DE1498581A1 - New method for the separation of liquids and solids by means of capillary liquid chromatography - Google Patents
New method for the separation of liquids and solids by means of capillary liquid chromatographyInfo
- Publication number
- DE1498581A1 DE1498581A1 DE19631498581 DE1498581A DE1498581A1 DE 1498581 A1 DE1498581 A1 DE 1498581A1 DE 19631498581 DE19631498581 DE 19631498581 DE 1498581 A DE1498581 A DE 1498581A DE 1498581 A1 DE1498581 A1 DE 1498581A1
- Authority
- DE
- Germany
- Prior art keywords
- liquid
- capillaries
- mentioned under
- liquid chromatography
- capillary
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000007788 liquid Substances 0.000 title claims description 11
- 239000007787 solid Substances 0.000 title claims description 9
- 238000003981 capillary liquid chromatography Methods 0.000 title claims description 3
- 238000000926 separation method Methods 0.000 title description 8
- 238000010828 elution Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 2
- 238000004811 liquid chromatography Methods 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 206010035148 Plague Diseases 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 238000004381 surface treatment Methods 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 235000001510 limonene Nutrition 0.000 description 2
- 229940087305 limonene Drugs 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- PKDBCJSWQUOKDO-UHFFFAOYSA-M 2,3,5-triphenyltetrazolium chloride Chemical compound [Cl-].C1=CC=CC=C1C(N=[N+]1C=2C=CC=CC=2)=NN1C1=CC=CC=C1 PKDBCJSWQUOKDO-UHFFFAOYSA-M 0.000 description 1
- MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 description 1
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005420 bog Substances 0.000 description 1
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/50—Conditioning of the sorbent material or stationary liquid
- G01N30/56—Packing methods or coating methods
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/60—Construction of the column
- G01N30/6052—Construction of the column body
- G01N30/6073—Construction of the column body in open tubular form
- G01N30/6078—Capillaries
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
Neues Verfahren zur Trennung von Flüssigkeiten und Festkörpern mittels kapillar-Flüssigkeits-Chromatographie.New process for separating liquids and solids by means of capillary liquid chromatography.
Aminosäuren werden heute üblicherweise nach der Methode von Ste## und Moore quantitativ bestimmt. Es handelt sich hierbei um eine co Co Ionenaustauschchromatographie, wobei je nach der Basizität der @ Aminosäure eine verschiedene Elutionszeit erfolgt. Diese Methoden ist vollautomatisch ausgestaltet worden,- entsprechende Apparaturen sind im Handel erhältlich. Der Nachteil dieses Verfahrens ist in einer relativ langen Analysenzeit von etwa 2 Tagen zu sehen. Die Gas-Ohromatographie hat sich für die Aminosäureanalyse nicht durchsetzen können, da sie zwar eine schnelle Trennung erlaubt, aber keine reproduzierbaren quantLtativen Werte erhalten werden. Ähnlich liegen die Verhältnisse bei der Papierchromatographie und der Chromatographie mit Säulen, die mit normalen Adsorbentien, wie Aluminiumoxid, Silikagel u.a. gefüllt sind.Amino acids are usually used today according to the method of Ste ## and peat bogs. This is a Co Co ion exchange chromatography, depending on the basicity of the @ amino acid, a different elution time takes place. These methods have been designed fully automatically - appropriate equipment are commercially available. The disadvantage of this procedure is a relatively long one Analysis time of about 2 days can be seen. Gas otromatography has become popular for that Amino acid analysis cannot enforce, as it allows a quick separation, but no reproducible quantitative values can be obtained. Lying similarly the relationships in paper chromatography and column chromatography, which are filled with normal adsorbents such as aluminum oxide, silica gel and others.
Die Nachteile oben genannter Verfahren lassen sich nun vermeiden, wenn man erfindungsgemäß mit Kapillaren nach dem Blüssigkeits-Festkörperprinzip arbeitet. Es handelt sich hierbei um ein vollständig neues Prinzip der Flüssigkeits-Chromatographie, das weit über die Aminosäureanalyse hinaus von Bedeutung ist. Da die Trennung sowohl von Festkörpern als auch von Flüssigkeiten möglich ist, wird dieses Verfahren nicht durch die Verdampfbarkeit einer Substanz begrenzt, wie dies bei der Gas-Chromatographie der Fall ist.The disadvantages of the above methods can now be avoided, if one according to the invention with capillaries according to the liquid-solid principle is working. This is a completely new principle of liquid chromatography, which is important far beyond the amino acid analysis. Since the separation is both of solids as well as liquids is possible, this method is not possible limited by the vaporizability of a substance, as is the case with gas chromatography the case is.
Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß die Innenwand einer Kapillare von 0,05 - 2mm Durchmesser aus Metall, Glas oder Kunststoff so vorbehandelt wird, daß eine aktive Oberfläehe entsteht. Im einfachsten Falle genügt es, z.B. eine Glaskapillare mit heißem Alkali zu behandeln, so daß eine schwammige Oberfläche entsteht, die sich als trennaktiv erweist. Andererseits können die Innenflächen der Kapillaren auch mit einem dünnen Film aus festem Adsorbens, z. B. Kohle, Molekularsieb, Silikagel oder mit einer beliebigen Blüssigkeit als Absorbens überzogen werden. Gemäß dem Schema der Apparatur in der Abbildung werden nun 0,1 bis IOyg der zu trennenden Substanz in einem Lösungsmittel eingegeben und die Säule mit einem Lösungsmittel oder einem Lösungsmittelgemisch durchspült. Sowohl polare als auch unpolare Lösungsmittel können Verwendung finden. Die Wahl hängt ausschileßlich von der experimentell bestimmten Wechselwirkung der zu trennon-@en Subst#nzen mit der aktiven Oberfläche der Kapillare ab. Es hierbei unerheblich, ob der Querschnitt der Kapillare kreisförmig, oval oder eckig ist. Je nach der Wechselwirkung der Substanzen werden sie durch die Säule mehr oder weniger fest gehalten-und treten am Ausgang getrennt aus. Die Trennung kann am Ausgang der Kapillarsäule durch kolorimetrische Messungen oder durch physikalische Meßmethoden üblicher Anordnung verfolgt werden und quantitativ der Gehalt bestimmt werden. Die Trennungen dauern gewöhnlich 1/2 - 3 Stunden bei Säulenlängen von 5 - 20m. Bei weniger kritischen Trennproblemen können Säulenlängen bis herab zu wenigen cm benutzt werden, wodurch auch die Elutionszelten entsprechend abgekürzt werden. Die Elutionszeiten können auch durch die Wahl eines polaren Lösungsmittels verringert werden. Das beschriebene Verfahren ist sowohl für Aminosäuren als auch für Zukker und beliebige andere anorganische oder organische Slüssigkeiten oder Festkörper anwendbar.The inventive method is characterized in that the Inner wall of a capillary with a diameter of 0.05 - 2mm made of metal, glass or plastic is pretreated so that an active surface is created. In the simplest case it is sufficient, for example, to treat a glass capillary with hot alkali so that a spongy Surface is created, which proves to be active in separation. On the other hand, the inner surfaces the capillaries with a thin film of solid adsorbent, e.g. B. coal, molecular sieve, Silica gel or coated with any liquid as an absorbent. According to the scheme of the apparatus in the figure, 0.1 to 10yg are now to be separated Substance entered in a solvent and the column with a solvent or a solvent mixture. Both polar and non-polar solvents can be used. The choice depends entirely on the experimental one Interaction of the substances to be separated with the active surface of the capillary away. It here it is irrelevant whether the cross-section of the capillary is circular, is oval or square. Depending on the interaction of the substances, they are through the column held more or less firmly - and emerge separately at the exit. the Separation can be done by colorimetric measurements or at the exit of the capillary column can be followed by physical measuring methods of the usual arrangement and quantitatively the salary can be determined. The separations usually last for 1/2 to 3 hours Column lengths from 5 to 20m. In the case of less critical separation problems, column lengths can be used down to a few cm, whereby the elution tents accordingly be abbreviated. The elution times can also be varied by choosing a polar solvent be reduced. The procedure described is for both amino acids and for sugar and any other inorganic or organic liquids or Solids applicable.
B e i s p i e l e : Beispiel 1: Zur Trennung der Aminosäuren Alanin, Glutaminsäure, G 1 ycin, Leucin, Cys-tein und Lysin wird eine konzentrierte methanolische Lösung, welche je lOOy der einzelnen Aminosäuren enthält, bei A in die Apparatur eingegeben. Die Säule besteht aus einer 5m-Kapillare von 0,4mm Durchmesser. Die Innenwand der Kapillare ist durch 3-stündiges Behandeln mit konsentriertem Ammoniak bei 30000 aktiviert worden. Nunmehr wird mit einer Lösung von Methyläthylketon:pyridin:Wasser:Eisessig 70:15:15:2 bei einem Durdhlauf des Lösungsmittelpfropfens von 10cm/min eluiert. Die in der Reihenfolge Lysin, Cystin, Glutaminsäure, Glycin, Alanin, leucin aus der Saule tretenden getrennten Substanzen werden kolorimetrisch nach Boissonas kontinuierlich bestimmt. Die Elution dauert etwa drei Stunden. Ein typisches Elutionsdiagramm zeigt Abb.2.Examples: Example 1: To separate the amino acids alanine, Glutamic acid, G 1 ycin, leucine, cys-teine and lysine is a concentrated methanolic Solution, each containing 100y of the individual amino acids, into the apparatus at A entered. The column consists of a 5m capillary with a diameter of 0.4mm. the The inner wall of the capillary is treated with concentrated ammonia for 3 hours has been activated at 30000. Now with a solution of methyl ethyl ketone: pyridine: water: glacial acetic acid 70: 15: 15: 2 eluted with a solvent plug flow of 10 cm / min. Those in the order lysine, cystine, glutamic acid, glycine, alanine, leucine from The separated substances entering the column are colorimetrically continuous according to Boissonas certainly. Elution takes about three hours. A typical elution diagram shows Fig 2.
Beispiel 2: Zur Trennung der Zucker Glukose, Xylose, Maltose wird eine im-Kapillare (0,2mm #), die wie in Beispiel 1 vorbehandelt ist, benutzt. Als Elutionsmittel findet n-Butanol-Eisessig-Wasser 60:30:10 Verwendung. Die Elutionszeit beträgt etwa 100 Minuten.Die Substanzen treten in der Reihenfolge Xylose, Glukose, Maltose aus ddr Säule und werden kolorimetrisch mit Triphenyltetrazoliumchlorid bestimmt.Example 2: To separate the sugars glucose, xylose, maltose is used an IM capillary (0.2mm #), which is pretreated as in Example 1, is used. as The eluent is n-butanol-glacial acetic acid-water 60:30:10. The elution time takes about 100 minutes. The substances occur in the order xylose, glucose, Maltose from DDR column and are colorimetrically with triphenyltetrazolium chloride certainly.
Beispiel 3: Zur Trennung von Terpenen (a-Pinen, Limonen, Cedren) )e 20@- @@llare henvtzt, deren Innenwand mit Polyäthylenglykol imprägniert ist. Als Elutionsflüssigkeit findet n-Hexan Verwendung. Die Terpene eluieren in der Reihenfolge Limonen, α-Pinen, Cedren und können durch ihren Brechungsindex bestimmt werden.Example 3: For the separation of terpenes (a-pinene, limonene, cedene) e 20 @ - @@ llare henvtzt, the inner wall of which is covered with polyethylene glycol impregnated is. N-Hexane is used as the elution liquid. The terpenes elute in in the order limonene, α-pinene, cedrene and can by their refractive index to be determined.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0072516 | 1963-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1498581A1 true DE1498581A1 (en) | 1969-01-23 |
Family
ID=6977480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631498581 Pending DE1498581A1 (en) | 1963-07-03 | 1963-07-03 | New method for the separation of liquids and solids by means of capillary liquid chromatography |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1498581A1 (en) |
| FR (1) | FR1403251A (en) |
| GB (1) | GB1076411A (en) |
| NL (1) | NL6407395A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2348730A1 (en) * | 1976-04-20 | 1977-11-18 | Technicon Instr | PROCESS FOR SEPARATION OF A PARTICULAR FRACTION OF A MIXTURE CONTAINING A LIQUID FRACTION |
| EP0309489A4 (en) * | 1987-04-15 | 1989-09-11 | Varian Associates | Fused-silica microbore packed chromatography column with chemically modified column wall. |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103657147B (en) * | 2012-09-20 | 2015-08-19 | 中国石油化工股份有限公司 | The method that oil product group composition is separated |
-
1963
- 1963-07-03 DE DE19631498581 patent/DE1498581A1/en active Pending
-
1964
- 1964-06-26 GB GB2657064A patent/GB1076411A/en not_active Expired
- 1964-06-29 NL NL6407395A patent/NL6407395A/xx unknown
- 1964-07-03 FR FR67008119A patent/FR1403251A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2348730A1 (en) * | 1976-04-20 | 1977-11-18 | Technicon Instr | PROCESS FOR SEPARATION OF A PARTICULAR FRACTION OF A MIXTURE CONTAINING A LIQUID FRACTION |
| EP0309489A4 (en) * | 1987-04-15 | 1989-09-11 | Varian Associates | Fused-silica microbore packed chromatography column with chemically modified column wall. |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1076411A (en) | 1967-07-19 |
| NL6407395A (en) | 1965-01-04 |
| FR1403251A (en) | 1965-06-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Scholer et al. | Antibiotika-Membranelektrode zur selektiven Erfassung von Ammoniumionenaktivitäten: Kurze Mitteilungen | |
| DE60002952T2 (en) | Process for the selective separation and purification of eicosapentaenoic acid and decosohexaenoic acid and their esters | |
| Barendse et al. | High-performance liquid chromatography of gibberellins | |
| DE4231149C1 (en) | Process for the further processing of technical processes in the molasses processing industry | |
| EP1143234B1 (en) | Method and device for detecting mercury | |
| DE69122280T2 (en) | Minimization of eluate bandwidths in liquid chromatography | |
| EP0645167A1 (en) | Process for obtaining pharmacological active compounds from complex substance mixtures | |
| DE1498581A1 (en) | New method for the separation of liquids and solids by means of capillary liquid chromatography | |
| van Beek et al. | Thin layer chromatography of bilobalide and ginkgolides A, B, C and J on sodium acetate impregnated silica gel | |
| DE1017596B (en) | Method and device for the continuous production of membrane filters | |
| DE2401620C3 (en) | Method for the spectrophotometric detection of zone boundaries, which are obtained in the isotachophoretic separation | |
| Frierson et al. | The separation of inorganic ions by paper partition chromatography | |
| DE3629056A1 (en) | Fungicidally active substance or substance mixture which can be isolated from the cuticula of spruce needles | |
| DE2755577C2 (en) | Process for obtaining the benzophenanthridine alkaloids, chelidonine, chelerythrine and sanguinarine from powdered plant material | |
| EP0082359B1 (en) | Process for the separation of mixtures from insulin, derivatives of insulin and, if required, impurities | |
| DE4042156C2 (en) | Process for the purification of mitomycin C. | |
| DE892228C (en) | Process for the chromatographic purification and fractionation of extracts containing corticoid hormones | |
| DD285113A5 (en) | METHOD FOR OBTAINING PURE HUMAN GROWTH HORMONE (HGH) | |
| DE1523037C3 (en) | Gradient shaped bodies for use in particular in three-dimensional chromatography | |
| DE951162C (en) | Purification and separation of B group vitamins by adsorption chromatography | |
| DE930651C (en) | Process for the purification and separation of the B group vitamins by partition chromatography | |
| Heftmann et al. | Argentation Thin-Layer Chromatography of the p-Nitrobenzyl Esters of Gibberellins and Their Precursors | |
| DE3824896A1 (en) | Method and apparatus for sample analysis in thin layer chromatography | |
| Schaffler et al. | A rapid quantitative method for the routine determination of oligosaccharides in cane molasses by thin-layer chromatography | |
| CH333229A (en) | Process for the continuous, chromatographic separation of multicomponent mixtures |