Miller Brewing Company

Millercoors LLC

Nissan Technical Center North America, Inc.

Hop Ting Resources, LLC

Coors Brewing Company

Miller Brewing International, Inc.

Patrick L Ting

Henry Goldstein

David S Ryder

Jay R Refling

Aki A Murakami

Michael A VanSanford

Etzer Chicoye

Lance T Lusk

John M Cowles

Matthew L Tripp

Sydney R Rader

John R Seabrooks

Jason Pratt

William G Schulze

Velta D Young

Lixin Zhu

Michael C Barney

Alfonso Navarro

Walter H Fly

Subba C Rao

Fran L Saunders

Conglin Peng

Etzer Chicove

Gary Goetzke

Regina Wilkinson, Legal Representative

Rhonda M Dannenberg

Hetvin A Wilkinson

Jacqueline A Laumann

John T Eplett, Iii

Gregory P Casey

Vinod K Chaudhary

Steven M Hoppe

Robert J Mizerak

John T Eplett

A method for preparing a hop acid mixture having an enantiomeric excess of a (+)-tetrahydro-&#x3b1;-acid is disclosed. In the method, a racemate of a tetrahydro-&#x3b1;-acid is contacted with an amine to form a precipitate having an enantiomeric excess of the (+)-tetrahydro-&#x3b1;-acid. A method for preparing a hop acid is also disclosed. In the method, a racemate of a tetrahydro-&#x3b1;-acid is contacted with an amine to form a precipitate comprising a (+)-tetrahydro-&#x3b1;-acid, and the (+)-tetrahydro-&#x3b1;-acid is isomerized to a hop acid selected from the group consisting of (+)-trans-tetrahydro-iso-&#x3b1;-acids, (&#x2212;)-cis-tetrahydro-iso-&#x3b1;-acids, and mixtures thereof, and reduced to (+)-trans-hexahydroiso-&#x3b1;-acids and (&#x2212;)-cis-hexahydroiso-&#x3b1;-acids. An additive for flavoring a malt beverage is also disclosed. The additive includes a bittering agent selected from the group consisting of (+)-trans-tetrahydro-iso-&#x3b1;-acids, (&#x2212;)-cis-tetrahydro-iso-&#x3b1;-acids, (+)-trans-hexahydroiso-&#x3b1;-acids, (&#x2212;)-cis-hexahydroiso-&#x3b1;-acids, and mixtures thereof.

Preparation of hop acids and their derivatives

Tetrahydro iso-&#x3b1;-acids and hexahydro iso-&#x3b1;-acids are prepared from &#x3b2;-acid resins in the presence of &#x3b1;-acids derivatives without the use of conventional organic solvents. Specifically, the hydrogenation and hydrogenolyzis step is performed using a liquefied hop resin composed of &#x3b2;-acids and &#x3b1;-acid derivatives, hydrogen, and a noble metal hydrogenation catalyst to form desoxytetrahydro &#x3b1;-acids and hydrogenated iso-&#x3b1;-acid derivatives (e. g., tetrahydroiso- and hexahydro iso-&#x3b1;-acids). The desoxytetrahydro &#x3b1;-acids are subsequently auto-oxidized and isomerized by the spent noble metal catalyst in an aqueous alkaline solution (without adding peracids, lead, calcium, or magnesium salts) into the desired tetrahydro iso-&#x3b1;-acids and hexahydro iso-&#x3b1;-acids.

Solvent-free processes for making light stable ISO-alpha-acids derivatives from both hop alpha-acids and beta-acids resins

A method for reducing the amount of beverage soluble metal ions in a diatomaceous earth filter aid is disclosed. The beverage soluble metal ions can be copper and/or iron. In the method, the diatomaceous earth filter aid is contacted with a hop compound selected from iso-alpha-acids, dihydroiso-alpha-acids, tetrahydroiso-alpha-acids, hexahydroiso-alpha-acids, alpha-acids, and beta-acids. The diatomaceous earth filter aid can also be contacted with and an acid other than the hop compound such as phosphoric acid. The iso-alpha-acids, dihydroiso-alpha-acids, tetrahydroiso-alpha-acids, hexahydroiso-alpha-acids, alpha-acids, or beta-acids bind the copper and iron metal ions and/or change the form of copper and iron in diatomaceous earth so the copper and iron are rendered substantially insoluble in a beverage such as beer. A method for filtering a beverage using the treated diatomaceous earth filter aid is also disclosed. A method for increasing the flavor stability of a malt beverage filtered with a diatomaceous earth filter aid is also disclosed.

Methods for reducing soluble metal ions in diatomaceous earth filter aids

Disclosed are methods for the production of light stable hop products, useful for the brewing of beer or ale to be stored in clear or green glass containers, which beer or ale will not develop objectionable flavor as a result of exposure to light. Light stable hop products are prepared by double extraction of liquid/supercritical COextracted hop solids with ethanol to remove alpha/iso-alpha-acids. Such alpha/iso-alpha-acids may be further removed from the ethanol extraction filtrate obtained in the double extraction process by subjecting such filtrate to an ion exchange medium, or precipitation by a metal ion, heavy metal ion, or alkali metal ion, or hydrogenation to provide an alpha/iso-alpha-acids free filtrate which may be added to the light stable double extracted hop solid residues obtained in the initial double extraction process.

Preparation of light stable hop products

Disclosed are methods for the production of light stable hops, useful for the brewing of beer or ale to be stored in clear or green glass containers, which beer or ale will not develop objectionable flavor as a result of exposure to light. Light stable hops are prepared by double extraction of liquid/supercritical COextracted hop solids with ethanol to remove alpha/iso-alpha-acids. Such alpha/iso-alpha-acids may be further removed from the ethanol extraction liquor obtained in the double extraction process by subjecting such liquor to an ion exchange medium, or precipitation by a metal ion, heavy metal ion, or alkali metal ion, to provide an alpha/iso-alpha-acid is free extraction liquor which may be added to the light stable hops residue obtained in the initial double extraction process.

Preparation of light stable hops

A method of making a fully hop flavored beverage employs a hop flavoring agent comprising an extract of hop solids, the hop solids being the residue of a first extraction of hops to remove the alpha acids. Preferably, liquid carbon dioxide is used for the first extraction of the hops and a polar solvent, such as ethanol or water, is used to extract the hop solids. Beverages made by the method and novel compositions for use in the method are also disclosed.

Method of preparing a fully kettle hop flavored beverage

The isolation and characterization of a group of odorless and non-volatile glycosides from extracted hops (hop solids which have been previously extracted with non-polar solvents) is disclosed. These glycosides are water soluble and consist of a group of aromatic compounds conjugated to mono-, di-, and trisaccharides. These glycosides are responsible for the formation of kettle hop flavor and taste through both chemical and biological transformations. When these glycosides are transformed, they yield an essence and flavorant which imparts a kettle hop flavor and taste when the essence and flavorant is added to an unhopped beer. These kettle hop flavor essences and flavorants provide economy, consistency, flexibility, quality, and convenience to the brewing process because only one unhopped wort is required to brew a stock of unhopped beer. The unhopped beer can then be dosed with the desired amount of kettle hop flavor essence and flavorant.

Methods of making and using purified kettle hop flavorants

A method of preparing tetrahydroiso-&agr;-acids from iso-&agr;-acids is disclosed wherein the reaction medium is a buffered, aqueous alcoholic solution. The method can also employ up to 85% w/w spent hydrogenation catalyst. The method advantageously avoids the formation of undesirable side products.

Method of hydrogenating iso-&agr; acids in a buffered solution

Carbon dioxide is used as a reaction solvent in the hydrogenation of organic compounds. The carbon dioxide is preferably a liquid or a supercritical fluid. The hydrogenation method can be used advantageously in methods for making tetrahydroiso-alpha-acids from alpha-acids, iso-alpha-acids, or beta-acids. If beta-acids are used to make tetrahydroiso-alpha-acids, an acidic lower alcohol is preferably added to the carbon dioxide reaction medium to act as a promoter.

Hydrogenation of hop soft resins using CO.sub.2

Unsaturated organic compounds, in particular .alpha.-acids and .beta.-acids, are purified prior to hydrogenation by mixing them with an adsorbent capable of adsorbing catalyst poisons, preferably activated carbon, and separating the adsorbent containing the catalyst poisons to recover the thus purified unsaturated organic compounds. A significant reduction in the use of hydrogenation catalyst is realized.

Purification of .alpha.-acids and .beta.-acids

A concentrated single phase aqueous alkaline solution of tetrahydroiso-.alpha.-acids having greater than 10% to about 45% w/w tetrahydroiso-.alpha.-acids is disclosed. A method of hydrogenating and formulating a starting solution of iso-.alpha.-acids to obtain such concentrated solutions of tetrahydroiso-.alpha.-acids is also disclosed.

Concentrated single phase aqueous solutions of

A method of making a light stable, hop flavored, fermented beverage of less bitterness having a comparable hop flavor to one prepared using whole hops consists of adding to a wort as the sole hopping material a solid hop residue obtained by extracting whole hops with liquid carbon dioxide, boiling the solid hop residue and wort mixture, removing the solids from the fermented mixture and fermenting the remaining liquid to obtain the beverage.

Method of preparing a full hop flavored beverage of low bitterness

Tetrahydroiso-.alpha.-acids are prepared from iso-.alpha.-acids metal salts by hydrogenating the salts in a reaction solvent of a lower alkanol containing about 5% to about 20% w/w water and in the presence of up to about 5-50 psig hydrogen and a hydrogenation catalyst at about 30.degree.-50.degree. C. to form tetrahydroiso-.alpha.-acids.

Preparation of tetrahydroiso-.alpha.-acids by the hydrogenation of the

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Brookfield, WI, United States of America

Patrick L Ting