NO172534B - PROCEDURE FOR SYNTHESIS OF 1,1,1,2-TETRACHLORETHANE BY HYDROCLORATION OF THE TRICHLORETHYL. - Google Patents
PROCEDURE FOR SYNTHESIS OF 1,1,1,2-TETRACHLORETHANE BY HYDROCLORATION OF THE TRICHLORETHYL. Download PDFInfo
- Publication number
- NO172534B NO172534B NO902167A NO902167A NO172534B NO 172534 B NO172534 B NO 172534B NO 902167 A NO902167 A NO 902167A NO 902167 A NO902167 A NO 902167A NO 172534 B NO172534 B NO 172534B
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- Norway
- Prior art keywords
- tetrachloroethane
- hydrochlorination
- trichlorethylene
- chloride
- synthesis
- Prior art date
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- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 6
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 22
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 14
- 238000007038 hydrochlorination reaction Methods 0.000 claims abstract description 13
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 4
- 150000005309 metal halides Chemical class 0.000 claims abstract description 4
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides 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
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- -1 antimony halides Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
- C07C19/043—Chloroethanes
- C07C19/055—Tetrachloroethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
Foreliggende oppfinnelse angår en fremgangsmåte for syntese av 1,1,1,2-tetrakloretan ved hydroklorering av trikloretylen. The present invention relates to a method for the synthesis of 1,1,1,2-tetrachloroethane by hydrochlorination of trichloroethylene.
1,1,1,2-tetrakloretan (CCI3CH2CI) er et produkt som benyttes som oppløsningsmiddel og spesielt som mellomprodukt ved organiske synteser. DE-PS 1 964 551 ("Chemical Abstracts" 76641 n, vol. 73) beskriver klorering av en blanding av 1,1,1-trikloretan (CCI3CH3) og trikloretylen (CHC1=CC12) for å oppnå en blanding av 1,2-dikloretan (CH2CICE2CI), penta-kloretan og 1,1,1,2-tetrakloretan. DE-PS 1 817 193 ("Chemical Abstracts" 123515 v, vol. 71) beskriver klorering av en blanding av 1,1-dikloretylen (CCl2=CH2) og 1,2-dikloretylen (CHC1=CHC1) for å fremstille en blanding av 1,1,1,2-tetrakloretan og 1,1,2,2-tetrakloretan (CHC12-CHC12). DE-PS 1 817 194 ("Chemical Abstracts" 123516 w, vol. 71) beskriver klorering av 1,1-dikloretylen for å fremstille 1,1,1,2-tetrakloretan. 1,1,1,2-Tetrachloroethane (CCI3CH2CI) is a product that is used as a solvent and especially as an intermediate in organic syntheses. DE-PS 1 964 551 ("Chemical Abstracts" 76641 n, vol. 73) describes the chlorination of a mixture of 1,1,1-trichloroethane (CCI3CH3) and trichloroethylene (CHC1=CC12) to obtain a mixture of 1,2 -dichloroethane (CH2CICE2CI), pentachloroethane and 1,1,1,2-tetrachloroethane. DE-PS 1 817 193 ("Chemical Abstracts" 123515 v, vol. 71) describes the chlorination of a mixture of 1,1-dichloroethylene (CCl2=CH2) and 1,2-dichloroethylene (CHC1=CHC1) to prepare a mixture of 1,1,1,2-tetrachloroethane and 1,1,2,2-tetrachloroethane (CHC12-CHC12). DE-PS 1 817 194 ("Chemical Abstracts" 123516 w, vol. 71) describes the chlorination of 1,1-dichloroethylene to prepare 1,1,1,2-tetrachloroethane.
US-PS 3 860 666 angår fremstilling av perkloretylen ved katalytisk klorering av etylen i et aluminium hvirvelsjikt. Det dannes også noe trikloretylen. En liten del av dette aluminium omdannes til aluminiumklorid og katalyserer hydroklorering av trikloretylen og 1,1,1,2-tetrakloretan. Trikloretylen representerer ikke mere enn noen prosent av utgangsblandingen fra hvirvelsjiktet og kun en liten del omdannes til 1,1,2-tetrakloretan. I industriell målestokk kan man ikke benytte aluminiumklorid som katalysator for hydroklorering av trikloretan til 1,1,1,2-tetrakloretan fordi trikloretan er ustabilt i nærvær av aluminiumklorid og man derved risikerer en dekomponering. US-PS 3,860,666 relates to the production of perchlorethylene by catalytic chlorination of ethylene in an aluminum fluidized bed. Some trichlorethylene is also formed. A small part of this aluminum is converted to aluminum chloride and catalyzes the hydrochlorination of trichloroethylene and 1,1,1,2-tetrachloroethane. Trichlorethylene does not represent more than a few percent of the output mixture from the fluidized bed and only a small part is converted to 1,1,2-tetrachloroethane. On an industrial scale, aluminum chloride cannot be used as a catalyst for the hydrochlorination of trichloroethane to 1,1,1,2-tetrachloroethane because trichloroethane is unstable in the presence of aluminum chloride and there is a risk of decomposition.
Man finner i en artikkel av M.S. Karasch, J.A. Norton og F.R. Mayo, "J. ORg. Chem." 3, 1938, s. 48-54 en hydroklorering av trikloretylen, katalysert av jern(III)klorid ved omgivelsestemperatur. Omdanningsgraden for trikloretylen går ikke ut over 49$ efter 6 timers reaksjon. One finds in an article by M.S. Karasch, J.A. Norton and F.R. Mayo, "J. ORg. Chem." 3, 1938, pp. 48-54 a hydrochlorination of trichloroethylene, catalyzed by ferric chloride at ambient temperature. The degree of conversion for trichlorethylene does not exceed 49$ after 6 hours of reaction.
US-PS 3 732 322 ("Chemical Abstracts" 4985 d, vol. 79) beskriver deshydroklorering av 1,1,1,2-tetrakloretan i nærvær av FeCl3 for å fremstille trikloretylen. På tross av at dette dokument viser enten en hydroklorering eller en deshydroklorering under virkning av FeCl3 har søkeren funnet en hydrokloreringsprosess for trikloretylen i nærvær av FeCl3 og under trykk. Denne prosess er selektiv for isomeren 1,1,1,2-tetrakloretan og den kan realiseres i industriell målestokk. Det er videre oppdaget at, i tillegg til jern-(Ill)klorid og aluminiumklorid som allerede nevnt, metalliske halogenider er hydrokloreringskatalysatorer for trikloretylen for selektivt å produsere 1,1,1,2-tetrakloretan. US-PS 3,732,322 ("Chemical Abstracts" 4985 d, vol. 79) describes the dehydrochlorination of 1,1,1,2-tetrachloroethane in the presence of FeCl 3 to produce trichloroethylene. Despite the fact that this document shows either a hydrochlorination or a dehydrochlorination under the action of FeCl3, the applicant has found a hydrochlorination process for trichlorethylene in the presence of FeCl3 and under pressure. This process is selective for the isomer 1,1,1,2-tetrachloroethane and it can be realized on an industrial scale. It has further been discovered that, in addition to ferric chloride and aluminum chloride as already mentioned, metallic halides are hydrochlorination catalysts for trichlorethylene to selectively produce 1,1,1,2-tetrachloroethane.
Foreliggende oppfinnelse angår således en fremgangsmåte for syntese av 1,1,1,2-tetrakloretan ved hydroklorering av trikloretylen og denne fremgangsmåte karakteriseres ved at man enten arbeider i nærvær av jern(III)klorid og under et trykk over det atmosfæriske, fortrinnsvis mellom 10 og 40 bar absolutt, eller i nærvær av aluminiumbromid, at hydrokloreringen gjennomføres ved en temperatur mellom 10 og 160°C og at man benytter metallhalogenidet i en mengde mellom 0,1 og 20 vekt-# og fortrinnsvis mellom 1 og 5 vekt-#, alt beregnet på mengden trikloretylen. The present invention thus relates to a method for the synthesis of 1,1,1,2-tetrachloroethane by hydrochlorination of trichlorethylene and this method is characterized by either working in the presence of iron (III) chloride and under a pressure above atmospheric, preferably between 10 and 40 bar absolute, or in the presence of aluminum bromide, that the hydrochlorination is carried out at a temperature between 10 and 160°C and that the metal halide is used in an amount between 0.1 and 20 wt-# and preferably between 1 and 5 wt-#, all calculated on the amount of trichlorethylene.
Hva angår reaksjoner i nærvær av jern(III)klorid er det som nevnt fordelaktig å arbeide ved et trykk over 5 bar absolutt og fortrinnsvis ved et trykk mellom 10 og 40 bar absolutt. Man går ikke utenfor oppfinnelsens ramme ved å arbeide ved et høyere trykk men tekniske vanskeligheter ved gjennomføringen gjør en slik prosess komplisert uten ytterligere fordeler. Temperaturen kan være en hvilken som helst men er fortrinnsvis mellom 10 og 160°C og aller helst mellom 20 og 100oC. With regard to reactions in the presence of iron (III) chloride, it is, as mentioned, advantageous to work at a pressure above 5 bar absolute and preferably at a pressure between 10 and 40 bar absolute. One does not go outside the scope of the invention by working at a higher pressure, but technical difficulties in the implementation make such a process complicated without further advantages. The temperature can be any but is preferably between 10 and 160°C and most preferably between 20 and 100°C.
I henhold til temperatur og trykk kan reaktantene være flytende eller gassformige. Det er foretrukket å arbeide i vannfritt medium. Reaktantene kan videre fortynnes i et oppløsningsmiddel forutsatt at de er inerte under betingel-sene for reaksjonen. According to temperature and pressure, the reactants can be liquid or gaseous. It is preferred to work in an anhydrous medium. The reactants can further be diluted in a solvent provided that they are inert under the conditions of the reaction.
Mengden jern(III )klorid ligger fortrinnsvis mellom 0,1 og 20$ aller helst mellom 1 og 5% beregnet på vekten av trikloretylen. The amount of iron(III) chloride is preferably between 0.1 and 20%, most preferably between 1 and 5% calculated on the weight of trichlorethylene.
Reaksjonen ifølge oppfinnelsen kan gjennomføres i en hvilken som helst innretning som sikrer kontakt mellom jern(III)-klorid og trikloretylen og saltsyre. Ved slutten av reaksjonen kan man eventuelt vaske reaksjonsmediet. Det oppnådde 1,1,2-tetrakloretan separeres for eksempel ved destillasjon. Når det gjelder hydroklorering i nærvær av metalliske halogenider bortsett fra jern(III)klorid og aluminiumklorid, arbeider man som antydet under de samme betingelser som ved jern(III)klorid bortsett fra at trykket ikke er nødvendig. Man kan også arbeide under trykk, det vil si et trykk over det atmosfæriske trykk. The reaction according to the invention can be carried out in any device which ensures contact between iron (III) chloride and trichlorethylene and hydrochloric acid. At the end of the reaction, the reaction medium can optionally be washed. The 1,1,2-tetrachloroethane obtained is separated, for example, by distillation. When it comes to hydrochlorination in the presence of metallic halides, apart from iron (III) chloride and aluminum chloride, as indicated, one works under the same conditions as with iron (III) chloride, except that the pressure is not necessary. One can also work under pressure, i.e. a pressure above atmospheric pressure.
Som eksempel på metalliske halogenider skal nevnes aluminiumbromid og gallium-, tinn-, molybden- og antimonhalogenidet. Man benytter fortrinnsvis aluminiumbromid. Mengden metall-halogenid er den samme som for jern(III)klorid. Examples of metallic halides include aluminum bromide and the gallium, tin, molybdenum and antimony halides. Aluminum bromide is preferably used. The amount of metal halide is the same as for ferric chloride.
De følgende eksempler skal illustrere oppfinnelsen. I disse eksempler blir reaksjonsblandingen ved slutten av reaksjonen vasket med vann og derefter analysert ved gassfasekromato-grafi. The following examples shall illustrate the invention. In these examples, the reaction mixture is washed with water at the end of the reaction and then analyzed by gas phase chromatography.
Eksempel 1 (ikke ifølge oppfinnelsen) Example 1 (not according to the invention)
Til en omrørt glassreaktor utstyrt med termometer, HC1-injektor og en tilbakeløpskjøler chargeres 2 mol tilsvarende 263 g trikloretylen, jern(III)klorid og man bringer det hele til 35°C og tilsetter 1 mol/t HC1. Hvis det har gått over en time uten reaksjon fortsettes injeksjonen av HC1 i samme hastighet men temperaturen i reaktoren bringes til 40° C. Efter 1 time ved 40°C fortsettes injeksjonen på 1 mol/t HC1 men temperaturen bringes til 60°C. Efter 1 time (det vil si 1 time ved 35°C, 1 time ved 40°C og 1 time ved 60°C) finner man 0,25$ CCI3CH2CI i reaktoren. De oppnådde resultater er anført i tabell I. Into a stirred glass reactor equipped with a thermometer, HC1 injector and a reflux cooler, 2 mol corresponding to 263 g of trichlorethylene, iron(III) chloride are charged and the whole is brought to 35°C and 1 mol/h HC1 is added. If more than an hour has passed without a reaction, the injection of HC1 is continued at the same rate but the temperature in the reactor is brought to 40°C. After 1 hour at 40°C, the injection of 1 mol/h HC1 is continued but the temperature is brought to 60°C. After 1 hour (ie 1 hour at 35°C, 1 hour at 40°C and 1 hour at 60°C) 0.25$ of CCI3CH2CI is found in the reactor. The results obtained are listed in Table I.
Eksempel 2 og 3 Examples 2 and 3
Til en 1 1 Inox reaktor chargeres 2 mol trikloretylen og katalysatoren; man tilfører EC1 under trykk som antydet i tabell I ved omgivelsestemperatur, man lukker autoklaven og bringer det hele til den antydede temperatur i den antydede tid som vist i tabell 1. Det maksimale trykk som oppnås i eksempel 2 er 60 bar og i eksempel 3 85 bar. 2 mol of trichlorethylene and the catalyst are charged to a 1 1 Inox reactor; EC1 is added under pressure as indicated in table I at ambient temperature, the autoclave is closed and everything is brought to the indicated temperature for the indicated time as shown in table 1. The maximum pressure achieved in example 2 is 60 bar and in example 3 85 bar.
Eksemplene 4 og 5 Examples 4 and 5
Til en 4 1 reaktor utstyrt med røreverk chargeres: A 4 1 reactor equipped with agitator is charged:
20 mol trikloretylen 20 moles of trichloroethylene
katalysator catalyst
og under det HC1 trykk som er angitt i tabell I holder man autoklaven ved den i tabell I viste temperatur i det tidsrom som er angitt. and under the HC1 pressure indicated in Table I, the autoclave is kept at the temperature shown in Table I for the time period indicated.
Eksempel 6 og 7 Examples 6 and 7
Man arbeider med den samme apparatur som i eksempel 1 og man chargerer: You work with the same equipment as in example 1 and you charge:
2 mol trikloretylen 2 moles of trichlorethylene
katalysator catalyst
hvorefter man bringer temperaturen til den ønskede verdi og tilsetter gassformig HC1 i en mengde av 0,5 mol/time. after which the temperature is brought to the desired value and gaseous HC1 is added in a quantity of 0.5 mol/hour.
Resultatene er vist i tabell I. The results are shown in Table I.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8906923A FR2647439A1 (en) | 1989-05-26 | 1989-05-26 | PROCESS FOR THE SYNTHESIS OF 1,1,1,2-TETRACHLORETHANE BY HYDROCHLORINATION OF TRICHLORETHYLENE |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO902167D0 NO902167D0 (en) | 1990-05-15 |
| NO902167L NO902167L (en) | 1990-11-27 |
| NO172534B true NO172534B (en) | 1993-04-26 |
| NO172534C NO172534C (en) | 1993-08-04 |
Family
ID=9382049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO902167A NO172534C (en) | 1989-05-26 | 1990-05-15 | PROCEDURE FOR SYNTHESIS OF 1,1,1,2-TETRACHLORETHANE BY HYDROCLORATION OF THE TRICHLORETHYL. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0399867B1 (en) |
| JP (1) | JPH0317028A (en) |
| KR (1) | KR920006537B1 (en) |
| CN (1) | CN1047490A (en) |
| AT (1) | ATE108758T1 (en) |
| CA (1) | CA2016845A1 (en) |
| DE (1) | DE69010773T2 (en) |
| DK (1) | DK0399867T3 (en) |
| ES (1) | ES2057466T3 (en) |
| FI (1) | FI902636A0 (en) |
| FR (1) | FR2647439A1 (en) |
| IE (1) | IE901882L (en) |
| NO (1) | NO172534C (en) |
| PT (1) | PT94162B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100338001C (en) * | 2004-11-17 | 2007-09-19 | 浙江莹光化工有限公司 | Production of 1,1,1,2-tetrafluoroethykane and pentafuoethane simultaneously |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE486345A (en) * | 1947-12-19 |
-
1989
- 1989-05-26 FR FR8906923A patent/FR2647439A1/en active Pending
-
1990
- 1990-05-09 ES ES90401225T patent/ES2057466T3/en not_active Expired - Lifetime
- 1990-05-09 AT AT90401225T patent/ATE108758T1/en not_active IP Right Cessation
- 1990-05-09 DK DK90401225.9T patent/DK0399867T3/en active
- 1990-05-09 EP EP90401225A patent/EP0399867B1/en not_active Expired - Lifetime
- 1990-05-09 DE DE69010773T patent/DE69010773T2/en not_active Expired - Fee Related
- 1990-05-11 KR KR1019900006748A patent/KR920006537B1/en not_active IP Right Cessation
- 1990-05-15 NO NO902167A patent/NO172534C/en unknown
- 1990-05-15 CA CA002016845A patent/CA2016845A1/en not_active Abandoned
- 1990-05-24 JP JP2135157A patent/JPH0317028A/en active Pending
- 1990-05-24 IE IE901882A patent/IE901882L/en unknown
- 1990-05-25 FI FI902636A patent/FI902636A0/en not_active IP Right Cessation
- 1990-05-25 PT PT94162A patent/PT94162B/en not_active IP Right Cessation
- 1990-05-26 CN CN90103796A patent/CN1047490A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK0399867T3 (en) | 1994-10-31 |
| ATE108758T1 (en) | 1994-08-15 |
| KR920006537B1 (en) | 1992-08-08 |
| NO902167D0 (en) | 1990-05-15 |
| NO172534C (en) | 1993-08-04 |
| ES2057466T3 (en) | 1994-10-16 |
| CN1047490A (en) | 1990-12-05 |
| JPH0317028A (en) | 1991-01-25 |
| IE901882L (en) | 1990-11-26 |
| EP0399867B1 (en) | 1994-07-20 |
| DE69010773D1 (en) | 1994-08-25 |
| NO902167L (en) | 1990-11-27 |
| FI902636A0 (en) | 1990-05-25 |
| PT94162B (en) | 1996-12-31 |
| CA2016845A1 (en) | 1990-11-26 |
| FR2647439A1 (en) | 1990-11-30 |
| PT94162A (en) | 1991-01-08 |
| DE69010773T2 (en) | 1995-03-09 |
| KR900017970A (en) | 1990-12-20 |
| EP0399867A1 (en) | 1990-11-28 |
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