DE1930341A1 - Chlorobenzene hydrolysis to give ortho and - para hydroxydiphenyl - Google Patents
Chlorobenzene hydrolysis to give ortho and - para hydroxydiphenylInfo
- Publication number
- DE1930341A1 DE1930341A1 DE19691930341 DE1930341A DE1930341A1 DE 1930341 A1 DE1930341 A1 DE 1930341A1 DE 19691930341 DE19691930341 DE 19691930341 DE 1930341 A DE1930341 A DE 1930341A DE 1930341 A1 DE1930341 A1 DE 1930341A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorobenzene
- hydroxydiphenyl
- percent
- weight
- hydrolysis
- 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 230000007062 hydrolysis Effects 0.000 title abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 title abstract description 6
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims abstract description 14
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- 229940031826 phenolate Drugs 0.000 claims abstract description 8
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims abstract description 7
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract description 4
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003513 alkali Substances 0.000 abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- -1 B. only about 1: 1 Chemical compound 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- MZRAYBSAMAGCRX-UHFFFAOYSA-N chembl261678 Chemical compound OC1=C(Cl)C=C(Cl)C=C1C1=CC=NN1 MZRAYBSAMAGCRX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Verfahren zur Erhöhung der Ausbeuten an o- und p-Hydroxydipenyl bei der alkalischen Hydrolyse von Chlorbenzol Die Erfindung bezieht sich auf ein Verfahren zur Erhöhung der Ausbeute an dem technisch wertvollen o- und p-Hydroxydiphenyl bei der Hydrolyse von Chlorbenzol mit Alkalihydroxid oder Alkaliphenolat in der Flüssigphase bei Temperaturen von etwa 350° bis etwa 450°C.Process for increasing the yields of o- and p-hydroxydipenyl the alkaline hydrolysis of chlorobenzene The invention relates to a process to increase the yield of the technically valuable o- and p-hydroxydiphenyl the hydrolysis of chlorobenzene with alkali hydroxide or alkali phenolate in the liquid phase at temperatures from about 350 ° to about 450 ° C.
Bei der Hydrolyse von Chlorbenzol mit verdünnter, in der Regel etwa 1o bis etwa 15 %iger, Alkali-, vorzugsweise natronlauge entsteht bekanntlich, J nach dem Verhältnis von Chlorbenzol zu Alkali, als Hauptreaktionsprodukt entweder Phenol oder Diphenyläther, und zwar ist die Ausbeute an Phenol umso höher, je höher der Alkaliüberschuß ist, und umgekehrt. Beträgt das Molverhältnis von Alkali zu Chlorbenzol z. B. nur etwa 1:1, so besteht das Reaktionsprodukt zu über 6o Gewichtsprozent aus Diphenyläther.In the hydrolysis of chlorobenzene with dilute, usually about It is known that 1o to about 15% alkali, preferably sodium hydroxide, is formed, J according to the ratio of chlorobenzene to alkali, as the main reaction product either Phenol or diphenyl ether, namely the higher the yield of phenol, the higher is the excess of alkali, and vice versa. The molar ratio of alkali is too Chlorobenzene e.g. B. only about 1: 1, the reaction product consists of more than 60 percent by weight from diphenyl ether.
Neben diesen beiden Hauptprodukten entstehen noch o und p-Hydroxydiphenyl in Mengen bis zu etwa 4 bzw. 1 Gewichtsprozent des Reaktionsproduktes. Da beide Verbindungen technische Bedeutung besitzen, kann ein Interesse daran bestehen, die Hydrolyse des Chlorbenzols, sei et zur Gewinnung von Phenol, sei es zur Gewinnung des technisch ebenfalls wertvollen Diphenyl äthers, so auszugestalten, daß als Nebenprodukte möglichst viel o- und p-Hydroxydiphenyl entstehen.In addition to these two main products, o and p-hydroxydiphenyl are also formed in amounts up to about 4 or 1 percent by weight of the reaction product. Since both Connections have technical importance, there may be an interest in the Hydrolysis of chlorobenzene, be it for the production of phenol, be it for the production of the technically equally valuable diphenyl ether to be designed so that as by-products as much as possible o- and p-hydroxydiphenyl are formed.
Dieses Ziel wird erfindungsgemäß dadurch erreicht, daß man die Hydrolyse des Chlorbenzols in Gegenwart von möglichst wenig Wasser, vorzugsweise in Abwesenheit von Wasser, durchführt.According to the invention, this aim is achieved by the hydrolysis of chlorobenzene in the presence of as little water as possible, preferably in its absence of water.
Dadurch läßt sich die Ausbeute an o-Hydroxydiphenyl bis zu etwa 15 Gewichtsprozent und an p-Hydroxydiphenyl bis zu etwa 4 Gewichtsprozent dea Reaktionsproduktes steigern.As a result, the yield of o-hydroxydiphenyl can be up to about 15 Percent by weight and p-hydroxydiphenyl up to about 4 percent by weight of the reaction product increase.
Erfindungsgemäß verwendet man daher als Verseifungsmittel eine konzentrierte Alkalilauge, insbesondere Natronlauge, oder/und Alkaliphenolat-Lösung oder trockenes Alkalihydroxid oder/und -phenolat.According to the invention, therefore, a concentrated saponification agent is used Alkaline lye, in particular sodium hydroxide solution, and / or alkali metal phenolate solution or dry Alkali hydroxide or / and phenolate.
Gegenstand der Ertindung ist deshalb ein Verfahren zur Erhöhung der Ausbeute an o- und p-Hydroxydiphenyl bei der alkalischen Hydrolyse von Chlorbenzol in der Flüssigphase bei Temperaturen von etwa 350°C bis etwa 450°C, vorzugsweise von 380° bis 420°C, das dadurch gekennzeichnet ist, daß man mit konzentrierter wäßriger Alkalibydroxid- oder/und -phenolat-Lösung oder mit wasserfreiem Alkalihydroxid oder/und -phenolat hydrolysiert Auch bei diesem Verfahren kann man äquivalente Mengen oder einen mehr oder weniger großen Überschuß an Alkali anwenden, Je nachdem, ob man Diphenyläther oder Phenol als Hauptprodukt erhalten möchte.The subject of the invention is therefore a method for increasing the Yield of o- and p-hydroxydiphenyl in the alkaline hydrolysis of chlorobenzene in the liquid phase at temperatures from about 350 ° C to about 450 ° C, preferably from 380 ° to 420 ° C, which is characterized in that one with concentrated aqueous Alkali hydroxide or / and phenolate solution or with anhydrous alkali hydroxide and / or -phenolat hydrolyzed Also in this process you can use equivalent amounts or use a more or less large excess of alkali, depending on whether you Would like to receive diphenyl ether or phenol as the main product.
Beispiel 1 In einem 2 l-Nickelautoklaven mit MagnethubrUhrer wird ein Gemisch von 336 g Chlorbenzol und 260 g 50 %iger wäßriger Natronlauge 2 Stunden auf 400°C erhitzt. Der Stlekstoff-Vordruck bei 20°C beträgt 50 atü, der Enddruck bei 400°C 168 atü.Example 1 In a 2 l nickel autoclave with a magnetic lift stirrer a mixture of 336 g of chlorobenzene and 260 g of 50% strength aqueous sodium hydroxide solution for 2 hours heated to 400 ° C. The pre-pressure of the steel at 20 ° C is 50 atmospheres, the final pressure at 400 ° C 168 atm.
Der Umsatz des Chlorbenzols beläuft sich auf etwa 95 %. Das Reaktionsprodukt (gewonnen durch Extraktion mit Methylenchlorid nach Ansäuern) enthält 54 Gewichtsprozent Diphenyläther, 26 Gewichtsprozent Phenol, 11 Gewichtsprozent 0-Hydroxydiphenyl und 1 Gewichtsprozent p-Hydroxydiphenyl.The conversion of chlorobenzene amounts to about 95%. The reaction product (obtained by extraction with methylene chloride after acidification) contains 54 percent by weight Diphenyl ether, 26 percent by weight phenol, 11 percent by weight 0-hydroxydiphenyl and 1 weight percent p-hydroxydiphenyl.
Beispiel 2 In einem 12 ml Nickel-Autoklaven mit Silber-Dichtung wird ein Gemisch von 5 g Chlorbenzol, 2 g Natriumhydroxid und 2 g Wasser 1 Stunde unter Schütteln auf 380°C erhitzt. Der Umsatz des Chlorbenzols beläuft sich auf etwa 80 %. Das Reaktionagemisch enthält 19 Gewichtsprozent Phenol, 6o,3 Gewichtsprozent Diphenyläther, 9,8 Gewichtsprozent o-Hydroxydiphenyl und 3,8 Gewichtsprozent p-Hydroxydiphenyl.Example 2 In a 12 ml nickel autoclave with a silver seal taking a mixture of 5 g of chlorobenzene, 2 g of sodium hydroxide and 2 g of water for 1 hour Shaking heated to 380 ° C. The conversion of chlorobenzene is around 80 %. The reaction mixture contains 19 percent by weight phenol, 6o.3 percent by weight Diphenyl ether, 9.8 percent by weight o-hydroxydiphenyl and 3.8 percent by weight p-hydroxydiphenyl.
Beispiel 3 Ein Gemisch von 300 g Phenol (3,19 Mol), 140 g Natriumhydroxid (3,5 Mol), loo g Wasser und 34o g Chlorbenzol (3,o2 Mol) wird im 2 1-Nickelautoklaven mit Magnethubrüherer 3 Stunden auf 400°C erhitzt. Dss Chlorbenzol ist quantitativ umgesetzt. Das seaktionsprodukt (gewonnen durch Extraktion mit Methylenchlorid nach Ansäuern) enthält 27 Gewichtaprozent Phenol,57 Gewichtsprozent Diphenyläther, 8,5 Gewichtsprozent o-Hydroxydiphenyl und 1,4 Gewichtsprozent p-Hydroxydiphenyl. Der Rest verteilte sich auf einige Nebenprodukte.Example 3 A mixture of 300 grams of phenol (3.19 moles), 140 grams of sodium hydroxide (3.5 mol), loo g water and 34o g chlorobenzene (3.02 mol) is in the 2 l nickel autoclave heated to 400 ° C for 3 hours with a magnet lift. The chlorobenzene is quantitative implemented. The reaction product (obtained by extraction with methylene chloride Acidification) contains 27 percent by weight phenol, 57 percent by weight diphenyl ether, 8.5 Percent by weight o-hydroxydiphenyl and 1.4 percent by weight p-hydroxydiphenyl. Of the The rest was distributed among some by-products.
Beispiel 4 Ein Gemisch von 4 g Chlorbenzol (0,035 Mol), 4 g Natriunhydroxidpulver (0,1 Mol) und ioo mg Kupferpulver wird in einem 12 ml-Nikkelautoklaven mit Kupferdichtung unter kräftigem Schütteln 1 Stunde auf 4200C erhitzt. Das Chlorbenzol ist dann nahezu vollständig umgesetzt. Nach der gaschromatographischen Analyse enthält das Reaktionsgemisch 73 Gewichtsprozent Phenol, 0,6 Gewichtsprozent Diphenyläther, 15 Gewichtsprozent o-Hydroxydiphenyl, 2,1 Gewlchtsprozent p-Hydroxydiphenyl und einige Nebenprodukte.Example 4 A mixture of 4 g chlorobenzene (0.035 mole), 4 g sodium hydroxide powder (0.1 mol) and 100 mg of copper powder is placed in a 12 ml nickel autoclave with Copper seal heated to 4200C for 1 hour while shaking vigorously. The chlorobenzene is then almost completely implemented. According to the gas chromatographic analysis contains the reaction mixture 73 percent by weight phenol, 0.6 percent by weight diphenyl ether, 15 percent by weight o-hydroxydiphenyl, 2.1 percent by weight p-hydroxydiphenyl and some by-products.
Beispiel 5 Im gleichen Autoklaven wie bei Beispiel 4 wird ein Gemisch von 4 g Chlorbenzol und 2 g Natriumhydroxidpulver 1 Stunde bei 420°C geschüttelt. Bei wieder vollständigem Umsatz des Chlorbenzolsenthält das Reaktionsgemisch 53 Gewichtsprozent Diphenyläther, 26 Gewichtsprozent Phenol, 13 Gewichtsprozent °-Hydroxydiphenyl und 2,5 Gewichtsprozent p-Hydroxydiphenyl.Example 5 In the same autoclave as in Example 4, a mixture shaken by 4 g of chlorobenzene and 2 g of sodium hydroxide powder for 1 hour at 420 ° C. When the chlorobenzene has been completely reacted again, the reaction mixture contains 53 Weight percent diphenyl ether, 26 weight percent phenol, 13 weight percent ° -hydroxydiphenyl and 2.5 weight percent p-hydroxydiphenyl.
Beispiel 6 Im Autoklaven wie bei Beispiel 4 wird ein Gemisch von 4 g Chlorbenzol und 1,5 g Natriumhydroxidpulver 1 Stunde bei 420°C geschüttelt. Im Reaktionsgemisch befinden sich danach 64,5 Gewichtsprozent Diphenyläther, 12 Gewichtsprozent Phenol, 13,6 Gewichtsprozent o-Hydroxydiphenyl und 2,7 Gewichtsprozent p-Hydpoxydiphenyl.Example 6 In the autoclave as in Example 4, a mixture of 4 g chlorobenzene and 1.5 g sodium hydroxide powder are shaken at 420 ° C for 1 hour. in the The reaction mixture then contains 64.5 percent by weight of diphenyl ether and 12 percent by weight Phenol, 13.6 percent by weight o-hydroxydiphenyl and 2.7 percent by weight p-hydroxydiphenyl.
Beispiel 7 Ein Gemisch von 4 g Natriumphenolat (0,345 Mol) und ml Chlorbenzol (0,0393 Mol) wird im 12 ml-Nickelautoklaven mit Kupferdichtung unter Schütteln 1 Stunde auf 4000C erhitzt. Das Reaktionsgemisch wird angesäuert und mit Methylenchlorid extrahiert.Example 7 A mixture of 4 g of sodium phenate (0.345 mol) and ml Chlorobenzene (0.0393 mol) is placed in a 12 ml nickel autoclave with a copper seal Shaking heated to 4000C for 1 hour. The reaction mixture is acidified and with Extracted methylene chloride.
Die gaschromatografische Analyse des Reaktionsproduktes ergibt, daß dasselbe 18 Gewichtsprozent Phenol, 61 Gewichtsprozent Diphenyläther, 12,6 Gewichtsprozent o-Hydroxydiphenyl, 2,5 Gewichtsprozent p-Hydroxydiphenyl und 4 Gewichtsprozent Chlorbenzol enthält.Gas chromatographic analysis of the reaction product shows that the same 18 weight percent phenol, 61 weight percent diphenyl ether, 12.6 weight percent o-hydroxydiphenyl, 2.5 percent by weight p-hydroxydiphenyl and 4 percent by weight chlorobenzene contains.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691930341 DE1930341A1 (en) | 1969-06-14 | 1969-06-14 | Chlorobenzene hydrolysis to give ortho and - para hydroxydiphenyl |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691930341 DE1930341A1 (en) | 1969-06-14 | 1969-06-14 | Chlorobenzene hydrolysis to give ortho and - para hydroxydiphenyl |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1930341A1 true DE1930341A1 (en) | 1970-12-17 |
Family
ID=5737052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691930341 Pending DE1930341A1 (en) | 1969-06-14 | 1969-06-14 | Chlorobenzene hydrolysis to give ortho and - para hydroxydiphenyl |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1930341A1 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337368A (en) * | 1980-04-21 | 1982-06-29 | The Franklin Institute | Reagent and method for decomposing halogenated organic compounds |
| WO1982003025A1 (en) * | 1981-03-05 | 1982-09-16 | Franklin Institute | Improved method for decomposition of halogenated organic compounds |
| US4417977A (en) * | 1982-09-30 | 1983-11-29 | The Franklin Institute | Removal of PCBS and other halogenated organic compounds from organic fluids |
| US4460797A (en) * | 1981-03-05 | 1984-07-17 | The Franklin Institute | Method for decomposition of halogenated organic compounds |
| US4471143A (en) * | 1980-04-21 | 1984-09-11 | The Franklin Institute | Composition for decomposing halogenated organic compounds |
| US4475000A (en) * | 1983-01-21 | 1984-10-02 | Ethyl Corporation | Process for producing 4,4'-dihydroxybiphenyl |
| US4490564A (en) * | 1983-04-22 | 1984-12-25 | Ethyl Corporation | Mixed solvent recovery of 4,4'-dihydroxybiphenyl |
| US4602994A (en) * | 1982-09-30 | 1986-07-29 | The Franklin Institute | Removal of PCBs and other halogenated organic compounds from organic fluids |
-
1969
- 1969-06-14 DE DE19691930341 patent/DE1930341A1/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337368A (en) * | 1980-04-21 | 1982-06-29 | The Franklin Institute | Reagent and method for decomposing halogenated organic compounds |
| US4400552A (en) * | 1980-04-21 | 1983-08-23 | The Franklin Institute | Method for decomposition of halogenated organic compounds |
| US4471143A (en) * | 1980-04-21 | 1984-09-11 | The Franklin Institute | Composition for decomposing halogenated organic compounds |
| WO1982003025A1 (en) * | 1981-03-05 | 1982-09-16 | Franklin Institute | Improved method for decomposition of halogenated organic compounds |
| US4460797A (en) * | 1981-03-05 | 1984-07-17 | The Franklin Institute | Method for decomposition of halogenated organic compounds |
| US4417977A (en) * | 1982-09-30 | 1983-11-29 | The Franklin Institute | Removal of PCBS and other halogenated organic compounds from organic fluids |
| US4602994A (en) * | 1982-09-30 | 1986-07-29 | The Franklin Institute | Removal of PCBs and other halogenated organic compounds from organic fluids |
| US4475000A (en) * | 1983-01-21 | 1984-10-02 | Ethyl Corporation | Process for producing 4,4'-dihydroxybiphenyl |
| US4490564A (en) * | 1983-04-22 | 1984-12-25 | Ethyl Corporation | Mixed solvent recovery of 4,4'-dihydroxybiphenyl |
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