NO130976B - - Google Patents
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- NO130976B NO130976B NO01091/72A NO109172A NO130976B NO 130976 B NO130976 B NO 130976B NO 01091/72 A NO01091/72 A NO 01091/72A NO 109172 A NO109172 A NO 109172A NO 130976 B NO130976 B NO 130976B
- Authority
- NO
- Norway
- Prior art keywords
- nitro
- acid
- furfurylidene
- sulfuric acid
- hydrazine
- Prior art date
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- -1 ureido- Chemical class 0.000 claims description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 12
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 2
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KVYKDNGUEZRPGJ-UHFFFAOYSA-N 1-Aminohydantoin Chemical compound NN1CC(=O)NC1=O KVYKDNGUEZRPGJ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BAOXJBYPTRZNSH-XBXARRHUSA-N [(e)-furan-2-ylmethylideneamino]urea Chemical compound NC(=O)N\N=C\C1=CC=CO1 BAOXJBYPTRZNSH-XBXARRHUSA-N 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 229960001907 nitrofurazone Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/08—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles
- B01J8/12—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with moving particles moved by gravity in a downward flow
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D57/00—Separation, other than separation of solids, not fully covered by a single other group or subclass, e.g. B03C
- B01D57/02—Separation, other than separation of solids, not fully covered by a single other group or subclass, e.g. B03C by electrophoresis
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/447—Systems using electrophoresis
- G01N27/44756—Apparatus specially adapted therefor
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/447—Systems using electrophoresis
- G01N27/44756—Apparatus specially adapted therefor
- G01N27/44769—Continuous electrophoresis, i.e. the sample being continuously introduced, e.g. free flow electrophoresis [FFE]
Description
Fremgangsmåte for fremstilling av N-(5-nitro-2-furfuryliden)-hydrazinforbindelser. Process for the preparation of N-(5-nitro-2-furfurylidene)-hydrazine compounds.
Foreliggende oppfinnelse vedrører en The present invention relates to a
fremgangsmåte for fremstilling av N-(5-nitro-2-f urfury liden) -hydrazinforbin-delser. process for the preparation of N-(5-nitro-2-furfurylidene)-hydrazine compounds.
Det er alminnelig kjent at N-(5-nitro-2 -f urfury liden) -hydrazinf orbindelser, sær-lig N- (5-nitro-2-furfuryliden) -1-aminohydantoin, N-(5-nitro-2-f urfury liden)-3-amino-2-oxazolidon og 5-nitro-2-furalde-hyd-semicarbazon, er verdifulle kjemote-rapeutiske midler. Tidligere er disse forbin-delser blitt fremstilt ved å kondensere 5-nitro-2-furaldehyd eller et derivat herav, It is generally known that N-(5-nitro-2-furfurylidene)-hydrazine compounds, especially N-(5-nitro-2-furfurylidene)-1-aminohydantoin, N-(5-nitro-2- (furfurylidene)-3-amino-2-oxazolidone and 5-nitro-2-furaldehyde-semicarbazone are valuable chemotherapeutic agents. In the past, these compounds have been prepared by condensing 5-nitro-2-furaldehyde or a derivative thereof,
som er i stand til under reaksj onsforhol-dene å danne 5-nitro-2-furaldehyd, med which is capable under the reaction conditions of forming 5-nitro-2-furaldehyde, with
en hensiktsmessig hydrazinforbindelse. 5-nitro-2-furaldehyd er blitt fremstilt ved an appropriate hydrazine compound. 5-nitro-2-furaldehyde has been produced by
nitrering av furfural. Dette har til følge nitration of furfural. This has consequences
bruken av eddiksyreanhydrid og medfører the use of acetic anhydride and entails
dannelsen av et mellomprodukt som om-dannes til 5-nitro-2-furaldehyd ved tilset-ning av en base eller et annet syrenøytra-liserende materiale. Denne fremgangsmåte the formation of an intermediate product which is converted to 5-nitro-2-furaldehyde by the addition of a base or another acid neutralizing material. This procedure
er beheftet med alvorlige ulemper. Eddiksyreanhydrid er kostbart og dets anvendelse resulterer i dannelsen av avfallspro-dukter, som medfører alvorlige problemer is fraught with serious disadvantages. Acetic anhydride is expensive and its use results in the formation of waste products, which cause serious problems
med hensyn til hva man skal gjøre med with regard to what to do with
disse produkter. Nødvendigheten av å omdanne nitreringsmellomproduktet til 5-ni-tro-2-furaldehyd forårsaker videre også en these products. Furthermore, the necessity to convert the nitration intermediate to 5-nitro-2-furaldehyde also causes a
komplikasjon som både er kostbar og som complication which is both costly and which
krever tid. requires time.
Det har nu vist seg at det er mulig å It has now been shown that it is possible to
unngå nødvendigheten av å bruke eddiksyreanhydrid ved fremstillingen av nitrerte avoiding the necessity of using acetic anhydride in the manufacture of nitrates
furanhydrazinderivater slik som angitt ovenfor. Dette kan oppnåes ved å bringe furfural til å reagere direkte med den ut-valgte hydrazinforbindelse og derpå å nitrere produktet fra denne reaksjon. En slik nitrering kan lett bevirkes ved anven-delsen av en blandet syre, dvs. en blanding av konsentrert salpetersyre og svovelsyre. furanhydrazine derivatives as indicated above. This can be achieved by causing furfural to react directly with the selected hydrazine compound and then nitrating the product from this reaction. Such nitration can easily be effected by the use of a mixed acid, i.e. a mixture of concentrated nitric acid and sulfuric acid.
Det faktum at dette kan gjøres, er over-raskende da forsøk på å nitrere furfural med blandingssyre hittil ikke har ført til tilfredsstillende resultater og dette antas å skyldes at furankjernen ødelegges (se f. eks. «The Furans» av Dunlop og Peters, New York, Reinhold, 1953, sidene 173—174). De reagerende stoffer som anvendes ved fremgangsmåten, er billige og lett tilgjen-gelige, og man unngår nødvendigheten av å omdanne nitreringsmellomproduktet til det ønskede sluttprodukt. The fact that this can be done is surprising as attempts to nitrate furfural with mixed acid have so far not led to satisfactory results and this is believed to be due to the destruction of the furan nucleus (see e.g. "The Furans" by Dunlop and Peters, New York, Reinhold, 1953, pages 173-174). The reactants used in the process are cheap and easily available, and the necessity to convert the nitration intermediate into the desired end product is avoided.
I overensstemmelse med oppfinnelsen tilveiebringes en fremgangsmåte for fremstilling av N-(5-nitro-2-furfuryliden)-hy-drazinf orbindelser av formelen: hvor A betyr en ureido-, 2,4-dioxo-l-imida-zolidyl- eller 2-oxo-3-oxazolidylgruppe, og fremgangsmåten er karakterisert ved at det til et i alt vesentlig vannfritt oppløs-ningsmiddel fortrinsvis konsentrert svovelsyre, som inneholder en furanforbindelse av formelen: In accordance with the invention, a method is provided for the preparation of N-(5-nitro-2-furfurylidene)-hydrazine compounds of the formula: where A means a ureido-, 2,4-dioxo-1-imidazolidyl- or 2 -oxo-3-oxazolidyl group, and the method is characterized in that to an essentially anhydrous solvent preferably concentrated sulfuric acid, which contains a furan compound of the formula:
tilsettes en blanding av konsentrert salpetersyre og svovelsyre, hvorunder forhol- a mixture of concentrated nitric acid and sulfuric acid is added, under which
dene opprettholdes slik at reaksjonsblan- they are maintained so that reaction mix-
dingens temperatur ikke overskrider 5° C, the object's temperature does not exceed 5° C,
og deretter utfelles fra reaksjonsblandingen det resulterende N-(nitro-2-furfuryliden)-hydrazin. and then the resulting N-(nitro-2-furfurylidene)-hydrazine is precipitated from the reaction mixture.
Ved utførelsen av oppfinnelsen kan In the execution of the invention can
nevnte furanforbindelse av formelen II said furan compound of the formula II
bare oppløses eller suspenderes i det i alt vesentlig vannfrie oppløsningsmiddel, og det tilsettes hertil en blanding av konsen- is simply dissolved or suspended in the essentially anhydrous solvent, and a mixture of concen-
trert salpetersyre og konsentrert svovel- concentrated nitric acid and concentrated sulphur-
syre. Reguleringen av temperaturen kan bevirkes ved ytre kjøling og ved at blandingssyren tilsettes gradvis. Etter at hele mengden av blandingssyren er blitt tilsatt, bråkjøles reaksjonsblandingen ved at den helles over is og den resulterende utfelling filtreres og vaskes med vann inntil den er syrefri. Videre vaskning med organiske oppløsningsmidler som ethylalkohol, ether, acid. The regulation of the temperature can be effected by external cooling and by gradually adding the mixed acid. After the entire amount of the mixed acid has been added, the reaction mixture is quenched by pouring it over ice and the resulting precipitate is filtered and washed with water until it is acid-free. Further washing with organic solvents such as ethyl alcohol, ether,
benzen eller lignende som ikke oppløser det på denne mtåe erholdte nitrofuran, kan utføres for å bevirke en ytterligere rens- benzene or the like, which does not dissolve the nitrofuran obtained in this way, can be carried out to effect a further cleaning
ning. Sluttproduktet tørkes sluttelig for å nothing. The end product is finally dried to
fjerne eventuelt flyktig residuum. remove any volatile residue.
For at oppfinnelsen lettere skal for- In order for the invention to more easily
ståes av fagfolk skal det i det følgende be- carried out by professionals, it must be explained in the following
skrives noen utførelseseksempler. some execution examples are written.
Eksempel 1 Example 1
Til 75 ml konsentrert svovelsyre som To 75 ml of concentrated sulfuric acid which
er avkjølt til 0—5° C, tilsettes gradvis 20,7 is cooled to 0-5° C, gradually add 20.7
g N- (f urfury liden) -1-aminohydantoin, fremstillet ved å la furfural reagere med 1-aminohydantoin på den måte som er kjent for å danne aldehydhydrazinkonden-seringsprodukter. Til denne blanding som holdes ved -2 til -5° C, tilsettes blandings- g N-(furfurylidene)-1-aminohydantoin, prepared by allowing furfural to react with 1-aminohydantoin in the manner known to form aldehyde hydrazine condensation products. To this mixture, which is kept at -2 to -5° C, is added the mixture
syre, fremstilt ved å blande 8,25 ml konsentrert salpetersyre og 16,5 ml konsentrert svovelsyre, under omrøring over en periode av 57 minutter. Etter at tilsetningen av blandingssyren er tilendebrakt, helles blan- acid, prepared by mixing 8.25 ml of concentrated nitric acid and 16.5 ml of concentrated sulfuric acid, with stirring over a period of 57 minutes. After the addition of the mixed acid has been completed, the mixed
dingen på is. Det gule faste stoff som ut- the thing on ice. The yellow solid that
felles, filtreres og vaskes syrefritt med vann og derpå med ethylalkohol og ether. Utfellingen tørkes ved 110° C. Det fåes 17,5 combined, filtered and washed acid-free with water and then with ethyl alcohol and ether. The precipitate is dried at 110° C. 17.5 is obtained
g (71 pst.) N-(5-nitro-2-furfuryliden)-l-aminohydantoin. g (71 percent) N-(5-nitro-2-furfurylidene)-1-aminohydantoin.
Eksempel 2 Example 2
Til 100 ml konsentrert svovelsyre av- To 100 ml of concentrated sulfuric acid of
kjølt til 0—5° C tilsettes gradvis 36,0 g N- cooled to 0-5° C, gradually add 36.0 g N-
(fufuryliden)-3-amino-2-oxazolidon, frem- (fufurylidene)-3-amino-2-oxazolidone, pro-
stilt ved å la furfural reagere med 3-ami-no-2-oxazoliden, på kjent måte for å danne aldehydrazinkondenseringsprodukter. Til den klare oppløsning som holdes ved prepared by reacting furfural with 3-amino-no-2-oxazolide, in a known manner, to form aldehyde-razine condensation products. To the clear resolution held by
-4 til 0° C, tilsettes over en periode av 57 minutter blandingssyre, som fremstilles ved å blande 13,4 ml konsentrert salpetersyre og 26,8 ml konsentrert svovelsyre. Etter at blandings-syretilsetningen er avsluttet, helles blan- -4 to 0° C, mixed acid is added over a period of 57 minutes, which is prepared by mixing 13.4 ml of concentrated nitric acid and 26.8 ml of concentrated sulfuric acid. After the mixed acid addition is finished, the mixed
dingen på is. Det gule faste stoff som ut- the thing on ice. The yellow solid that
felles, filtreres og vaskes syrefritt med vann og derpå med deler av ethylalkohol og ether. Det tørkes ved 65° C. Det fåes 37,1 combined, filtered and washed acid-free with water and then with portions of ethyl alcohol and ether. It is dried at 65° C. 37.1 is obtained
g (82,5 pst.) N-(5-nitro-2-furfuryliden)-3-amino-2-oxazolidon. g (82.5 percent) N-(5-nitro-2-furfurylidene)-3-amino-2-oxazolidone.
Eksempel 3 Example 3
Til 85 ml konsentrert svovelsyre av- To 85 ml of concentrated sulfuric acid of-
kjølt til 0—5° C tilsettes 21,0 g furaldehyd-semicarbazon. Til denne blanding som hol- cooled to 0-5° C, 21.0 g of furaldehyde semicarbazone are added. To this mixture as hol-
des ved ^-1 til -^3° C tilsettes under omrøring over en tidsperiode av 40 minutter blandingssyre fremstilt ved å blande 9,2 ml konsentrert salpetersyre og 18,4 ml konsentrert svovelsyre. Etter at blandingssyre-tilsetningen er tilendebrakt, helles blandin- des at ^-1 to -^3° C, mixed acid prepared by mixing 9.2 ml of concentrated nitric acid and 18.4 ml of concentrated sulfuric acid is added with stirring over a period of 40 minutes. After the mixed acid addition has been completed, the mixed
gen på is og det faste stoff som utfelles, filtreres. Det filtrerte stoff vaskes syrefritt med vann og derpå med deler av alkohol og ether. Det tørkes ved 65° C. Det fåes 5,7 gen on ice and the solid substance that precipitates is filtered. The filtered substance is washed acid-free with water and then with portions of alcohol and ether. It is dried at 65° C. 5.7 is obtained
g (21 pst.) 5-nitro-2-furaldehyd-semicar- g (21 percent) 5-nitro-2-furaldehyde-semicar-
bazon. Omkrystalliseringen kan bevirkes under anvendelse av dimethylsulfoxyd som oppløsningsmiddel. bazon. The recrystallization can be effected using dimethylsulfoxide as solvent.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7111180A FR2131859B1 (en) | 1971-03-30 | 1971-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO130976B true NO130976B (en) | 1974-12-09 |
| NO130976C NO130976C (en) | 1975-03-19 |
Family
ID=9074431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1091/72A NO130976C (en) | 1971-03-30 | 1972-03-29 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3829370A (en) |
| BE (1) | BE781424A (en) |
| BR (1) | BR7201749D0 (en) |
| CA (1) | CA985209A (en) |
| CH (1) | CH543305A (en) |
| DE (1) | DE2215761A1 (en) |
| FR (1) | FR2131859B1 (en) |
| GB (1) | GB1338543A (en) |
| IT (1) | IT959581B (en) |
| LU (1) | LU65075A1 (en) |
| NL (1) | NL7203835A (en) |
| NO (1) | NO130976C (en) |
| SU (1) | SU487476A3 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935092A (en) * | 1971-12-14 | 1976-01-27 | Rhone-Poulenc-Textile | Purification of a chloride solution |
| US3994799A (en) * | 1973-04-17 | 1976-11-30 | Yao Shang J | Blood and tissue detoxification apparatus |
| US3989613A (en) * | 1973-05-16 | 1976-11-02 | The Dow Chemical Company | Continuous balanced flow fixed boundary electrophoresis |
| US3972791A (en) * | 1974-05-06 | 1976-08-03 | Harold Stern | Fractionation of proteins by electrical means |
| US3923426A (en) * | 1974-08-15 | 1975-12-02 | Alza Corp | Electroosmotic pump and fluid dispenser including same |
| US4115225A (en) * | 1977-07-22 | 1978-09-19 | Ionics, Inc. | Electrodialysis cell electrode reversal and anolyte recirculation system |
| US4276140A (en) * | 1980-01-10 | 1981-06-30 | Ionics Inc. | Electrodialysis apparatus and process for fractionating protein mixtures |
| DE3040470A1 (en) * | 1980-10-27 | 1982-06-03 | Siemens AG, 1000 Berlin und 8000 München | METHOD AND DEVICE FOR INDIRECTLY OXIDATING UREA |
| JPS58147639A (en) * | 1982-02-26 | 1983-09-02 | Hideyuki Nishizawa | Separation by continuous electric migration and its device |
| US4394246A (en) * | 1982-05-24 | 1983-07-19 | Mcdonnell Douglas Corporation | Electrophoresis apparatus with flow control |
| DE3337669C2 (en) * | 1983-10-17 | 1989-09-21 | Carl Schleicher & Schuell Gmbh & Co Kg, 3352 Einbeck | Device for the electroelution of electrically charged macromolecules |
| DE3337668C2 (en) * | 1983-10-17 | 1985-12-05 | Carl Schleicher & Schuell Gmbh & Co Kg, 3352 Einbeck | Process for the electroelution of electrically charged macromolecules |
| FR2567914B1 (en) * | 1984-07-19 | 1989-04-07 | Univ Languedoc | METHOD FOR THE CONTINUOUS RECOVERY OF METAL CATIONS FROM DILUTED SOLUTIONS AND APPARATUS FOR IMPLEMENTING SAME |
| FR2568485B1 (en) * | 1984-08-06 | 1990-03-23 | Rhone Poulenc Rech | PROTEIN-CONTAINING ELECTROPHORESIS APPARATUS FOR USE, IN PARTICULAR FOR FRACTIONATION OF HUMAN PLASMA |
| US4668361A (en) * | 1985-05-24 | 1987-05-26 | Dorr-Oliver Incorporated | Dialyzing electrofilter with improved electrode |
| US4834862A (en) * | 1988-09-12 | 1989-05-30 | Duke University | Ampholyte separation method and apparatus |
| GB2225339A (en) * | 1988-11-15 | 1990-05-30 | Aligena Ag | Separating electrically charged macromolecular compounds by forced-flow membrane electrophoresis |
| US5336387A (en) * | 1990-09-11 | 1994-08-09 | Bioseparations, Inc. | Electrical separator apparatus and method of counterflow gradient focusing |
| US5662813A (en) * | 1994-10-21 | 1997-09-02 | Bioseparations, Inc. | Method for separation of nucleated fetal erythrocytes from maternal blood samples |
| AUPP790898A0 (en) * | 1998-12-23 | 1999-01-28 | Life Therapeutics Limited | Renal dialysis |
| DE10063097B4 (en) * | 2000-12-18 | 2007-04-19 | Becton, Dickinson And Co. | electrophoresis |
| EP3474006A1 (en) * | 2017-10-19 | 2019-04-24 | Université de Liège | Microchip for free flow electrophoresis |
-
1971
- 1971-03-30 FR FR7111180A patent/FR2131859B1/fr not_active Expired
-
1972
- 1972-03-22 NL NL7203835A patent/NL7203835A/xx unknown
- 1972-03-24 BR BR1749/72A patent/BR7201749D0/en unknown
- 1972-03-27 SU SU1762202A patent/SU487476A3/en active
- 1972-03-28 GB GB1445972A patent/GB1338543A/en not_active Expired
- 1972-03-28 US US00238764A patent/US3829370A/en not_active Expired - Lifetime
- 1972-03-29 NO NO1091/72A patent/NO130976C/no unknown
- 1972-03-29 LU LU65075D patent/LU65075A1/xx unknown
- 1972-03-29 BE BE781424A patent/BE781424A/en unknown
- 1972-03-29 CA CA138,533A patent/CA985209A/en not_active Expired
- 1972-03-29 CH CH468072A patent/CH543305A/en not_active IP Right Cessation
- 1972-03-30 DE DE19722215761 patent/DE2215761A1/en active Pending
- 1972-03-30 IT IT22647/72A patent/IT959581B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2131859B1 (en) | 1974-03-08 |
| BR7201749D0 (en) | 1973-11-01 |
| GB1338543A (en) | 1973-11-28 |
| FR2131859A1 (en) | 1972-11-17 |
| LU65075A1 (en) | 1972-12-07 |
| BE781424A (en) | 1972-09-29 |
| CH543305A (en) | 1973-10-31 |
| CA985209A (en) | 1976-03-09 |
| IT959581B (en) | 1973-11-10 |
| NO130976C (en) | 1975-03-19 |
| SU487476A3 (en) | 1975-10-05 |
| NL7203835A (en) | 1972-10-03 |
| US3829370A (en) | 1974-08-13 |
| DE2215761A1 (en) | 1972-10-12 |
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