US3876714A - Chloroprene removal from pyrolyzed 1,2-dichlorethane - Google Patents

Chloroprene removal from pyrolyzed 1,2-dichlorethane Download PDF

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US3876714A
US3876714A US113985A US11398571A US3876714A US 3876714 A US3876714 A US 3876714A US 113985 A US113985 A US 113985A US 11398571 A US11398571 A US 11398571A US 3876714 A US3876714 A US 3876714A
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dichlorethane
liquid
phase
vinyl chloride
treating
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Guillaume Coppens
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Solvay SA
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Solvay SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives

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  • ABSTRACT In a process for treating the raw gaseous products of [30] Foreign Application Priority Data the pyrolysis of 1,2-dichlorethane to form vinyl chlo- Feb. 20. I970 Belgium x5450 3 Procedure for 6limimiliflg Chloroprene involving the steps of cooling the raw gaseous product com- 521 u.s. Cl 260/656 R ing from the Py y rsarrtion under Pressure above 51 lm. Cl.
  • the present invention relates to a process for treating the raw gaseous product coming from the pyrolysis of l,2-dichlorethane into vinyl chloride.
  • the 1,2dichlorethane which still contains certain impurities, such as chloroprene, is then purified before being recycled to the pyrolysis.
  • the purification is effected by distillation in two successive columns in such a manner as to eliminate fractions having a boiling point below 83C and fractions having a boiling point greater than 83C.
  • the pressure of the chloroprene then proves to be very troublesome.
  • the concentration of chloroprene at the top of the column is increased, and this chloroprene can polymerize after its concentration reaches 5 percent by weight.
  • the polymer formed provokes the blocking of conduits and condensers which necessitates frequent stoppages and cleanings.
  • a further object of the invention is to simplify the purification of l,2-dichlorethane.
  • a further object of the invention is to provide an improved method for removing chloroprene from the 1,2- dichlorethane which was not converted during the pyrolysis operation.
  • the present invention is based essentially on applicants discovery of a procedure for eliminating the chloroprene accompanying the nonconverted l,2- dichlorethane leaving the pyrolysis region without introducing any supplemental steps, such as have been heretofore proposed.
  • the invention is thus directed to a process for the treatment of the raw gaseous product derived from the pyrolysis of l,2-dichlorethane into vinyl chloride, which process includes the following steps: cooling the gaseous product (issuing from the pyrolysis) under a pressure greater than atmospheric pressure in order to obtain a gaseous phase and a liquid phase, treating this liquid phase with chlorine in an amount of 0.0l-5 percent by weight with respect to the l,2-dichlorethane which was not converted during the pyrolysis, and sep arating the mixture obtained into its various constituents.
  • the present invention is directed to a process for the treatment of the raw gaseous product coming from the pyrolysis of the l,2-dichlorethane and containing principally vinyl chloride, in a mixture with hydrogen chloride, unconverted l,2-dichlorethane, and small quantities of chloroprene, the process being for the purpose of obtaining pure vinyl chloride and including the following steps: cooling of the product coming from the pyrolysis of the l,2-dichlorethane to a temperature between 0 and 300 C by quenching with liquid l,2-dichlorethane at a pressure greater than atmospheric pressure and generally between I and 30 kg/cm condensing the cooling mixture obtained in the cooling step at a pressure generally between I and 30 ltg/cm and a temperature between 0 and C so as to obtain a liquid phase principally containing 1.2- dichlorethane, vinyl chloride, a small quantity of hydrogen chloride and small quantities of chloroprene, and a gaseous
  • the gaseous product coming from the pyrolysis of the l,2-dichlorethane contains also a small amount of butadiene
  • the latter is divided during the condensation between the gaseous phase and the liquid phase obtained and it is then advantageous to add a supple mental step of washing the gaseous phase obtained during the condensing step with a part of the liquid mixture obtained during the treating step in a manner to obtain a gaseous phase which is practically free of butadiene, the washing liquid being then returned to the treating step where it is treated with chlorine.
  • the raw product coming from the pyrolysis is condensed in two steps, according to the process described in Belgian Pat. No. 720,894 the gaseous product coming from the pyrolysis is first of all cooled, by being brought into contact with liquid l,2- dichlorethane, under a pressure of 1-30 kg/cm and preferably 4-20 kg/cm to a temperature of between and 300C and preferably l00200C; and the gase ous mixture thus obtained is condensed, under a pressure of between l30 kg/cm and preferably 4-20 kg/cm to a temperature of between 0 and 100C and preferably between 20 and 80 in order to obtain a gaseous phase and a liquid phase.
  • the liquid phase obtained mainly contains 1,2- dichlorethane, vinyl chloride, hydrogen chloride and impurities, such as chloroprene and butadiene.
  • the gaseous phase contains hydrogen chloride, vinyl chloride, and a fraction of the light impurities present in the liquid phase, such as butadienev Chlorine is introduced into the liquid phase thus ob tained and this liquid phase remains in a reservoir with out it being necessary to add thereto any reactant whatsoever.
  • a chlorination catalyst such as ferric chloride or any other known chlorination catalyst, as disclosed in the text by P. H. Groggins, Unit Processes in Organic Synthesis, McGraw-Hill, 1958, page 265.
  • the quantities of chlorine utilized are between 0.01 and 5 percent by weight with respect to the 1,2- dichlorethane which was not converted during the pyrolysis and the quantity of chlorine is preferably between 0.02 and 1 percent by weight with respect to that l,2 dichlorethane.
  • one part of the liquid phase treated with chlorine can be utilized to wash in a countercurrent flow the gaseous phase obtained during the condensation stage in order to eliminate the residual impurities.
  • the liquid product coming from the washing column is then treated again with chlorine, preferably in the same reservoir as that in which the liquid phase coming from the condensation step is treated.
  • the constituents of the liquid phase treated with chlorine and including essentially hydrogen chloride, vinyl chloride and unconverted 1,2-dichl0rethane, can then be separated in any manner known per se. It is possible, for example, to distill the hydrogen chloride and the vinyl chloride in two successive distillation columns.
  • the hydrogen chloride can be distilled at a temperature of between 80 and +C and at a pressure of between 1 and 30 kglcm
  • the vinyl chloride can be distilled at a temperature of between 14and +60C and a pressure of between 1 and 10 kg/cm".
  • the dichlorethane obtained is then purified in its turn by distillation in two successive columns permitting elimination of the fractions having a boiling point below 83C and the fractions having a boiling point above 83C.
  • the distillation column which permits the elimination of fractions whose boiling point at atmospheric pressure is below 83C operates at a temperature of between 40 and 120C and at a pressure of be tween 0.5 and 3 kg/cm".
  • the distillation column which permits the elimination of fractions whose boiling point at atmospheric pressure is greater than 83C operates at a temperature between 60 and 130C and at a pressure of between 0.5 and 3 kg/cm
  • FIG. 1 is a block diagram of a first embodiment of apparatus for carrying out the method according to the invention.
  • FIG. 2 is a view similar to that of FIG. 1 showing another embodiment of apparatus for carrying out the method according to the invention.
  • a pyrolysis oven 1 is maintained at a temperature of 500C and under a pressure of the order of l l kg/cm
  • the oven which may be furnished with a packing of inert material having a silica base, is supplied with pure 1,2- dichlorethane.
  • the product from this oven which com prises, mainly, e.g., 5 to 45 percent by volume of vinyl chloride, 5 to 45 percent by volume of hydrogen chloride, 10 to percent by volume of nonconverted 1,2- dichlorethane, up to 3 percent by volume of chloroprene and up to 0.2 percent by volume of butadiene, passes to a condenser 2 where it is quenched to bring its temperature to around 150C, and then cooled to about 40C, to obtain a liquid and a gaseous phase.
  • a condenser 2 where it is quenched to bring its temperature to around 150C, and then cooled to about 40C, to obtain a liquid and a gaseous phase.
  • the gaseous phase which is withdrawn via conduit 3 contains from 5 to 45 percent by volume of vinyl chloride, from 55 to percent by volume of hydrogen chloride and from 0 to 0.2 percent by volume of butadiene and is fed into column 4. There is no change in butadiene content in conduit 3 and butadiene goes unchanged into the final vinyl chloride.
  • the liquid phase flows via conduit 5 from the bottom of condenser 2 under a pressure of the order of 10 kg/cm and passes into a storage device 7.
  • This liquid phase almost entirely comprises 1,2-dichlorethane, vinyl chloride, a small amount, e.g. from 1 to 20 mole percent, of hydrogen chloride, 0 to 0.2 mole percent of butadiene, up to 4 mole percent of chloroprene, and.
  • the storage device 7 may be a suitable vessel provided with an inlet and outlet so as to avoid back-mixing of the liquid; this vessel may be made, for example, of steel, alloys, cladded steel or enamelled steel. Via the conduit 6 there is simultaneously introduced into the storage device 7 about 0.015 percent by weight of chlorine with respect to the 1,2-dichlorethane.
  • the liquid phase which remains in the storage device 7 contains essentially 1,2- dichlorethane, vinyl chloride and a little hydrogen chloride.
  • the butadiene present in the product entering unit 2 is divided equally between conduits 3 and 5 while the chloroprene is mainly collected in conduit 5.
  • the liquid phase in conduit 8 which phase is maintained in the presence of chlorine, is virtually free from chloroprene and butadiene; it contains l,2-dichlorethane, 20-80 mole percent; hydrogen chloride, 1-20 mole percent; vinyl chloride, l-50 mole percent.
  • Hydrogen chloride is removed from the top of column 4 at around -30C under a pressure of 10 kg/cm while a liquid phase, removed via line 9 from a heater maintained at 90C, is directed to column 10.
  • Vinyl chloride is separated in column 10 at 40C under a pressure of kg/cm and carried off via the head of column 10, while the base of the column, maintained at l50C, contains virtually only 1,2-dichlorethane and heavy products consisting mainly of chlorinated C products.
  • the components at the base of the column are conveyed by line 11 into the column 12 where the light impurities having a boiling point below 83C are separated, in the head of the column, and removed via line 13, while the 1,2-dichlorethane containing only heavy products is conveyed via line 14 into column 15.
  • column 15 the pure l,2-dichlorethane in a condition to be recycled is removed from the head of that column and conveyed via line 17, while at the base of the column the heavy products are collected and carried off via line 16.
  • the columns 4, l0, l2 and I5 are well known to those skilled in the art and may be provided with any kind of trays or packing. Columns and trays for 4, l0, l2 and IS may be made ofa suitable material, such as steel, stainless steel and also Ni-alloys, e.g. inconel, hastelloy and monel.
  • FIG. 2 When the initial butadiene concentration, at the output of the pyrolysis, is greater than ten parts per million with respect to the vinyl chloride and when it is desired to obtain a vinyl chloride which is free of butadiene, it is advantageous to utilize an apparatus of the type illustrated in FIG. 2.
  • This apparatus is identical with that of FIG. I with the exception that it also includes a countercurrent washing column 3' connected to receive the material passing through line 3 and to wash this material in a countercurrent flow with a liquid phase taken from the conduit 8.
  • the liquid passing through column 3' is returned to the input of storage device 7 where it is again brought into contact with chlorine.
  • a reduction is effected in the quantity of butadiene present in the gaseous phase conveyed via line 3" to the column 4.
  • FIGS. 1 and 2 represent only examples of apparatus which can be employed for carrying out the process of the present invention and that other forms of apparatus can be employed.
  • means could be provided for subjecting the gaseous phase leaving the head of the washing column, or tower, 3' to another countercurrent washing by another liquid fraction taken from conduit 8, etc.
  • This example of a process according to the invention is based on the actual operation of an apparatus having the form illustrated in FIG. 1.
  • THe pyrolysis oven 1 is maintained at around 500C under a pressure of the order of l 1 kg/cm This oven is supplied with pure l,2-dichlorethane.
  • the products exiting from this oven and which contain essentially vinyl chloride, hydrogen chloride and nonconverted l,2-dichlorethane (50 percent mole) pass to condenser 2 where they undergo first of all a quenching which brings their, temperature to about l50C.
  • the gaseous mixture thus obtained is cooled to 40C under a pressure of the order of 10 kg/cm in order to produce a liquid phase and a gaseous phase.
  • the gaseous phase, which exits via line 3 and which contains vinyl chloride, hydrogen chloride and a small quantity of butadiene, is conveyed to column 4.
  • the liquid phase removed via line 5 from the bottom of condenser 2 has the following composition:
  • Components 7 ( by weight vinyl chloride 29.4 I ,2-dichlorethane 60.] l l -dichlorethane 0.02 HCI l0.l chloroprene 0.0l trichlorethylene 0.27 butadiene 0.00003 1 ,2.4-trichlorobutane 0.024 I ,2-dichlorobutane 0.0 l 8 l l ,Z-trichlorethane 0.006 remaining components 0162 It is noted from a comparison of the above tables that the concentrations of chloroprene and butadiene in the product leaving storage device 7 are greatly reduced.
  • vinyl chloride is separated at 40C and under a pressure of 5 kg/cm while the base of the column, maintained at C, supplies essentially l,2-dichlorethane and chlorinated C products, the material provided by the base of the column being delivered to line 11.
  • the boiler of column which is at a z p of 100C furnishes essen dichlorethane, vinyl chloride, hydrogen chloride, chlob t d' th tlally chlorinated C products. Also as the result of the iizi z f j f gszg ig ggg fi mz g ggf z ig g introduction of chlorine into storage device 7, practip g the raw gaseous product to form a liquid mixture, the cally no tarry residues are found to appear in the boiler of column 15.
  • the wash liquid gaseous product commg from pyrolifsls under a from column 3' is either separately treated with chlopressure ,than atmosphel'lc to Obtam i F 'I rine in storage device 7 or is treated therein in admixphase i a Phase; "eating the resumng hquld ture with fresh condensate from condenser 2. There is phase chlofme "K amount of between?
  • a process as defined in claim 2 wherein said step id fin Applicable methods of rapid coolmg are of cooling is carried out as to'obtain a gaseous phase well known to those iramlllflr with lhls T p 60 and a liquid phase at a temperature of between 0 and ferred manner is to mix the hot gases emeggmg fro m C d comprising the further step of washing the the Pyrolysis Oven at a lemp'iraml'e of 400 to C gaseous phase produced by said cooling step with part With a liquid having a temperature of f 300 C f of the liquid mixture produced by said treating step, consisting mainly of l,2diChl0r t l'la In y device and subsequently returning the liquid employed in said which brings in close contact liquid and gas such as a 65 washing step to be subjected anew to said treating step.
  • a process for treating the raw gaseous product of the pyrolysis of l,2-dichlorethane, which product contains principally vinyl chloride in mixture with hydrogen chloride, non-converted l,2-dichlorethane and small quantities of chloroprene comprising the steps of:
  • step (d) separating the liquid mixture obtained by step (d) by distillation to obtain polymerizable vinyl chloride; and f. separating the gaseous phase obtained by said condensing step, by distillation, for obtaining polymerizable vinyl chloride.
  • each of the liquid phase and gaseous phase produced by said con densing step additionally contains a small quantity of butadiene, and said treating step produces a liquid mixture which is also substantially free of butadiene; and comprising the further step of washing the gaseous phase produced by said condensing step with a portion of the liquid mixture produced by said treating step for obtaining a gaseous phase substantially free of butadiene, and subsequently again subjecting said portion of the liquid mixture to said treating step.
  • a process according to claim 1 which comprises maintaining the chlorine in admixture with the liquid condensate for a period sufficient to remove all but at most a negligible quantity of chloroprene from said liquid condensate.

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US113985A 1970-02-20 1971-02-09 Chloroprene removal from pyrolyzed 1,2-dichlorethane Expired - Lifetime US3876714A (en)

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CA (1) CA955960A (cs)
DE (1) DE2101464A1 (cs)
ES (1) ES388118A1 (cs)
FI (1) FI53300C (cs)
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GB (1) GB1323038A (cs)
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094915A (en) * 1974-08-16 1978-06-13 The Lummus Company Recovery of 12-dichloroethane from vinyl chloride production effluent
US4119674A (en) * 1976-08-30 1978-10-10 The Dow Chemical Company Process for production of 1,1,1-trichloroethane and vinylidene chloride
JPS5517333A (en) * 1978-07-25 1980-02-06 Tokuyama Soda Co Ltd Vaporization of low-boiling residue discharged from production process of vinyl chloride monomer
US4252749A (en) * 1975-11-19 1981-02-24 Stauffer Chemical Company Production of 1,2-dichloroethane with purification of dichloroethane recycle
US4257850A (en) * 1979-01-31 1981-03-24 Hoechst Aktiengesellschaft Purification of 1,2-dichloroethane recovered in the incomplete thermal cracking to vinyl chloride
US4760206A (en) * 1986-10-17 1988-07-26 The B. F. Goodrich Company Process for removing butadiene from vinyl chloride in a quench tower
US5507921A (en) * 1994-12-14 1996-04-16 Westlake Monomers Corporation Method for quenching a gas stream in the production of vinyl chloride monomer
US6160189A (en) * 1995-05-02 2000-12-12 Ppg Industries Ohio, Inc. Reducing the monovinyl acetylene and/or butadiene content of impure vinyl chloride
US20040267064A1 (en) * 2001-10-17 2004-12-30 Beatrice Rondot Method for obtaining polymerisable vinyl chloride from a raw product derived from the pyrolysis of 1 2-dichloroethane
US20070112233A1 (en) * 2005-11-17 2007-05-17 Lg Chem, Ltd. Apparatus for preparing vinyl chloride by pyrolysis of 1,2-dichloroethane and method of preparing vinyl chloride using the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2211429B1 (cs) * 1972-12-27 1976-08-27 Rhone Progil
DE2754891C3 (de) * 1977-12-09 1981-02-26 Wacker-Chemie Gmbh, 8000 Muenchen Verfahren zur Reinigung von nichtumgesetztem 1.2-Dichloräthan aus der Vinylchloridherstellung

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125607A (en) * 1964-03-17 Purification op vinyl chloride
US3142709A (en) * 1961-05-22 1964-07-28 Monsanto Co Purification of vinyl chloride

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125607A (en) * 1964-03-17 Purification op vinyl chloride
US3142709A (en) * 1961-05-22 1964-07-28 Monsanto Co Purification of vinyl chloride

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4094915A (en) * 1974-08-16 1978-06-13 The Lummus Company Recovery of 12-dichloroethane from vinyl chloride production effluent
US4252749A (en) * 1975-11-19 1981-02-24 Stauffer Chemical Company Production of 1,2-dichloroethane with purification of dichloroethane recycle
US4119674A (en) * 1976-08-30 1978-10-10 The Dow Chemical Company Process for production of 1,1,1-trichloroethane and vinylidene chloride
JPS5517333A (en) * 1978-07-25 1980-02-06 Tokuyama Soda Co Ltd Vaporization of low-boiling residue discharged from production process of vinyl chloride monomer
US4257850A (en) * 1979-01-31 1981-03-24 Hoechst Aktiengesellschaft Purification of 1,2-dichloroethane recovered in the incomplete thermal cracking to vinyl chloride
US4760206A (en) * 1986-10-17 1988-07-26 The B. F. Goodrich Company Process for removing butadiene from vinyl chloride in a quench tower
US5507921A (en) * 1994-12-14 1996-04-16 Westlake Monomers Corporation Method for quenching a gas stream in the production of vinyl chloride monomer
US5558746A (en) * 1994-12-14 1996-09-24 Westlake Monomers Corporation Apparatus for quenching a gas stream in the production of vinyl chloride monomer
US6160189A (en) * 1995-05-02 2000-12-12 Ppg Industries Ohio, Inc. Reducing the monovinyl acetylene and/or butadiene content of impure vinyl chloride
US20040267064A1 (en) * 2001-10-17 2004-12-30 Beatrice Rondot Method for obtaining polymerisable vinyl chloride from a raw product derived from the pyrolysis of 1 2-dichloroethane
US6979754B2 (en) * 2001-10-17 2005-12-27 Arkema Method for obtaining polymerizable vinyl chloride from a raw product derived from the pyrolysis of 1,2-dichloroethane
US20070112233A1 (en) * 2005-11-17 2007-05-17 Lg Chem, Ltd. Apparatus for preparing vinyl chloride by pyrolysis of 1,2-dichloroethane and method of preparing vinyl chloride using the same

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NO135025B (cs) 1976-10-18
BE746270A (fr) 1970-08-20
FR2080645A1 (cs) 1971-11-19
FR2080645B1 (cs) 1973-12-07
FI53300B (cs) 1977-12-30
NO135025C (cs) 1977-01-26
FI53300C (fi) 1978-04-10
DE2101464A1 (de) 1971-09-16
GB1323038A (en) 1973-07-11
NL7100999A (cs) 1971-08-24
CA955960A (en) 1974-10-08
ES388118A1 (es) 1973-05-01
AT305960B (de) 1973-03-26

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