CA1099289A - Preparation of hop extract - Google Patents
Preparation of hop extractInfo
- Publication number
- CA1099289A CA1099289A CA295,222A CA295222A CA1099289A CA 1099289 A CA1099289 A CA 1099289A CA 295222 A CA295222 A CA 295222A CA 1099289 A CA1099289 A CA 1099289A
- Authority
- CA
- Canada
- Prior art keywords
- extract
- extraction
- acids
- hop
- hops
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000284 extract Substances 0.000 title claims abstract description 91
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 83
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 73
- 239000007788 liquid Substances 0.000 claims abstract description 53
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims description 67
- 235000008694 Humulus lupulus Nutrition 0.000 claims description 47
- 239000001993 wax Substances 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 7
- 239000003925 fat Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 8
- 241000218228 Humulus Species 0.000 description 48
- 244000025221 Humulus lupulus Species 0.000 description 45
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000013405 beer Nutrition 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 13
- 239000012535 impurity Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910052742 iron Inorganic materials 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229920001864 tannin Polymers 0.000 description 3
- 239000001648 tannin Substances 0.000 description 3
- 235000018553 tannin Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229930002875 chlorophyll Natural products 0.000 description 2
- 235000019804 chlorophyll Nutrition 0.000 description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- WYUYEJNGHIOFOC-VVTVMFAVSA-N 2-[(z)-1-(4-methylphenyl)-3-pyrrolidin-1-ylprop-1-enyl]pyridine;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C\CN1CCCC1 WYUYEJNGHIOFOC-VVTVMFAVSA-N 0.000 description 1
- 241000543381 Cliftonia monophylla Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- 101100286668 Mus musculus Irak1bp1 gene Proteins 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 1
- 241000950638 Symphysodon discus Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000061 acid fraction Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- VTVVPPOHYJJIJR-UHFFFAOYSA-N carbon dioxide;hydrate Chemical compound O.O=C=O VTVVPPOHYJJIJR-UHFFFAOYSA-N 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012632 extractable Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 101150032953 ins1 gene Proteins 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000009991 pite Nutrition 0.000 description 1
- 244000293655 pite Species 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C3/00—Treatment of hops
- C12C3/04—Conserving; Storing; Packing
- C12C3/08—Solvent extracts from hops
- C12C3/10—Solvent extracts from hops using carbon dioxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Extraction Or Liquid Replacement (AREA)
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1944/77A GB1575827A (en) | 1977-01-18 | 1977-01-18 | Preparation of hop extract |
| GB1944/77 | 1977-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1099289A true CA1099289A (en) | 1981-04-14 |
Family
ID=9730787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA295,222A Expired CA1099289A (en) | 1977-01-18 | 1978-01-18 | Preparation of hop extract |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4218491A (en:Method) |
| AT (1) | AT359018B (en:Method) |
| AU (1) | AU517660B2 (en:Method) |
| BE (1) | BE863013A (en:Method) |
| CA (1) | CA1099289A (en:Method) |
| CH (1) | CH634346A5 (en:Method) |
| DE (1) | DE2801843A1 (en:Method) |
| FR (1) | FR2377448A1 (en:Method) |
| GB (1) | GB1575827A (en:Method) |
| NZ (1) | NZ186251A (en:Method) |
| YU (1) | YU10578A (en:Method) |
| ZA (1) | ZA78328B (en:Method) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH649778A5 (de) * | 1978-06-20 | 1985-06-14 | Mueller Adam | Verfahren zum isomerisieren von alpha-saeuren in einem hopfenextrakt. |
| US4395431A (en) * | 1979-05-15 | 1983-07-26 | Carlton And United Breweries Limited | Processing of hop resins and similar materials |
| ZA802802B (en) * | 1979-05-24 | 1981-05-27 | Brewing Patents Ltd | Preparation of hop extracts rich in particular constituents |
| DE3119454A1 (de) * | 1981-05-15 | 1982-12-09 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verfahren zur herstellung von konzentrierten extrakten aus frischen pflanzen oder teilen davon, insbesondere frischen kuechenkraeutern |
| US4507329A (en) * | 1982-02-03 | 1985-03-26 | S. S. Steiner, Inc. | Mixed solvent extraction of hops |
| US4550198A (en) * | 1982-11-04 | 1985-10-29 | Georgia Tech Research Institute | Purification of terephthalic acid by supercritical fluid extraction |
| DE3346776A1 (de) * | 1983-12-23 | 1985-07-04 | Hopfen-Extraktion Barth & Co, 8069 Wolnzach | Verfahren zur extraktion von hopfeninhaltsstoffen |
| DE3413869A1 (de) * | 1984-04-12 | 1985-10-17 | Hopfenextraktion HVG Barth, Raiser & Co, 8069 Wolnzach | Verfahren zur entcoffeinierung von schwarzem tee |
| DE3414562A1 (de) * | 1984-04-17 | 1985-10-24 | Skw Trostberg Ag, 8223 Trostberg | Verfahren zum abscheiden von mittels hochdruckextraktion gewonnenen stoffen |
| AT389034B (de) * | 1984-06-15 | 1989-10-10 | Gyoergy Dr Timar | Verfahren zur herstellung von patronen zur bereitung von kohlensaeurehaltigen getraenken |
| DE3632401A1 (de) * | 1986-09-24 | 1988-04-07 | Barth Raiser Hopfenextraktion | Verfahren zur extraktion unpolarer inhaltsstoffe aus hopfen |
| US4962275A (en) * | 1990-02-21 | 1990-10-09 | United States Of America As Represented By The Secretary Of Commerce | Method and apparatus for supercritical fluid extraction solution separation |
| JP3155003B2 (ja) * | 1990-11-06 | 2001-04-09 | サントリー株式会社 | ホップエキスの製造法および該方法により得られるホップエキス |
| US5120557A (en) * | 1991-06-21 | 1992-06-09 | Owades Joseph L | Preparation of a non-alcoholic malt beverage |
| GB2289055A (en) * | 1994-04-28 | 1995-11-08 | Steiner Hops Ltd | Extraction of hops |
| US6020019A (en) * | 1996-03-26 | 2000-02-01 | Miller Brewing Company | Hydrogenation of hop soft resins using CO2 |
| US6407143B1 (en) | 1999-12-22 | 2002-06-18 | Sandia Corporation | Method and solvent composition for regenerating an ion exchange resin |
| EP1747822A1 (en) * | 2005-07-28 | 2007-01-31 | Linde Aktiengesellschaft | Cooling / heating system for CO2 cleaning machine |
| US8048304B2 (en) * | 2007-12-27 | 2011-11-01 | Dynasep Llc | Solvent extraction and recovery |
| TWI630018B (zh) * | 2015-09-07 | 2018-07-21 | 喬治 斯特徹夫 | 萃取裝置及萃取方法 |
| EP4186374A1 (en) | 2021-11-24 | 2023-05-31 | Herbolea Biotech S.p.A. | Bitter acids concentrate, method of obtaining the same and use thereof |
| DE102022119594A1 (de) * | 2022-08-04 | 2024-02-15 | Simon H. Steiner, Hopfen, Gesellschaft mit beschränkter Haftung | Verfahren zur Herstellung einer Hopfenextrakt-Emulsion, damit hergestellte Hopfenextrakt-Emulsion, Lebensmittel und entsprechende Verwendungen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2127618C2 (de) | 1971-06-03 | 1973-06-14 | Hag Ag | Verfahren zur Gewinnung von Hopfenextrakten |
| CA1047436A (en) * | 1974-06-11 | 1979-01-30 | Brewing Patents Limited | Preparation of hop oil |
| YU242277A (en) * | 1976-10-13 | 1982-06-30 | Brewing Patents Ltd | Process for preparing an iso-alpha-acid preparation |
| GB1557123A (en) * | 1977-04-29 | 1979-12-05 | Distillers Co Carbon Dioxide | Method and apparatus for reparing extracts of hops and other materials |
-
1977
- 1977-01-18 GB GB1944/77A patent/GB1575827A/en not_active Expired
-
1978
- 1978-01-17 US US05/870,084 patent/US4218491A/en not_active Expired - Lifetime
- 1978-01-17 DE DE19782801843 patent/DE2801843A1/de not_active Ceased
- 1978-01-18 ZA ZA00780328A patent/ZA78328B/xx unknown
- 1978-01-18 CA CA295,222A patent/CA1099289A/en not_active Expired
- 1978-01-18 BE BE184396A patent/BE863013A/xx not_active IP Right Cessation
- 1978-01-18 AU AU32523/78A patent/AU517660B2/en not_active Expired
- 1978-01-18 YU YU00105/78A patent/YU10578A/xx unknown
- 1978-01-18 CH CH53278A patent/CH634346A5/de not_active IP Right Cessation
- 1978-01-18 AT AT36378A patent/AT359018B/de not_active IP Right Cessation
- 1978-01-18 FR FR7801371A patent/FR2377448A1/fr active Granted
- 1978-01-18 NZ NZ186251A patent/NZ186251A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT359018B (de) | 1980-10-10 |
| US4218491A (en) | 1980-08-19 |
| CH634346A5 (de) | 1983-01-31 |
| ATA36378A (de) | 1980-03-15 |
| GB1575827A (en) | 1980-10-01 |
| NZ186251A (en) | 1979-11-01 |
| BE863013A (fr) | 1978-07-18 |
| YU10578A (en) | 1982-06-30 |
| AU517660B2 (en) | 1981-08-20 |
| FR2377448A1 (fr) | 1978-08-11 |
| FR2377448B1 (en:Method) | 1982-05-28 |
| ZA78328B (en) | 1979-01-31 |
| DE2801843A1 (de) | 1978-07-27 |
| AU3252378A (en) | 1979-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |