DE2832267C2 - - Google Patents
Info
- Publication number
- DE2832267C2 DE2832267C2 DE2832267A DE2832267A DE2832267C2 DE 2832267 C2 DE2832267 C2 DE 2832267C2 DE 2832267 A DE2832267 A DE 2832267A DE 2832267 A DE2832267 A DE 2832267A DE 2832267 C2 DE2832267 C2 DE 2832267C2
- Authority
- DE
- Germany
- Prior art keywords
- caffeine
- resin
- beans
- total
- extract
- 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
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 70
- 229920005989 resin Polymers 0.000 claims description 36
- 239000011347 resin Substances 0.000 claims description 36
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims description 35
- 229960001948 caffeine Drugs 0.000 claims description 35
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 19
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 17
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 17
- 239000000284 extract Substances 0.000 claims description 15
- 238000001179 sorption measurement Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 6
- 238000005342 ion exchange Methods 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 239000002952 polymeric resin Substances 0.000 claims description 4
- 229920001059 synthetic polymer Polymers 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 9
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 9
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 9
- 229940074393 chlorogenic acid Drugs 0.000 description 9
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 9
- 235000001368 chlorogenic acid Nutrition 0.000 description 9
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 9
- 230000008929 regeneration Effects 0.000 description 9
- 238000011069 regeneration method Methods 0.000 description 9
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 6
- 241000533293 Sesbania emerus Species 0.000 description 5
- 244000013123 dwarf bean Species 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 235000021331 green beans Nutrition 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 235000002187 Coffea robusta Nutrition 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- -1 chlorogenic acid ions Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940069765 bean extract Drugs 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 235000021384 green leafy vegetables Nutrition 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- XXFQGNXPWZSRRK-UHFFFAOYSA-N sodium;n-chlorobenzenesulfonamide Chemical compound [Na+].ClNS(=O)(=O)C1=CC=CC=C1 XXFQGNXPWZSRRK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/20—Reducing or removing alkaloid content; Preparations produced thereby; Extracts or infusions thereof
- A23F5/22—Reducing or removing alkaloid content from coffee extract
- A23F5/223—Reducing or removing alkaloid content from coffee extract using flocculating, precipitating, adsorbing or complex-forming agents, or ion-exchangers
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Tea And Coffee (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3285977 | 1977-08-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2832267A1 DE2832267A1 (de) | 1979-02-15 |
| DE2832267C2 true DE2832267C2 (en, 2012) | 1988-06-16 |
Family
ID=10345080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782832267 Granted DE2832267A1 (de) | 1977-08-05 | 1978-07-22 | Verfahren zum entfernen von koffein aus gruenen kaffeebohnen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4364964A (en, 2012) |
| AT (1) | AT366238B (en, 2012) |
| BE (1) | BE869504A (en, 2012) |
| CA (1) | CA1115593A (en, 2012) |
| CH (1) | CH637272A5 (en, 2012) |
| DE (1) | DE2832267A1 (en, 2012) |
| FR (1) | FR2399212A1 (en, 2012) |
| GB (1) | GB2001838B (en, 2012) |
| IT (1) | IT1097628B (en, 2012) |
| NL (1) | NL187665C (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4237288A (en) * | 1979-05-17 | 1980-12-02 | Societe D'assistance Technique Pour Produits Nestle S.A. | Decaffeination of fatty materials |
| NL8104854A (nl) * | 1981-10-27 | 1983-05-16 | Douwe Egberts Tabaksfab | Werkwijze voor het decaffeineren van groene koffiebonen. |
| DE3313339A1 (de) * | 1983-04-13 | 1984-10-18 | Kord Beteiligungsgesellschaft mbH & Co KG, 2000 Hamburg | Verfahren zur herstellung von entcoffeinierten genussmitteln |
| US4820537A (en) * | 1987-03-13 | 1989-04-11 | General Foods Corporation | Method for decaffeinating coffee with a supercritical fluid |
| US4837038A (en) * | 1988-02-02 | 1989-06-06 | Nestec Sa | Decaffeination process |
| US5043178A (en) * | 1988-02-09 | 1991-08-27 | Kraft General Foods, Inc. | Method for the extraction of roasted and ground coffee |
| US4911941A (en) * | 1988-08-05 | 1990-03-27 | General Foods Corporation | Method for decaffeinating coffee with a supercritical fluid |
| US4956429A (en) * | 1989-03-01 | 1990-09-11 | Penick Corporation | Method of making a coca leaf flavor extract |
| US5021253A (en) * | 1989-12-13 | 1991-06-04 | The Dow Chemical Company | Decaffeination of liquid medium |
| DE4010826A1 (de) * | 1990-04-04 | 1991-10-17 | Jacobs Suchard Ag | Verfahren und vorrichtung zur entcoffeinierung von kaffee, insbesondere rohkaffee |
| US5443709A (en) * | 1993-12-17 | 1995-08-22 | Imsco, Inc. | Apparatus for separating caffeine from a liquid containing the same |
| PT776607E (pt) * | 1995-12-07 | 2002-06-28 | Nestle Sa | Polimero de absorcao de cafeina |
| EP1632135A1 (en) * | 2004-08-18 | 2006-03-08 | Nestec S.A. | Inert, glassy matrices for the stabilization of aroma in soluble coffee |
| US20100112181A1 (en) * | 2008-10-30 | 2010-05-06 | Matthew Joel Taylor | Recovery of Antioxidants from Decaffeination Process |
| EP4327666A1 (de) | 2022-08-26 | 2024-02-28 | ANKA Angewandte Kaffeetechnologie GmbH | Verfahren und vorrichtung zur herstellung entkoffeinierter rohkaffeebohnen und koffein unter einsatz von adsorberharzen sowie entsprechende verwendungen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108876A (en) * | 1961-05-09 | 1963-10-29 | Duncan Coffee Company | Manufacture of decaffeinated instant coffee |
| US3620756A (en) * | 1969-02-17 | 1971-11-16 | Procter & Gamble | Nonfoaming and nonscumming instant coffee |
| US4031251A (en) * | 1975-01-08 | 1977-06-21 | Societe D'assistance Technique Pour Produits Nestle S.A. | Decaffeination of vegetable material |
| CA1083880A (en) * | 1975-06-24 | 1980-08-19 | Gary L. Hickernell | Method for decaffeinating green coffee |
| DE2637197C2 (de) * | 1976-08-18 | 1983-01-27 | Hag Ag, 2800 Bremen | Verfahren zum Entzug von Coffein aus coffeinhaltigen Naturstoffen mit einem überkritischen Extraktionsmittel |
| US4113888A (en) * | 1977-02-24 | 1978-09-12 | General Foods Corporation | Adsorption process |
| US4113887A (en) * | 1977-02-24 | 1978-09-12 | General Foods Corporation | Adsorption process |
| NL7807214A (nl) * | 1977-08-06 | 1979-02-08 | D E J Int Research | Werkwijze voor de selectieve extractie van een oplos- bare component uit een vast korrelvormig materiaal, dat een aantal oplosbare componenten bevat. |
-
1978
- 1978-07-03 NL NLAANVRAGE7807208,A patent/NL187665C/xx not_active IP Right Cessation
- 1978-07-20 CH CH781878A patent/CH637272A5/de not_active IP Right Cessation
- 1978-07-22 DE DE19782832267 patent/DE2832267A1/de active Granted
- 1978-07-24 AT AT0534778A patent/AT366238B/de not_active IP Right Cessation
- 1978-07-31 CA CA308,462A patent/CA1115593A/en not_active Expired
- 1978-08-02 FR FR7822798A patent/FR2399212A1/fr active Granted
- 1978-08-04 IT IT26530/78A patent/IT1097628B/it active
- 1978-08-04 BE BE7857193A patent/BE869504A/xx not_active IP Right Cessation
- 1978-08-04 GB GB7832293A patent/GB2001838B/en not_active Expired
-
1980
- 1980-08-27 US US06/181,899 patent/US4364964A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4364964A (en) | 1982-12-21 |
| BE869504A (nl) | 1979-02-05 |
| FR2399212A1 (fr) | 1979-03-02 |
| GB2001838A (en) | 1979-02-14 |
| DE2832267A1 (de) | 1979-02-15 |
| FR2399212B1 (en, 2012) | 1984-10-05 |
| AT366238B (de) | 1982-03-25 |
| IT7826530A0 (it) | 1978-08-04 |
| NL7807208A (nl) | 1979-02-07 |
| GB2001838B (en) | 1982-01-13 |
| NL187665C (nl) | 1991-12-16 |
| ATA534778A (de) | 1981-08-15 |
| IT1097628B (it) | 1985-08-31 |
| CH637272A5 (de) | 1983-07-29 |
| CA1115593A (en) | 1982-01-05 |
| NL187665B (nl) | 1991-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |