BE1013616A3 - Chlorination ethylene cracking hydrocarbons obtained. - Google Patents

Chlorination ethylene cracking hydrocarbons obtained. Download PDF

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Publication number
BE1013616A3
BE1013616A3 BE9800788A BE9800788A BE1013616A3 BE 1013616 A3 BE1013616 A3 BE 1013616A3 BE 9800788 A BE9800788 A BE 9800788A BE 9800788 A BE9800788 A BE 9800788A BE 1013616 A3 BE1013616 A3 BE 1013616A3
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BE
Belgium
Prior art keywords
chlorination
ethylene
cracking
products
dichloroethane
Prior art date
Application number
BE9800788A
Other languages
French (fr)
Inventor
Michel Strebelle
Andre Petitjean
Original Assignee
Solvay
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Publication date
Application filed by Solvay filed Critical Solvay
Priority to BE9800788A priority Critical patent/BE1013616A3/en
Priority to AU11554/00A priority patent/AU1155400A/en
Priority to PCT/EP1999/008145 priority patent/WO2000026164A1/en
Priority to ARP990105384 priority patent/AR020965A1/en
Application granted granted Critical
Publication of BE1013616A3 publication Critical patent/BE1013616A3/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/148Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/14808Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with non-metals as element
    • C07C7/14825Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with non-metals as element halogens
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/013Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/02Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Le procédé concerne la chloration de l'éthylène en présence de produits tels que l'hydrogène et des hydrocarbures saturés.The process relates to the chlorination of ethylene in the presence of products such as hydrogen and saturated hydrocarbons.

Description

       

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  Chloration d'éthylène obtenu pour cracking d'hydrocarbures 
La présente invention concerne un procédé de cracking de produits pétroliers simplifié qui est couplé à une chloration de l'éthylène. 



   A ce jour, on effectue toujours le cracking de divers produits pétroliers lourds pour former de l'éthylène. Celui-ci est séparé des sous-produits légers tels que l'hydrogène, le méthane et l'éthane par des procédés coûteux et complexes. 



   Par ailleurs, plusieurs voies de valorisation directe d'éthane en chlorure de vinyle sont connues dans la littérature : - oxychloration d'éthane en lit fluide et valorisation des sous-produits - chloration non catalytique à haute température - oxychloration en bain de sels fondus. 



  Aucune n'a toutefois trouvé d'application industrielle jusqu'à présent. 



   D'autre part, il est également connu que le vapocraquage d'éthane conduit à un mélange riche en éthylène. En effet, on observe une sélectivité proche de 80 % pour une conversion d'éthane de l'ordre de 70 %. L'investissement d'un tel type de craquage est malheureusement très lourd et n'a donc pas abouti à un procédé industriellement utilisable de cracking directement dédicacé à une production de 1, 2-dichloréthane et de chlorure de vinyle. 



   La présente invention a pour but d'alléger le coût d'un vapocraqueur en renonçant à des séparations complexes et sans intérêt pour la fabrication de 1,2dichloréthane. A cet effet une étape de chloration de   l'éthylène   en présence des impuretés habituellement obtenues permet de séparer le produit utile sous forme de 1,2-dichloréthane. 



   Le procédé de l'invention a pour avantages qu'il ne nécessite : pas de valorisation des produits lourds, - pas de séparation de   l'éthylène   du mélange éthylène-éthane-méthane et hydrogène. 



   Un autre avantage réside dans le fait que l'on peut récupérer l'éthane et le recycler au four de craquage. Pour ce faire on utilise de préférence un procédé par absorption désorption dans un solvant organique chloré. Des exemples de tels solvants organiques chlorés sont le 1,   2-dichloréthane,   le tétrachlorure de carbone ou le chlorobenzène. Le 1,2-dichloréthane convient particulièrement bien dans le procédé de l'invention. 

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   Plus particulièrement l'invention se rapporte à un procédé dans lequel on chlore de l'éthylène en présence des impuretés obtenues lors du cracking de produits pétroliers en particulier, lors du cracking (ou vapocraquage) d'éthane. 



  Cette réaction est réalisée de manière remarquablement sélective dans une phase liquide (de préférence du 1,   2-dichloréthane   essentiellement) contenant un catalyseur dissous tel que   Fez13 ou   un autre acide de Lewis. On peut avantageusement combiner ce catalyseur à des catalyseurs tels que des chlorures alcalins. Un couple ayant donné de bons résultats est le couple   FeCI3   avec du   LiCI   comme système catalytique. 



   Dans ces conditions, on observe que l'on obtient essentiellement du 1,2dichloroéthane par chloration additive de l'éthylène et qu'il y a inhibition des réactions de substitution conduisant à la formation de 1, 1,2-trichloréthane ainsi qu'à des réactions de chloration du méthane, de l'éthane et de l'hydrogène. Ceci permettant d'éviter des séparations complexes de l'éthylène des produits co-produits lors d'un cracking de produits pétroliers et particulièrement d'un vapocracking produisant de l'éthane et de   l'éthylène.   



   Le procédé de chloration selon l'invention est de préférence conduit à des températures comprises entre 30 et   150  C.   De bons résultats ont été obtenus tant à une température inférieure au point d'ébullition à pression atmosphérique ou même à une pression supérieure à la pression atmosphérique. Ces dispositions permettent le cas échéant de récupérer utilement la chaleur de réaction. 



   En outre on opère le procédé de l'invention généralement dans un milieu liquide organique chloré. De préférence ce milieu liquide organique chloré, également appelé pied liquide, est du 1,   2-dichloréthane.   



   Le mélange contenant l'éthylène ainsi que le chlore (lui-même pur ou dilué) peuvent être introduits par tout dispositif connu dans le milieu réactionnel. 



  Il est par exemple connu (Brevet DE 4026882) que ces réactifs peuvent être introduits séparément. On peut tirer avantage d'une introduction séparée du mélange riche en oléfine pour accroître sa pression partielle et faciliter sa dissolution qui constitue souvent une étape limitante du procédé. 



   Le chlore est ajouté en quantité suffisante pour convertir l'essentiel de l'éthylène et sans nécessiter l'ajout d'un excès de chlore non converti. Le rapport   C12/C2H4   mis en oeuvre est de préférence compris entre 1,2 et 0,8 et de préférence entre 1, 05 et 0,95   mol/mol.   

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   Les produits chlorés obtenus contiennent essentiellement du 1,2dichloréthane ainsi que des sous-produits tels que le 1,1,   2-trichloroéthane   ou de petites quantités de produits de chloration de l'éthane ou du méthane. 



  L'épuration du 1,2-dichoréthane s'opère suivant des modes connus et permet en général d'exploiter la chaleur de la réaction de chloration. 



   Les produits non convertis (C2H6, CH4, CO et   H)   sont alors soumis à une séparation plus aisée que celle qui aurait été nécessaire pour séparer de l'éthylène pur au départ du mélange initial. Plutôt qu'une distillation qui requiert des pressions élevées et une source considérable de froid, on réalise de préférence la séparation de l'éthane à recycler au four de cracking grâce à un cycle d'absorption désorption dans un solvant adéquat. De tels solvants sont habituellement choisis parmi le 1, 2-dichloréthane, le chloroforme voire le chlore. 



   Le procédé peut comprendre en outre des étapes connues des procédés de cracking tels que : - l'élimination de l'eau du vapocraquage avec les lourds - l'élimination des contaminants soufrés - l'hydrogénation de dérivés indésirables tels que par exemple l'acétylène qui conduirait à une formation accrue de lourds à l'étape de chloration. 



   Les gaz non convertis à la chloration peuvent, après récupération de l'éthane, être valorisé comme combustible au four de cracking. Il en va de même pour la fraction lourde de cracking.



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 EMI1.1
 



  Chlorination of ethylene obtained for cracking of hydrocarbons
The present invention relates to a simplified cracking process for petroleum products which is coupled to chlorination of ethylene.



   To date, cracking of various heavy petroleum products is still carried out to form ethylene. This is separated from light by-products such as hydrogen, methane and ethane by costly and complex processes.



   In addition, several ways of direct upgrading of ethane to vinyl chloride are known in the literature: - oxychlorination of ethane in a fluid bed and upgrading of by-products - non-catalytic chlorination at high temperature - oxychlorination in a bath of molten salts.



  None have found industrial application so far.



   On the other hand, it is also known that steam cracking of ethane leads to a mixture rich in ethylene. Indeed, a selectivity close to 80% is observed for an ethane conversion of the order of 70%. The investment of such a type of cracking is unfortunately very heavy and therefore has not resulted in an industrially usable cracking process directly dedicated to the production of 1, 2-dichloroethane and vinyl chloride.



   The object of the present invention is to lighten the cost of a steam cracker by dispensing with complex and irrelevant separations for the manufacture of 1,2dichloroethane. To this end, a stage of chlorination of ethylene in the presence of the impurities usually obtained makes it possible to separate the useful product in the form of 1,2-dichloroethane.



   The process of the invention has the advantages that it does not require: no recovery of heavy products, - no separation of ethylene from the ethylene-ethane-methane and hydrogen mixture.



   Another advantage is that the ethane can be recovered and recycled in the cracking furnace. To do this, a absorption desorption process in a chlorinated organic solvent is preferably used. Examples of such chlorinated organic solvents are 1, 2-dichloroethane, carbon tetrachloride or chlorobenzene. 1,2-Dichloroethane is particularly suitable in the process of the invention.

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   More particularly, the invention relates to a process in which ethylene is chlorinated in the presence of the impurities obtained during the cracking of petroleum products in particular, during the cracking (or steam cracking) of ethane.



  This reaction is carried out remarkably selectively in a liquid phase (preferably 1,2-dichloroethane essentially) containing a dissolved catalyst such as Fez13 or another Lewis acid. This catalyst can advantageously be combined with catalysts such as alkali chlorides. A couple which has given good results is the FeCI3 couple with LiCI as catalytic system.



   Under these conditions, it is observed that essentially 1,2dichloroethane is obtained by additive chlorination of ethylene and that there is inhibition of substitution reactions leading to the formation of 1,2,2-trichloroethane as well as chlorination reactions of methane, ethane and hydrogen. This makes it possible to avoid complex separations of ethylene from the co-produced products during a cracking of petroleum products and in particular of a vapocracking producing ethane and ethylene.



   The chlorination process according to the invention is preferably carried out at temperatures between 30 and 150 C. Good results have been obtained both at a temperature below the boiling point at atmospheric pressure or even at a pressure above the pressure atmospheric. These provisions allow, if necessary, to usefully recover the heat of reaction.



   In addition, the process of the invention is generally carried out in a chlorinated organic liquid medium. Preferably, this chlorinated organic liquid medium, also called liquid base, is 1,2-dichloroethane.



   The mixture containing ethylene as well as chlorine (itself pure or diluted) can be introduced by any known device into the reaction medium.



  It is for example known (Patent DE 4026882) that these reagents can be introduced separately. One can take advantage of a separate introduction of the mixture rich in olefin to increase its partial pressure and facilitate its dissolution which often constitutes a limiting step of the process.



   Chlorine is added in sufficient quantity to convert most of the ethylene without requiring the addition of excess unconverted chlorine. The C12 / C2H4 ratio used is preferably between 1.2 and 0.8 and preferably between 1.05 and 0.95 mol / mol.

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   The chlorine products obtained essentially contain 1,2dichloroethane as well as by-products such as 1,1,2-trichloroethane or small amounts of chlorination products of ethane or methane.



  The purification of 1,2-dichorethane takes place according to known modes and generally makes it possible to exploit the heat of the chlorination reaction.



   The unconverted products (C2H6, CH4, CO and H) are then subjected to an easier separation than that which would have been necessary to separate pure ethylene from the initial mixture. Rather than a distillation which requires high pressures and a considerable source of cold, it is preferable to separate the ethane to be recycled in the cracking furnace by means of a desorption absorption cycle in a suitable solvent. Such solvents are usually chosen from 1, 2-dichloroethane, chloroform or even chlorine.



   The process can also comprise steps known from cracking processes such as: - the elimination of water from steam cracking with heavy products - the elimination of sulfur-containing contaminants - the hydrogenation of undesirable derivatives such as for example acetylene which would lead to increased formation of heavy in the chlorination stage.



   The gases not converted to chlorination can, after recovery of the ethane, be valued as fuel in the cracking furnace. The same goes for the heavy cracking fraction.


    

Claims (4)

REVENDICATIONS 1 - Procédé de cracking de produits pétroliers couplé à une production de 1, 2-dichloréthane caractérisé en ce que l'éthylène obtenu lors de ce procédé est séparé des autres produits par une étape de chloration.  CLAIMS 1 - Process for cracking petroleum products coupled with the production of 1, 2-dichloroethane, characterized in that the ethylene obtained during this process is separated from the other products by a chlorination step. 2 - Procédé selon la revendication 1 caractérisé en ce que cette chloration s'opère en milieu liquide en présence d'un catalyseur tel que FeC13 ou d'autres acides de Lewis éventuellement combinés à des co-catalyseurs tels que des chlorures alcalins.    2 - Process according to claim 1 characterized in that this chlorination takes place in a liquid medium in the presence of a catalyst such as FeC13 or other Lewis acids optionally combined with co-catalysts such as alkali chlorides. 3-Procédé selon la revendication 1 caractérisé en ce que l'on opère la chloration à une température comprise entre 30 et 150 C.  3-A method according to claim 1 characterized in that one operates the chlorination at a temperature between 30 and 150 C. 4 - Procédé selon l'une quelconque des revendications 1 et 2 caractérisé en ce que l'étape de chloration est effectuée dans un pied liquide de 1, 2-dichloréthane    4 - Method according to any one of claims 1 and 2 characterized in that the chlorination step is carried out in a liquid base of 1, 2-dichloroethane
BE9800788A 1998-10-30 1998-10-30 Chlorination ethylene cracking hydrocarbons obtained. BE1013616A3 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE9800788A BE1013616A3 (en) 1998-10-30 1998-10-30 Chlorination ethylene cracking hydrocarbons obtained.
AU11554/00A AU1155400A (en) 1998-10-30 1999-10-21 Ethylene chlorination obtained by hydrocarbon cracking
PCT/EP1999/008145 WO2000026164A1 (en) 1998-10-30 1999-10-21 Ethylene chlorination obtained by hydrocarbon cracking
ARP990105384 AR020965A1 (en) 1998-10-30 1999-10-25 PROCEDURE FOR HYDROCARBON CRACHING COUPLED TO A PRODUCTION OF 1,2-DICHLOROETHANE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE9800788A BE1013616A3 (en) 1998-10-30 1998-10-30 Chlorination ethylene cracking hydrocarbons obtained.

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BE1013616A3 true BE1013616A3 (en) 2002-05-07

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Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10159615A1 (en) 2001-12-05 2003-06-12 Basf Ag Process for the preparation of 1,2-dichloroethane
FR2880019B1 (en) * 2004-12-23 2007-03-09 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
US7732649B2 (en) * 2004-12-23 2010-06-08 Solvay (Societe Anonyme) Process for the manufacturing of 1,2-dichloroethane
MX2007007778A (en) * 2004-12-23 2007-08-21 Solvay Process for the manufacture of 1,2-dichloroethane.
EA015748B1 (en) * 2004-12-23 2011-12-30 Солвей (Сосьете Аноним) Process for the manufacture of 1,2-dichloroethane
JP2008525380A (en) * 2004-12-23 2008-07-17 ソルヴェイ(ソシエテ アノニム) Process for producing 1,2-dichloroethane
FR2883870B1 (en) * 2005-04-01 2007-05-25 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
FR2883871B1 (en) * 2005-04-01 2008-09-05 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
FR2902784B1 (en) 2006-06-23 2008-09-05 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
FR2902787B1 (en) * 2006-06-26 2008-09-05 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
FR2902785B1 (en) * 2006-06-26 2008-08-08 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
FR2902786B1 (en) * 2006-06-26 2008-08-29 Solvay PROCESS FOR PRODUCING 1,2-DICHLOROETHANE
EP2130815A1 (en) 2008-06-03 2009-12-09 SOLVAY (Société Anonyme) Process for the manufacture of at least one ethylene derivative compound
EP2096095A1 (en) 2008-02-28 2009-09-02 SOLVAY (Société Anonyme) Process for the manufacture of at least one ethylene derivative compound
EP2130810A1 (en) 2008-06-03 2009-12-09 SOLVAY (Société Anonyme) Process for the manufacture of 1,2-dichloroethane and of at least one ethylene derivative compound different from 1,2-dichloroethane
EP2130814A1 (en) 2008-06-03 2009-12-09 SOLVAY (Société Anonyme) Process for the manufacture of at least one ethylene derivative compound
EP2130813A1 (en) 2008-06-03 2009-12-09 SOLVAY (Société Anonyme) Process for the manufacture of at least one ethylene derivative compound
WO2011067237A2 (en) 2009-12-03 2011-06-09 Solvay Sa Process for the manufacture of at least one ethylene derivative compound
PE20130169A1 (en) 2009-12-03 2013-03-09 Solvay PROCESS FOR THE MANUFACTURE OF AT LEAST ONE COMPOUND DERIVED FROM ETHYLENE
EP2594547A1 (en) 2011-11-17 2013-05-22 Solvay Sa Process for the manufacture of at least one ethylene derivative compound from bioethanol

Citations (4)

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Publication number Priority date Publication date Assignee Title
GB301009A (en) * 1927-06-18 1928-11-19 Ig Farbenindustrie Ag Improvements in the manufacture and production of halogenated hydrocarbon products, and analogous substances
US2043932A (en) * 1932-07-02 1936-06-09 Shell Dev Production of halogenated organic compounds
GB1096594A (en) * 1964-04-01 1967-12-29 Kureha Chemical Ind Co Ltd A process for manufacturing dichloroethane
NL6901398A (en) * 1969-01-29 1969-11-25

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
SU433116A1 (en) * 1971-12-13 1974-06-25 METHOD FOR ETHANE ESCAPE FROM ETHANE-RTHYLENE UFRACTION

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB301009A (en) * 1927-06-18 1928-11-19 Ig Farbenindustrie Ag Improvements in the manufacture and production of halogenated hydrocarbon products, and analogous substances
US2043932A (en) * 1932-07-02 1936-06-09 Shell Dev Production of halogenated organic compounds
GB1096594A (en) * 1964-04-01 1967-12-29 Kureha Chemical Ind Co Ltd A process for manufacturing dichloroethane
NL6901398A (en) * 1969-01-29 1969-11-25

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WO2000026164A1 (en) 2000-05-11
AR020965A1 (en) 2002-06-05
AU1155400A (en) 2000-05-22

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