GB2095245A - Chlorination of alkanes - Google Patents

Chlorination of alkanes Download PDF

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Publication number
GB2095245A
GB2095245A GB8207073A GB8207073A GB2095245A GB 2095245 A GB2095245 A GB 2095245A GB 8207073 A GB8207073 A GB 8207073A GB 8207073 A GB8207073 A GB 8207073A GB 2095245 A GB2095245 A GB 2095245A
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Priority to GB8207073A priority patent/GB2095245A/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/093Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/093Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/15Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
    • C07C17/152Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons
    • C07C17/154Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons of saturated hydrocarbons

Abstract

A process for the selective production of chlorinated hydrocarbons comprises contacting an alkane having 2 or more carbon atoms, chlorine and optionally a source of molecular oxygen in the vapour phase at a temperature above 275 DEG C in the presence of a catalyst comprising a zeolite. It is useful for the production of vinyl chloride from ethane.

Description

SPECIFICATION Production of chlorinated hydrocarbons The present invention relates to a process for the selective production of chlorinated hydrocarbons by the chlorination and/or oxychlorination of alkanes.

British Patent 1,172,002 describes a process for the chlorination of hydrocarbons which comprises contacting a mixture of hydrocarbon and chlorine with a zeolite catalyst at a temperature of 500C to 2500C temperatures of from 650C to 1 500C being most preferred. Although this patent envisages the use of a wide variety of both hydrocarbon starting materials and zeolites (including metal exchanged zeolites), the only exemplification relates to the chlorination of ethane and of propane. Each of the aforesaid alkane starting materials give rise to a wide spectrum of chlorinated products (including about 48% of unknown product from propane and 67% unknown product from ethane) and there is no marked selectivity to any particular chlorinated product.

We have now found a catalytic process which is effective for the selective production of chlorinated hydrocarbons from alkanes.

According to the present invention we provide a process for the selective production of chlorinated hydrocarbons which comprises contacting an alkane having 2 or more carbon atoms, chlorine and optionally a source of molecular oxygen in the vapour phase at a temperature about 2 75 OC in the presence of a catalyst comprising a zeolite.

The process of the invention is especially applicable to the selective production of vinyl chloride from ethane, chlorine and oxygen.

A wide range of zeolites may be employed as catalysts, providing they are stable under chlorination and oxychlorination conditions. Suitable zeolites include X-type zeolites (e.g. as described in UK Patent 1,450,411; US Patent 2,882,244), Y-type zeolites (e.g. as described in US Patent 3,130,007), and zeolite Nu-2 (as described in our copending UK Application No 8040782).

The zeolite catalysts are preferably partially or wholly exchanged with metal cations, for example one or more of copper, silver, magnesium, zinc, manganese, cobalt, nickel and lanthanide ions. The preferred catalysts comprise zeolites which are partially or wholly exchanged with silver and/or manganese cations, more preferably silver and manganese cations.

It will be appreciated that during chlorination the aforesaid metal cations, which may be present as metals or metal compounds e.g. oxides, may be partially or wholly converted under the reaction conditions to chloride during the course of the reaction.

The process of the invention is applicable to a range of alkane starting materials having 2 or more carbon atoms, more particularly alkanes having 2 to 4 carbon atoms, for example ethane.

The catalysts may be employed in fixed, moving or fluidised beds of the appropriate size.

The reaction temperature is suitably in the range 275-5000C, and preferably between 300 and 5000C, for example 3500C to 4500 C.

The reaction is normally carried ou under atmospheric or superatmospheric pressure, e.g. at a pressure in the range 1 to 100 bars.

The process is preferably carried out in the presence of a source of molecular oxygen, e.g. oxygen itself or oxygen enriched air since this minimises coking problems and aids zeolite stability. It is especially preferable to use oxygen in order to obtain vinyl chloride selectively from ethane. Useful chlorination will however, take place in the absence of oxygen. An inert diluent such as nitrogen may also be present.

The molar ratios of alkane to chlorine are suitably in the range 10 to 1 to 1 to 10, for example 1 to 1.

The molar ratios of alkane to oxygen (when present) are suitably in the range 100 to 1 to 1 to 1, for example 2 to 1.

The products of the reaction may be isolated and used as such or, if desired, may be recycled wholly or partially to the chlorination reaction in order to increase the yield of specific chlorinated products.

The invention is illustrated by the following Examples.

EXAMPLE 1 A Y type zeolite of formula Na2O.A1203.5. 1 SiO2 was saturated with 10 ml of 50% Mn(NO3)2.6 H20 solution for 16 hours and then filtered and washed thoroughly with water. The white solid was then treated with 10 ml of 80% AgNO3 solution for 1 6 hours, filtered, washed, dried at 1 200C for 1 6 hours and then calcined at 4500C for 1 6 hours. The resulting catalyst was shown by analysis to contain 18.9% silver and 2.4% manganese. After grinding to 20-30 mesh size the catalyst was packed as a 10 cm bed in a 6.3 mm O.D. microreactor tube surrounded by a resistively heated furnace and connected to an on-line GLC system.After treatment in flowing chlorine at 4000C, the catalyst was tested with ethane over a range of gas feed compositions and temperatures. The results are shown in Table 1.

A comparative example was carried out at 4000C in which the silver/manganese/zeolite catlayst was replaced by an equal quantity of pumice ground to the same mesh size. The results are shown in Table 2. A comparison of these results with those shown in Table 1 illustrates the greater selectivity to vinyl chloride when using the silver/manganese/zeolite catalyst.

EXAMPLE 2 A catalyst was prepared as in Example 1 but from offretite zeolite, analysis showing the resultant material to contain 12.1% silver and 0.6% manganese. The following results were obtained with a feed mixture of chlorine, ethane and air at 365"C.

EXAMPLE 3 The sodium form of X type zeolite (Molecular sieve 1 3X) was exchanged with silver and manganese by contacting for 24 hours with an equimolar concentrated solution of manganous and silver nitrates. After filtration, the zeolite was washed and dried at 4500C overnight. The resultant powder was found to contain 23.9 weight % silver and 3.4 weight % manganese. The catalyst was tested as in Example 1 to give the results presented in Table 4.

TABLE 1 <img class="EMIRef" id="027056878-00030001" />

Slectivity <SEP> % <tb> Gas <SEP> feed <SEP> (ml/min) <tb> Reaction <SEP> Conversion <SEP> Trans <SEP> Cis <tb> Temp. <SEP> C <SEP> C2H6 <SEP> Air <SEP> Cl2 <SEP> (C2H6 <SEP> mol <SEP> %) <SEP> VC <SEP> C2H4 <SEP> EtCl <SEP> Dichlor <SEP> Dichlor <SEP> EDC <SEP> ss-Tri <SEP> CO2 <tb> 375 <SEP> 2 <SEP> 10 <SEP> 2 <SEP> 53.9 <SEP> 43.3 <SEP> 21.1 <SEP> 0.9 <SEP> 5.1 <SEP> 11.5 <SEP> 4.3 <SEP> 3.0 <SEP> 9.1 <tb> 400 <SEP> 2 <SEP> 20 <SEP> 2 <SEP> 40.8 <SEP> 35.8 <SEP> 18.0 <SEP> 0.6 <SEP> 5.4 <SEP> 11.3 <SEP> 17.8 <SEP> 1.7 <SEP> 7.3 <tb> TABLE 2 <img class="EMIRef" id="027056878-00030002" />

Selectivity <SEP> % <SEP> Gas <SEP> feed <SEP> (ml/min) <tb> Reaction <SEP> Conversion <SEP> Trans <SEP> Cis <tb> Temp. <SEP> C <SEP> C2H6 <SEP> Air <SEP> Cl2 <SEP> (C2H6 <SEP> mol <SEP> %) <SEP> VC <SEP> C2H4 <SEP> EtCl <SEP> Dichlor <SEP> Dichlor <SEP> EDC <SEP> ss-TRi <SEP> Co2 <tb> 350 <SEP> 5 <SEP> 25 <SEP> 5 <SEP> 18.8 <SEP> - <SEP> 0.6 <SEP> 90.1 <SEP> - <SEP> - <SEP> 3.6 <SEP> - <SEP> 0.6 <tb> 420 <SEP> 5 <SEP> 25 <SEP> 5 <SEP> 14.4 <SEP> 0.3 <SEP> 5.8 <SEP> 87.9 <SEP> - <SEP> - <SEP> 4.0 <SEP> 0.6 <SEP> 0.4 <tb> Notes on Table 1 and 2 VC = vinyl chloride EDC = ethylene dichloride Trans dichlor = trans dichloroethylene ss-tri = ss-trichloroethane Cis dichlor = cis dichlorethylene TABLE 3 <img class="EMIRef" id="027056878-00040001" />

Selectivity <SEP> % <tb> Gas <SEP> feed <SEP> (ml/min) <tb> Conversion <SEP> Trans <SEP> Cis <tb> C2H6 <SEP> Air <SEP> Cl2 <SEP> (C2H6 <SEP> mol <SEP> %) <SEP> VC <SEP> C2H4 <SEP> EtCl <SEP> Dichlor <SEP> Dichlor <SEP> EDC <SEP> ss-tri <SEP> CO2 <tb> 2 <SEP> 10 <SEP> 2 <SEP> 67.6 <SEP> 46.2 <SEP> 16.9 <SEP> 0.6 <SEP> 5.2 <SEP> 13.6 <SEP> 6.1 <SEP> 1.6 <SEP> 7.6 <tb> 2 <SEP> 10 <SEP> 1 <SEP> 47.7 <SEP> 45.6 <SEP> 22.7 <SEP> 0.8 <SEP> 3.9 <SEP> 10.3 <SEP> 3.5 <SEP> 2.3 <SEP> 8.6 <tb> Notes on Table 3 VC = vinyl chloride Trans dichlor = trans dichloroethylene EDC = ethylene dichloride Cis dichlor = cis dichlorethylene ss-tri = ss-trichloroethane TABLE 4 <img class="EMIRef" id="027056878-00040002" />

Gas <SEP> feed <SEP> (ml/min) <tb> Conversion <tb> Trans <SEP> Cis <tb> C2H6 <SEP> Air <SEP> Cl2 <SEP> VC <SEP> C2H4 <SEP> EtCl <SEP> Dichlor <SEP> dichlor <SEP> EDC <SEP> TRI <SEP> CO2 <tb> 2 <SEP> 10 <SEP> 3 <SEP> 81 <SEP> 10 <SEP> 31 <SEP> 44 <SEP> - <SEP> - <SEP> 2.6 <SEP> - <SEP> 2 <tb> 2 <SEP> 10 <SEP> 4 <SEP> 99 <SEP> 34 <SEP> 28 <SEP> 18 <SEP> - <SEP> - <SEP> 7 <SEP> 0.5 <SEP> 2 <tb> 2 <SEP> 10 <SEP> 6 <SEP> 42 <SEP> 25 <SEP> 1 <SEP> 3 <SEP> 10 <SEP> 8 <SEP> 2.6 <SEP> 2 <tb> 2 <SEP> 10 <SEP> 8 <SEP> 100 <SEP> 11 <SEP> 0.3 <SEP> - <SEP> 18 <SEP> 32 <SEP> 4 <SEP> 21 <SEP> 10 <tb> TRI = Trichloroethylene

Claims (7)

1. A process for the selective production of chlorinated hydrocarbons which comprises contacting an alkane having 2 or more carbon atoms, chlorine and optionally a source of molecular oxygen in the vapour phase at a temperature above 2750C in the presence of a catalyst comprising a zeolite.
2. A process according to claim 1 wherein ethane, chlorine and oxygen are contacted in the presence of the catalyst to form vinyl chloride.
3. A process according to claim 1 or claim 2 wherein the catalyst comprises a zeolite that has been partially or wholly exchanged with silver and/or manganese cations.
4. A process according to any one of the preceding claims wherein the reaction temperature is in the range 3000 to 5000 C.
5. A process according to any one of the preceding claims wherein the molar ratio of alkane to chlorine is in the range 10:1 to 1:10.
6. A process according to any one of the preceding claims wherein the molar ratio of alkane to oxygen is in the range 100:1 to 1:1.
7. A process according to claim 1 substantially as hereinbefore described with reference to the foregoing Examples.
GB8207073A 1981-03-19 1982-03-11 Chlorination of alkanes Withdrawn GB2095245A (en)

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106356A1 (en) * 1982-10-18 1984-04-25 The Dow Chemical Company Catalytic process for producing saturated dihalohydrocarbons
US5663472A (en) * 1985-07-22 1997-09-02 University Of Southern California Production of alkenes
US5705728A (en) * 1990-12-06 1998-01-06 Occidental Chemical Corporation Process for the production of ethylene and mixture containing ethylene
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US7880041B2 (en) 2004-04-16 2011-02-01 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US8008535B2 (en) 2004-04-16 2011-08-30 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US8053616B2 (en) 2006-02-03 2011-11-08 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106356A1 (en) * 1982-10-18 1984-04-25 The Dow Chemical Company Catalytic process for producing saturated dihalohydrocarbons
US5663472A (en) * 1985-07-22 1997-09-02 University Of Southern California Production of alkenes
US5705728A (en) * 1990-12-06 1998-01-06 Occidental Chemical Corporation Process for the production of ethylene and mixture containing ethylene
US8415512B2 (en) 2001-06-20 2013-04-09 Grt, Inc. Hydrocarbon conversion process improvements
US7838708B2 (en) 2001-06-20 2010-11-23 Grt, Inc. Hydrocarbon conversion process improvements
US7964764B2 (en) 2003-07-15 2011-06-21 Grt, Inc. Hydrocarbon synthesis
US7847139B2 (en) 2003-07-15 2010-12-07 Grt, Inc. Hydrocarbon synthesis
US8173851B2 (en) 2004-04-16 2012-05-08 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US7880041B2 (en) 2004-04-16 2011-02-01 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US8642822B2 (en) 2004-04-16 2014-02-04 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor
US7674941B2 (en) 2004-04-16 2010-03-09 Marathon Gtf Technology, Ltd. Processes for converting gaseous alkanes to liquid hydrocarbons
US8008535B2 (en) 2004-04-16 2011-08-30 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to olefins and liquid hydrocarbons
US8232441B2 (en) 2004-04-16 2012-07-31 Marathon Gtf Technology, Ltd. Process for converting gaseous alkanes to liquid hydrocarbons
US9206093B2 (en) 2004-04-16 2015-12-08 Gtc Technology Us, Llc Process for converting gaseous alkanes to liquid hydrocarbons
US8053616B2 (en) 2006-02-03 2011-11-08 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US7883568B2 (en) 2006-02-03 2011-02-08 Grt, Inc. Separation of light gases from halogens
US8921625B2 (en) 2007-02-05 2014-12-30 Reaction35, LLC Continuous process for converting natural gas to liquid hydrocarbons
US7998438B2 (en) 2007-05-24 2011-08-16 Grt, Inc. Zone reactor incorporating reversible hydrogen halide capture and release
US8282810B2 (en) 2008-06-13 2012-10-09 Marathon Gtf Technology, Ltd. Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery
US8415517B2 (en) 2008-07-18 2013-04-09 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8273929B2 (en) 2008-07-18 2012-09-25 Grt, Inc. Continuous process for converting natural gas to liquid hydrocarbons
US8367884B2 (en) 2010-03-02 2013-02-05 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US9133078B2 (en) 2010-03-02 2015-09-15 Gtc Technology Us, Llc Processes and systems for the staged synthesis of alkyl bromides
US8198495B2 (en) 2010-03-02 2012-06-12 Marathon Gtf Technology, Ltd. Processes and systems for the staged synthesis of alkyl bromides
US8815050B2 (en) 2011-03-22 2014-08-26 Marathon Gtf Technology, Ltd. Processes and systems for drying liquid bromine
US8436220B2 (en) 2011-06-10 2013-05-07 Marathon Gtf Technology, Ltd. Processes and systems for demethanization of brominated hydrocarbons
US8829256B2 (en) 2011-06-30 2014-09-09 Gtc Technology Us, Llc Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons
US8802908B2 (en) 2011-10-21 2014-08-12 Marathon Gtf Technology, Ltd. Processes and systems for separate, parallel methane and higher alkanes' bromination
US9193641B2 (en) 2011-12-16 2015-11-24 Gtc Technology Us, Llc Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems

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