DE314364C - - Google Patents
Info
- Publication number
- DE314364C DE314364C DENDAT314364D DE314364DA DE314364C DE 314364 C DE314364 C DE 314364C DE NDAT314364 D DENDAT314364 D DE NDAT314364D DE 314364D A DE314364D A DE 314364DA DE 314364 C DE314364 C DE 314364C
- Authority
- DE
- Germany
- Prior art keywords
- erythrene
- isoprene
- erythren
- purification
- oxidizing agent
- 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.)
- Active
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 230000001264 neutralization Effects 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 4
- ZJRXSAYFZMGQFP-UHFFFAOYSA-N Barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N butylene glycol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 ethylene, propylene Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14833—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds
- C07C7/14841—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with metals or their inorganic compounds metals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Erythren bildet sich oft neben verschiedenen ungesättigten Verbindungen, die sehr schwierig zu entfernen sind. Nach einem geschützten Verfahren zur Reinigung von Isopren wird in der Weise verfahren, daß rohes, Amylene enthaltendes Isopren bei normaler oder erhöhter Temperatur in Lösung oder für sich der Einwirkung eines neutralen oder basischen Oxydationsmittels oder eines Alkali- bzw. Erdalkalimetallen, ihrer Mischungen, Legierungen . oder Amalgame oder dem Oxydationsmittel und dem Metall gleichzeitig oder nacheinander ausgesetzt wird, worauf das unverändert bleibende reine Isopren aus der Mischung der Reaktionsprodukte auf üblichem Wege, wie z. B. durch einfache Destillation, entfernt wird. Es wurde gefunden, daß Erythren auf demselben Wege leicht gereinigt werden kann, wie der für die Reinigung des Isoprens vorstehend angegebene. Am vorteilhaftesten wird das rohe Erythren bei normaler Temperatur oder unter Erwärmen mit einem Oxydationsmittel von basischer oder neutraler Reaktion, z.B. mit Benzoyl- oder Bariumsuperoxyd, oder mit einer Mischung von Bariumsuperoxyd und metallischem Natrium behandelt. Das Erythren, das ohne Veränderung zurückbleibt, kann jetzt nach der Destillation in chemisch reinem Zustande erhalten werden, natürlich unter der Voraussetzung, daß es keine Kohlen-Wasserstoffe der Grenzreihe enthalten hat. Die gesättigten Kohlenwasserstoffe üben aber* bei Polymerisation des Erythrens zum entsprechenden Kautschuk keine störende Wirkung aus.Erythrene often forms alongside various unsaturated compounds that are very difficult to remove. According to a protected process for the purification of isoprene, the procedure is that crude isoprene containing amylenes is exposed to the action of a neutral or basic oxidizing agent or an alkali or alkaline earth metal, their mixtures, alloys at normal or elevated temperatures. or amalgams or the oxidizing agent and the metal is exposed simultaneously or successively, whereupon the unchanged pure isoprene from the mixture of the reaction products in the usual way, such as. B. is removed by simple distillation. It has been found that erythrene can be easily purified in the same way as that given above for the purification of isoprene. The raw erythrene is most advantageously treated at normal temperature or with heating with an oxidizing agent with a basic or neutral reaction, for example with benzoyl or barium peroxide, or with a mixture of barium peroxide and metallic sodium. The erythrene, which remains unchanged, can now be obtained in a chemically pure state after distillation, provided, of course, that it did not contain any hydrocarbons of the limit series. However, the saturated hydrocarbons do not have a disruptive effect * when the erythrene polymerizes to form the corresponding rubber.
Das beschriebene Verfahren kann für die Reinigung desjenigen rohen Erythrens mit Vorteil benutzt weiden, das sich bei der Dehydratation des 1,3-Butylenglycols mittels der üblichen wasserabspaltenden Mittel, wie ^0 z. B. des Aluminiumoxydes bzw. des roten Phosphors usw., oder mittels Sulfanilsäure bildet (vgl. darüber Berichte des II. Mendelejeffschen Kongresses, Heft 3, Seite 6, Vortrag von I. Ostromisslensky, gehalten am 21. Dezember 1911). Dieses rohe Erythren enthält gewöhnlich in geringer Menge Äthylen, Propylen, die Butylene, Acetylen und andere ungesättigte Verbindungen, die nach dem .beschriebenen Verfahren sehr leicht und quan- g0 titativ entfernt werden können.The method described can be used with advantage for the purification of that crude erythrene, which is produced in the dehydration of 1,3-butylene glycol by means of the usual dehydrating agents, such as ^ 0 z. B. of aluminum oxide or red phosphorus etc., or by means of sulfanilic acid (cf. reports of the II. Mendelejeff Congress, volume 3, page 6, lecture by I. Ostromisslensky, given on December 21, 1911). This crude Erythren usually contains a small amount of ethylene, propylene, the butylenes, acetylene and other unsaturated compounds and quantum 0 can be removed after the tatively .beschriebenen method very easy g.
100 g des rohen,Erythrens werden mit 5 g des Bariumsuperoxydes vermischt und in einem zugeschmolzenen Rohre' etwa 10 Tage bei normaler Temperatur sich selbst überlassen. Es bildet sich dabei ein weißer Niederschlag der Oxydationsprodukte. Aus dem Gefäße läßt sich das reine Erythren quantitativ überdestillieren.100 g of the raw, erythrene are mixed with 5 g of the barium superoxide mixed and in a sealed tube for about 10 days Left to its own devices at normal temperature. A white one forms in the process Precipitation of the oxidation products. Pure Erythren can be extracted from the vessel distill quantitatively over.
Beispiel 2.
Dieselbe Mischung wie in Beispiel 1 wirdExample 2.
The same mixture as in Example 1 is used
ungefähr 24 Stunden auf 50° erwärmt. Die weitere Behandlung" erfolgt wie in Beispiel 1.warmed to 50 ° for about 24 hours. the further treatment "takes place as in example 1.
von Isopren auch auf
Erythren anwendbar ist.of isoprene too
Erythren is applicable.
die Reinigung vonthe cleaning of
100 £ des Erythrens, 5 g des Benzoylsuperoxydes oder eines Terpenozonides und 3 g Natriumürahtes werden unter Schütteln wie' in Beispiel 1 oder Beispiel 2 behandelt.100 pounds of erythrene, 5 g of benzoyl peroxide or a terpenozonide and 3 g of sodium sauté are shaken like ' treated in Example 1 or Example 2.
Es war nicht vorauszusehen, daß das schon geschützte analoge Verfahren zur ReinigungIt could not be foreseen that the already protected analogous process for cleaning
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE314364C true DE314364C (en) |
Family
ID=567185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT314364D Active DE314364C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE314364C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435524A (en) * | 1941-04-18 | 1948-02-03 | Polymerisable Products Ltd | Making acetylenic alcohols and intermediate formed therein |
-
0
- DE DENDAT314364D patent/DE314364C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435524A (en) * | 1941-04-18 | 1948-02-03 | Polymerisable Products Ltd | Making acetylenic alcohols and intermediate formed therein |
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