DE553280C - Process for the preparation of mercuration products of benzene - Google Patents
Process for the preparation of mercuration products of benzeneInfo
- Publication number
- DE553280C DE553280C DEI35941D DEI0035941D DE553280C DE 553280 C DE553280 C DE 553280C DE I35941 D DEI35941 D DE I35941D DE I0035941 D DEI0035941 D DE I0035941D DE 553280 C DE553280 C DE 553280C
- Authority
- DE
- Germany
- Prior art keywords
- benzene
- mercuration
- products
- preparation
- acetic acid
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 2
- 229910000474 mercury oxide Inorganic materials 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/12—Aromatic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Merkurierungsprodukten des Benzols Durch das Patent 548 902 wird ein Verfahren zur Darstellung von Merkurierungsprodukten des Benzols geschützt. Es besteht darin, daß man die Reaktionsteilnehmer, Merduriacetat und Benzol, unter Zusatz von über i 5o' siedenden Lösemitteln, welche die Reaktionstemperatur auf das Optimum erhöhen, ohne unter diesen Bedingungen selbst merkuriert zu werden, unter gewöhnlichem Druck in offenen Gefäßen bei Temperaturen bis höchstens i35° aufeinander einwirken läßt.Process for the preparation of mercuration products of benzene by patent 548,902 discloses a method for the preparation of mercuration products protected from benzene. It consists in getting the reactant, merduriacetate and benzene, with the addition of solvents boiling over 150 ', which lower the reaction temperature increase to the optimum without being noticed under these conditions, under normal pressure in open vessels at temperatures not exceeding i35 ° can act on each other.
Es wurde nun gefunden, daß man bei diesem Verfahren vorteilhaft die hochsiedenden Lösemittel durch Eisessig ersetzen kann. Durch diesen Zusatz von Eisessig wird die Merkurierung begünstigt, so daß sich die Reaktion unter gewöhnlichem Druck in offenen Gefäßen schon bei Temperaturen, die wesentlich niedriger liegen als die im Patent 548 902 angegebenen, durchführen läßt, z. B. ist bei der Merkurierung des Benzols eine Temperatur von 85 bis. 95° für eine glatte Durchführung der Reaktion ausreichend.It has now been found that in this process the high-boiling solvents can advantageously be replaced by glacial acetic acid. This addition of glacial acetic acid promotes mercuration, so that the reaction can be carried out under normal pressure in open vessels at temperatures which are considerably lower than those specified in patent 548 902 , e.g. B. is at the mercuration of benzene a temperature of 85 to. 95 ° is sufficient for the reaction to run smoothly.
Das beschriebene Verfahren bedeutet einen bemerkenswerten technischen Fortschritt. Denn vor den bekannten Verfahren zur Merkurierung des Benzols hat es den großen Vorzug, daß die im technischen Großbetrieb bei der Verarbeitung von Qued'ksilb:ersalzen und Eisessig in Druckgefäßen auftretenden Schwierigkeiten damit vermieden werden können. Beispiel 54 kg Quecksilberoxyd werden mit i ooo 1 Eisessig und 4001 Handelsbenzol unter Rückfluß 2 bis 3 Stunden auf go bis 95° erhitzt. Nach dem Abdestillieren des überschüssigen Benzols und Eisessigs bleibt das gebildete Phenylqweclz:#silbera£etat als feste Kristallmasse in einer Ausbeute von 96 % der Theorie (berechnet auf das angewandte Quecksilberoxyd) zurück.The process described is a remarkable technical one Progress. Because before the known process for the mercuration of benzene it was the great advantage that they are salted in large-scale technical operations when processing Qued'ksilb and glacial acetic acid in pressure vessels can thus be avoided can. Example 54 kg of mercury oxide are mixed with 100 liters of glacial acetic acid and 400 liters of commercial benzene heated to 95 ° under reflux for 2 to 3 hours. After distilling off the Excess benzene and glacial acetic acid leave the phenyl molecule formed: silver residue as a solid crystal mass in a yield of 96% of theory (calculated on the applied mercury oxide).
Man kann die Komponenten auch in anderen Verhältnisasen mit gleich gutem Erfolg aufeinander einwirken lassen. Weitere Herabsetzung der Temperatur hat eine Erhöhung der Reaktionszeit zur Folge.The components can also be used in other proportions with the same allow good success to interact. Has further lowering the temperature result in an increase in the response time.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35941D DE553280C (en) | 1928-08-08 | 1928-10-30 | Process for the preparation of mercuration products of benzene |
| US401378A US1879206A (en) | 1928-10-30 | 1929-10-21 | Process of preparing phenyl mercuric acetate |
| FR37531D FR37531E (en) | 1928-08-08 | 1929-10-25 | Process for obtaining mercury products from aromatic hydrocarbons |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI35181D DE548902C (en) | 1928-08-08 | 1928-08-08 | Method of Mercurying Benzene |
| DEI35941D DE553280C (en) | 1928-08-08 | 1928-10-30 | Process for the preparation of mercuration products of benzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE553280C true DE553280C (en) | 1932-06-23 |
Family
ID=32327385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI35941D Expired DE553280C (en) | 1928-08-08 | 1928-10-30 | Process for the preparation of mercuration products of benzene |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE553280C (en) |
| FR (1) | FR37531E (en) |
-
1928
- 1928-10-30 DE DEI35941D patent/DE553280C/en not_active Expired
-
1929
- 1929-10-25 FR FR37531D patent/FR37531E/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR37531E (en) | 1930-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1186968B (en) | Process for the preparation of diamino-1,1'-dianthraquinonylene | |
| DE553280C (en) | Process for the preparation of mercuration products of benzene | |
| DE941909C (en) | Process for the preparation of N, N'-diaethanol-piperazine | |
| DE930751C (en) | Process for the preparation of terephthalic acid from p-xylylene dichloride | |
| DE809551C (en) | Process for the production of pure cyclohexanol | |
| DE573983C (en) | Process for the preparation of oxyalkylamines | |
| DE717952C (en) | Process for the preparation of adipic acid, its homologues and halogen substitution products | |
| DE524188C (en) | Process for the preparation of benzoylated aromatic amines | |
| DE441179C (en) | Process for reducing organic compounds | |
| DE470503C (en) | Process for the preparation of anthraquinone derivatives | |
| DE856888C (en) | Process for the production of 1,5-dichloropentane | |
| DE595135C (en) | Process for the preparation of N-alkyl perhydrocarbazoles | |
| DE701953C (en) | Process for the production of aromatic carboxylic acid chlorides | |
| DE542801C (en) | Process for the production of real Kuepen dyes | |
| DE515540C (en) | Process for the preparation of diacidyl derivatives of meta-xylene | |
| DE603808C (en) | Process for the preparation of oxyaethylated (ª † -alkoxy-ª ‰ -oxypropyl) -aminobenzenes | |
| DE576388C (en) | Process for the preparation of camphene | |
| DE679340C (en) | Process for the preparation of dehydrobinaphthylenediimine | |
| DE480848C (en) | Process for the production of 2íñ3-diaminoanthraquinone | |
| DE512821C (en) | Process for the preparation of 1, 1-dianthraquinonyl-2, 2-diurethane, its derivatives and, if appropriate, condensation products | |
| DE734741C (en) | Process for the production of permanent ferrous iron solutions | |
| DE806668C (en) | Process for the preparation of p-aminodialkylanilines | |
| DE370974C (en) | Process for the preparation of the hydrogenation products of naphthalene and its derivatives | |
| DE275048C (en) | ||
| DE1079065B (en) | Process for the preparation of 1- (4-oxyphenyl) -butanone- (3) |