DE1018043B - Process for the production of ª-phenyl-ethyl alcohol - Google Patents
Process for the production of ª-phenyl-ethyl alcoholInfo
- Publication number
- DE1018043B DE1018043B DED16573A DED0016573A DE1018043B DE 1018043 B DE1018043 B DE 1018043B DE D16573 A DED16573 A DE D16573A DE D0016573 A DED0016573 A DE D0016573A DE 1018043 B DE1018043 B DE 1018043B
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- carried out
- phenyl
- water
- styrene oxide
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229940067107 phenylethyl alcohol Drugs 0.000 title description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 16
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims 2
- ZCCKUOITFYNSQG-UHFFFAOYSA-N styrene;hydrate Chemical compound O.C=CC1=CC=CC=C1 ZCCKUOITFYNSQG-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- -1 styrene halohydrin Chemical class 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GCXHSBQTVXCWBK-UHFFFAOYSA-N 1,2-dichloroethylbenzene Chemical compound ClCC(Cl)C1=CC=CC=C1 GCXHSBQTVXCWBK-UHFFFAOYSA-N 0.000 description 1
- XWCQSILTDPAWDP-UHFFFAOYSA-N 2-chloro-1-phenylethanol Chemical compound ClCC(O)C1=CC=CC=C1 XWCQSILTDPAWDP-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008261 styrofoam Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
- C07C33/22—Benzylalcohol; phenethyl alcohol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von ß-Phenyl-äthyl-alkohol Es ist bekannt, durch katalytische Hydrierung von Styroloxydß-Phenyl-äthyl-alkohol herzustellen. Hierbei wird das Styro-loxyd in reiner Form mit Wasserstoff in Gegenwart von Katalysatoren hydriert. Es ist ferner bekannt, diese Hydrierung in Gegenwart von Alkohol, z. B. Methanol, als Lösungsmittel vorzunehmen. Beide Verfahren haben keinen Eingang in die Technik gefunden, da Nebenreaktionen auftreten und störende Nebenprodukte gebildet werden.Process for the production of ß-phenyl-ethyl alcohol It is known by catalytic hydrogenation of styrene oxide ß-phenyl-ethyl alcohol. Here, the styrofoam is in pure form with hydrogen in the presence of catalysts hydrogenated. It is also known to carry out this hydrogenation in the presence of alcohol, e.g. B. Methanol as a solvent. Both procedures have no entrance in found the technique because side reactions occur and disruptive byproducts are formed will.
Es ist außerdem bekannt, ß-Phenyl-ä.thyl-alkohol durch katalytische Hydrierung von Styrolhalohydrin, welches auch durch Styroldihalogenid verunreinigt sein kann, in flüssiger Phase herzustellen. Bei diesem Verfahren bildet sich unter der Einwirkung von konzentriertem Alkali aus dem Styrolhalohydrin zunächst Styroloxyd, welches dann sofort zu ß-Phenyläthyl-alkohol reduziert wird.It is also known to use ß-phenyl-Ä.thyl-alcohol by catalytic Hydrogenation of styrene halohydrin, which is also contaminated with styrene dihalide can be to produce in the liquid phase. In this process, under forms the action of concentrated alkali from the styrene halohydrin initially styrene oxide, which is then immediately reduced to ß-phenylethyl alcohol.
Es wurde nun gefunden, daß die katalytische Hydrierung von Styroloxyd besonders vorteilhaft so durchgeführt werden kann, daß man das Styroloxyd vorher mit Wasser verrührt. Hierbei ist es vorteilhaft, die Behandlung mit Wasserstoff in Gegenwart höherer Drucke, z. B. zwischen 20 und 200 at, durchzuführen.It has now been found that the catalytic hydrogenation of styrene oxide can be carried out particularly advantageously so that the styrene oxide beforehand stirred with water. It is advantageous here to treat with hydrogen in the presence of higher pressures, e.g. B. between 20 and 200 at to perform.
Der Erfolg der Reaktion wird von dem Verteilungsgrad des Styroloxyds in Wasser beeinflußt. Daher empfiehlt es sich, das Gemisch intensiv zu rühren und hierbei gegebenenfalls geringe Mengen emulgierend wirkender Stoffe zuzusetzen.The success of the reaction depends on the degree of distribution of the styrene oxide affected in water. It is therefore advisable to stir the mixture intensively and add small amounts of emulsifying substances if necessary.
Als geeignete Hydrierungskatalysatoren haben sich unter anderem feinverteiltes Nickel, Kobalt, Platin oder Palladium erwiesen. Auch aktive Kohle ist ein guter Katalysator. Die katalytisch wirkenden Metalle können unter Umständen in an sich bekannter Weise auf inaktiven Trägersubstanzen, wie Siliciumdioxyd, Aluminiumoxyd oder Kieselgur, niedergeschlagen sein.Finely divided substances, among others, have proven to be suitable hydrogenation catalysts Nickel, cobalt, platinum or palladium have been proven. Active coal is also a good one Catalyst. The catalytically active metals can under certain circumstances in itself known way on inactive carrier substances such as silicon dioxide, aluminum oxide or diatomaceous earth, be dejected.
Um die Hydrierung des Styroloxyds mit Wasserstoff zu erleichtern und Nebenreaktionen auszuschließen, hat es sich als zweckmäßig erwiesen, dem Reaktionsgemisch geringe Mengen alkalisch wirkender Stoffe, z. B. Natriumhydroxyd oder Natriu,mcarbonat, zuzusetzen.To facilitate the hydrogenation of the styrene oxide with hydrogen and To exclude side reactions, it has proven to be expedient to add the reaction mixture small amounts of alkaline substances, e.g. B. sodium hydroxide or sodium carbonate, to add.
Unter den angegebenen Bedingungen verläuft die Hydrierung in kurzer Zeit und mit fast quantitativer Ausbeute, ohne Bildung von störenden Nebenprodukten. Der erzielte technische Fortschritt tritt auch gegenüber dem Verfahren, nach welchem ß-Phenyl-äthyl-allcohol aus Styrolhalohydrin, welches auch durch Styroldiha,logenid verunreinigt sein kann, durch katalytische Hydrierung hergestellt wird, deutlich in Erscheinung. So kann beispielsweise die erfindungsgemäßeHydrierung, weil sie in ganz schwach alkalischer Lösung durchgeführt wird, in Druckgefäßen aus jedem beliebigen. Material stattfinden. Die Anwendung von besonders widerstandsfähigen, korrosionsfesten Apparaturen ist nicht erforderlich. Da ferner das erfindungsgemäße Verfahren mit halogenfreien Stoffen, d. h. in Abwesenheit von Styroldihalogeniden, durchgeführt wird, tritt eine Vergiftung des Katalysators nicht ein, was eine erhebliche Einsparung und eine Verkürzung der Hydrierungszeit bedeutet. Außerdem läßt sich hierdurch selbst ohne besondere Reinigung ein viel reineres und besser riechendes Produkt herstellen. Diese Vorteile werden durch die im Beispiel 2 angeführten Vergleichsversuche gezeigt.The hydrogenation takes place in a short time under the specified conditions Time and with almost quantitative yield, without the formation of disruptive by-products. The technical progress achieved also occurs compared to the method according to which ß-Phenyl-ethyl-alcohol from styrene halohydrin, which is also produced by styrene diha, logenide may be contaminated, is produced by catalytic hydrogenation, clearly in appearance. For example, hydrogenation according to the invention can, because it is carried out in very weakly alkaline solution, in pressure vessels from each any. Material take place. The use of particularly resistant, Corrosion-resistant equipment is not required. Furthermore, since the inventive Process with halogen-free substances, d. H. in the absence of styrene dihalides, is carried out, poisoning of the catalyst does not occur, which is considerable Saving and shortening the hydrogenation time means. In addition, can as a result, even without special cleaning, a much purer and better smelling one Manufacture product. These advantages are demonstrated by the comparative tests listed in Example 2 shown.
Beispiel 1 100 Teile Styroloxyd werden mit 500 Teilen Wasser, 2 Teilen N atriumcarbonat und 3 Teilen Raney-Nickel in einem druckfesten Gefäß unter Rühren und einem Wasserstoffdruck von 50 at bei 50° bis zur Druckkonstanz gerührt. Nach ungefähr 30 Minuten ist die Wasserstoffaufnahme beendigt. Bei der nachfolgenden Aufarbeitung durch Destillation erhält man ß-Phenyl-äthyl-allcohol in nahezu quantitativer Ausbeute.Example 1 100 parts of styrene oxide are mixed with 500 parts of water, 2 parts N atrium carbonate and 3 parts of Raney nickel in a pressure-tight vessel with stirring and a hydrogen pressure of 50 at at 50 ° until the pressure was constant. To hydrogen uptake is complete in about 30 minutes. In the following Working up by distillation gives ß-phenyl-ethyl-alcohol in an almost quantitative manner Yield.
Beispiel 2 (Vergleichsversuch) Ein Gemisch von 110 g Styroldichlorid und 255 g Styrolchlorhydrin wird mit 328g 33o/oiger Natronlauge und wenig Raney-Nickel im Rühra.utolclav bei Zimmertemperatur und einem maximalen Wasserstoffdruck von 25 at zur Reaktion gebracht, bis kein Wasserstoff mehr aufgenommen wird: Der Ansatz wird im Scheidetrichter mit 41 Äther aufgearbeitet. Es wird viermal mit Wasser gewaschen. Dabei bilden: sich unliebsame Emulsionen, die die Arbeit merklich behindern. Nach dem Trocknen und Abdampfen des Äthers verbleibt eine rötlich gefärbte Flüssigkeit, die zur Abtrennung der farbigen und harzigen Bestandteile im Hickrnannkolben ausdestilliert wird (Ölbad bis 200°), wobei 173,5 g einer farblosen Flüssigkeit zwischen 40 und 90° (die vor 40° anfallenden Anteile an Kohlenwasserstoffen werden verworfen) und 11 mm abdestillieren, während 17,8 g eines harzigen Rückstandes im Kolben verbleiben. Das Destillat wird nun einer sorgfältigen Rektifikation in der Widmerkolonne unterworfen. Dabei gehen bei 11 mm Hg bis 54° noch 11,2 g Kohlenwasserstoffe über, dann steigt die Temperatur rasch auf 96 bis 97°, wobei insgesamt 155 g einer einheitlichen Fraktion übergehen. Die Substanz enthält jedoch noch Chlor (Substanz 1), wogegen das Infrarotspektrum kaum von demjenigen des reinen Phenyläthylalkohols verschieden ist.Example 2 (comparative experiment) A mixture of 110 g of styrene dichloride and 255 g of styrene chlorohydrin are mixed with 328 g of 33% sodium hydroxide solution and a little Raney nickel in the Rühra.utolclav at room temperature and a maximum hydrogen pressure from 25 at reacted until no more hydrogen is absorbed: The approach is worked up in a separating funnel with 41 ether. It is washed four times with water. This creates: unpleasant emulsions which noticeably hinder the work. To the drying and evaporation of the ether leaves a reddish colored liquid, which is distilled out in the Hickrnann flask to separate the colored and resinous components is (oil bath up to 200 °), 173.5 g of a colorless liquid between 40 and 90 ° (the proportions of hydrocarbons occurring before 40 ° are discarded) and Distill off 11 mm, while 17.8 g of a resinous residue remain in the flask. The distillate is then subjected to careful rectification in the Widmer column. At 11 mm Hg up to 54 °, 11.2 g of hydrocarbons pass over, then rise the temperature rapidly increased to 96 to 97 °, with a total of 155 g of a uniform fraction pass over. However, the substance still contains chlorine (substance 1), whereas the infrared spectrum is hardly different from that of pure phenylethyl alcohol.
Die Substanz 1 wird nun zur Entfernung von chlorhaltigen Produkten über die Calciumchloridverbindung gereinigt, wobei 25,3 g nicht addiert werden. Diese Substanz siedet bei 11 mm zwischen 88 und 95° und enthält viel Chlor. Die destillierte Substanz wird nochmals mit CaC12 verrieben, abgenutscht und mit Petroläther gewaschen, wobei nochmals 3 g an das CaC12 addiert werden. Die Additionsverbindung wird mit Eiswasser zersetzt und mit Äther ausgezogen. In der Widmerkolonne geht bei 11 mm Hg die gesamte Substanz bis auf einen geringen Rückstand zwischen 96 und 97° über (Substanz 2). Diese Substanz zeigt keine Reaktion, mehr auf Chlor, ist aber in bezug auf den Geruch dem aus Styroloxyd durch Reduktion mit Raney-Nickel in Wasser erhaltenen Phenyläthylalkohol noch weit unterlegen. Maximalausbeute 6611/o.Substance 1 is now used to remove products containing chlorine Purified via the calcium chloride compound, 25.3 g not being added. This substance boils between 88 and 95 ° at 11 mm and contains a lot of chlorine. the The distilled substance is rubbed again with CaC12, suction filtered and with petroleum ether washed, another 3 g of the CaC12 being added. The addition connection is decomposed with ice water and extracted with ether. Go in the Widmer column at 11 mm Hg all of the substance except for a slight residue between 96 and 97 ° above (substance 2). This substance no longer reacts to chlorine but with regard to the odor, that of styrene oxide by reduction with Raney nickel Phenylethyl alcohol obtained in water is still far inferior. Maximum yield 6611 / o.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED16573A DE1018043B (en) | 1953-12-15 | 1953-12-15 | Process for the production of ª-phenyl-ethyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED16573A DE1018043B (en) | 1953-12-15 | 1953-12-15 | Process for the production of ª-phenyl-ethyl alcohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1018043B true DE1018043B (en) | 1957-10-24 |
Family
ID=7035402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED16573A Pending DE1018043B (en) | 1953-12-15 | 1953-12-15 | Process for the production of ª-phenyl-ethyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1018043B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE907169C (en) * | 1950-12-14 | 1954-03-22 | Polak & Schwarz S Essencefabri | Process for the preparation of 2-phenylaethanol- (1) |
-
1953
- 1953-12-15 DE DED16573A patent/DE1018043B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE907169C (en) * | 1950-12-14 | 1954-03-22 | Polak & Schwarz S Essencefabri | Process for the preparation of 2-phenylaethanol- (1) |
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