DE1270040B - Process for the production of ninhydrin - Google Patents
Process for the production of ninhydrinInfo
- Publication number
- DE1270040B DE1270040B DEP1270A DER0038160A DE1270040B DE 1270040 B DE1270040 B DE 1270040B DE P1270 A DEP1270 A DE P1270A DE R0038160 A DER0038160 A DE R0038160A DE 1270040 B DE1270040 B DE 1270040B
- Authority
- DE
- Germany
- Prior art keywords
- ninhydrin
- production
- water
- bromine
- methylmercaptoindanedione
- 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 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 title description 13
- 239000000460 chlorine Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 241000282376 Panthera tigris Species 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 3
- WFFZGYRTVIPBFN-UHFFFAOYSA-N 3h-indene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)CC2=C1 WFFZGYRTVIPBFN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
Int. Cl.: Int. Cl .:
C 07cC 07c
Deutsche Kl.: 12 ο-25German class: 12 ο-25
Nummer: 1270 040Number: 1270 040
Aktenzeichen: P 12 70 040.2-42File number: P 12 70 040.2-42
Anmeldetag: 19. Juni 1964 Filing date: June 19, 1964
Auslegetag: 12. Juni 1968Opening day: June 12, 1968
Es ist bekannt, daß man Ninhydrin herstellen kann, indem man z. B. Indandion-(1,3) mit Selendioxyd oxydiert, 2-Brom-2-nitroindandion-(l,3) thermisch zersetzt oder p-Naphthochinon mit Sauerstoff oxydiert oder 2-Chlor-2-methylmercaptoindandion-(l,3) mit siedendem Wasser hydrolysiert.It is known that ninhydrin can be prepared by e.g. B. Indanedione (1,3) oxidized with selenium dioxide, 2-Bromo-2-nitroindandione- (l, 3) decomposed thermally or oxidized p-naphthoquinone with oxygen or 2-chloro-2-methylmercaptoindandione- (1,3) hydrolyzed with boiling water.
Alle bekannten Verfahren besitzen entscheidende Nachteile, da sie entweder von schwer zugänglichen Produkten ausgehen, auf Grund von Nebenreaktionen mit niedrigen Ausbeuten verlaufen, die Aufreinigung des entstandenen Ninhydrins schwierig ist, arbeitsintensive mehrstufige Reaktionsfolgen notwendig sind oder wie im Fall des 2-Chlor-2-methylmercaptoindandion-(l,3) ein vielstündiges Erhitzen in für eine technische Herstellung unrentabel großer Verdünnung erforderlich ist, erhebliche Geruchsbelästigung durch Bildung des giftigen Methylmercaptans auftritt und ferner schwer verhindert werden kann, daß sich beträchtliche Mengen Phthalsäure bilden.All known methods have significant disadvantages, since they are either difficult to access Run out of products due to side reactions with low yields, the purification of the ninhydrin formed is difficult, labor-intensive multi-stage reaction sequences are necessary or, as in the case of 2-chloro-2-methylmercaptoindanedione- (1.3), heating for many hours for a technical Production unprofitable large dilution is required, considerable odor nuisance through Formation of the poisonous methyl mercaptan occurs and, moreover, it is difficult to prevent considerable Forms quantities of phthalic acid.
Insbesondere konnte ein Nacharbeiten der Versuche zur Hydrolyse des 2-Chlor-2-methylmercaptoindandions (J. Org. Chem. 28 [1963], S. 1896) die günstigen Ausbeuteangaben (100 °/0) nicht bestätigen, vielmehr wurde nur eine Ausbeute von 50,8 °/0 erhalten.In particular, a reworking of the attempts to hydrolyze the 2-chloro-2-methylmercaptoindandions (J. Org Chem 28 [1963] S. 1896th.,) Could not confirm the favorable yield information (100 ° / 0), but only a yield of 50.8 ° / 0 obtained.
Es wurde nun überraschenderweise gefunden, daß man eine sonst bei Oxydationen von 2-substituierten Indandion-(1,3)-Derivaten leicht eintretende Molekülverdoppelung vermeiden kann und in hoher Ausbeute Ninhydrin erhält, wenn man 2-Hydroxy-2-methylmercaptoindandion-(l,3) in wäßriger Suspension etwa bei Raumtemperatur mit Chlor oder Brom oxydiert. Vorteilhafterweise geht man so vor, daß man 2-Hydroxy-2-methylmercaptoindandion-(l,3) in Wasser suspendiert, mit Chlor oder Brom oxydiert und das sich kristallin abscheidende Ninhydrin nach bekannten Verfahren abtrennt. Nebenprodukte können durch Extraktion mit einem geeigneten organischen Lösungsmittel entfernt werden. Als organisches Lösungsmittel ist vor allem Chloroform geeignet.It has now been found, surprisingly, that one would otherwise oxidize 2-substituted Indanedione (1,3) derivatives can easily avoid molecular doubling and in high yield Ninhydrin is obtained when 2-hydroxy-2-methylmercaptoindanedione- (l, 3) oxidized in aqueous suspension at about room temperature with chlorine or bromine. It is advantageous to proceed in such a way that 2-hydroxy-2-methylmercaptoindanedione (l, 3) suspended in water, oxidized with chlorine or bromine and the ninhydrin which separates out in crystalline form according to known methods Process separates. By-products can be removed by extraction with a suitable organic solvent removed. A particularly suitable organic solvent is chloroform.
Ein Überschuß von Chlor oder Brom als Oxydationsmittel führt nicht zur Bildung von Nebenprodukten. Überschüssiges Halogen kann nach Beendigung der Reaktion durch einen Gasstrom, ζ. Β. durch Stickstoff oder Luft, verdrängt werden. Das auskristallisierte Ninhydrin wird abgesaugt und getrocknet.An excess of chlorine or bromine as an oxidizing agent does not lead to the formation of by-products. After the reaction has ended, excess halogen can be removed by a stream of gas, ζ. Β. by nitrogen or air, to be displaced. The ninhydrin which has crystallized out is filtered off with suction and dried.
Das als Ausgangsstoff verwendete 2-Hydroxy-2-methylmercaptoindandion-(l,3) kann nach den deutschen Patenten 1 207 381 und 1 229 080 hergestellt werden, indem man Phthalsäureester mit Dimethylsulfoxyd in Gegenwart von Alkalialkoholaten umsetzt und das entstehende Zwischenprodukt mit wäßriger Schwefelsäure umlagert oder auf 2-Chlor- oder 2-Brom-Verfahren zur Herstellung von NinhydrinThe 2-hydroxy-2-methylmercaptoindanedione (l, 3) used as starting material can be prepared according to German patents 1 207 381 and 1 229 080 by mixing phthalic acid esters with dimethyl sulfoxide in Reacts the presence of alkali alcoholates and the intermediate product formed with aqueous sulfuric acid rearranged or on 2-chloro or 2-bromine processes for the production of ninhydrin
Anmelder:Applicant:
Riedel-de Haen Aktiengesellschaft, 3016 SeelzeRiedel-de Haen Aktiengesellschaft, 3016 Seelze
Als Erfinder benannt:
Dr.-Ing. Horst Liebig,
Dr. rer. nat. Heinrich Pfetzing,
3052 Bad NenndorfNamed as inventor:
Dr.-Ing. Horst Liebig,
Dr. rer. nat. Heinrich Pfetzing,
3052 Bad Nenndorf
methylmercaptoindandion-(l,3) Wasser einwirken läßt.methylmercaptoindandione- (l, 3) water can act.
10 g 2-Hydroxy-2-methylmercaptoindandion-(l,3) werden in etwa 100 ml Wasser suspendiert. Anschließend wird so lange Chlor eingeleitet, bis ein Überschuß in der Lösung verbleibt. Dabei entsteht zunächst eine klare Lösung, aus der Ninhydrin auskristallisiert.10 g of 2-hydroxy-2-methylmercaptoindandione- (l, 3) are suspended in about 100 ml of water. Afterward chlorine is passed in until an excess remains in the solution. First of all, a clear solution from which ninhydrin crystallizes out.
Die abgeschiedenen Kristalle werden abgesaugt, mit wenig Wasser gewaschen, die Mutterlauge mit Chloroform extrahiert und im Vakuum eingeengt, wobei sich weiteres Ninhydrin abscheidet, das wie oben isoliert wird.The deposited crystals are filtered off with suction, washed with a little water, the mother liquor with chloroform extracted and concentrated in vacuo, further ninhydrin separating out, which is isolated as above will.
Nach dem Trocknen erhält man insgesamt 7,2 g = 84,2 % der Theorie Ninhydrin vom Schmelzpunkt 239 bis 2400C.After drying, a total of 7.2 g = 84.2% of theory of ninhydrin with a melting point of 239 to 240 ° C. is obtained.
10 g 2-Hydroxy-2-methylmercaptoindandion-(l,3) werden in etwa 75 ml Wasser suspendiert und unter mechanischem Rühren so lange tropfweise mit elementarem Brom versetzt, bis ein Überschuß erkennbar bleibt.10 g of 2-hydroxy-2-methylmercaptoindandione- (l, 3) are suspended in about 75 ml of water and under Elemental bromine is added dropwise to mechanical stirring until an excess can be seen remain.
Aus der zunächst entstehenden klaren Lösung scheidet sich Ninhydrin kristallin aus, das durch Absaugen, Waschen mit Wasser und Trocknen isoliert wird. Die entstehende, mit dem Waschwasser vereinigte Mutterlauge wird mit Chloroform extrahiert, im Vakuum eingeengt und das sich abscheidende kristalline Ninhydrin wie oben isoliert.Ninhydrin precipitates in crystalline form from the initially resulting clear solution, which by suction, Wash with water and dry is isolated. The resulting mother liquor combined with the wash water is extracted with chloroform, concentrated in vacuo and the crystalline ninhydrin which separates out isolated as above.
Insgesamt erhält man 6,3 g = 73,5 °/0 der Theorie Ninhydrin vom Schmelzpunkt 239 bis 2400C.Overall, one obtains 6.3 g = 73.5 ° / 0 of theory ninhydrin of melting point 239-240 0 C.
809 559/496809 559/496
Claims (1)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER38122A DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DER38123A DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DEP1270A DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
| CH681365A CH461472A (en) | 1964-06-12 | 1965-05-14 | Process for the production of ninhydrin |
| GB24588/65A GB1035180A (en) | 1964-06-12 | 1965-06-10 | Process for the preparation of ninhydrin |
| FR20546A FR1437103A (en) | 1964-06-12 | 1965-06-11 | Process for the preparation of ninhydrin |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER38122A DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DER38123A DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DEP1270A DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1270040B true DE1270040B (en) | 1968-06-12 |
Family
ID=27212157
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38122A Pending DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DER38123A Pending DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
| DEP1270A Pending DE1270040B (en) | 1964-06-12 | 1964-06-19 | Process for the production of ninhydrin |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER38122A Pending DE1229080B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-methylmercapto-indandione (1, 3) derivatives |
| DER38123A Pending DE1207381B (en) | 1964-06-12 | 1964-06-12 | Process for the preparation of 2-hydroxy-2-methylmercapto-indandione- (1, 3) |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH461472A (en) |
| DE (3) | DE1229080B (en) |
| FR (1) | FR1437103A (en) |
| GB (1) | GB1035180A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3385894A (en) * | 1965-06-30 | 1968-05-28 | Shulton Inc | Oxidation of activated methylene group containing compounds to the corresponding carbonyl compounds |
| CN108047018B (en) * | 2017-12-12 | 2022-07-22 | 上海三爱思试剂有限公司 | Synthetic method of ninhydrin |
-
1964
- 1964-06-12 DE DER38122A patent/DE1229080B/en active Pending
- 1964-06-12 DE DER38123A patent/DE1207381B/en active Pending
- 1964-06-19 DE DEP1270A patent/DE1270040B/en active Pending
-
1965
- 1965-05-14 CH CH681365A patent/CH461472A/en unknown
- 1965-06-10 GB GB24588/65A patent/GB1035180A/en not_active Expired
- 1965-06-11 FR FR20546A patent/FR1437103A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1207381B (en) | 1965-12-23 |
| DE1229080B (en) | 1966-11-24 |
| FR1437103A (en) | 1966-04-29 |
| CH461472A (en) | 1968-08-31 |
| GB1035180A (en) | 1966-07-06 |
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