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US4302479A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of iso-alpha-acid-containing hop extracts

Assignee: Solvay Solutions UK Ltd
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Filing: 1980-05-27
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Granted: 1981-11-24
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Expires: 2000-05-27
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Abstract

Abstract When preparing hop extract containing iso-alpha-acids, improved yield of iso-alpha-acids is obtained by contacting a solution of extracted alpha-acids in a water-immiscible non-polar liquid with a sufficiently strong aqueous solution of acid to provide a pH of less than 1 in an aqueous phase that separates from the non-polar liquid. After contacting with the acid, the alpha-acids are isomerized such as by forming alpha acid salts and heating the salts.

Inventors

  • 👤 Anthony M. Humphrey
  • 👤 Anthony Lewis

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 14:28
CPC Classifications
C; C12; C12C; C12C3/00; C12C3/12; C12C3/04; C12C3/08

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 151 words
In the method for the preparation of an isomerized hop extract which consists essentially in extracting alpha-acids from hops with a solvent for alpha-acids to form an alpha-acid-containing hop extract, contacting a solution of said alpha-acids in a water immiscible, non-polar liquid with a base selected from the hydroxides and carbonates of sodium and potassium whereby said base and said alpha-acids react to form salts of the alpha-acids, heating said salts to effect isomerisation thereof, and transferring said isomerised salts, into an aqueous, alkaline phase, the improvement which consists in that a solution of the alpha-acids in a water immiscible non-polar liquid is contacted, prior to conversion into the salt form, with a sufficiently strong aqueous solution of acid to provide a pH of less than 1 in an aqueous phase that separates from said water-immiscible non-polar liquid after contacting said solution of alpha acids with said aqueous solution of acid.
Claim 2
Dependent Claim 151 words
In the method for the preparation of an isomerized hop extract which consists essentially in extracting alpha-acids from hops with a solvent for alpha-acids to form an alpha-acid-containing hop extract, contacting a solution of said alpha-acids in a water immiscible, non-polar liquid with a base selected from the hydroxides and carbonates of sodium and potassium whereby said base and said alpha-acids react to form salts of the alpha-acids, heating said salts to effect isomerisation thereof, and transferring said isomerised salts, into an aqueous, alkaline phase, the improvement which consists in that a solution of the alpha-acids in a water immiscible non-polar liquid is contacted, prior to conversion into the salt form, with a sufficiently strong aqueous solution of acid to provide a pH of less than 1 in an aqueous phase that separates from said water-immiscible non-polar liquid after contacting said solution of alpha acids with said aqueous solution of acid.
Claim 3
Dependent Claim 29 words
A method according to claim 1 wherein the alpha-acids are extracted from the hops with a solvent selected from the group consisting of liquid hydrocarbons, halocarbons and carbon dioxide.
Claim 4
Dependent Claim 27 words
A method according to claim 2 wherein the alpha-acid-containing hop extract is recovered from the extracting solvent by evaporation of said solvent prior to contacting with acid.
Claim 5
Dependent Claim 14 words
A method according to claim 1 wherein said non-polar liquid is a liquid hydrocarbon.
Claim 6
Dependent Claim 14 words
A method according to claim 4 wherein said liquid hydrocarbon is a petroleum hydrocarbon.
Claim 7
Dependent Claim 14 words
A method according to claim 4 wherein said liquid hydrocarbon is a terpene hydrocarbon.
Claim 8
Dependent Claim 14 words
A method according to claim 1 wherein said non-polar liquid is hop essential oil.
Claim 9
Dependent Claim 19 words
A method according to claim 4 wherein said liquid hydrocarbon has a boiling point between 80° and 200° C.
Claim 10
Dependent Claim 15 words
A method according to claim 1 wherein said aqueous solution of acid is hydrochloric acid.
Claim 11
Dependent Claim 24 words
A method according to claim 1 wherein said aqueous solution of acid is selected from the group consisting of phosphoric, sulphuric and trichloroacetic acid.
Claim 12
Dependent Claim 20 words
A method according to claim 1 wherein said aqueous solution of acid contains a proportion of a water miscible alcohol.
Claim 13
Dependent Claim 92 words
A method according to claim 1 wherein said aqueous phase having a pH less than 1 is separated from said non-polar liquid and said alpha-acids in said non-polar liquid are contacted with a base selected from the group consisting of substantially anhydrous hydroxides and carbonates of potassium and sodium, to form a precipitate of the alkali metal salts of the alpha-acids, said salts are heated to isomerise said salts and said isomerised salts are transferred to said aqueous alkaline phase after isomerisation by contacting said salts with sufficient water to dissolve them.
Claim 14
Dependent Claim 15 words
A method according to claim 12 wherein said base is a substantially anhydrous potassium alkali.
Claim 15
Dependent Claim 13 words
A method according to claim 13 wherein said potassium alkali is potassium carbonate.
Claim 16
Dependent Claim 18 words
A method according to claim 12 wherein the isomerisation occurs at a temperature between 100° and 150° C.
Claim 17
Dependent Claim 67 words
A method according to claim 12 wherein said base is said hydroxide or carbonate of potassium and said alpha-acids are recovered, after isomerisation, by contacting said salts in said non-polar liquid with an aqueous phase having a pH after said contacting sufficient to extract the iso-alpha-acids as their potassium salts into the aqueous phase but insufficient to extract beta-acids as their potassium salts into the aqueous phase.
Claim 18
Dependent Claim 18 words
A method according to claim 14 wherein the pH of said aqueous phase is between 8 and 9.5.
Claim 19
Independent Claim 142 words
A method for the preparation of isomerised hop extract which consists essentially in contacting a solution of an alpha-acid-containing hop extract in a non-polar, water-immiscible liquid having a boiling point greater than 100° C. with a sufficiently strong aqueous solution of acid to produce an aqueous phase after said contacting having a pH of less than 1, separating said aqueous phase from said liquid, contacting said liquid with a substantially anhydrous base selected from the group consisting of the hydroxides and carbonates of sodium and potassium to precipitate salts of the alpha-acids, heating said salts in said liquid at a temperature between 100° C. and 150° C., to form salts of iso-alpha-acids, contacting said salts of iso-alpha-acids with sufficient water to dissolve them at a pH between about 8 and 9.5, and separating an aqueous solution of iso-alpha-acid salts from said liquid.
Claim 20
Independent Claim 142 words
A method for the preparation of isomerised hop extract which consists essentially in contacting a solution of an alpha-acid-containing hop extract in a non-polar, water-immiscible liquid having a boiling point greater than 100° C. with a sufficiently strong aqueous solution of acid to produce an aqueous phase after said contacting having a pH of less than 1, separating said aqueous phase from said liquid, contacting said liquid with a substantially anhydrous base selected from the group consisting of the hydroxides and carbonates of sodium and potassium to precipitate salts of the alpha-acids, heating said salts in said liquid at a temperature between 100° C. and 150° C., to form salts of iso-alpha-acids, contacting said salts of iso-alpha-acids with sufficient water to dissolve them at a pH between about 8 and 9.5, and separating an aqueous solution of iso-alpha-acid salts from said liquid.
Claim 21
Independent Claim 185 words
A method for the preparation of isomerised hop extract which consists essentially in extracting hops with a volatile solvent for alpha acids, evaporating said solvent to form a hop extract containing alpha-acids, beta-acids and hop oils, dissolving said extract in a water-immiscible non-polar liquid contacting said extract in said liquid with a sufficiently strong aqueous solution of acid to produce an aqueous phase that separates from said liquid having a pH below 1, separating said aqueous phase from said non-polar liquid, contacting said liquid with sufficient substantially anhydrous potassium carbonate to form potassium salts of said alpha-acids, but not to form potassium salts of said beta-acids, heating said salts while in said non-polar liquid to isomerise said salts of said alpha-acids to form potassium salts of iso-alpha-acids, contacting said isomerised salts in said non-polar liquid with sufficient water to dissolve said salts of iso-alpha-acids at a pH insufficient to convert said beta-acids to the salt form, and in the presence of sufficient non-polar, water-immiscible liquid to retain said beta-acids in said non-polar liquid, and separating said liquid from an aqueous phase containing said iso-alpha-acid salts.
Claim 22
Independent Claim 185 words
A method for the preparation of isomerised hop extract which consists essentially in extracting hops with a volatile solvent for alpha acids, evaporating said solvent to form a hop extract containing alpha-acids, beta-acids and hop oils, dissolving said extract in a water-immiscible non-polar liquid contacting said extract in said liquid with a sufficiently strong aqueous solution of acid to produce an aqueous phase that separates from said liquid having a pH below 1, separating said aqueous phase from said non-polar liquid, contacting said liquid with sufficient substantially anhydrous potassium carbonate to form potassium salts of said alpha-acids, but not to form potassium salts of said beta-acids, heating said salts while in said non-polar liquid to isomerise said salts of said alpha-acids to form potassium salts of iso-alpha-acids, contacting said isomerised salts in said non-polar liquid with sufficient water to dissolve said salts of iso-alpha-acids at a pH insufficient to convert said beta-acids to the salt form, and in the presence of sufficient non-polar, water-immiscible liquid to retain said beta-acids in said non-polar liquid, and separating said liquid from an aqueous phase containing said iso-alpha-acid salts.
Claim 23
Dependent Claim 14 words
A method according to claim 19 wherein said volatile solvent is liquid carbon dioxide.
Claim 24
Independent Claim 22 words
A method according to either of claims 19 and 20 wherein said non-polar, water-immiscible solvent is hop oil contained by said extract.
Claim 25
Dependent Claim 23 words
A method according to claim 21 wherein said hop oil is recovered by steam distillation from said extract and at least partially recycled.
Claim 26
Independent Claim 86 words
A method for the production of isomerised hop extract which consists essentially in contacting a solution of hop extract containing alpha-acids in a non-polar, water-immiscible liquid with a sufficiently strong aqueous solution of acid to provide an aqueous phase having a pH of less than 1, separating said aqueous phase from said liquid, contacting said liquid with sufficient aqueous alkali to extract said alpha-acids from said liquid as their salts, separating said aqueous alkali containing said salts from said liquid and subsequently isomerising said alpha-acid salts.
Claim 27
Independent Claim 86 words
A method for the production of isomerised hop extract which consists essentially in contacting a solution of hop extract containing alpha-acids in a non-polar, water-immiscible liquid with a sufficiently strong aqueous solution of acid to provide an aqueous phase having a pH of less than 1, separating said aqueous phase from said liquid, contacting said liquid with sufficient aqueous alkali to extract said alpha-acids from said liquid as their salts, separating said aqueous alkali containing said salts from said liquid and subsequently isomerising said alpha-acid salts.

References Cited (Backward Citations)

US3532504A Cited
US3558326A Cited
US3875316A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-11-23 1985-05-25 1985-11-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-11-23 1989-05-25 1989-11-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-11-23 1993-05-25 1993-11-24 $7700.00 Window Closed / Lapsed

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