DE1905561A1 - Perhalogenated benzenes from hexachloro - cyclopentadiene - Google Patents
Perhalogenated benzenes from hexachloro - cyclopentadieneInfo
- Publication number
- DE1905561A1 DE1905561A1 DE19691905561 DE1905561A DE1905561A1 DE 1905561 A1 DE1905561 A1 DE 1905561A1 DE 19691905561 DE19691905561 DE 19691905561 DE 1905561 A DE1905561 A DE 1905561A DE 1905561 A1 DE1905561 A1 DE 1905561A1
- Authority
- DE
- Germany
- Prior art keywords
- halogen
- weight
- parts
- perhalogenated
- benzenes
- 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
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 150000001555 benzenes Chemical class 0.000 title claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229940073584 methylene chloride Drugs 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 239000011261 inert gas Substances 0.000 abstract description 2
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- AWLHOCSHUCRWFB-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(dichloromethyl)benzene Chemical compound ClC(Cl)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AWLHOCSHUCRWFB-UHFFFAOYSA-N 0.000 description 3
- -1 dichlorocarbenes Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229950005228 bromoform Drugs 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N iodoform Chemical compound IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CEOCDNVZRAIOQZ-UHFFFAOYSA-N pentachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1Cl CEOCDNVZRAIOQZ-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 description 1
- BBEAZDGZMVABIC-UHFFFAOYSA-N 1,1,1,3,3,3-hexachloropropane Chemical compound ClC(Cl)(Cl)CC(Cl)(Cl)Cl BBEAZDGZMVABIC-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- ZULBFSSEZXLFIV-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl ZULBFSSEZXLFIV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
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 Herstellung perhalogenierter Benzole Es ist aus Chem03er. Band 101, 1968, S. 1407 - 1413 beannt, daß man aus hexachlorcyclopentadien und Dichlorcarbenen Hexachlorbenzol erhält. Bei dieser Beaktion benötigt man Chloroform mit einem Überschuß an äthylenoxid und Tetraäthylammoniumbromid. Man erhält Hexachlorbenzol in einer Ausbeute von nur 5 %. Process for the production of perhalogenated benzenes It is from Chem03er. Volume 101, 1968, pp. 1407-1413 beannt that from hexachlorocyclopentadiene and dichlorocarbenes Hexachlorobenzene receives. This reaction requires chloroform in excess of ethylene oxide and tetraethylammonium bromide. Hexachlorobenzene is obtained in one Yield of only 5%.
Es wurde nun gefunden, daß man perhalogenierte Benzole auf sehr einfache Weise herstellen kann, wenn man Hexachlorcyclopentadien mit halogenierten Kohlenwasserstoffen der allgemeinen Formel I worin R für Wasserstoff, Halogen der niedere halogenierte Alkylgruppen steht und die Reste R¹, R², und R³ Wasserstoff oder Halogen bedeuten, wobei mindestons einer der Reste R, R¹, R² und R³ ein Halogenatom sein muß und wobei R und R¹ gemeinsam auch für eine an @s@ Kohlenstoffaton doppelt gebundene Dihalegenmethylaagruppe stchen können, bei erhöhter Temporature in Abwesenheit von Katalysatoren unsetzt.It has now been found that perhalogenated benzenes can be produced in a very simple manner if hexachlorocyclopentadiene is used with halogenated hydrocarbons of the general formula I. wherein R is hydrogen, halogen, the lower halogenated alkyl groups and the radicals R¹, R², and R³ are hydrogen or halogen, where at least one of the radicals R, R¹, R² and R³ must be a halogen atom and where R and R¹ together also represent one at @ s @ carbon atom doubly bonded dihalegene methyl group, sets in at increased temp in the absence of catalysts.
Ala Halogen k@@@en Fluor, Chlor, Brem und Jod in Betracht. Als halogenierte Alkylgr@ppen vorsugswoise solche mit 1 oder 2 Echlenstoffat@n@n. Ala Halogen k @@@ en fluorine, chlorine, brem and iodine into consideration. As halogenated Alkylgr @ ppen vorsugswoise those with 1 or 2 Echlenstoffat @ n @ n.
Die bei dem Verfahren erhältlichen perhalogenierten Benzole entsprechen der allgemeinen Formel wobei R4 und R5 für gleiche oder verschiedene Halogenatome stehen und wobei einer der Reste R4 oder R5 auch für einen niederen Perhalogen-Alkylrest stehen kann.The perhalogenated benzenes obtainable in the process correspond to the general formula where R4 and R5 stand for identical or different halogen atoms and where one of the radicals R4 or R5 can also stand for a lower perhalo-alkyl radical.
Als für das Verfahren Verwendung findende Halogen-Kohlenwasserstoffe seien beispielsweise genannt: Methylchlorid, Methylenchlorid, Chloroform, Bromoform, Tetrachlorkohlenstoff, Methylenbromid, Methylbromid, Methyljodid, Pentachlorbenzalchlorid, Pentachlorbenzylchlorid, Pentachloräthan, Hexachlorpropan, Tribrommethan, Trijodmethan, 1,1,1-Trichloräthan, 1,1,2,2-Tetrachloräthan und Pentachlorpropan und Tetrachloräthylen.As halogen hydrocarbons used for the process are for example: methyl chloride, methylene chloride, chloroform, bromoform, Carbon tetrachloride, methylene bromide, methyl bromide, methyl iodide, pentachlorobenzal chloride, Pentachlorobenzyl chloride, pentachloroethane, hexachloropropane, tribromomethane, triiodomethane, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane and pentachloropropane and tetrachlorethylene.
Die Ausgangskomponenten Herachlorcyclopentadien und halogenierte Kohlenwasserstoffe der Formel I werden in annähernd stöchiometrischen Mengenverhältnissen oder mit einem Überschuß der einen oder anderen Komponente miteinander umgesetzt.The starting components herachlorocyclopentadiene and halogenated hydrocarbons of formula I are in approximately stoichiometric proportions or with reacted with one another in an excess of one or the other component.
Das erfindungsgenäße Verfahren vird in Gegenwart oder in Abwesenheit von inerten Gasen (z.B. Stickstoff, CO2), zweckmäßigerweise bei Temperaturen zwischen 200 und 800° durchgeführt; bevorzugt wird die Reaktion bei Temperaturen zwischen 400 und 700° durchgeführt, wobei drucklos, unter vermindertem Druck oder unter geringem Überdru@k in der Gasphase gearbeitet wird. Im allgemeinen ist es vorteilhaft, die Ausgangskemponenten gemeinsan in stöchiometrischen Mengen zu erhitzen, oder eine der Komponenten als Lösungsmittel zu verwenden.The process according to the invention is carried out in the presence or in the absence of inert gases (e.g. nitrogen, CO2), expediently at temperatures between 200 and 800 ° carried out; the reaction is preferred at temperatures between 400 and 700 ° carried out, with pressureless, under reduced pressure or under low pressure Overpressure is carried out in the gas phase. In general, it is advantageous to use the Starting components to be heated together in stoichiometric amounts, or a of the components to be used as a solvent.
Die Umsetzung erfolgt in einem Reaktionsgefäß, bevorzugt in einem Rohr, unter Verwendung eines der üblichen gegenüber den Reaktionskomponenten inerten Materials wie z.B. Nickel, Tantal, Quarz oder bei Abwesenheit von fluor in Glasapparaturen.The reaction takes place in a reaction vessel, preferably in one Tube, using one of the usual inert to the reaction components Materials such as nickel, tantalum, quartz or in the absence of fluorine in glass equipment.
Es muß als ausgesprochen überraschend angesehen werden, daß die perhalogenierten Benzole bei dem vorliegenden Verfahren trotz Abwesenhei7t von Katalysatoren in guten Ausbeuten erhalten werden.It must be regarded as extremely surprising that the perhalogenated In the present process, benzenes are good in spite of the absence of catalysts Yields can be obtained.
In den nachfolgenden Beispielen beziehen sich die Temperaturangaben auf °C.In the following examples, the temperature data relate to to ° C.
Beispiel 1: Durch ein senkrecht stehendes Rohr aus inertem Material ( das durch eine Elektroheizung auf 6000 erhitzt wirdo werden 272 Gewichtsteile Hexachlorcyclopentadien und 177 Gewich teile Chloroform in 2 Stdn. durchgetropft. Als Reaktionsprodukt erhält man 18-5 Gewichtsteile Rexachlorbenzol neben 58 Gewichtsteilen nicht umgesetzten Hexachlorcyclopentadien. Das entspricht einer Ausbeute von 85 % bei einem Umsatz von 79 %.Example 1: Through a vertical pipe made of inert material (which is heated to 6000 by an electric heater so becomes 272 parts by weight Hexachlorocyclopentadiene and 177 parts by weight of chloroform in 2 hours. Dripped through. The reaction product obtained is 18-5 parts by weight of rexachlorobenzene in addition to 58 parts by weight unreacted hexachlorocyclopentadiene. This corresponds to a yield of 85 % with a conversion of 79%.
Beispiel 2: Durch ein auf 6000 erhitztes Rohr aus inertem Material leitet man 272 Gewichtsteile Hexachlorcyclopentadien und 128 Gewichts teile Dichlormethan. Das Reaktionsprodukt enthält 78 Gewichtsteile Hexachlorbenzol und 4 Gewichtsteile Pentachlorbenzol. Daneben wurden 127 Gewichtsteile Hexychlorcyclopentadien zurückgewonnen. Des Pentachlorbenzol zeigte den F 85 - 870 und erwies sich durch Vergleich des IR-Spektrums mit einer authentischen Probe als identisch.Example 2: Through a tube made of inert material heated to 6000 272 parts by weight of hexachlorocyclopentadiene and 128 parts by weight of dichloromethane are passed. The reaction product contains 78 parts by weight of hexachlorobenzene and 4 parts by weight Pentachlorobenzene. In addition, 127 parts by weight of hexychlorocyclopentadiene were recovered. The pentachlorobenzene had the F 85-870 and was proven by comparing the IR spectrum as identical to an authentic sample.
Beispiel 3: 600 Gewichtsteile Hexachlorcydlopentadien und 66 Gewichtsteile Pentachlorbenzalchlorid (F 116 » 1180) werden in 41/2 Stunden durch ein auf 500° erhitztes Rohr geleitet. Man erhält neben Hexachlorcyclopentadien 72 Gewichtsteile Hexachlorbenzol und 10 Gewichtsteile nicht umgesetztes pentachlorbenzalchlorid.Example 3: 600 parts by weight of hexachlorocydlopentadiene and 66 parts by weight Pentachlorobenzal chloride (F 116 »1180) are in 41/2 hours by a to 500 ° heated pipe passed. In addition to hexachlorocyclopentadiene, 72 parts by weight are obtained Hexachlorobenzene and 10 parts by weight do not converted pentachlorobenzal chloride.
Beispiel 4: 272 Gewichtsteile Hexachlorcyclopentadien werden im Gemisch mit 300 Gewichtsteilen Tetrachlorkohlenstoff in 3 Stdn. durch ein auf 600° erhitztes Rohr getropft. Man erhält neben 131 Gewichtsteilen nicht umgesetztem Hexachlorcyclopentadien 135 Gewichtsteile Hexachlorbenzol. Das entspricht einer Ausbeute von 92 % bei 48 % Umsatz.Example 4: 272 parts by weight of hexachlorocyclopentadiene are mixed with 300 parts by weight of carbon tetrachloride in 3 hours. Through a heated to 600 ° Pipe dripped. In addition to 131 parts by weight of unreacted hexachlorocyclopentadiene, this is obtained 135 parts by weight of hexachlorobenzene. This corresponds to a yield of 92% for 48 % Sales.
Beispiel 5: 272 Gewichtsteile Hexachlorcyclopentadien und 83 Gew. Tle. Perchloräthylen werden bei 600° in einem schwachen Stickstoffstrom durch ein leeres Quarzrohr innerhalb von 1,3 Stdn. durchgetropft. Aus dem Reaktionsgemisch können durch Kristallsation 70 Gew. Tle. Hexachlorbenzol mit einem Schmelzpunkt von 227 - 228° abgetrannt werden.Example 5: 272 parts by weight of hexachlorocyclopentadiene and 83 parts by weight. Tle. Perchlorethylene are at 600 ° in a gentle stream of nitrogen through a empty quartz tube dripped through within 1.3 hours. From the reaction mixture 70 parts by weight of hexachlorobenzene with a melting point can be obtained by crystallization can be separated from 227 - 228 °.
Durch Destillation gewinnt man 145 Gew. Tle. Herachlorcyclopentadien im Siedebereich von 110 - 120° bei 14 mm Hg neben Forchloräthylen Siedebereich 69 - 71° bei 14 mm Hg zurück. Es sind also 47 % Hexachlorcyclopentadien umgesetzt, wovon 53 % in Hexachlorbenzol umgewandelt wurden.145 parts by weight of herachlorocyclopentadiene are obtained by distillation in the boiling range of 110 - 120 ° at 14 mm Hg in addition to forchlorethylene boiling range 69 - 71 ° back at 14 mm Hg. So there are 47% hexachlorocyclopentadiene converted, of which 53% was converted to hexachlorobenzene.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691905561 DE1905561A1 (en) | 1969-02-05 | 1969-02-05 | Perhalogenated benzenes from hexachloro - cyclopentadiene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691905561 DE1905561A1 (en) | 1969-02-05 | 1969-02-05 | Perhalogenated benzenes from hexachloro - cyclopentadiene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1905561A1 true DE1905561A1 (en) | 1970-08-20 |
Family
ID=5724349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691905561 Pending DE1905561A1 (en) | 1969-02-05 | 1969-02-05 | Perhalogenated benzenes from hexachloro - cyclopentadiene |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1905561A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008048562A1 (en) | 2008-09-23 | 2010-04-29 | Knorr-Bremse Systeme für Schienenfahrzeuge GmbH | Valve arrangement for braking and auxiliary device control of a pneumatic brake system of a vehicle |
-
1969
- 1969-02-05 DE DE19691905561 patent/DE1905561A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008048562A1 (en) | 2008-09-23 | 2010-04-29 | Knorr-Bremse Systeme für Schienenfahrzeuge GmbH | Valve arrangement for braking and auxiliary device control of a pneumatic brake system of a vehicle |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68927110T2 (en) | Process for the preparation of 1,1,1-trifluoro-2,2-dichloroethane | |
| DE69001623T2 (en) | Process for the preparation of fluorine-oxy-fluorosulfonyl compounds by direct fluorination of fluorine-beta sultones. | |
| DE69304987T2 (en) | Process for the production of pentafluoroethane by disproportionation of tetrafluoro-chloroethane | |
| US2192143A (en) | Fluorination process | |
| DE69424948T2 (en) | METHOD FOR THE PRODUCTION OF FLUORINATED PROPANES AND PENTANS | |
| EP0442087A1 (en) | Process for preparing saturated fluorinated hydrocarbons without chlorine | |
| US5608126A (en) | Process for preparing 1,1,1,3,3-pentafluoropropane | |
| DE68917597T2 (en) | CATALYTIC HYDROFLUORATION PROCESS. | |
| DE68919697T2 (en) | CATALYTIC HYDROFLUORATION OF ALKENES. | |
| DE1905561A1 (en) | Perhalogenated benzenes from hexachloro - cyclopentadiene | |
| DE68917596T2 (en) | METHOD FOR HYDROFLUORING ALKANS WITH THE AID OF THE TAX5 CATALYSTS. | |
| EP0407990B1 (en) | Method for the production of 1,1,1-trifluoro-2,2-dichloroethane under high pressure | |
| DE1817193C3 (en) | Process for the simultaneous production of symmetrical and asymmetrical tetrachloroethane | |
| DE1283829B (en) | Process for the production of tetrachlorethylene | |
| DE69702961T2 (en) | PRODUCTION OF 1,1-DIFLUORETHANE | |
| DE2105907A1 (en) | Process for the fluorination of organic compounds with another halogen atom | |
| DE1132901B (en) | Process for the preparation of pyrophoric silicon and polysilicon halides | |
| JP2760862B2 (en) | Novel branched perfluoroalkyl halides and their preparation | |
| DE1900706C3 (en) | 1-alkyl-4-oxaphosphorinanes and a process for the preparation of 4oxaphosphorinanes | |
| CH630053A5 (en) | METHOD FOR PRODUCING A MIXTURE FROM M-ARYLOXYBENZYL CHLORIDE AND M-ARYLOXYBENZALCHLORIDE. | |
| DE2223806C3 (en) | ||
| DE2719021A1 (en) | 1,1,1-Tri:fluoro-2-chloro-ethane prodn. - from tri:chloro-ethylene and hydrogen fluoride using arsenic or antimony cpd. catalyst | |
| DE1071691B (en) | Process for the production of Trichloräthylen unid or or Tetriacbloirät'hylien | |
| US3704307A (en) | Process for the preparation of 3-chloro-4-methoxy-phenylisocyanate | |
| DE890504C (en) | Process for the preparation of diorganodihalosilanes |