydrogen source in the solution is D2O present in the solution at a molar ratio to total solution of at least 0.1 percent. 42. The method of claim 21, wherein a quantity of 50 picomoles or more of the peptide or protein is present in the solution. 43. The method of claim 21, wherein the heavy hydrogen donor is reduced dithiothreitol that is present in the solution at a concentration of at least 1 μM. 44. The method of claim 21, wherein the solvent-accessible, reduced carbon atom is in a side chain of a residue on the peptide or protein. 45. The method of claim 21, wherein the residue is aliphatic. 46. The method of claim 21, wherein the solvent-accessible, reduced carbon is the Cαcarbon of a glycine residue in the peptide or protein. 47. The method of claim 21, wherein the solution further comprises an internal reference. 48. The method of claim 47, wherein the internal reference is a free amino acid. 49. The method of claim 47, wherein the internal reference is 50 picomoles, or more, of free leucine in the solution. 50. The method of claim 21, wherein the pH of the solution is determined by a buffer present in the solution, with the provisos that: (i) the buffer is not reactive with hydroxyl radical or solvated electrons; and (ii) the pH is such that the hydrogen atom donor is not stripped of its reactive hydrogen. 51. The method of claim 50, wherein the buffer is selected from the group consisting of phosphate and cacodylate. 52. The method of claim 21, wherein the solution is aqueous. 53. The method of claim 29, wherein the total equivalent concentration of hydroxyl radical is generated by radiolysis or pulse radiolysis. 54. A method of labeling solvent-accessible, reduced carbon atoms in a peptide or protein with deuterium, the method comprising: generating a hydrogen atom abstractor in a substantially oxygen free solution comprising the peptide or protein, a deuterium source, and a heavy hydrogen donor, for a time and under conditions effective to label said solvent-accessible, reduced carbon atoms, the hydrogen atom abstractor reacting with said solvent-accessible, reduced carbon atoms to form corresponding carbon-centered radicals and the heavy hydrogen donor donating a deuterium to each said corresponding carbon-centered radical. 55. The method of claim 54, wherein the solution is substantially oxygen free when at least five percent of the solvent-accessible, reduced carbon atoms in the peptide or protein are labeled with deuterium dur
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이 특허에 인용된 특허 (180)
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