Method for mitigating conversion of volatile terpene species

Abstract

The conversion of nocaol to nocaene in terpene blends is mitigated or prevented by substantially or completely separating nocaol, such as α-nocaol, from compounds present in the terpene blend that catalyze the chemical reaction of nocaol to nocaene, and / or by at least partially neutralizing compounds present in the terpene blend that catalyze the chemical reaction of nocaol to nocaene. Methods for preparing terpene blends, terpene blends, flavoring compositions containing terpene blends, beverages and foods containing flavoring compositions, flavoring compositions containing terpene blends, and flavored products containing flavoring compositions are also disclosed.

Description

[0001] This application is a divisional application of Chinese invention patent application filed on October 29, 2021, with application number 202180072882.0 and entitled "Method for reducing the conversion of volatile terpenoids". Technical Field

[0002] This disclosure relates to mitigating the conversion of volatile terpenes into undesirable compounds. More specifically, this disclosure relates to methods for mitigating or preventing the conversion of nootkatol to nootkatene, methods for preparing terpene blends, terpene blends, and beverage, food, and flavoring products containing terpene blends. Background Technology

[0003] Nootkatone is a blend of volatile essential oils derived from grapefruit and Alaskan yellowcedar trees. Nootkatone oil blends are commonly used as citrus flavoring agents in food and beverages, and as flavoring ingredients. Regarding food and beverage products, α-nocatol is widely considered a key component in nootkatone oil blends because it contributes to their acceptable sensory properties.

[0004] Nocarbamate-containing terpene blends may also contain fatty acids and other high-boiling-point impurities that catalyze the reaction of nocarbamate to nocarene. Fractional distillation of the nocarbamate-containing terpene blends is necessary to prepare the final commercially viable nocarbone oil blends suitable for sale to consumers. During the fractional distillation process, the nocarbamate-containing terpene blends are heated at elevated temperatures for a sustained period. The elevated temperature triggers the fatty acids and other high-boiling-point impurities present in the terpene blends to catalyze the undesirable reaction of nocarbamate to nocarene. This results in a decrease in the level of nocarbamate and an increase in the level of nocarene in the terpene blend. The decreased nocarbamate level or increased nocarene level alters the flavor characteristics of the nocarbone oil blend, making it unsuitable for current market expectations.

[0005] Nocaenes formed continuously during batch and fractional distillation will contaminate the distillate fraction throughout the distillation process and prevent the production of high-quality terpene blends. The terpene blends desired in the market contain little or no nocaenes. The presence of nocaenes above a certain level in terpene blends will affect sensory properties, consumer satisfaction, and may lead to consumer rejection based on analytical specifications.

[0006] Since some nocarbamate oil blends contain fatty acids and other high-boiling-point impurities that catalyze the undesirable reaction of nocarbamate to nocarene, there is a need in the art to develop methods for processing feedstock nocarbamate oil blends that maintain the desired α-nocarbamate content while minimizing nocarene formation. Summary of the Invention

[0007] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene is provided, comprising providing a feed containing at least one nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, and (i) separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene, or (ii) neutralizing at least a portion of the at least one compound that catalyzes the conversion of nocaol to nocaene.

[0008] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene is provided, comprising providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, and separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene.

[0009] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene is provided, comprising providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, and neutralizing at least a portion of the at least one compound that catalyzes the conversion of nocaol to nocaene.

[0010] According to certain illustrative embodiments, a method for preparing terpene blends is also provided, comprising providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, treating the feed to mitigate or prevent the conversion of nocaol to nocaene, and fractionally distilling a second feed containing nocaol.

[0011] According to certain illustrative embodiments, a method for preparing a terpene blend includes providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, treating the feed to mitigate or prevent the conversion of nocaol to nocaene by (i) separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene to produce a second feed containing nocaol or (ii) neutralizing at least a portion of the at least one compound that catalyzes the conversion of nocaol to nocaene, and fractional distilling the feed or the second feed.

[0012] According to certain illustrative embodiments, a method for preparing a terpene blend includes providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, treating the feed to mitigate or prevent the conversion of nocaol to nocaene by separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene to produce a second feed containing nocaol, and fractionally distilling the second feed containing nocaol.

[0013] According to certain illustrative embodiments, a method for preparing a terpene blend includes providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene, treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compound present in the feed that catalyzes the conversion of nocaol to nocaene, and fractionally distilling the treated feed.

[0014] According to certain embodiments, a terpene blend prepared according to a method comprising: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion of nocaol to nocaene by (i) separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene to produce a second feed containing nocaol; or (ii) neutralizing at least a portion of the at least one compound that catalyzes the conversion of nocaol to nocaene; and fractional distilling the feed or the second feed.

[0015] According to certain embodiments, the terpene blend is prepared by a method comprising: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion of nocaol to nocaene by separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene to produce a second feed containing nocaol; and fractionating the second feed by distillation.

[0016] According to certain illustrative embodiments, the terpene blend is prepared by a method comprising: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compound present in the feed that catalyzes the conversion of nocaol to nocaene; and fractionally distilling the treated feed.

[0017] According to certain illustrative embodiments, a beverage or food comprising a beverage or food base and a terpene blend is provided, the terpene blend being prepared by: treating a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene to mitigate or prevent the conversion of nocaol to nocaene, and fractional distilling the feed.

[0018] According to certain illustrative embodiments, a beverage or food comprises a beverage or food base and a terpene blend, the terpene blend being prepared by: treating a feed containing nocaol and at least one compound catalyzing the conversion of nocaol to nocaene by separating at least a portion of nocaol from a compound in the feed that catalyzes the conversion of nocaol to nocaene to produce a second feed containing nocaol, thereby mitigating or preventing the conversion of nocaol to nocaene; and fractionating the second feed by distillation.

[0019] According to certain illustrative embodiments, a beverage or food comprises a beverage or food base and a terpene blend, the terpene blend being prepared by: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compound present in the feed that catalyzes the conversion of nocaol to nocaene; and fractionating the treated feed by distillation.

[0020] Also disclosed are flavor compositions comprising a terpene blend prepared according to the method of the present disclosure and a flavor base.

[0021] Food or beverage products comprising terpene blends prepared according to the methods of this disclosure, or flavoring compositions comprising said terpene blends and flavoring product bases, are also disclosed.

[0022] The method for preparing food or beverage products is also disclosed, which includes mixing a terpene blend or a flavoring composition containing a terpene blend prepared according to the method of the present disclosure with a food or beverage product base.

[0023] According to certain illustrative embodiments, the fragrance product comprises a fragrance product base and a terpene blend, which is prepared by treating a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene to mitigate or prevent the conversion of nocaol to nocaene, and by fractional distillation of the treated feed.

[0024] According to certain illustrative embodiments, the fragrance product comprises a fragrance product base and a terpene blend, which is prepared by: treating a feed containing nocaol and at least one compound catalyzing the conversion of nocaol to nocaene by separating at least a portion of nocaol from a catalyst compound in the feed that catalyzes the conversion of nocaol to nocaene to produce a second feed containing nocaol; and fractional distilling the second feed.

[0025] According to certain illustrative embodiments, the fragrance product comprises a fragrance product base and a terpene blend, which is prepared by: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compound present in the feed that catalyzes the conversion of nocaol to nocaene; and fractionally distilling the treated feed.

[0026] Also disclosed are fragrance compositions comprising a terpene blend prepared according to the method of this disclosure and a fragrance base.

[0027] The disclosure also discloses flavored products comprising terpene blends prepared according to the methods of this disclosure, or flavor compositions comprising said terpene blends and flavor product bases.

[0028] The method for preparing a flavored product is also disclosed, which includes mixing a terpene blend or a fragrance composition containing a terpene blend prepared according to the method of this disclosure with a fragrance product base.

[0029] The use of terpene blends as flavorings in flavored products is also provided, said terpene blends being prepared by treating a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene to mitigate or prevent the conversion of nocaol to nocaene, and by fractional distillation of the treated feed.

[0030] According to certain illustrative embodiments, the use of terpene blends as flavorings in flavored products is provided, said terpene blends being prepared by: treating a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene by separating at least a portion of nocaol from a catalyst compound in the feed to produce a second feed containing nocaol, thereby mitigating or preventing the conversion of nocaol to nocaene; and fractional distilling the second feed.

[0031] According to certain illustrative embodiments, the use of terpene blends as flavoring agents in beverages or food products is provided, said terpene blends being prepared by: treating a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene by separating at least a portion of nocaol from a catalyst compound in the feed to produce a second feed containing nocaol, thereby mitigating or preventing the conversion of nocaol to nocaene; and fractional distilling the second feed.

[0032] According to certain illustrative embodiments, the use of terpene blends as flavorings in flavored products is provided, said terpene blends being prepared by: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compound present in the feed that catalyzes the conversion of nocaol to nocaene; and fractionally distilling the treated feed.

[0033] According to certain illustrative embodiments, the use of terpene blends as flavoring agents in beverages or food products is provided, said terpene blends being prepared by: providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; treating the feed to mitigate or prevent the conversion by neutralizing at least a portion of the compound present in the feed that catalyzes the conversion of nocaol to nocaene; and fractionating the treated feed by distillation. Detailed Implementation

[0034] The raw material terpene blend may contain nocarboxyl. As used herein, the term "nocarboxyl" includes α-nocarboxyl and β-nocarboxyl. According to some embodiments, the raw material terpene blend includes at least one nocarboxyl. According to an illustrative embodiment, the raw material terpene blend contains α-nocarboxyl. According to other illustrative embodiments, the raw material terpene blend contains β-nocarboxyl. According to yet another illustrative embodiment, the raw material terpene blend contains both α-nocarboxyl and β-nocarboxyl.

[0035] Nocaol-containing terpene blends may also contain acid compounds and other high-boiling-point impurities, which catalyze the reaction of nocaol to nocaene at elevated temperatures utilized in typical fractional distillation of the terpene blends to prepare nocaketone blends for use as flavoring or fragrance ingredients. A method for mitigating or preventing the conversion of nocaol to nocaene during high-temperature fractional distillation of nocaol-containing terpene blends, typically prior to fractional distillation, is disclosed, reducing the amount of nocaene formed during fractional distillation to a commercially acceptable level.

[0036] According to certain embodiments, the raw material terpene blend used in the method according to this disclosure contains at least α-nocarboxol and at least one compound or molecule catalyzing the chemical reaction from α-nocarboxol to nocarene. According to certain illustrative embodiments, the raw material terpene blend may contain more than one nocarboxol, such as a mixture of α-nocarboxol and β-nocarboxol, and at least one compound or molecule catalyzing the chemical reaction from α-nocarboxol to nocarene. According to further illustrative embodiments, the raw material blend may contain α-nocarboxol, β-nocarboxol, β,γ-nocarbone, nocarene, nocarbone, and valenene, and at least one compound or molecule catalyzing the chemical reaction from α-nocarboxol to nocarene.

[0037] According to certain embodiments, the feedstock terpene blend can be prepared by microbial fermentation using suitable microorganisms capable of performing fermentation processes to produce a terpene blend containing at least one nocaol. This disclosure is not limited to the use of terpene blends prepared by microbial fermentation, and the feedstock blend may contain nocaol already extracted from grapefruit, Alaskan cypress, vetiver, or a composition containing a sesquiterpene substrate such as valenene, which can be oxidized to nocaol by any oxidation method including but not limited to chemical oxidation, enzymatic oxidation, or whole-cell biotransformation. Methods for the enzymatic oxidation of sesquiterpene substrates to oxidized sesquiterpenes (e.g., to nocaol and / or nocaconone) are disclosed in WO 2016 / 029187 and WO 2016 / 029153, both of which are hereby incorporated by reference.

[0038] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene includes separating a portion of the nocaol present in the feed (such as a feed containing a blend of raw material terpenes) from one or more compounds that are also present in the material feed and catalyze the chemical conversion of nocaol to nocaene.

[0039] According to certain illustrative embodiments, methods for mitigating or preventing the conversion of nocaol to nocaene include neutralizing acidic compounds present in terpene blends or feeds containing nocaol that catalyze the chemical conversion of nocaol to nocaene.

[0040] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene includes neutralizing an acidic compound present in a terpene blend containing nocaol that catalyzes the chemical conversion of nocaol to nocaene, and subsequently separating a portion of the nocaol from the remaining compound that catalyzes the chemical conversion of nocaol to nocaene.

[0041] According to the method of the present invention for mitigating or preventing the conversion of nocaol to nocaene, nocaol is separated from or neutralized with one or more compounds that catalyze the reaction from nocaol to nocaene in a shorter time period and at a lower temperature than that obtainable by fractional distillation of a nocaol-containing feedstock terpene blend.

[0042] The desired terpene (including α-nocarol) is separated from or neutralized from the catalyst compounds catalyzing the conversion of nocarol to nocarene, such that the terpene blend can be fractionally distilled at elevated temperatures for an extended period of time without substantially losing the total amount of nocarol recovered from the fractional distillation process. According to certain illustrative embodiments, the treatment step of separating or neutralizing the desired terpene from or neutralizing the catalyst compounds present in the feed terpene blend reduces the loss of the total amount of nocarol recovered after fractional distillation to 10% by weight or less, compared to the expected recovery of nocarol after fractional treatment without first performing the disclosed treatment step.

[0043] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene includes separating at least a portion of nocaol and other desired terpenes present in a terpene feed containing a terpene blend from one or more compounds present in the terpene feed containing a terpene blend that catalyze the conversion of nocaol to nocaene.

[0044] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene includes providing a feed containing nocaol, other desired terpene substances, and at least one compound that catalyzes the conversion of nocaol to nocaene. At least a portion of the nocaol present in the terpene feed is separated from the at least one compound that catalyzes the conversion of nocaol to nocaene and further processed.

[0045] According to certain illustrative embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene includes providing a feed containing a blend of terpenes (including nocaol), other desired terpenes, and at least one compound that catalyzes the conversion of nocaol to nocaene. At least a portion of the nocaol and at least a portion of the other desired terpenes present in the terpene feed are separated from at least one compound that catalyzes the conversion of nocaol to nocaene.

[0046] According to certain illustrative embodiments, one or more compounds present in the feed material that catalyze the conversion of nocaol to nocaene comprise at least one acid. The acid may comprise any acid-containing molecule that catalyzes the conversion of nocaol to nocaene. The acid includes inorganic (mineral) acids and organic acids. According to certain embodiments, the acid catalyzing the conversion of nocaol to nocaene comprises a fatty acid. For example, but not limited to, the fatty acid may comprise a carboxylic acid and a hydrocarbon tail having 2 to 28 carbon atoms. The hydrocarbon tail may be straight-chain or branched and may contain a cyclic structure. This includes short-chain fatty acids, medium-chain fatty acids, and long-chain fatty acids. The fatty acid may be selected from saturated or unsaturated fatty acids. The hydrocarbon tail of an unsaturated fatty acid may contain one or more double bonds. The hydrogen atom adjacent to the double bond of the hydrocarbon tail of the unsaturated fatty acid may be in a cis or trans configuration. According to certain embodiments, and without limitation, illustrative examples of the at least one fatty acid are selected from nonanoic acid (C9:0), decanoic acid (C10:0), undecanoic acid (C11:0), lauric acid (C12:0), tridecanoic acid (C13:0), myristic acid (C14:0), pentadecanoic acid (C15:0), palmitic acid (C16:0), linoleic acid (C18:2), oleic acid (C18:1), transoleic acid (C18:1), stearic acid (C18:0), and combinations thereof.

[0047] According to certain embodiments, the step of separating the acid from a terpene feed containing nocaol and an acid catalyzing the conversion of nocaol to nocaene includes a distillation process. According to the disclosed method, the distillation includes one-stage distillation. According to certain embodiments, the one-stage distillation process is carried out at 25°C. o C to 260 o The pot temperature at C is 25°C. o C to 140 o The process is carried out at a vapor temperature of C and a pressure of 0 to 50 mmHg for 60 to 180 minutes. According to other embodiments, the single-stage distillation process is carried out at 140... o C to 240 o C, reactor temperature, 40 o C to 130 o The process is carried out for 80 to 130 minutes at a vapor temperature of C and a pressure of 0 to 20 mmHg. According to other embodiments, the single-stage distillation process is carried out at 160... o C to 200 o C is the temperature of the vessel, 75 o C to 120 o The test was conducted at a vapor temperature of C and a pressure of 0 to 1 mmHg for 90 to 110 minutes.

[0048] According to certain illustrative embodiments, the conversion of nocaol to nocaene is mitigated by treating a feed containing nocaol and compounds that catalyze the conversion of nocaol to nocaene with the addition of an alkali. The alkali has chemical properties of neutralizing acids or increasing the pH of the liquid. Adding an alkali to the feed neutralizes at least a portion of the compounds present in the feed that catalyze the conversion of nocaol to nocaene, thereby mitigating or preventing the conversion to nocaene.

[0049] The base added to a feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene may be selected from any base capable of at least partially or completely neutralizing the one or more acidic compounds. According to some illustrative embodiments, the base added to the feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene to at least partially neutralize the acid comprises at least one nitrogen-containing compound. According to some illustrative embodiments, the nitrogen-containing compound added to the feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene to at least partially neutralize the acid comprises at least one amine. According to some illustrative embodiments, the amine compound added to the feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene to at least partially neutralize the acid comprises at least one alkylamine. According to some illustrative embodiments, the amine compound added to the feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene to at least partially neutralize the acid comprises at least one secondary or tertiary amine. According to certain illustrative embodiments, the amine compound added to a feed containing nocaol and one or more acidic compounds that catalyze the conversion of nocaol to nocaene to at least partially neutralize the acid comprises at least one trialkylamine. Non-limitingly, and by way of illustration only, the tertiary amine may be selected from one or more of trioctylamine, tri-dodecylamine, and combinations thereof. According to other embodiments, the base added to a feed containing nocaol and one or more acidic compounds that catalyze the conversion of nocaol to nocaene may be selected from hydroxide bases. Non-limitingly, and by way of illustration only, hydroxide bases include ammonium hydroxide, calcium hydroxide, lithium hydroxide, magnesium hydroxide, potassium hydroxide, sodium hydroxide, and mixtures thereof.

[0050] According to other illustrative embodiments, the nitrogen-containing compound added to a feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene to at least partially neutralize the acid includes ammonia. According to some embodiments, ammonia is introduced as a gas into the feed by allowing gaseous ammonia to flow into the feed containing nocarbamate and one or more acidic compounds that catalyze the conversion of nocarbamate to nocarene to at least partially neutralize the acid. According to some embodiments, the step of allowing ammonia gas to flow into the feed containing nocarbamate and one or more acidic compounds includes bubbling the ammonia gas into the feed.

[0051] According to some embodiments, a method for mitigating or preventing the conversion of nocaol to nocaene includes providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene. At least a portion of the nocaol and one or more desired terpenes present in the feed are separated from the at least one compound by distillation, and the nocaol is collected as a distillate. According to some embodiments, at least a portion of the nocaol and one or more desired terpenes present in the feed are separated from the at least one compound by single-stage distillation, and the nocaol is collected as a distillate.

[0052] According to certain embodiments, a method for preparing a nocaketone composition includes providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene. The feed is then treated to mitigate or prevent the conversion of nocaol to nocaene by separating the nocaol from the feed through distillation to produce a second feed containing nocaol and other desired terpenes, and by collecting the nocaol as a distillate. The treated feed containing the collected nocaol distillate is subsequently subjected to fractional distillation.

[0053] According to some embodiments, a method for preparing a nocaketone composition includes providing a feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene. The feed is treated by adding an alkali to neutralize the compound present in the feed that catalyzes the conversion of nocaol to nocaene to mitigate or prevent the conversion. The treated feed is then subjected to fractional distillation to produce the nocaketone composition.

[0054] According to certain embodiments, by pretreating a feed containing nocaol and a compound that catalyzes the chemical conversion of nocaol to nocaene, by separating at least a portion of the nocaol from the compound present in the feed that catalyzes the reaction of nocaol to nocaene, or by neutralizing the compound present in the feed that catalyzes the reaction of nocaol to nocaene with a neutralizing compound or molecule (such as a base), or by first separating at least a portion of the nocaol from the compound present in the feed that catalyzes the reaction of nocaol to nocaene, and then neutralizing the compound present in the feed that catalyzes the reaction of nocaol to nocaene with a neutralizing compound or molecule, the amount of nocaol retained in the terpene blend after fractional distillation is at least 50% by weight, or at least 45% by weight, or at least 40% by weight, or at least 35% by weight, or at least 30% by weight, or at least 25% by weight, or at least 20% by weight, or at least 15% by weight, or at least 10% by weight.

[0055] According to certain embodiments, the terpene blend after the fractional distillation step contains 1% by weight or less nocaene, by pretreating a feed containing nocaol and a compound that catalyzes the chemical conversion of nocaol to nocaene, by separating at least a portion of the nocaol from the compound present in the feed that catalyzes the reaction of nocaol to nocaene, or by neutralizing the compound present in the feed with a neutralizing compound or molecule (such as a base), or by first separating at least a portion of the nocaol from the compound present in the feed that catalyzes the reaction of nocaol to nocaene, and then neutralizing the compound present in the feed with a neutralizing compound or molecule. According to other illustrative embodiments, the terpene blend prepared according to the disclosed method contains 0.9% or less, 0.8% or less, 0.7% or less, 0.6% or less, 0.5% or less, 0.4% or less, 0.3% or less, 0.2% or less, or 0.1% or less of nocarne.

[0056] The distillate fractions that can be used to prepare terpene blends are also disclosed, comprising at least 50 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 45 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 40 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 35 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 30 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 25 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 20 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 15 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 10 wt% α-nocarbamol and 1 wt% or less nocarne.

[0057] According to certain embodiments, the distillate fraction used to prepare the terpene blend contains at least 50 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 45 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 40 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 35 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 30 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 25 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 20 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 15 wt% α-nocarbamol and 0.5 wt% or less nocarne, or at least 10 wt% α-nocarbamol and 0.5 wt% or less nocarne.

[0058] According to other illustrative embodiments, the distillate fraction used to prepare the terpene blend contains at least 50% by weight α-nocarboxol and 1% by weight or less nocarne, or at least 45% by weight α-nocarboxol and 0.25% by weight or less nocarne, or at least 40% by weight α-nocarboxol and 0.25% by weight or less nocarne, or at least 35% by weight α-nocarboxol and 0.25% by weight or less nocarne, or at least 3% by weight α-nocarboxol and 0.25% by weight or less nocarne. 0% by weight of α-nocarbamate and 0.25% by weight or less of nocarne, or at least 25% by weight of α-nocarbamate and 0.25% by weight or less of nocarne, or at least 20% by weight of α-nocarbamate and 0.25% by weight or less of nocarne, or at least 15% by weight of α-nocarbamate and 0.25% by weight or less of nocarne, or at least 10% by weight of α-nocarbamate and 0.25% by weight or less of nocarne.

[0059] According to other illustrative embodiments, the distillate fraction used to prepare the terpene blend contains at least 50 wt% α-nocarbamol and 1 wt% or less nocarne, or at least 45 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 40 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 35 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 30 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 25 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 20 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 15 wt% α-nocarbamol and 0.1 wt% or less nocarne, or at least 10 wt% α-nocarbamol and 0.1 wt% or less nocarne.

[0060] Terpene blends prepared according to the disclosed method are also disclosed. The terpene blends may comprise fractionated distillates prepared according to the method of this disclosure, or may comprise blends of distillate fractions prepared according to the method of this disclosure, to obtain one or more terpenes at desired concentrations.

[0061] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 40 to about 60% by weight of nocarbone, or about 40 to about 55% by weight of nocarbone, or about 40 to about 50% by weight of nocarbone, or about 45 to about 55% by weight of nocarbone, or about 48 to about 52% by weight of nocarbone, or about 49 to about 51% by weight of nocarbone.

[0062] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 5 to about 25 weight percent of α-nocarol, or about 5 to about 20 weight percent of α-nocarol, or about 5 to about 15 weight percent of α-nocarol, or about 5 to about 10 weight percent of α-nocarol, or about 10 to about 25 weight percent of α-nocarol, or about 10 to about 20 weight percent of α-nocarol, or about 10 to about 15 weight percent of α-nocarol, or about 12 to about 20 weight percent of α-nocarol, or about 13.5 to about 17.5 weight percent of α-nocarol, or about 15 to about 25 weight percent of α-nocarol, or about 15 to about 20 weight percent of α-nocarol.

[0063] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 0.001 to about 5% by weight of β-nocarboxol, or 0.01 to about 5% by weight of β-nocarboxol, or 0.05 to about 5% by weight of β-nocarboxol, or 0.1 to about 5% by weight of β-nocarboxol, or 0.25 to about 5% by weight of β-nocarboxol, or 0.5 to about 5% by weight of β-nocarboxol, or 0.75 to about 5% by weight of β-nocarboxol, or 0.3 to about 0%. 6% by weight of β-nocarboxol, or 0.35 to about 0.45% by weight of β-nocarboxol, or 1 to about 5% by weight of β-nocarboxol, or 1.5 to about 5% by weight of β-nocarboxol, or 2 to about 5% by weight of β-nocarboxol, or 2.5 to about 5% by weight of β-nocarboxol, or 3 to about 5% by weight of β-nocarboxol, or 3.5 to about 5% by weight of β-nocarboxol, or 4 to about 5% by weight of β-nocarboxol, or 4.5 to about 5% by weight of β-nocarboxol.

[0064] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 0.1 to about 5% by weight of β,γ-nocarbone, or about 0.25 to about 5% by weight of β,γ-nocarbone, or about 0.5 to about 5% by weight of β,γ-nocarbone, or about 0.75 to about 5% by weight of β,γ-nocarbone, or about 1 to about 5% by weight of β,γ-nocarbone, or about 1.5 to about 5% by weight of β,γ-nocarbone, or about The terpene blend may contain 2 to 5% by weight of β,γ-norcarne, or about 2.5 to 5% by weight of β,γ-norcarne, or about 3 to 5% by weight of β,γ-norcarne, or about 3.5 to 5% by weight of β,γ-norcarne, or about 4 to 5% by weight of β,γ-norcarne, or about 4.5 to 5% by weight of β,γ-norcarne, or about 2 to 3% by weight of β,γ-norcarne, or about 2.5 to 3% by weight of β,γ-norcarne. According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 5% or less by weight of β,γ-norcarne, or about 4% or less by weight of β,γ-norcarne, or about 3% or less by weight of β,γ-norcarne, or about 2% or less by weight of β,γ-norcarne, or about 1% or less by weight of β,γ-norcarne.

[0065] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 0.01 to about 1 wt% of nocardene, or 0.02 to about 1 wt% of nocardene, or 0.03 to about 1 wt% of nocardene, or 0.04 to about 1 wt% of nocardene, or 0.05 to about 1 wt% of nocardene, or 0.06 to about 1 wt% of nocardene, or 0.07 to about 1 wt% of nocardene, or 0.08 to about 1 wt% of nocardene, or 0.09 to about 1 wt% of nocardene, or 0.1 to about 1 wt% of nocardene, or 0.15 to about 1 wt% of nocardene, or 0.2 to about 1 wt% of nocardene, or 0.25 to about 1 wt% of nocardene. Or 0.3 to about 1.25% by weight of nocarne, or 0.3 to about 1% by weight of nocarne, or 0.35 to about 1% by weight of nocarne, or 0.4 to about 1% by weight of nocarne, or 0.45 to about 1% by weight of nocarne, or 0.5 to about 1% by weight of nocarne, or 0.55 to about 1% by weight of nocarne, or 0.6 to about 1% by weight of nocarne, or 0.65 to about 1% by weight of nocarne, or 0.7 to about 1% by weight of nocarne, or 0.75 to about 1% by weight of nocarne, or 0.8 to about 1% by weight of nocarne, or 0.85 to about 1% by weight of nocarne, or 0.9 to about 1% by weight of nocarne, or 0.95 to about 1% by weight of nocarne.

[0066] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may contain about 0.001 to about 15 weight percent of varenene, or about 0.01 to about 15 weight percent of varenene, or about 0.025 to about 15 weight percent of varenene, or about 0.05 to about 15 weight percent of varenene, or about 0.075 to about 15 weight percent of varenene, or about 0.1 to about 15 weight percent of varenene, or about 0.25 to about 15 weight percent of varenene. The alkene, or about 0.5 to about 15 weight percent of walene, or about 0.75 to about 15 weight percent of walene, or about 0.03 to about 1.5 weight percent of walene, or about 0.03 to about 0.55 weight percent of walene, or about 0.4 to about 1.5 weight percent of walene, or about 1 to about 15 weight percent of walene, or about 5 to about 15 weight percent of walene, or about 10 to about 15 weight percent of walene, or about 5 to about 10 weight percent of walene.

[0067] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may comprise about 5 to about 25% by weight of α-nocarol, about 0.001 to about 5% by weight of β-nocarol, about 0.1 to about 5% by weight of β,γ-nocarone, about 40 to about 60% by weight of nocarone, about 0.01 to about 1% by weight of nocarne, and about 0.001 to about 15% by weight of valenene.

[0068] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may comprise about 12 to about 20 weight percent of α-nocarol, about 0.3 to about 0.6 weight percent of β-nocarol, about 2.5 to about 3 weight percent of β,γ-nocarone, about 48 to about 52 weight percent of nocarone, about 0.3 to about 1.2 weight percent of nocarene, and about 0.4 to about 1.5 weight percent of valenene.

[0069] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may comprise about 12 to about 20 weight percent of α-nocarol, about 0.3 to about 0.6 weight percent of β-nocarol, about 2.5 to about 3 weight percent of β,γ-nocarone, about 48 to about 52 weight percent of nocarone, about 0.3 to about 1.2 weight percent of nocarene, about 0.4 to about 1.5 weight percent of valenene, about 0.2 to about 0.5 weight percent of 1,10-dihydronocarone, and about 25 to about 30 weight percent of other sesquiterpenes.

[0070] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may comprise about 13.5 to about 17% by weight of α-nocarol, about 0.35 to about 0.45% by weight of β-nocarol, about 0.55 to about 1.4% by weight of β,γ-nocarone, about 49 to about 51% by weight of nocarone, about 0.3 to about 1% by weight of nocarne, and about 0.03 to about 0.55% by weight of valenene.

[0071] According to certain illustrative embodiments, based on the total weight of the terpene blend, the terpene blend may comprise about 13.5 to about 17% by weight of α-nocarol, about 0.35 to about 0.45% by weight of β-nocarol, about 0.55 to about 1.4% by weight of β,γ-nocarone, about 49 to about 51% by weight of nocarone, about 0.3 to about 1% by weight of nocarene, about 0.03 to about 0.55% by weight of valenene, about 0.2 to about 0.35% by weight of 1,10-dihydronocarone, and about 25 to about 30% by weight of other sesquiterpenes.

[0072] Fragrance compositions containing terpene blends prepared according to this disclosure may further include one or more additional fragrance compounds.

[0073] According to certain illustrative embodiments, without limitation, additional fragrance compounds may include one or more aldehyde compounds, one or more balsamic compounds, one or more different citrus compounds, one or more floral compounds, one or more fruity compounds, one or more gourmand compounds, one or more green compounds, one or more marine compounds, one or more moss compounds, one or more musk compounds, one or more piney compounds, one or more spicy compounds, and / or one or more woody compounds, or combinations thereof.

[0074] By way of illustration and not limitation, suitable aldehyde compounds include saturated alkyl aldehydes, including but not limited to ALDEHYDE C12 MNA (2-methylundecyl); ALDEHYDE C8 OCTYLIC (octanal); ALDEHYDE C9 (nonanal); ALDEHYDE C6 HEXYLIC (hexanal); CALYPSONE (6-methoxy-2,6-dimethyloctanal); ALDEHYDE C7 HEPTYLIC (heptanal); ALDEHYDE C10 decanal; ALDEHYDE C12 dodecanal; acetaldehyde; n-butyraldehyde; isobutyraldehyde. In one embodiment, the saturated alkyl aldehyde is selected from the group consisting of ALDEHYDE C12 MNA and CALYPSONE.

[0075] In another embodiment, suitable odor-reducing materials include unsaturated alkyl aldehydes, including but not limited to DECEN-1-AL, CIS-4 ((Z)-decano-4-enal); DECENAL-4-TRANS ((E)-decano-4-enal); DECENAL-9 (9-decenoal), MELONAL (2,6-dimethylheptano-5-enal); CYCLAL C (2,4-dimethylcyclohexyl-3-enal); NONADIENAL ((2E,6Z)-non-2,6-dienal); PINOACETALDEHYDE (3-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)propanal); SHISOLIA (4-vinylcyclohexyl-1-enal); MACEAL (bicyclo[2.2.2]oct-5-en-2-carboxal); cinnamaldehyde; citronellol; trans-2-hexenal; trans-2-decenal, cis-3-hexenal, and cis-4-heptenal. In one embodiment, the unsaturated alkyl aldehyde is selected from the group consisting of MELONAL, CYCLAL C, SHISOLIA, and MACEAL.

[0076] In another embodiment, suitable odor-reducing materials include aromatic aldehydes, including but not limited to anisaldehyde; AUBEPINE PARA CRESOL (4-methoxybenzaldehyde), FLORHYDRAL (3-(3-isopropylphenyl)butanal); benzaldehyde; PHENYL PROPIONIC ALDEHYDE (3-phenylpropanal); and TOLYL ALDEHYDE PARA (4-methylbenzaldehyde).

[0077] By way of illustration and not limitation, suitable citrus compounds may include citral, citronellol, L-citronellol, decanal, limonene, myrcene, sweet orange aldehyde, bergamot oil, grapefruit oil, lemon oil, lime oil, and / or orange oil.

[0078] As an illustration and not a limitation, suitable floral compounds may include anisyl acetate, anisaldehyde, benzyl acetate, bourgeonal, butyl acetate, cyclamen aldehyde, cyclohexyl lactone, δ-dihydrodamascone, farnesal, L-farnesal, farnesol, anthocyanin, geraniol, gernaylacetate, piperaldehyde, methyl dihydrojasmone, heliobouquet, hexylcinnamaldehyde, hexyl salicylate, indole, α-ionone, β-ionone, isopropoxyethylsalicylate, jasmodione, cis-jasmone, kovanol, lauryl alcohol, linalool, linalyl acetate, mayol, and methyl dihydrojasmone. dihydrojasomante), γ-methyl ionone, methoxycucurbitaldehyde, nerol, nerolione, nerol acetate, 2-pentylcyclopentanone, phenoxanol, phenoxyethyl isobutyrate, phenylacetaldehyde, phenylethanol, oxidized rose, suzaral, methyl decenol, geranium oil, lavender oil, rose oil, and / or ylang-ylang oil. Fruity aroma compounds can be C-C16 aldehydes, allyl hexanoate, allyl cyclohexylpropionate, allyl heptaate, amyl acetate, benzaldehyde, L-citronellol acetate, L-citronellol nitrile, cyclacet, damascenone, β-decanolide, γ-decanolide, diethyl malonate, dimethylphenylethyl methanol, dimethyl sulfide, γ-dodecanolide, ethyl acetate, ethyl butyrate, ethyl hexanoate, ethyl decadienotate, ethyl-2-methylbutyrate, ethyl acetoacetate, ethyl propionate, florol, hexyl acetate, hexyl isobutyrate, isoamyl acetate, jasmolactone, manzanate, melon aldehyde, methyl heptaketone, γ-nonanolide, γ-octanolide, phenylethyl isobutyrate, raspberry ketone, ringonol, thesaron, toluenealdehyde, γ-undecanolate lactone, vanoris, and / or verdox.

[0079] By way of illustration and not limitation, suitable edible flavor compounds may include caprylic acid, coumarin, ethylfraison, ethyl vanillin, ethyl maltol, filbertone, furanone, guaiacol, maple furanone, 2-acetylpyrazine, 2,5-dimethylpyrazine, and / or vanillin.

[0080] By way of illustration and not limitation, suitable green compounds may include dynasty ketone, gempenene, trans-2-hexenal, cis-3-hexenol, hexen-1-ol, cis-3-hexenyl acetate, cis-3-hexenyl butyrate, cis-3-hexenyl salicylate, liffarome, octyryne methyl carbonate, 2,6-nonadienal, oxane, oleinone, styrax acetate, privet aldehyde, undecavertol, violet methyl carbonate, vionil, and / or violet leaf extract.

[0081] By way of illustration and not limitation, suitable musk compounds may include asterolone, ambretone, ambroxanone, cyclopentadecanolone, galaxolide, habanolide, hymex, (1'R)-3-methyl-5-(2,2,3-trimethylcyclopentan-1-yl)-2-pentanone, muscenone, musk T, L-muscenone, and / or tuna musk.

[0082] By way of illustration and not limitation, suitable pine resin compounds may include α-pinene, β-pinene, and mixtures thereof.

[0083] By way of illustration and not limitation, suitable spice compounds may include β-caryophyllene, cinnamaldehyde, cuminaldehyde, eugenol, isoeugenol, perillaldehyde, cardamom oil, clove oil, ginger extract and / or black pepper extract.

[0084] By way of illustration and not limitation, suitable woody compounds may include amber core, amber extreme, ambroxan, sandalwood, cedanol, ebony alcohol, hindinol, juniper alcohol, Javanol, norlimbanol dextro, saffron alcohol, patchone, polyambrol, α-pinene, β-pinene, sandalmysore core, santalex T, orbitone, cedar oil, patchouli oil, sandalwood oil, and / or vetiver oil.

[0085] The terpene blends disclosed herein can be included in a variety of food and beverage products.

[0086] The terpene blends disclosed herein can be included in a variety of food products that will benefit from citrus aroma and / or flavor.

[0087] Muffins (e.g., English muffins), biscuits (e.g., savory biscuits, baked biscuits, whole wheat biscuits, etc.), rolls (e.g., soft rolls, dinner rolls, crescent rolls), biscuits (e.g., buttermilk biscuits, cobbler biscuits), pie crusts, breads (e.g., focaccia, bruschetta, sourdough bread, soda bread, breadsticks, cornbread, etc.), bagels, brownies, cookies, turnovers, donuts, cakes, shortbread, pies, scones, etc.

[0088] Without limitation, and by way of illustration only, exemplary dairy products include ice cream, instant ice cream, ice cream desserts, frozen yogurt, milk, fresh / pasteurized milk, whole fresh / pasteurized milk, semi-skimmed fresh / pasteurized milk, long-life / UHT milk, whole long-life / UHT milk, semi-skimmed long-life / UHT milk, non-fat long-life / UHT milk, goat milk, condensed / evaporated milk, plain condensed / evaporated milk, flavored, functional and other condensed milk, flavored milk beverages, dairy-only flavored milk beverages, soy milk, yogurt beverages, fermented milk beverages, coffee creamer / whitening agent, milk powder, flavored milk powder beverages, cream, yogurt, plain / natural yogurt, flavored yogurt, fruit yogurt, probiotic yogurt, yogurt beverages and other dairy-based desserts.

[0089] Without limitation, and only as a limitation, exemplary palatable food products include savory snacks (potato chips, crisps, nuts, tortilla-tostada, pretzels, cheese snacks, corn snacks, potato snacks, instant popcorn, microwaveable popcorn, pork rinds, nuts, crackers, cracker snacks, breakfast cereals, meat, cured meat, lunch / breakfast meat, tomato products, peanut butter, soup, canned vegetables, pasta sauce, and palatable biscuits, crackers, and bread substitutes).

[0090] Without limitation, and by way of illustration only, sweet products include breakfast cereals, ready-to-eat (“rte”) cereals, family breakfast cereals, oatmeal, muesli, other rte cereals, children’s breakfast cereals, and hot cereals.

[0091] The terpene blends and / or flavoring compositions comprising terpene blends of this disclosure can be included in citrus beverages. Suitable citrus beverages include, but are not limited to, alcoholic citrus cocktails, citrus-flavored beverages, citrus liqueurs, citrus-flavored sodas, citrus-flavored soft drinks, citrus-flavored water, citrus-flavored still water, citrus-flavored carbonated water, etc. The terpene blends and / or flavoring compositions comprising terpene blends of this disclosure can be included in tropical flavoring compositions or in foods and beverages containing tropical flavorings (such as, for example, coconut, guava, kiwi, mango, papaya, passion fruit, and pineapple flavorings), which contain citrus components.

[0092] Terpene blends and flavoring compositions containing terpene blends can be used in personal care products such as pharmaceuticals, cosmetics and toiletries.

[0093] When used in cosmetics and toiletries, these formulations may be used in any of the "Reported Product Categories" listed in the Cosmetic, Toiletries and Fragrance Association's "International Dictionary and Handbook of Cosmetic Ingredients," and in conjunction with any one or more ingredients listed for the Reported Product Categories. Reported Product Categories include: aftershave lotions, baby washes, oils, powders and creams, various baby products, baby shampoos, basecoats and undercoats, bath capsules, bath oils, tablets and salts, various bath formulations, bath soaps and detergents, beard softeners, blush, body and hand formulations, foaming bath liquids, cleansing products, colognes and eau de toilettes. Water), cuticle softener, teeth cleaner, deodorant, hair removal agent, rinse, eye wash, various eye makeup products, eye makeup remover, eyeshadow, eyebrow pencil, eyeliner, face and neck products, face powder, feminine hygiene deodorant, foot powder and spray, foundation, various fragrance products, hair bleach, hair dye spray, various hair dye products, hair conditioner, hair dye and colorant, hair shine with colorant, hair products, hair rinse, hair shampoo, hair spray, hair straightener, hair dye, hair wave set, tanning products, leg and body lotion, lipstick, makeup base, cosmetic fixative, cosmetic products, various nail care products, mascara, men's talcum powder, moisturizing products, mouthwash and breath freshener, nail cream and lotion, nail extender, nail polish and nail polish remover, nail polish Polish and nail enamel, nighttime skin care products, various oral hygiene products, face masks, perfumes, permanent waves, various personal hygiene products, pressed powder, preshave lotion, blush, sachets, shampoos, shaving creams, various shaving products, shaving soaps, various skin care products, skin fresheners, tanning gels, creams and liquids, various tanning products, sonic agents, dressings and other hair styling aids.

[0094] "Oral care" or "oral hygiene" products may include any product applied to the oral cavity for the purpose of cleaning, freshening, healing, deodorizing the oral cavity or any part thereof. Without limitation, and by way of illustration only, such oral care and oral hygiene compositions include toothpaste, tooth gel, tooth powder, teeth whitening products, oral cleansers, mouthwash, mouthwash compositions, lozenges, dental floss, toothpicks, anti-plaque and anti-gingivitis compositions, throat lozenges, throat drops, compositions for treating nasal symptoms, cold symptoms, and for relieving cold symptoms.

[0095] The nocarboxone oil compositions disclosed herein can be included in a variety of other consumer products. Non-limitingly, and by way of illustration only, consumer products may be selected from fine fragrances, home care products, and air care products.

[0096] According to certain illustrative embodiments, and without limitation, fine fragrance products may be selected from parfum, extrait de parfum, eau de parfum, millesime, parfum de toilette, eau de toilette, eau de cologne, body spray, aftershave, body mists, and baby cologne.

[0097] According to certain illustrative embodiments, and without limitation, household care products may be selected from fabric conditioners, fabric softeners, laundry detergents, laundry additives, rinsing additives, bleach, dryer sheets, perfume beads, car care products, dishwashing liquids, and hard surface cleaners.

[0098] According to certain illustrative embodiments, and without limitation, air care products may be selected from candles, aerosols, air fresheners, liquid electric air fresheners, fragrance diffusers, gel air fresheners, insertable air fresheners, insertable oil and wax melts.

[0099] Example

[0100] The following examples illustrate exemplary embodiments of the disclosed method in further detail and explain methods for mitigating or preventing the conversion of α-nocarboxol to nocarne in terpene blends. These examples should not be construed as limiting methods for mitigating the chemical conversion of α-nocarboxol to nocarne in terpene blend feedstocks, methods for preparing terpene blends, terpene blends, flavoring compositions, fragrance compositions, beverage products, food products, fragrance products, methods for preparing beverage products, methods for preparing food products, and methods for preparing flavored products.

[0101] Comparative Example 1

[0102] A blend of citrus terpenes containing approximately 1.61% total fatty acids was fractionally distilled under full vacuum. Table 1A below shows the initial amounts of each component in the terpene blend, as well as the amounts of each component recovered from a high-temperature fractional distillation process typically used to prepare nocarne blends for use as flavoring and fragrance ingredients. Table 1B below shows the temperature and composition of the distillate fractions during fractional distillation.

[0103] Table 1A

[0104]

[0105] Table 1B

[0106]

[0107] The results of fractional distillation showed that the mass of nocaol decreased significantly during the fractional distillation process, while the mass of nocaene increased accordingly. Nocaene was present at >= 1% in each distillate fraction except the first fraction, providing evidence of its continuous formation throughout the fractional distillation process.

[0108] Comparative Example 2 / Example 3-4

[0109] A sample of the feedstock blend containing approximately 1.61% total fatty acids of the same citrus terpenes used in Comparative Example 1 was evaluated to determine the effect of simple single-stage distillation (Example 3) or treatment of the feedstock terpene blend with an alkaline material (Example 4) on the catalytic reaction of α-nocarbamol to nocarene. 5% by weight of trioctylamine was added as an alkaline material to the terpene blend of Example 4. The sample was subjected to reflux at 1 ATM and at temperatures up to 130°C. o Heating under a nitrogen pad at C for five hours. Tables 2A-2C below show the amounts (in grams) of nocaol, nocaene, nocaconone, and other components present in the terpene blend that were loaded into the reaction vessel (i.e., flask) and recovered after heat treatment.

[0110] Table 2A

[0111] Comparative / Control Example 2

[0112]

[0113] Table 2B

[0114] Example 3

[0115]

[0116] Table 2C

[0117] Example 4

[0118]

[0119] Both the simple distillate (Example 3) and the amine spike (Example 4) resulted in less nocarne formation and less nocarol retention. A conversion from nocarol to nocarne did occur in Examples 3 and 4, but to a much smaller extent compared to Comparative / Control Example 2. The simple distillation performed (Example 3) did carry a limited amount of undesirable high-boiling material, including a certain level of acidity. Based on these results, without being bound by any particular theory, the carryover of acidity and other high-boiling materials could be further reduced or even eliminated if the process were terminated at a lower pot temperature, which would improve nocarol stability beyond the results shown above for Example 3. Alternatively, as in Example 4, a larger addition of a tertiary amine to the feed terpene blend could result in greater nocarol stability and less nocarne formation.

[0120] Examples 5-6

[0121] According to embodiments of this disclosure, a feed blend of citrus terpenes containing approximately 1.61% total fatty acids was processed. Two samples of the same citrus terpene feed blend were fractionally distilled after a simple single-stage distillation (Example 5) or after the addition of 5% by weight of trioctylamine to the terpene blend (Example 6). Tables 3A and 3C below show the temperature and composition of the distillate fractions during fractional distillation. Tables 3B-3D below show the amounts (in grams) of nocaol, nocaene, nocaketone, and other components present in the terpene blend that were loaded into the reaction vessel (i.e., flask) and recovered after heat treatment.

[0122] Table 3A (Example 5)

[0123]

[0124] Table 3B

[0125]

[0126] Table 3C (Example 6)

[0127]

[0128] Table 3D

[0129]

[0130] The yields of α-nocarol increased from 43% (Table 1A, Comparison / Control) to 86% and 93%, respectively, for both amine-spiked fractions (Example 6) and simple distillate fractionation (Example 5). Both simple distillation and amine pretreatment effectively preserved α-nocarol and reduced nocarne formation during fractional distillation. It is believed that the tertiary amine buffered the sample pH to prevent acid-catalyzed reactions, and that simple distillation separated the desired terpenes from higher-boiling fatty acids. The nocarne concentrations in the distillate fractions in Tables 3A and 3C were generally much lower than those from distillations of untreated terpene blend samples.

[0131] It should be understood that when a range of values ​​is described in this disclosure, it is intended that any and every value (including endpoints) within that range be considered as already disclosed. For example, a “range of 50 to 100” for a component will be interpreted as indicating each and every possible number along the continuum of 50 to 100. It should be understood that the inventor recognizes and understands that any and all values ​​within that range are considered as already specified, and that the inventor owns the entire range and all values ​​within that range.

[0132] In this disclosure, the term “about” used in conjunction with a value includes the value and has a meaning defined by the context. For example, it includes at least the degree of error associated with the measurement of a particular value. Those skilled in the art will understand that the term “about” as used herein to refer to the amount of the value “about” produces the desired level of effectiveness in the compositions and / or methods of this disclosure. Those skilled in the art will further understand that the boundaries and limits of the value “about” relating to the percentage, amount, or quantity of any component in the embodiments can be determined by varying the value, determining the effectiveness of the composition for each value, and determining the range of values ​​that produce compositions with the desired level of effectiveness according to this disclosure. The term “about” is further used to reflect the possibility that the composition may contain trace amounts of other materials that do not alter the effectiveness or safety of the composition.

[0133] Any percentage by weight of components disclosed herein is specified as appropriate based on the total weight of the terpene blend, flavoring composition, fragrance composition, food product, beverage product, or flavored product. Those skilled in the art will understand that the total weight percentage of a particular blend, composition, or product may not exceed 100%. For example, those skilled in the art will readily recognize and understand that a beverage product comprising 50 to 95% by weight of a beverage base and 5 to 50% by weight of a terpene-based flavoring composition will not exceed 100%. Those skilled in the art will understand that the amounts of these components can be adjusted to include desired amounts of components without exceeding 100% by weight of the blend, composition, or product.

[0134] The foregoing provides a broad description of many different embodiments of this disclosure. The description should be interpreted as exemplary only and does not describe every possible embodiment, as describing every possible embodiment would be impractical, if not impossible. It should be understood that any feature, characteristic, component, composition, ingredient, product, step, or method described herein can be deleted, combined, or replaced, in whole or in part, with any other feature, characteristic, component, composition, ingredient, product, step, or method described herein.

[0135] While methods for mitigating the chemical conversion of α-nocarboxol to nocarne in terpene blend feeds, methods for preparing terpene blends, terpene blends, flavoring compositions, flavoring compositions, beverage products, food products, flavoring products, methods for preparing beverage products, methods for preparing food products, and methods for preparing flavored products have been described in conjunction with various illustrative embodiments, it should be understood that other similar embodiments can be used or modifications and additions can be made to the described embodiments to achieve the same function. Furthermore, various illustrative embodiments can be combined to produce desired results. Therefore, methods for mitigating the chemical conversion of α-nocarboxol to nocarne in terpene blend feeds, methods for preparing terpene blends, terpene blends, flavoring compositions, flavoring compositions, beverage products, food products, and flavoring products should not be limited to any single embodiment, but should be interpreted in breadth and scope according to the statement of the appended claims. It should be understood that the embodiments described herein are merely exemplary, and those skilled in the art can make changes and modifications without departing from the spirit and scope of the invention. All such changes and modifications are intended to be included within the scope of the invention as described above. Furthermore, all disclosed embodiments are not necessarily in an either-or manner (in the alternative), as various embodiments of the invention can be combined to provide the desired results.

Claims

1. A method for mitigating or preventing the conversion of nocaol to nocaene, comprising: A feed containing nocaol and at least one compound that catalyzes the conversion of nocaol to nocaene; and (i) separating at least a portion of the nocaol from the at least one compound that catalyzes the conversion of nocaol to nocaene, or (ii) neutralizing at least a portion of the at least one compound that catalyzes the conversion of nocaol to nocaene.

2. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 1, wherein the feed comprises a blend of volatile terpenes, the volatile terpenes comprising α-nocaol.

3. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 1, wherein the compound catalyzing the conversion of nocaol to nocaene comprises at least one fatty acid.

4. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 3, wherein the at least one fatty acid is selected from saturated and unsaturated fatty acids having 2 to 28 carbon atoms.

5. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 1, wherein the step of separating the nocaol comprises distillation.

6. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 5, wherein the distillation comprises single-stage distillation.

7. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 5, wherein an alkali is added to the feed prior to the distillation.

8. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 5, wherein the distillation step includes fractional distillation after (i) or (ii).

9. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 7, wherein the base is a nitrogen-containing compound.

10. The method for mitigating or preventing the conversion of nocaol to nocaene as described in claim 9, wherein the nitrogen-containing compound comprises an amine.

11. The method of claim 10 for mitigating or preventing the conversion of nocaol to nocaene, wherein the amine comprises a tertiary amine.

12. A beverage or food comprising a beverage or food base and a terpene blend prepared by any one of claims 1 to 11.

13. A flavoring composition comprising a base material and a terpene blend prepared by any one of claims 1 to 11.

14. Use of the terpene blend prepared by any one of claims 1 to 11 as a flavoring agent in beverages or food products.

15. A terpene blend comprising, based on the total weight of the terpene blend, about 12 to about 20% by weight of α-nocarol, about 0.3 to about 0.6% by weight of β-nocarol, about 2.5 to about 3% by weight of β,γ-nocarone, about 48 to about 52% by weight of nocarone, about 0.3 to about 1.2% by weight of nocarne, and about 0.4 to about 1.5% by weight of valenene.

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