Odorants for carbon dioxide, odorized carbon dioxide, and methods

Abstract

Odorized fluids comprising a fluid and an odorizing agent are disclosed. Odorizing agents capable of containing sulfur, odorized materials, and methods of odorizing materials such as fluids are disclosed. The fluid can be carbon dioxide. The odorizing agent can comprise a thioether and / or a mercaptan. The odorizing agent can be effective at relatively low concentrations. The odorizing agent can be distinguishable from other commonly used odorizing agents.

Description

Citation of relevant applications

[0001] This application claims the benefit and priority of U.S. Provisional Patent Application No. 63 / 631,506, filed on April 3, 2025, and filed on April 9, 2024, the entire disclosure of which is incorporated herein by reference. Technical Field

[0002] This disclosure relates to odorants for fluids such as carbon dioxide, odorizing fluids, and methods for odorizing fluids such as carbon dioxide. Background Technology

[0003] Many technologies involve capturing and / or storing fluids such as carbon dioxide. In recent years, the amount of carbon dioxide captured and / or stored has increased, thereby increasing exposure risks, particularly when transporting captured and / or stored carbon dioxide through densely populated areas. Carbon dioxide and other gases can cause one or more hazards, such as asphyxiation.

[0004] Various technologies are used to detect gas leaks (such as carbon dioxide), including those relying on infrared cameras, manual inspections, drones, and so on.

[0005] There is still a need for improved methods of odorizing fluids, as well as odorants for fluids, including odorants that are effective at relatively low concentrations, odorants that are olfactorily distinguishable from other widely used odorants, or combinations thereof. Summary of the Invention

[0006] This summary is provided to introduce, in a simplified form, various concepts that will be further described in the following detailed description. This summary is not intended to identify essential or necessary features of the claimed subject matter, nor is it intended to limit the scope of the claimed subject matter.

[0007] In one aspect, odorants are provided, such as odorants for fluids that may contain carbon dioxide. In some embodiments, the odorant comprises one or more sulfides, one or more thiols, or combinations thereof. The one or more sulfides may include diethyl sulfide, dimethyl sulfide, propyl sulfide, tetrahydrothiophene, ethyl methyl sulfide, or combinations thereof. In some embodiments, the one or more thiols are selected from tert-butyl mercaptan, ethyl mercaptan, n-butyl mercaptan, sec-butyl mercaptan, n-propyl mercaptan, 2-propyl mercaptan, etc. β -Mercaptoethanol or combinations thereof.

[0008] On the other hand, odorizing materials, such as odorizing fluids (also referred to as odorizing compositions), are provided. The odorizing fluid may contain odorized carbon dioxide. In some embodiments, the odorizing material comprises a fluid and an odorant dispersed in the fluid. The fluid may contain carbon dioxide. The odorant may contain one or more sulfides, one or more thiols, or combinations thereof. The odorant may be present in the odorizing material in any effective amount, including but not limited to about 1 part per trillion to about 0.1% by weight or a concentration of about 1 part per trillion to about 100 parts per million.

[0009] In another aspect, odorization methods are provided, such as methods for odorizing a fluid, which may contain carbon dioxide. In some embodiments, these methods include providing a fluid, and contacting the fluid with an odorant to produce odor. The provision of the fluid may include a capture fluid, a storage fluid, or a combination thereof.

[0010] Additional aspects will be set forth in part in the description which follows, and in part will be apparent from the description, or may be learned by practicing the aspects described herein. The advantages described herein can be realized and obtained by the elements and combinations particularly pointed out in the appended claims. It should be understood that the foregoing general description and the following detailed description are exemplary and explanatory only, and not restrictive.

[0011] definition To more clearly define the terms used herein, the following definitions are provided. Unless otherwise specified, the following definitions apply to this disclosure. If a term is used in this disclosure but is not specifically defined herein, the definition in the IUPAC Compendium of Chemical Terminology, 2nd Edition (1997) may be applied, provided that the definition does not conflict with any other disclosure or definition applied herein, or render any claim to which the definition is applied ambiguous or invalid. If any definition or usage provided in any document incorporated herein by reference conflicts with the definition or usage provided herein, the definition or usage provided herein shall prevail.

[0012] Because various features of the subject matter of this disclosure have been described, one or more combinations of different features can be contemplated within a particular aspect. For each aspect of each feature disclosed herein, all combinations are considered, whether or not a particular combination is explicitly described, provided they do not adversely affect the design, composition, system, process, or method described herein. Therefore, unless expressly stated to the contrary, any aspect of the features disclosed herein can be combined to describe and disclose an inventive design, composition, system, process, or method consistent with the entire disclosure.

[0013] Although compositions and methods are described as “comprising” various components or steps, they may also be described as “consisting substantially of various components or steps” or “component of various components or steps” unless otherwise stated.

[0014] Unless otherwise specified, the terms “including,” “with,” and “having” as used herein are defined as encompassing (i.e., open-ended language).

[0015] The terms “a / an” and “described” are intended to include plural alternatives, such as at least one / an. For example, unless otherwise stated, the disclosure of “fluid,” “sulfide,” etc., means to cover one or more of the fluid, sulfide, etc., or mixtures or combinations thereof.

[0016] This document discloses various numerical ranges. When an applicant discloses or claims protection for any type of range, unless otherwise stated, the applicant intends to individually disclose or claim protection for every possible number that such range can reasonably cover, including the endpoints of the range and any subranges and combinations thereof covered therein. For example, by disclosing a ratio of about 45:55 to about 55:45, the applicant intends to individually list 45:55, 46:54, 47:53, 48:52, 49:51, 50:50, 51:49, 52:48, 53:57, 54:46, and 55:45, including any subranges and combinations thereof covered therein, and these methods of describing such ranges are interchangeable. Furthermore, all numerical endpoints of the ranges disclosed herein are approximate unless excluded by attached conditions. As a representative example, if the applicant states that one or more steps in the process disclosed herein can be performed at temperatures ranging from 10°C to 75°C, unless otherwise stated, this range should be interpreted as covering temperatures ranging from “about” 10°C to “about” 75°C.

[0017] Values ​​or ranges herein may be expressed as “about,” from “about” a specific value, and / or to “about” another specific value. When expressing such values ​​or ranges, other disclosed embodiments include the specific value, from one specific value, and / or to another specific value. Similarly, when a value is expressed as an approximation using the antecedent “about,” it should be understood that the specific value forms another embodiment. It should be further understood that numerous values ​​are disclosed herein, and each value, in addition to being stated as the value itself, is also disclosed herein as “about” the specific value. On the other hand, each use of the term “about” may independently represent ±20% of the value, ±15% of the value, ±10% of the value, ±5% of the value, or ±3% of the value.

[0018] Thus, if an applicant chooses for any reason to claim less than the full measure of what is disclosed, for example, to take into account references that the applicant can not have known at the time of filing the application, the applicant reserves the right to specify or exclude any individual member of any such group of values or ranges of values (including any sub-range or combination of sub-ranges within the group) that can be claimed, according to the scope or in any similar manner. Moreover, if an applicant chooses for any reason to claim less than the full measure of what is disclosed, for example, to take into account references that the applicant can not have known at the time of filing the application or prior disclosures, the applicant reserves the right to specify or exclude any individual substituent, analog, compound, ligand, structure, or group thereof, or any member of a claimed group.

[0019] For any particular compound or group disclosed herein, unless otherwise specified, any name or structure presented (general or specific) is intended to encompass all conformational isomers, regioisomers, stereoisomers, and mixtures thereof that can arise from a particular set of substituents. Unless otherwise indicated, the name or structure also encompasses all enantiomers, diastereomers, and other optical isomers (if any), whether in enantiomeric or racemic forms, as well as mixtures of stereoisomers, as known to one of skill in the art. For example, general reference to a “C6alkane,” “hexane,” or “hexanes” includes n-hexane, 2-methylpentane, 3-methylpentane, 2,2-dimethylbutane, and 2,3-dimethylbutane; and general reference to a “C4alkyl” or “butyl” includes n-butyl, sec-butyl, iso-butyl, and t-butyl.

[0020] When used to describe a group, for example, when referring to a substituted analog of a particular group, the term “substituted” is intended to describe a compound or group in which any non-hydrogen moiety formally replaces a hydrogen in the group or compound, and is intended to be non-limiting. A compound or group can also be referred to herein as “unsubstituted” or an equivalent term such as “non-substituted,” referring to the original group or compound. “Substituted” is intended to be non-limiting and includes inorganic substituents or organic substituents, as specified and understood by one of ordinary skill in the art.

[0021] The terms "contact product," "contacting," and the like are used herein to describe compositions and methods in which components are contacted together in any order, in any manner, and for any length of time, unless otherwise specified. For example, components can be contacted by blending or mixing. Further, unless otherwise specified, contacting of any component can occur in the presence or absence of any other component of the compositions and methods described herein. Additional materials or components can be combined by any suitable method. Further, the term "contact product" includes mixtures, blends, solutions, slurries, reaction products, and the like, or combinations thereof. Although "contact product" can and often does include reaction products, it is not required that the individual components react with one another. Similarly, "contacting" two or more components can result in a reaction product or reaction mixture. Thus, depending on the circumstances, the "contact product" can be a mixture, a reaction mixture, or a reaction product.

[0022] The term "alkyl" is used herein according to the definition specified by IUPAC: a monovalent radical formed by the removal of one hydrogen atom from an alkane. Unless otherwise indicated, alkyl groups can be straight or branched.

[0023] "Cycloalkane" as used herein is a saturated cyclic hydrocarbon with or without side chains, such as cyclobutane, cyclopentane, cyclohexane, methylcyclopentane, and methylcyclohexane. Other designators can be used to indicate the presence of particular groups in the cycloalkane, if any (e.g., halogenated cycloalkane indicates the presence of one or more halogen atoms replacing an equivalent number of hydrogen atoms in the cycloalkane).

[0024] The term "hydrocarbyl" is used herein according to the definition specified by IUPAC: a monovalent radical formed by the removal of one hydrogen atom from a hydrocarbon (i.e., a group containing only carbon and hydrogen). Thus, hydrocarbyl groups include alkyl (straight chain or branched), cycloalkyl, alkenyl, aryl, and the like. Non-limiting examples of hydrocarbyl groups include methyl, ethyl, butyl, hexyl, phenyl, tolyl, propenyl, and the like.

[0025] The term "independently" when used herein in reference to the selection of substituents indicates that two differently labeled substituents selected from the same group of substituents, e.g., R 1 and R 2 may be the same or different.

[0026] The abstract of the present application is not intended to interpret the scope of the claims or the scope of subject matter disclosed herein, but is provided merely for purposes of summarizing the technical disclosures made in order to comply with 37 C.F.R. § 1.72(b) to enable the United States Patent and Trademark Office and the public generally to quickly determine the nature and gist of the technical disclosures. Moreover, no title herein is intended to serve as an interpretation of the scope of the claims or the scope of subject matter disclosed herein.

[0027] All publications mentioned herein are incorporated herein by reference to describe and disclose, for example, constructs and methods described in the publications that can be used in connection with the presently described application. The publications discussed throughout this document are provided solely for their disclosure prior to the filing date of the present application. Nothing herein is to be construed as an admission that the inventors are not entitled to antedate such disclosure by virtue of prior application.

[0028] Those skilled in the art will readily recognize a number of modifications which can be made to the example embodiments disclosed herein without materially departing from the novel teachings and advantages of the disclosure according to this disclosure. Accordingly, all such modifications are intended to be included within the scope of the disclosure as defined in the following claims. The disclosures of patents and other publications are provided solely for their disclosure prior to the filing date of the present application. Nothing herein is to be construed as an admission that the inventors are not entitled to antedate such disclosure by virtue of prior application. DETAILED DESCRIPTION

[0029] The present disclosure relates to odorants, methods of making odorants, and methods of odorizing materials, such as fluids, which can include carbon dioxide.

[0030] Odorants Odorants of the present disclosure can include one or more sulfides, one or more thiols, or a combination thereof. For example, an odorant can include (i) one sulfide, (ii) two different sulfides, (iii) one sulfide and one thiol, (iv) one sulfide and two different thiols, (v) two different sulfides and one thiol, (vi) one thiol, (vii) two different thiols, and so on. The one or more sulfides and the one or more thiols can include any of those known in the art and / or any of those provided herein.

[0031] Odorants can include sulfur in any total amount. For example, sulfur can be present in a total concentration of about 20 wt% to about 60 wt%, about 30 wt% to about 50 wt%, or about 35 wt% to about 45 wt%, based on the total weight of the odorant, such as the total weight of the one or more sulfides and the one or more thiols.

[0032] Sulfides and thiols In some embodiments, the one or more sulfides of the odorant include one or more compounds of Formula (I) and / or Formula (II), and the one or more thiols include one or more compounds of Formula (III): Formula (I); Formula (II); Equation (III); Where R 1 R 2 R 3 and R 4 Independently selected from unsubstituted or substituted C1-C 10 Hydrocarbon groups, of which R 3 Independent selection of unsubstituted or substituted C1-C 10 The hydrocarbon group is divalent; or R is present in the hydrocarbon group. 1 R 2 R 3 and R 4 Independently selected from unsubstituted or substituted C1-C 10 Alkyl groups, wherein the alkyl group is relative to R 3 Independent selection of unsubstituted or substituted C1-C 10 Alkyl groups are divalent.

[0033] In some implementation schemes, R 1 R 2 R 3 Or R 4 At least one of them is independently C1-C8 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl, or C2 alkyl. 1 R 2 R 3 Or R 4 At least one of them can be a straight-chain unsubstituted or substituted C1-C 10 Alkyl, or branched unsubstituted or substituted C1-C 10 Alkyl group. In some embodiments, R 1 R 2 R 3 Or R 4 At least one of them is independently replaced by a hydroxyl group.

[0034] Each of the compounds of formula (I), formula (II), and / or formula (III) may independently be present in the odorant in any effective amount. In some embodiments, each of the compounds of formula (I), formula (II), and / or formula (III) is present in the odorant in an amount of at least 0.1% by weight, at least 1% by weight, at least 5% by weight, at least 10% by weight, at least 20% by weight, at least 30% by weight, at least 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, or at least 90% by weight, based on the weight of the odorant.

[0035] One or more sulfides may include any one or more of the following sulfides:

[0036] One or more thiols may include any or more of the following thiols:

[0037] In some implementations, the odorant includes diethyl sulfide (DES). β - Mercaptoethanol (BME) or combinations thereof. DES and BME may be present in the odorant in any weight ratio, such as about 10:90 to about 90:10, about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 60:40, about 45:55 to about 55:45, or about 50:50 (DES:BME).

[0038] In some embodiments, the odorant includes dimethyl sulfide (DMS), tert-butyl mercaptan (TBM), or combinations thereof. DMS and TBM may be present in the odorant in any weight ratio, such as about 10:90 to about 90:10, about 20:80 to about 80:20, about 25:75 to about 75:25, about 30:70 to about 70:30, about 40:60 to about 60:40, about 45:55 to about 55:45, or about 50:50 (DMS:TBM).

[0039] Sterilizing materials This disclosure also provides odorizing materials (or compositions). The odorizing materials may comprise a fluid (such as carbon dioxide) and any odorant provided herein. The odorant may be dispersed (e.g., uniformly or non-uniformly) in the fluid.

[0040] The odorizing material can be any fluid (such as carbon dioxide) and in any phase (i.e., liquid, gas, etc.). The fluid can be a supercritical fluid.

[0041] Odorants can be present in the odorized material in any effective amount, such as amounts detectable by a person with a normal sense of smell. In some embodiments, the odorant is present in the odorized material at concentrations of: about 1 part per trillion to about 0.1 wt%, about 1 part per trillion to about 0.08 wt%, about 1 part per trillion to about 0.06 wt%, about 1 part per trillion to about 0.04 wt%, about 1 part per trillion to about 0.02 wt%, about 1 part per trillion to about 100 parts per million, about 100 parts per trillion to about 100 parts per million, about 1,000 parts per trillion to... About 100 parts per million, about 10,000 parts per trillion to about 100 parts per million, about 100,000 parts per trillion to about 100 parts per million, about 1 part per million to about 100 parts per million, about 10 parts per million to about 100 parts per million, about 20 parts per million to about 100 parts per million, about 30 parts per million to about 100 parts per million, about 40 parts per million to about 100 parts per million, or about 50 parts per million to about 100 parts per million (by weight).

[0042] Methods of adding odor This document also provides methods for odorizing materials such as fluids (e.g., carbon dioxide). These methods may include providing a fluid and contacting the fluid with an odorant (such as the odorant provided herein) to produce an odorized material.

[0043] The provision of fluids may include capture fluids, storage fluids, or combinations thereof. Fluids may be captured using any known technology or equipment, such as those known for capturing carbon. Fluid capture may include post-combustion carbon capture processes, pre-combustion carbon capture processes, or oxy-fuel combustion processes.

[0044] Before, during, and / or after the methods provided herein, fluids and / or odorized materials may be pressurized, stored, and / or transported.

[0045] Contact between the fluid and the odorant can be achieved in any manner using any known technology or equipment. One or both of the fluid and the odorant may be pressurized and / or supplied in a stream form before, during, and / or after contact with the odorant. Before, during, and / or after contact with the odorant, the odorant may be in a liquid phase, a gas phase, or a combination thereof. Therefore, contact between the fluid and the odorant may include dispensing the odorant using a liquid metering device. The liquid metering device can achieve a desired concentration of the odorant present in the odorized material. Contact between the fluid and the odorant may include atomizing the odorant.

[0046] The provision of the fluid may include providing a container in which the fluid is disposed. When the fluid is present in the container, contact between the fluid and the odorant may include disposing of the odorant in the container, such as by means of a liquid meter or other device.

[0047] In some embodiments, the provision of the fluid includes providing a first flow containing the fluid, and contact between the fluid and the odorant may include contacting the first flow and a second flow containing the odorant.

[0048] Example This disclosure is further illustrated by the following embodiments, which should not be construed as limiting the scope of the technology in any way. After reading this description, various other aspects, embodiments, modifications, and equivalents will arise in those skilled in the art without departing from the spirit of this disclosure or the scope of the appended claims.

[0049] Example 1 Odor evaluation group characterization One drop of each odorant was placed on a cotton swab, which was then placed inside a wafted glass bottle. Each expert panel member assessed the odor intensity of each odorant on a scale from 1 (very weak) to 10 (very strong) and provided a brief description of the odor. The results indicated that diethyl sulfide had a relatively high odor intensity and a distinct odor description compared to dimethyl sulfide and tetrahydrothiophene.

[0050] Odor evaluations were conducted in a randomized order, and between tests of each odorant, a dedicated team member smelled ground coffee in a sealed container to establish an olfactory baseline.

[0051] The results of this embodiment are provided in the table below. The odorant abbreviations in the table are as follows: tetrahydrothiophene (THT), isopropyl mercaptan (IPM), diethyl sulfide (DES), ethyl mercaptan (EM), n-propyl mercaptan (NPM), n-butyl mercaptan (NBM), dimethyl sulfide (DMS), and tert-butyl mercaptan (TBM).

[0052] Example 2 Preparation of odorant In this embodiment, a series of odorants were prepared, which contained the following components and sulfur content:

[0053] A series of odorants were also prepared, in which dimethyl sulfide in samples 1-5 in the table above was replaced with diethyl sulfide.

[0054] Example 3 Odor detection threshold study In this embodiment, an odor detection threshold study was conducted for diethyl sulfide (DES) in carbon dioxide. This embodiment involved mixing carbon dioxide and DES in air to determine the concentration of DES that could be detected by an odor assessment expert panel.

[0055] The table below provides the research parameters and results for this embodiment.

[0056] In this embodiment, carbon dioxide was added to the air at 1,000 ppm (which is 20% of the 8-hour TWA exposure limit established by OSHA). DES was also introduced into the mixture at concentrations from zero up to those detectable by members of the expert panel. In this embodiment, it was found that in a mixture with 1,000 ppm carbon dioxide in the air, all members of the expert panel could statistically detect 500 ppb (0.5 ppm) of DES.

[0057] Calculations were performed to determine the appropriate concentration of DES in the liquid carbon dioxide so that, if the mixture were released into the atmosphere and evaporated, the DES concentration would be 500 ppb when the carbon dioxide concentration in the air reaches 1,000 ppm. This calculation was performed because carbon dioxide is typically transported via pipelines while in a liquid state.

[0058] When performing this calculation, the DES concentration was determined to be as high as approximately 0.1% by weight in liquid carbon dioxide, which is significantly higher than the concentrations required for some other odorants, such as natural gas odorants. This difference is believed to be related not only to the detection threshold but also to the density of carbon dioxide in liquid form.

[0059] aspect The following are the non-restrictive aspects: Aspect 1. An odorant for fluids such as carbon dioxide, said odorant comprising, substantially comprising, or comprising of one or more thioethers, one or more thiols, or combinations thereof.

[0060] Aspect 2. The odorant as described in Aspect 1, wherein the one or more thioethers comprise, are substantially composed of, or are composed of, compounds of formula (I) and / or formula (II), and the one or more thiols comprise, are substantially composed of, or are composed of, the compounds of formula (III): Formula (I); Equation (II); Equation (III); Where R 1 R 2 R 3 and R4 Independently selected from unsubstituted or substituted C1-C 10 Hydrocarbon groups, of which R 3 Independent selection of the unsubstituted or substituted C1-C 10 The hydrocarbon group is divalent; or Where R 1 R 2 R 3 and R 4 Independently selected from unsubstituted or substituted C1-C 10 Alkyl groups, wherein the alkyl group is relative to R 3 Independent selection of the unsubstituted or substituted C1-C 10 Alkyl groups are divalent.

[0061] Aspect 3. The odorant as described in any of the preceding aspects, wherein sulfur is present at a total concentration of about 20% to about 60% by weight, about 30% to about 50% by weight, or about 35% to about 45% by weight, based on the total weight of the odorant, such as the total weight of the one or more thioethers and the one or more thiols.

[0062] Aspect 4. The odorant as described in any of the preceding aspects, wherein R 1 R 2 R 3 Or R 4 At least one of them is independently C1-C8 alkyl, C1-C6 alkyl, C1-C5 alkyl, C1-C4 alkyl, C1-C3 alkyl or C2 alkyl.

[0063] Aspect 5. The odorant as described in any of the preceding aspects, wherein R 1 R 2 R 3 Or R 4 At least one of them is independently a straight-chain unsubstituted or substituted C1-C 10 alkyl.

[0064] Aspect 6. The odorant as described in any of the preceding aspects, wherein R 1 R 2 R 3 Or R 4 At least one of them is independently a branched, unsubstituted or substituted C1-C 10 alkyl.

[0065] Aspect 7. The odorant as described in any of the preceding aspects, wherein R 1 R 2 R 3 Or R 4 At least one of them is independently replaced by a hydroxyl group.

[0066] Aspect 8. The odorant as described in any of the preceding aspects, wherein the one or more sulfides comprise one or more of the following, consist substantially of one or more of the following, or consist of one or more of the following:

[0067] Aspect 9. The odorant as described in any of the preceding aspects, wherein said one or more thiols comprise one or more of the following, consist substantially of one or more of the following, or consist of one or more of the following:

[0068] Aspect 10. The odorant as described in any of the preceding aspects, wherein the odorant comprises, is substantially composed of, or is composed of diethyl sulfide (DES). β -Mercaptoethanol (BME) or combinations thereof.

[0069] Aspect 11. The odorant as described in aspect 10, wherein the DES and the BME are present in a weight ratio (DES:BME) of about 10:90 to about 90:10, about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 60:40, about 45:55 to about 55:45, or about 50:50.

[0070] Aspect 12. The odorant as described in any of the preceding aspects, wherein the odorant comprises, is substantially composed of, or is composed of dimethyl sulfide (DMS), tert-butyl mercaptan (TBM), or a combination thereof.

[0071] Aspect 13. The odorant as described in aspect 12, wherein the dimethyl sulfide and the tert-butyl mercaptan are present in a weight ratio (DMS:TBM) of about 10:90 to about 90:10, about 20:80 to about 80:20, about 25:75 to about 75:25, about 30:70 to about 70:30, about 40:60 to about 60:40, about 45:55 to about 55:45, or about 50:50.

[0072] Aspect 14. The odorant as described in any of the preceding aspects, wherein each of the compounds of formula (I), formula (II) and / or formula (III) is present in the odorant independently in an amount of at least 0.1% by weight, at least 1% by weight, at least 5% by weight, at least 10% by weight, at least 20% by weight, at least 30% by weight, at least 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, or at least 90% by weight, based on the weight of the odorant.

[0073] Aspect 15. An odorant material (or composition) comprising, substantially consisting of, or consisting of: a fluid, such as carbon dioxide; and an odorant as described in any one of Aspects 1 to 14.

[0074] Aspect 16. The odorant material as described in any of the preceding aspects, wherein the odorant is dispersed (e.g., uniformly or non-uniformly) in the fluid.

[0075] Aspect 17. The odorizing material as described in any of the preceding aspects, wherein the odorizing agent is present in the odorizing material at the following concentrations: about 1 part per trillion to about 0.1 wt%, about 1 part per trillion to about 0.08 wt%, about 1 part per trillion to about 0.06 wt%, about 1 part per trillion to about 0.04 wt%, about 1 part per trillion to about 0.02 wt%, about 1 part per trillion to about 100 parts per million, about 100 parts per trillion to about 100 parts per million, about 100 parts per trillion 1,000 to about 100 parts per million, about 10,000 to about 100 parts per million, about 100,000 to about 100 parts per million, about 1 to about 100 parts per million, about 10 to about 100 parts per million, about 20 to about 100 parts per million, about 30 to about 100 parts per million, about 40 to about 100 parts per million, or about 50 to about 100 parts per million (by weight).

[0076] Aspect 18. The odorizing material as described in any of the preceding aspects, wherein the fluid is a gas.

[0077] Aspect 19. The odorizing material as described in any of the preceding aspects, wherein the fluid is a supercritical fluid.

[0078] Aspect 20. An odorization method comprising, substantially comprising, or comprising: providing a fluid, and contacting the fluid with an odorant as described in any of the preceding aspects to generate an odorized material, such as an odorized material as described in any of the preceding aspects.

[0079] Aspect 21. The method of any of the preceding aspects, wherein the provision of the fluid comprises capturing the fluid.

[0080] Aspect 22. The method of aspect 21, wherein the capture of the fluid comprises a post-combustion carbon capture process, a pre-combustion carbon capture process, or an oxygen fuel combustion process.

[0081] Aspect 23. The method of any of the preceding aspects, wherein the fluid comprises, is substantially composed of, or is composed of carbon dioxide.

[0082] Aspect 24. The method as described in any of the preceding aspects, further comprising pressurizing the fluid and / or the odorizing material, storing the fluid and / or the odorizing material, or a combination thereof.

[0083] Aspect 25. The method of any of the preceding aspects, wherein the odorant is in a liquid phase, a gas phase, or a combination thereof before, during, and / or after the contact between the fluid and the odorant.

[0084] Aspect 26. The method of any of the preceding aspects, wherein the contact between the fluid and the odorant comprises dispensing the odorant using a liquid meter.

[0085] Aspect 27. The method of any of the preceding aspects, wherein the contact between the fluid and the odorant comprises atomizing the odorant.

[0086] Aspect 28. The method of any of the preceding aspects, wherein the contact between the fluid and the odorant disperses the odorant (e.g., uniformly or non-uniformly) in the fluid.

[0087] Aspect 29. The method of any of the preceding aspects, wherein the provision of the fluid includes providing a container in which the fluid is disposed.

[0088] Aspect 30. The method of aspect 29, wherein the contact between the fluid and the odorant comprises placing the odorant in the container.

[0089] Aspect 31. The method of any of the preceding aspects, wherein the provision of the fluid comprises providing a first flow containing the fluid.

[0090] Aspect 32. The method of aspect 31, wherein the contact between the fluid and the odorant comprises contacting the first flow and a second flow containing the odorant.

Claims

1. An odor-enhancing material comprising: Fluids containing carbon dioxide; and An odorant dispersed in the fluid, the odorant comprising one or more sulfides, one or more thiols, or combinations thereof; wherein: The odorant is present in the odorized material at a concentration of about 1 part per trillion (by weight) to about 0.1% by weight.

2. The odorizing material as claimed in claim 1, wherein the odorizing agent comprises diethyl sulfide.

3. The odorizing material as claimed in claim 1, wherein the odorizing agent comprises diethyl sulfide, dimethyl sulfide, propyl sulfide, tetrahydrothiophene, ethyl methyl sulfide, or combinations thereof.

4. The odorizing material of claim 1, wherein the odorizing agent comprises (a) diethyl sulfide and (b) dimethyl sulfide, propyl sulfide, tetrahydrothiophene, ethyl methyl sulfide or a mixture thereof.

5. The odorizing material of claim 1, wherein the one or more sulfides comprise one or more compounds of formula (I) and / or formula (II): Equation (I); Equation (II); Where R 1 R 2 and R 3 Independently selected from unsubstituted or substituted C1-C 10 Alkyl groups, wherein the alkyl group is relative to R 3 Independent selection of the unsubstituted or substituted C1-C 10 Alkyl groups are divalent.

6. The odorizing material of claim 1, wherein the one or more thiols comprise one or more compounds of formula (III): Equation (III); Where R 4 Selected from unsubstituted or substituted C1-C 10 alkyl.

7. The odorizing material as described in claim 6, wherein R 4 It is replaced by a hydroxyl group.

8. The odorizing material as claimed in claim 1, wherein the odorizing agent comprises tert-butyl mercaptan, ethyl mercaptan, n-butyl mercaptan, sec-butyl mercaptan, n-propyl mercaptan, 2-propyl mercaptan, β -Mercaptoethanol or combinations thereof.

9. The odorizing material as claimed in claim 1, wherein the odorizing agent comprises diethyl sulfide, β -Mercaptoethanol or combinations thereof.

10. The odor-enhancing material of claim 9, wherein the diethyl sulfide and the β - Diethyl sulfide in a ratio of approximately 10:90 to approximately 90:10: mercaptoethanol β -Mercaptoethanol exists in a weight ratio.

11. The odorizing material of claim 1, wherein the odorizing agent comprises dimethyl sulfide, tert-butyl mercaptan, or a combination thereof.

12. The odorizing material of claim 11, wherein the dimethyl sulfide and the tert-butyl mercaptan are present in a weight ratio of about 10:90 to about 90:10 of dimethyl sulfide:tert-butyl mercaptan.

13. The odorizing material according to any one of claims 1 to 12, wherein the odorizing agent is present in the odorizing material at the following concentrations: about 1 part per trillion to about 0.08 wt%, about 1 part per trillion to about 0.06 wt%, about 1 part per trillion to about 0.04 wt%, about 1 part per trillion to about 0.02 wt%, about 1 part per trillion to about 100 parts per million, about 100 parts per trillion to about 100 parts per million, about 1,000 parts per trillion to about 100 parts per million, about 10,000 parts per trillion to about 100 parts per million, about 100,000 parts per trillion to about 100 parts per million, about 1 part per million to about 100 parts per million, about 10 parts per million to about 100 parts per million, about 20 parts per million to about 100 parts per million, about 30 parts per million to about 100 parts per million, about 40 parts per million to about 100 parts per million, or about 50 parts per million to about 100 parts per million. (by weight) 14. A method for adding odor, the method comprising: Provides a fluid containing carbon dioxide; and The fluid and the odorant are brought into contact to produce an odorized material; The odorant described herein comprises one or more sulfides, one or more thiols, or a combination thereof.

15. The method of claim 14, wherein the provision of the fluid includes capturing the fluid.

16. The method of claim 14 or 15, further comprising pressurizing the odorizing material, storing the odorizing material, or a combination thereof.

17. The method of any one of claims 14 to 16, wherein the odorant is in a liquid phase, a gas phase, or a combination thereof before, during, and / or after the contact between the fluid and the odorant.

18. The method of any one of claims 14 to 17, wherein the contact between the fluid and the odorant comprises dispensing the odorant using a liquid meter.

19. The method of any one of claims 14 to 17, wherein the contact between the fluid and the odorant comprises atomizing the odorant.

20. The method of any one of claims 14 to 19, wherein the provision of the fluid comprises providing a container in which the fluid is disposed, and wherein the contact between the fluid and the odorant comprises disposing of the odorant in the container.

21. The method of any one of claims 14 to 19, wherein the provision of the fluid comprises providing a first flow containing the fluid, and wherein the contact of the fluid with the odorant comprises contacting the first flow and a second flow containing the odorant.

22. The method of any one of claims 14 to 21, wherein the odorizing material is the odorizing material of any one of claims 1 to 13.

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