CA1097688A - Obtention d'iso-d-acides - Google Patents

Obtention d'iso-d-acides

Info

Publication number: CA1097688A
Authority: CA; Canada
Prior art keywords: acids; extract; iso; alpha; hops
Prior art date: 1976-10-13
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

Application number

CA288,549A

Other languages

English (en)

Inventor

Nigel A. Bath

Derek R. J. Laws

Colin S. Ennis

John A. Pickett

Alfred G. Wheldon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Brewing Patents Ltd

Original Assignee

Brewing Patents Ltd

Priority date (The priority date 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 date listed.)

1976-10-13

Filing date

1977-10-12

Publication date

1981-03-17

1976-10-13 Priority claimed from GB42613/76A external-priority patent/GB1576729A/en

1977-10-12 Application filed by Brewing Patents Ltd filed Critical Brewing Patents Ltd

1981-03-17 Application granted granted Critical

1981-03-17 Publication of CA1097688A publication Critical patent/CA1097688A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
239000002253 acid Substances 0.000 claims abstract description 182
239000000284 extract Substances 0.000 claims abstract description 157
235000008694 Humulus lupulus Nutrition 0.000 claims abstract description 74
239000007788 liquid Substances 0.000 claims abstract description 74
238000000034 method Methods 0.000 claims abstract description 69
238000006317 isomerization reaction Methods 0.000 claims abstract description 29
238000002360 preparation method Methods 0.000 claims abstract description 27
238000001914 filtration Methods 0.000 claims abstract description 11
238000009835 boiling Methods 0.000 claims abstract description 8
239000012670 alkaline solution Substances 0.000 claims abstract description 6
229910002092 carbon dioxide Inorganic materials 0.000 claims description 91
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 40
239000000243 solution Substances 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 20
239000001569 carbon dioxide Substances 0.000 claims description 18
239000000463 material Substances 0.000 claims description 12
238000001704 evaporation Methods 0.000 claims description 10
230000008020 evaporation Effects 0.000 claims description 9
239000003513 alkali Substances 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
230000020477 pH reduction Effects 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
238000000605 extraction Methods 0.000 abstract description 66
235000013405 beer Nutrition 0.000 abstract description 47
235000019658 bitter taste Nutrition 0.000 abstract description 4
238000000855 fermentation Methods 0.000 abstract description 2
230000004151 fermentation Effects 0.000 abstract description 2
150000002894 organic compounds Chemical class 0.000 abstract 1
241000218228 Humulus Species 0.000 description 72
244000025221 Humulus lupulus Species 0.000 description 70
239000003921 oil Substances 0.000 description 41
239000011347 resin Substances 0.000 description 32
229920005989 resin Polymers 0.000 description 32
150000007513 acids Chemical class 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 16
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
238000007792 addition Methods 0.000 description 12
239000012535 impurity Substances 0.000 description 11
239000003960 organic solvent Substances 0.000 description 11
238000003860 storage Methods 0.000 description 11
229920001864 tannin Polymers 0.000 description 9
239000001648 tannin Substances 0.000 description 9
235000018553 tannin Nutrition 0.000 description 9
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
229910052802 copper Inorganic materials 0.000 description 8
239000010949 copper Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000010438 heat treatment Methods 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
230000008901 benefit Effects 0.000 description 6
229930002875 chlorophyll Natural products 0.000 description 6
235000019804 chlorophyll Nutrition 0.000 description 6
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 6
229910052742 iron Inorganic materials 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000012546 transfer Methods 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000007789 gas Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003925 fat Substances 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
235000019634 flavors Nutrition 0.000 description 4
239000012530 fluid Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000001993 wax Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
229910001385 heavy metal Inorganic materials 0.000 description 3
239000008188 pellet Substances 0.000 description 3
238000012545 processing Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000003889 chemical engineering Methods 0.000 description 2
238000006243 chemical reaction Methods 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
238000013461 design Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960000443 hydrochloric acid Drugs 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
238000004064 recycling Methods 0.000 description 2
239000013557 residual solvent Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000000341 volatile oil Substances 0.000 description 2
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
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
241000331231 Amorphocerini gen. n. 1 DAD-2008 Species 0.000 description 1
OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
101100328884 Caenorhabditis elegans sqt-3 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000237074 Centris Species 0.000 description 1
241000543381 Cliftonia monophylla Species 0.000 description 1
241000518994 Conta Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
229930183974 Humulinic acid Natural products 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241000694408 Isomeris Species 0.000 description 1
241001233242 Lontra Species 0.000 description 1
229910001209 Low-carbon steel Inorganic materials 0.000 description 1
241000489861 Maximus Species 0.000 description 1
101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
208000007542 Paresis Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
-1 alkali metal salts Chemical class 0.000 description 1
235000019568 aromas Nutrition 0.000 description 1
238000006701 autoxidation reaction Methods 0.000 description 1
238000010923 batch production Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000000287 crude extract Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
229940079920 digestives acid preparations Drugs 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000002706 hydrostatic effect Effects 0.000 description 1
238000009413 insulation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229940046892 lead acetate Drugs 0.000 description 1
150000002739 metals Chemical class 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
238000002156 mixing Methods 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
238000013021 overheating Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
208000012318 pareses Diseases 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
238000007699 photoisomerization reaction Methods 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000003405 preventing effect Effects 0.000 description 1
230000005180 public health Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000011172 small scale experimental method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000013022 venting Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing 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)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Health & Medical Sciences (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Food Science & Technology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Extraction Or Liquid Replacement (AREA)

CA288,549A 1976-10-13 1977-10-12 Obtention d'iso-d-acides Expired CA1097688A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB42613/76		1976-10-13
GB42613/76A GB1576729A (en)	1976-10-13	1976-10-13	Method of making an iso-acid preparation from hops
GB18480/77		1977-05-03
GB1848077		1977-05-03

Publications (1)

Publication Number	Publication Date
CA1097688A true CA1097688A (fr)	1981-03-17

Family

ID=26253412

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA288,549A Expired CA1097688A (fr)	1976-10-13	1977-10-12	Obtention d'iso-d-acides

Country Status (8)

Country	Link
AT (1)	AT360468B (fr)
AU (1)	AU512851B2 (fr)
CA (1)	CA1097688A (fr)
CH (1)	CH630956A5 (fr)
DE (1)	DE2745829C2 (fr)
FR (1)	FR2367822A1 (fr)
NZ (1)	NZ185423A (fr)
YU (1)	YU242277A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1575827A (en) *	1977-01-18	1980-10-01	Brewing Patents Ltd	Preparation of hop extract
DE2827002B2 (de)	1978-06-20	1980-09-04	Adam Dr. 8421 St Johann Mueller	Verfahren zum Behandeln von Hopfen mit CO2 als Extraktionsmittel
DE2920765C2 (de) *	1979-05-22	1986-10-23	Müller, Adam, Dr., 8421 St Johann	Verfahren zur Herstellung eines isomerisierten Hopfenextraktes
DE3126490C2 (de) *	1981-07-04	1985-02-21	Miller Brewing Co., Milwaukee, Wis.	Verfahren zur Herstellung eines Hopfenpräparates
DE3235847C2 (de) *	1981-11-11	1996-05-30	Sueddeutsche Kalkstickstoff	Verfahren zur Extraktion von Hopfen
DK163185A (da) *	1984-04-12	1985-10-13	Scottish & Newcastle Breweries	Fremgangsmaade til fremstilling af oel med foroeget bitterhed
DE3513169A1 (de) *	1985-04-12	1986-10-16	Hopstabil Hopfenverarbeitungs-Gesellschaft mbH, 8069 Wolnzach	Verfahren zur herstellung von isohumulonen
KR101113162B1 (ko) *	2002-08-14	2012-06-20	지더블유 파마 리미티드	식물물질로부터 약제학적 활성성분의 추출의 개량

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2127618C2 (de) *	1971-06-03	1973-06-14	Hag Ag	Verfahren zur Gewinnung von Hopfenextrakten
GB1423129A (en) *	1971-08-04	1976-01-28	Bush Boake Allen Ltd	Isomerised hop extracts
JPS5020697B2 (fr) *	1971-09-04	1975-07-17

1977
- 1977-10-10 YU YU242277A patent/YU242277A/xx unknown
- 1977-10-11 AU AU29566/77A patent/AU512851B2/en not_active Expired
- 1977-10-12 CA CA288,549A patent/CA1097688A/fr not_active Expired
- 1977-10-12 DE DE19772745829 patent/DE2745829C2/de not_active Expired
- 1977-10-13 AT AT734577A patent/AT360468B/de not_active IP Right Cessation
- 1977-10-13 FR FR7730832A patent/FR2367822A1/fr active Granted
- 1977-10-13 CH CH1250977A patent/CH630956A5/de not_active IP Right Cessation
- 1977-10-13 NZ NZ18542377A patent/NZ185423A/xx unknown

Also Published As

Publication number	Publication date
CH630956A5 (en)	1982-07-15
AU512851B2 (en)	1980-10-30
DE2745829A1 (de)	1978-04-20
AT360468B (de)	1981-01-12
ATA734577A (de)	1980-06-15
FR2367822A1 (fr)	1978-05-12
FR2367822B1 (fr)	1982-05-28
NZ185423A (en)	1980-03-05
YU242277A (en)	1982-06-30
AU2956677A (en)	1979-04-26
DE2745829C2 (de)	1984-12-20

Legal Events

Date	Code	Title	Description
1998-03-17	MKEX	Expiry

Publication	Publication Date	Title
US4212895A (en)	1980-07-15	Production of iso-α-acid
US4218491A (en)	1980-08-19	Hop extraction with carbon dioxide
US4644084A (en)	1987-02-17	Preparation of tetrahydroisohumulones
US4590296A (en)	1986-05-20	Process for separation of beta-acids from extract containing alpha-acids and beta-acids
CA1097688A (fr)	1981-03-17	Obtention d'iso-d-acides
US5073396A (en)	1991-12-17	Beer flavored with a non-acidic hop-flavor fraction
US4324810A (en)	1982-04-13	Hop extracts and method of preparation
US4666731A (en)	1987-05-19	Separation of the constituents of CO2 hop extracts
CA1132068A (fr)	1982-09-21	Production d'acides iso-alpha
EP0679419B1 (fr)	2000-02-02	Extraction du houblon
US4844939A (en)	1989-07-04	Separation of the constitutents of CO2 hop extracts
US4344978A (en)	1982-08-17	Preparation of hop extracts rich in particular constituents
CA1245171A (fr)	1988-11-22	Methode pour augmenter l'amertume de la biere
US3852477A (en)	1974-12-03	Recovering flavor and aroma substances from fermentation gases
Irwin et al.	1985	An investigation of the relationships between hopping rate, time of boil, and individual alpha-acid utilization
Dickenson	1979	The relationship of dimethyl sulphide levels in malt, wort and beer
US6080844A (en)	2000-06-27	Process for the recovery and purification of a recombinant protein from a cell
US3821418A (en)	1974-06-28	Preparation of alcoholic malt beverages
Gardner	1993	Commercial scale extraction of alpha-acids and hop oils with compressed CO2
EP0173479B1 (fr)	1989-11-29	Extraction et isomérisation d'acides alpha d'extraits de houblon
US4507329A (en)	1985-03-26	Mixed solvent extraction of hops
Laws et al.	1977	Production of solvent-free isomerized extracts
EP0061877A2 (fr)	1982-10-06	Procédé et appareil pour l'obtention d'un extrait de houblon
GB1042798A (en)	1966-09-14	Process for preparation of a fermented beverage
Sharpe et al.	1980	Pilot Plant Extraction of Hops with Liquid Carbon Dioxide and the Use of These Extracts in Pilot and Production Scale Brewing a