CTNF 18/495,421 CTNF 69838 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claims 14, 17-18 and 22 rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, regards as the invention. With respect to claims 14 and 22, the derivatizing agent is not defined and covers anything from a pure compound such as the benzyl bromide of claim 11 to the benzyl bromide dissolved in water or an organic solvent such as chloroform, acetone or ethanol or a solution in one or more of those solvents and a phase transfer catalyst, surfactant or other agent designed to increase the solubility of either the sulfur compound, the derivatizing agent or the derivative in the solvent. Due to the scope of the derivatization agent, it is not clear if the claim language requiring the formation of a derivatized sulfur-containing compound is an attempt to limit the derivatization agent to something capable of forming a salt with one or more of the compounds listed in claim 1, attempting to exclude the presence of a phase transfer catalyst, surfactant or other agent designed to increase the solubility of either the sulfur compound or its derivative in the solvent from being part of the derivatization agent or requiring the derivatized sulfur-containing compound to have a particular structure. For examination purposes, the claim language will be treated as covering all possibilities. In claims 17 and 22 a second analysis step is performed after a first analysis step. In the second analysis step, derivatized sulfur-containing compounds that were not soluble in the derivatizing agent are treated to make them soluble in the derivatizing agent and then the treatment soluble derivatized sulfur containing compounds are analyzed. Since the derivatizing agent soluble and derivatizing agent insoluble derivatized sulfur-containing compounds form at the same time, it is not clear if the first and second analysis steps are performed on the whole sample or if there is some sort of separation step to separate the derivatizing agent insoluble derivatized sulfur-containing compounds from the derivatizing agent soluble derivatized sulfur-containing compounds. Claim 18 is dependent from claim 17 and fails to correct the deficiency of claim 17. 07-07-aia AIA 07-07 The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – 07-08-aia AIA (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. 07-15 AIA Claim s 1-2, 5, 13, 16 and 21 are rejected under 35 U.S.C. 102( a)(1 ) as being anticipated by Bulatov (Journal of Flow Injection Analysis 2006). In the paper Bulatov teaches a stepwise injection analysis (SWIA) method for determination of hydrogen sulfide in natural gas. The determination is based on absorption of hydrogen sulfide into open to the air reaction tube with 2% zinc acetate solution, stepwise injection of the reagents to the reaction tube to form a methylene blue and subsequent measurement of the downstream colored product at 670 nm. The open to the air reaction tube is a part of hydraulic system and has PTFE granules to increase a surface area during the gas sample bubbling. Nitrogen was purged to the reaction tube for enhanced mixing. All experimental manipulations were controlled by software. The absorbing solution has an absorption efficiency of >98% at a sampling flow rate of 0.3 l/min. This method provides a linear working range of 0.5 to 20 mg/m 3 with a relative standard deviation of 2.5 % (n=10) at the 5 mg/m3 level for 3 liters of gas sample and concentration time of 10 min. The determination limit of 0.1 mg/m 3 was achieved using 3 liters of gas sample and time of one cycle of 18.5 min. Table 1 provides conditions for the determination of hydrogen sulfide in natural gas. These conditions include contacting the gas sample or liquefied petroleum gas sample comprising one or more sulfur-containing compounds with a derivatization agent to form one or more derivatized sulfur-containing compounds; and analyzing the gas sample or liquefied petroleum gas sample comprising one or more derivatized sulfur-containing compounds to determine the sulfur-content; wherein the method determines the total concentration of the one or more sulfur-containing compounds in the gas sample or liquefied petroleum gas sample, wherein the one or more sulfur-containing compounds are selected from hydrogen sulfide, carbonyl sulfide, carbon disulfide, mercaptans, dialkyl sulfides, and combinations thereof. The specific sampling procedure is given on page 104. With respect to claim 2, the title is clear that the gas sample or liquefied petroleum gas sample is a natural gas sample. With respect to claim 5, the title is also clear that the gas sample or liquefied petroleum gas sample comprises hydrogen sulfide. With respect to claim 13, the fact that no precipitate is mentions indicated that the one or more of the derivatized sulfur-containing compounds are soluble in the derivatization agent. With respect to claim 16, the fact that table 1 and the sampling procedure teach that the derivative is analyzed using a calibration graph means that analyzing the gas sample or liquefied petroleum gas sample comprises a first analysis step, wherein: the first analysis step comprises analyzing the one or more derivatized sulfur-containing compounds that are soluble in the derivatization agent. With respect to claim 21, the fact that derivatives of the hydrocarbon in the natural gas sample are not mentioned and/or taught as separated from the hydrogen sulfide derivative means that the derivatization agent does not react with hydrocarbons present in the gas sample or liquefied petroleum gas sample, wherein the hydrocarbons are selected from methane, ethane, propane, butane, pentane, hexane, heptane, octane, benzene, toluene, xylenes, and combinations thereof . 07-20-aia AIA The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action: A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made. 07-23-aia AIA The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows: 1. Determining the scope and contents of the prior art. 2. Ascertaining the differences between the prior art and the claims at issue. 3. Resolving the level of ordinary skill in the pertinent art. 4. Considering objective evidence present in the application indicating obviousness or nonobviousness. 07-20-02-aia AIA This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. 07-21-aia AIA Claim s 1-8, 10-13, 15-16 and 19-21 are rejected under 35 U.S.C. 103 as being unpatentable over Myung (Journal of Chromatography A 1997) in view of Li (European Food Research and Technology 2017) and further in view of Kawahara (Analytical Chemistry 1968), Floberg (Journal of Chromatography 1980), Wu (Journal of Chromatography 1981), Funazo (Journal of Chromatography 1985), Halket (European Journal of Mass Spectrometry 2004), Maity (Journal of Molecular Catalysis A: Chemical 2006) or Mateo-Vivaracho (Journal of Chromatography A 2007). In the paper Myung teaches a gas chromatographic–mass spectrometric method for developed for the determination of mercaptan odorants (dimethyl sulfide, tert-butylmercaptan, tetrahydrothiophene) in natural gas. The gas sample was introduced into the 0.5 ml volume of a sampling loop, separated on a 50 m capillary column coated with 5% phenylmethylsilicone and detected by a mass spectrometer. Natural gas samples collected from 124 sites were analyzed and the concentration of added odorants was found to be between 9.7 and 66.2 ppm (w/w). The detection limit of each odorant was below 1 ppm (w/w). The advantages of the developed technique were lower detection limits, elimination of interference peaks by introducing into the sampling loop system and selected-ion monitoring mode, and reduced total analysis time. The intra-day and inter-day precision of the established method was R.S.D.,5% (n55). Myung does not teach contacting the gas sample or liquefied petroleum gas sample comprising one or more sulfur-containing compounds with a derivatization agent to form one or more derivatized sulfur-containing compounds prior to the analyzing step . In the paper Li describes the development of stable isotope dilution assays for the quantitation of the food odorants hydrogen sulfide, methanethiol, ethanethiol, and propane‑1‑thiol. Relevant to the instant claims are the last full paragraph of page 70 and the paragraph bridging pages 70-71, teaching that to facilitate the quantitation of hydrogen sulfide and short-chain alkane-1-thiols, their conversion into less reactive and less volatile derivatives is an alternative to the direct analysis of the compounds. This approach includes some basic advantages. No headspace sampling equipment is needed, the sampling amount is not limited, thus allowing to increase the sensitivity if necessary, and stable derivatives are no longer susceptible to disulfane formation. For hydrogen sulfide (u = 34), an increased molecular mass further adds to the advantages of the derivatization approach due to an improved gas chromatographic retention and a lower noise during GC–MS. Due to the high nucleophilicity of thiols, particularly under alkaline conditions when present as thiolates, electron-deficient alkenes, such as α,β-unsaturated ketones, acrylnitrile, and vinylpyridines, are commonly used as derivatization reagents. In the paper Kawahara teaches the microdetermination of derivatives of mercaptans by means of electron capture gas chromatography. The second paragraph on page 1009 teaches the detection of mercaptans by gas chromatography using a silver ion titration cell. This method had a sensitivity of 1 ppm of mercaptan sulfur. The paragraph bridging the columns of page 1009 teaches that because of the numerous contaminants in the weak acid fraction, a highly selective method is required. Thus, the conversion of phenol and mercaptan to a derivative which can exhibit electron capture response seemed desirable for their measurement. The paragraph prior to the experimental section starting on page 1009 teaches that ethers and thioethers, derived from phenols and mercaptans, respectively, with a-bromo-2,3,4,5,6-pentafluorotoluene, exhibit excellent electron capture response. This property accounts for excellent measurements in the presence of impurities. Only phenols, mercaptans, and acids will react rapidly with the fluoro-organic reagent under the described conditions. Derivatives of phenols and mercaptans are stable in water and are amenable to gas-liquid chromatographic separations. The paragraph bridging pages 1009-10010 teaches the preparation of the thioethers. The last paragraph on page 1010 teaches that the derivatives provide the following advantages: excellent stability in aqueous solution, excellent response to electron capture detector and specificity in presence of impurities, suitability to gas chromatographic separations, and analyses at trace concentrations of phenols and mercaptans. In the paper Floberg teaches a gas chromatography-mass spectrometry method for quantitation of the thyreostatic agent methimcola in plasma (see the structure given in figure 1). The drug was transferred from the plasma sample and derivatized in one step by extractive alkylation. Either of two alkylating agents benzyl chloride or pentafluorobenzyl bromide were used. The first full paragraph on page 65 teaches the extractive alkylation method used. In the paper Wu teaches the electron capture gas chromatographic determination of sulfide as a pentafluorobenzyl derivative. The second paragraph on page 312 teaches that the are several methods for measuring sulfide in water including a gas chromatography method. in addition to this, the paragraph teaches that there is still a need for a specific and more sensitive method for quantitation of sulfide in complicated matrices. The following paragraph teaches that a new approach based on detector-oriented derivatization of sulfide, as bis(pentatluorobenzy1) sulfide, is described for quantitative analysis of inorganic sulfide (S2-) down to ppb* levels. The results indicate that the method is specific and highly sensitive. The procedure section on page 313 describes the room temperature derivative formation. In the paper Funazo teaches a new derivatizing agent, pentafluorobenzyl p-toluenesulphonate, has been synthesized and is designed to enhance the volatility of analytes and introduce a detector-oriented tag into the molecules for gas chromatography (GC) with electron-capture detection. The derivatization of several inorganic anions was studied, and a new GC method for their simultaneous determination has been developed. Bromide, iodide, cyanide, thiocyanate, nitrite, nitrate and sulfide can be simultaneously derivatized to their pentafluorobenzyl derivatives using tetra-n-amylammonium chloride as the phase transfer catalyst. The derivatives were subsequently determined by GC with flame ionization detection. This method has also been applied to the determination of carboxylic acids or phenols, the derivatives of which were identified using mass spectrometry. The derivatives from bromide, iodide, cyanide, thiocyanate, nitrite, nitrate and sulfide were pentafluorobenzyl bromide, pentafluorobenzyl iodide, pentafluorobenzyl cyanide, pentafluorobenzyl thiocyanate, a-nitro-2,3,4,5,6-pentafluorotoluene, pentafluorobenzyl nitrate and bis(pentafluorobenzy1) sulfide, respectively. The effects of added acid or base, and of the reaction time, on the pentafluorobenzylation were discussed. the paragraph bridging pages 27-218 teaches the room temperature derivatization method. In the paper page 7 of Halket teaches that for alkylation of mercapto groups (SH – thiols), these groups possess a more acidic character than analogous alcohols and are more easily alkylated by the same reagents. The paragraph bridging pages 1-2 teaches that a number of reagents have been suggested for the preparation of alkyl derivatives: among these are alkyl (methyl, ethyl, propyl etc.) bromides or iodides and benzyl bromide and its substituted or fluorinated analogs. With respect to alkylation of alcoholic OH groups, page 7 teaches that pentafluorobenzyl ethers of alcohols may be obtained by the reaction of an alcohol with pentafluorobenzyl bromide in the presence of anhydrous K2CO3 (see the similar reaction of acids). Other benzyl ethers may be prepared in a similar way. In addition to K2CO3, other basic compounds (KOH, NaOH) may be involved. In the paper Maity investigated the reaction of benzyl chloride with ammonium sulfide under liquid–liquid phase transfer catalysis. The reaction between benzyl chloride and aqueous ammonium sulfide was carried out in an organic solvent – toluene, using tetrabutylammonium bromide (TBAB) as phase transfer catalyst (PTC). Two products, namely dibenzyl sulfide (DBS) and benzyl mercaptan (BM), were identified in the reaction mixture. The selectivity of DBS was maximized by changing various parameters such as NH 3 /H 2 S mole ratio, stirring speed, catalyst loading, concentration of benzyl chloride, volume of aqueous phase, and temperature. Section 2.5 on page 115 teaches that all the samples from the organic phase were analyzed by gas–liquid chromatography. In the paper Mateo-Vivaracho teaches the quantitative determination of wine polyfunctional mercaptans at nanogram per liter level by gas chromatography–negative ion mass spectrometric analysis of their pentafluorobenzyl derivatives. A fast method for the determination of aroma-powerful polyfunctional thiols at nanogram per liter level has been developed and applied to wine. A small volume of wine (6 mL) was extracted with 1.5mL of benzene containing four internal standards. Pentafluorobenzyl derivatives of mercaptans were formed in the extract by adding small amounts (100 mg L -1 ) of pentafluorobenzyl bromide and a strong alkali: 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After washing with a water:methanol (5:1) solution 0.5M in HCl, 20 L of the extract was directly injected into a gas chromatograph. Derivatives were detected by negative ion mass spectrometry. The method makes it possible to simultaneously determine 2-furfurylthiol (2-furanmethanethiol) (FFT), 4-mercapto-4-methyl-2-pentanone (MP), 3-mercaptohexylacetate (MHA) and 3-mercaptohexanol (MH). Section 2.2 on page 243 teaches the derivatization method. The conclusion of page 250 teaches that the present method resolves some of the limitations of previous procedures for the analysis of polyfunctional mercaptans at an ultratrace level. Although the method is not fully automated, it is relatively fast and simple, requires a small volume of sample and the number of compounds that can be determined simultaneously is higher than that of a previous report. Leaving aside 2-methyl-3-furanthiol, for which inconsistent results were found, the linear range is satisfactory, and the sensitivity is very good. The proposed procedure makes use of the formation of derivatives in a benzene extract, and although the procedure has been validated for wine, it should be expected that it be useful for the analysis of these compounds in different matrixes. With respect to the above claims, it would have been obvious to one of ordinary skill in the art at the time the application was filed to modify the method of Myung by contacting the sulfur compounds in the gas or liquefied gas with a derivatizing agent such as benzyl chloride, benzyl bromide or pentafluorobenzyl bromide as taught by one or more of Kawahara, Floberg, Wu, Funazo, Halket, Maity or Mateo-Vivaracho because of the increase in sensitivity afforded by the derivatives as taught by Kawahara, Floberg, Wu, Funazo, Halket, Maity or Mateo-Vivaracho and the additional advantages taught by Li for the use of derivatives compared to direct analysis of the sulfur compounds . 12-151-08 AIA 07-43 12-51-08 Claim 9 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. 07-43-01 AIA Claim 22 would be allowable if rewritten or amended to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), 2nd paragraph, set forth in this Office action. 07-43-02 AIA Claim s 14 and 17-18 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims. 13-03-01 AIA The following is a statement of reasons for the indication of allowable subject matter: the art of record fails to teach or fairly suggest the derivatizing agent of claim 9 or that some of the derivatives would be insoluble in the derivatizing agent . 07-96 AIA The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. The additionally cited art is related to various alkylating agents and their use for sulfur containing compounds . Any inquiry concerning this communication or earlier communications from the examiner should be directed to Arlen Soderquist whose telephone number is (571)272-1265. The examiner can normally be reached 1st week Monday-Thursday, 2nd week Monday-Friday. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Lyle Alexander can be reached at (571)272-1254. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. 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If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /ARLEN SODERQUIST/Primary Examiner, Art Unit 1797 Application/Control Number: 18/495,421 Page 2 Art Unit: 1797 Application/Control Number: 18/495,421 Page 3 Art Unit: 1797 Application/Control Number: 18/495,421 Page 4 Art Unit: 1797 Application/Control Number: 18/495,421 Page 5 Art Unit: 1797 Application/Control Number: 18/495,421 Page 6 Art Unit: 1797 Application/Control Number: 18/495,421 Page 7 Art Unit: 1797 Application/Control Number: 18/495,421 Page 8 Art Unit: 1797 Application/Control Number: 18/495,421 Page 9 Art Unit: 1797
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