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US 7,4l3,758B2 56 solids and the second alcohol solvent, and separating the mixture of the treated hop solids and the second alcohol solventintohop solidsresiduesandasecond?ltrateincluding alpha/iso-alpha acids, Wherein a light stable hop product comprising the hop solids residues is formed. Preferably,thehopsolidsareobtainedbyextractingWhole hops or hop pellets With carbon dioxide. HoWever, the term “hop solids” as used herein means the solid hop residue obtained by extracting Whole hops or hop pellets With any solvent such as hexane, carbon dioxide (liquid or supercriti cal), alcohol (e.g., ethanol), Water, or an alcohol/Water mix ture, or the solid hop residue recovered after boiling Whole hops or hop pellets in a breWing kettle. The hop solids residues formed in the method may be concentrated using techniques such as evaporation. The hop solids residues or concentrated hop solids residues formed in themethodmay bemixedWithanadditiveselectedfromhop oil fractions, beta-acid rich fractions, light stable bittering agents and mixtures of any of these additives. The?rstalcoholsolventandthesecondalcoholsolvent 20 used in the method are preferably selected from the group consisting of ethanol and aqueous ethanol solutions. The ?rst alcohol solvent and the second alcohol solvent may be the same or different depending on the ?nal light stable hop productsought.Inoneversionoftheinvention,the?rst25 alcohol solvent and the second alcohol solvent are selected from aqueous ethanol solutions having an ethanol concentra tionof5% to95%. Inanotherversionoftheinvention,the?rst alcohol solvent and the second alcohol solvent are selected fromaqueousethanolsolutionshavinganethanolconcentra 30 tionofgreaterthan90%. Instilanotherversionoftheinven tion, the ?rst alcohol solvent and the second alcohol solvent are selected from aqueous ethanol solutions having an etha nolconcentrationof95% orgreater. TheinventionisnotlimitedtothetreatmenthopsolidsWith 35 a?rstalcoholsolventtoformoncetreatedhop solidsandthen the treatment of the once treated hop solids With a second alcoholsolvent.Thehop solidsmay beextractedanynumber of times using the same or different alcohol solvents. For example,thehopsolidsmaybetreatedWithanalcoholsol 40 vent three, four, ?ve or even more times depending on the hop productsought. The ?rst ?ltrate and the second ?ltrate (and any other ?ltrates) produced in the method can then be subjected to furtherprocessing.Inoneversionoftheinvention,atleastone 45 of the ?rst ?ltrate and the second ?ltrate (and any other ?ltrates) is contacted With an ion exchange resin to remove alpha/iso-alpha-acids from the ?ltrate. An e?iuent is col lected after contacting the ?ltrate or ?ltrates With the ion exchangeresin.Preferably,thee?iuentisessentiallyfreeof 50 alpha/iso-alpha-acids.Thee?iuentisthenmixedWiththehop solidsresiduesproducedbythemethodsuchthatalightstable hopproductincludingthehopsolidsresiduesandthee?iuent isformed. This lightstablehop productmay be concentrated (e.g.,byevaporation)toproduceaconcentratedmixtureof55 the hop solids residues and the ef?uent. The concentrated or unconcentrated mixture may be mixed With an additive selected from the group consisting of hop oil fractions, beta acidrichfractions,lightstablebitteringagentsandmixtures thereof.Inanexampleembodiment,theionexchangeresinis60 in chloride, hydroxide, or acetate ion form such that dissoci ated alpha/iso-alpha-acid ions exchange With these anions (Cl‘, OH‘, and acetate ion) on the resins. In another version of the invention, at least one of the ?rst ?ltrateandthesecond?ltrate(andanyother?ltrates)ismixed 65 With a metal ion that complexes With alpha/iso-alpha acids to form metal ion-alpha/iso-alpha acids complexes. The metal ion-alpha/iso-alphaacidscomplexesarethenseparatedfrom themixturetoformanother?ltrate.This?ltrateisthenmixed Withthehopsolidsresiduesproducedbythemethodsuchthat a light stable hop product including the hop solids residues and this ?ltrate is formed. This light stable hop product may be concentrated (e.g., by evaporation) to produce a concen tratedmixtureofthehop solidsresiduesandthis?ltrate.The concentrated or unconcentrated mixture may be mixed With an additive selected from the group consisting of hop oil fractions,beta-acidrichfractions,lightstablebitteringagents and mixtures thereof. In an example embodiment, the metal ionthatcomplexesWithalpha/iso-alphaacidsisformedfrom a compound selected from the group consisting of calcium carbonate,calciumhydroxide,magnesiumhydroxide,mag nesium carbonate, magnesium acetate, Zinc sulfate, Zinc acetate,andmixturesthereof. In stilanotherversion ofthe invention, atleastone ofthe ?rst ?ltrate and the second ?ltrate (and any other ?ltrates) is subjected to hydrogenation to reduce the alpha/iso-alpha acidsinthe?ltrateor?ltrates.Suchhydrogenatedalpha/iso alphaacidsareknoWntobelightstable.Any ofthe?ltrate(s) includinghydrogenatedalpha/iso-alphaacidsarethenmixed Withthehopsolidsresiduesproducedbythemethodsuchthat a light stable hop product including the hop solids residues andthe?ltrate(s)isformed.Thislightstablehopproductmay be concentrated (e.g., by evaporation) to produce a concen trated mixture of the hop solids residues and the ?ltrate(s). The concentrated or unconcentrated mixture may be mixed With an additive selected from the group consisting ofhop oil fractions,beta-acidrichfractions,lightstablebitteringagents andmixturesthereof.Inanexampleembodiment,thehydro genation is carried out using a palladium and/or platinum catalyst, and using hydrogen at a pressure in the range of 5-100psig. Thelightstablehopproductproducedbythemethodofthe invention, in concentrated or unconcentrated form, and includingornotincludingtheadditivesdescribedabove,may be used in knoWn methods for preparing a fermented malt beverage. For example, the light stable hop product may be addedaWort,priortoorduringboiling,andtheWortmay fermented to produce a fermented malt beverage. EXAMPLES The folloWing Examples have been presented in order to furtherillustratetheinventionandarenotintendedtolimitthe invention in any Way. Example 1 A thermaldecompositionofhopsolidsinthepresenceof hot airWas unsuccessful, and most residual amounts of alpha acidsWereconvertedintoiso-alpha-acids,resultinginalight unstableproduct.DirectisomeriZationandreductionoftrace amountsofalpha-acidstolightstablerho-iso-alpha-acids(or dihydro iso-alpha-acids) in an aqueous hop solid slurry Was attempted,employingacausticsodiumborohydridesolution (NaBH4). Results Were inconsistent, and high performance liquid chromatography (HPLC) analysis indicated that the reductioninalpha-acidcontentWasineffectiveduetointer ference of hop solid materials. Example2 Since it is knoWn that trace amounts of alpha/iso-alpha acids(about0.1-0.5Weightpercent)seemtobindverytightly Within the hop cellulose matrix, thus making a direct chemiPDF Image | PREPARATION OF LIGHT STABLE HOP PRODUCTS
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