Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/12—Organo silicon halides
  • C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/12—Organo silicon halides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/12—Organo silicon halides
  • C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
  • C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/12—Organo silicon halides
  • C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
  • C07F7/123—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-halogen linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/12—Organo silicon halides
  • C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
  • C07F7/125—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving both Si-C and Si-halogen linkages, the Si-C and Si-halogen linkages can be to the same or to different Si atoms, e.g. redistribution reactions

Definitions

• the present invention pertains to methods for synthesizing fluorosilicon compounds such as cyanoalkyldifluoromethylsilanes and cyanoalkyldimethylfluorosilanes.
• Fluorosilicon compounds such as cyanoalkyldifluoromethylsilanes and cyanoalkyldimethylfluorosilanes are useful in various applications such as battery fabrication, semiconductor deposition, fluorosilicone glass formation, and semiconductor etching agents. The development of economically viable and industrially practical methods for synthesizing such compounds would therefore be of great interest.
• One aspect of the invention provides a method of making 3-cyanopropyldimethylfluorosilane, comprising:
• reaction of fluorodimethylsilane and allyl cyanide may be carried out in the presence of a hydrosilylation catalyst, such as an organoplatinum coordination complex (e.g., Karstedt's catalyst).
• a hydrosilylation catalyst such as an organoplatinum coordination complex (e.g., Karstedt's catalyst).
• Also provided by the invention is a method of making 3-cyanopropyldimethylfluorosilane comprising a step of reacting bis(3-cyanopropyl)tetramethyldisiloxane and boron trifluoride.
• the boron trifluoride may be in the form of a Lewis base complex, such as an etherate complex.
• Yet another aspect of the invention furnishes a method of making 3-cyanopropyldifluoromethylsilane comprising a step of reacting allyl cyanide and difluoromethylsilane.
• the difluoromethylsilane may be prepared by reacting a cyclic siloxane containing silicon atoms bearing hydrogen and methyl substituents (e.g., 2,4,6,8-tetramethylcyclotetrasiloxane) with boron trifluoride.
• the reaction of allyl cyanide and difluoromethylsilane may be catalyzed using a hydrosilylation catalyst.
• the invention provides a method of making a cyanoalkyldifluoromethylsilane (e.g., 3-cyanopropyldifluooromethylsilane or 2-cyanoethyldifluoromethylsilane), comprising a step of reacting a cyanoalkyldichloromethylsilane with ammonium bifluoride.
• a cyanoalkyldifluoromethylsilane e.g., 3-cyanopropyldifluooromethylsilane or 2-cyanoethyldifluoromethylsilane
• the above-described reactions may be conducted in the presence of a solvent, in particular an inert organic solvent such as toluene, that forms an azeotrope with water. Removal of water from the compound that is the desired synthetic target is facilitated, since such solvent permits any residual water which may be present in the reaction product mixture to be separated by azeotropic distillation with the solvent.
• a solvent in particular an inert organic solvent such as toluene
• the compound 3-cyanopropyldimethylfluorosilane (sometimes referred to herein as “F1S 3 MN”) has the chemical structure NCCH 2 CH 2 CH 2 Si(CH 3 ) 2 F and thus has a cyanopropyl group, two methyl groups and a fluorine atom bonded to a silicon atom.
• F1S 3 MN is prepared by first synthesizing fluorodimethylsilane [HSiF(CH 3 ) 2 ] by reacting tetramethyldisiloxane [(H 3 C) 2 Si—O—Si(CH 3 ) 2 ] with boron trifluoride (BF 3 ), which acts as a fluorinating agent, to yield fluorodimethylsilane and then reacting the fluorodimethylsilane thereby obtained with allyl cyanide (H 2 C ⁇ CH—CH 2 —CN).
• boron trifluoride may be supplied in any suitable form, including in neat or solvated form.
• a Lewis base complex of BF 3 is employed, such as an etherate complex.
• boron trifluoride diethyl etherate (BF 3 .OEt 2 ) may be utilized.
• the stoichiometry of BF 3 to tetramethyldisiloxane may be varied and optimized using standard experimental procedures, but typically the molar ratio of BF 3 to tetramethyldisiloxane is advantageously within the range of from about 0.3:1 to about 1:1.
• Procedures for reacting tetramethyldisiloxane and boron trifluoride diethyl etherate are known in the art and may be readily adapted for use in the present invention (see, for example, J. Chem.
• the boron trifluoride is added to a solution of the tetramethyldisiloxane in an inert solvent such as an aromatic hydrocarbon.
• the solvent may be a solvent such as toluene that is capable of forming an azeotrope with water.
• the use of such a solvent is advantageous since it permits removal of water from the reaction product as an azeotrope with the solvent, thereby leading to an isolated F1S 3 MN product having a very low water content, which is highly desirable.
• the reaction mixture may be maintained at a temperature effective to achieve the desired reaction of the starting material to selectively yield the desired fluorodimethylsilane within a practicably short period of time.
• reaction temperatures of from about 30° C. to about 100° C. and reaction times of from about 1 to about 10 hours may be employed.
• the desired product, fluorodimethylsilane is relatively volatile and thus may be recovered from the reaction mixture by methods such as distillation.
• the next step of the above-mentioned method involves reacting the fluorodimethylsilane with allyl cyanide.
• the molar ratio of fluorodimethylsilane to allyl cyanide may be from about 0.7:1 to about 1.3:1, for example.
• the reaction is carried out in the presence of a hydrosilylation catalyst, in particular a platinum-containing catalyst such as an organoplatinum coordination complex having activity as a hydrosilylation catalyst.
• Karstedt's catalyst which is an organoplatinum compound derived from divinyl-containing disiloxane (by treatment of chloroplatinic acid with divinyltetramethyldisiloxane), is an example of a suitable catalyst for this purpose.
• suitable hydrosilylation catalysts include, for example, Wilkinson's catalyst (tris(triphenylphosphine)rhodium (I) chloride), the cobalt carbonyl complex Co 2 (CO) 8 , and H 2 PtCl 6 (Speier's catalyst).
• Wilkinson's catalyst tris(triphenylphosphine)rhodium (I) chloride
• the cobalt carbonyl complex Co 2 (CO) 8 cobalt carbonyl complex Co 2 (CO) 8
• H 2 PtCl 6 Speier's catalyst
• the allyl cyanide may be charged to a suitable reaction vessel, optionally together with one or more inert solvents such as an aromatic hydrocarbon (preferably a solvent such as toluene that is capable of forming an azeotrope with water, thereby permitting the removal of water from the reaction product as a toluene/water azeotrope) and/or a hydrosilylation catalyst.
• an aromatic hydrocarbon preferably a solvent such as toluene that is capable of forming an azeotrope with water, thereby permitting the removal of water from the reaction product as a toluene/water azeotrope
• a hydrosilylation catalyst preferably a solvent such as toluene that is capable of forming an azeotrope with water, thereby permitting the removal of water from the reaction product as a toluene/water azeotrope
• the fluorodimethylsilane may then be added to and combined with the contents of the reaction vessel. The addition of the fluorod
• a first portion of the fluorodimethylsilane may be added (optionally, in an incremental fashion) and the resulting mixture then permitted to react for a period of time before adding a second portion of the fluorodimethylsilane.
• the reaction mixture may be maintained, for example, at a temperature of from about 70° C. to about 120° C.
• the desired product, 3-cyanopropyldimethylfluorosilane may be recovered from the reaction product mixture and purified by any suitable method, such as fractional distillation or the like.
• residual water may be removed by azeotropic distillation from the reaction product, if a solvent such as toluene is present which is capable of forming an azeotrope with water.
• 3-cyanopropyldimethylfluorosilane is prepared by a process comprising a step of reacting bis(3-cyanopropyl)tetramethyldisiloxane and boron trifluoride.
• Bis(3-cyanopropyl)tetramethyldisiloxane [NCCH 2 CH 2 CH 2 (CH 3 ) 2 SiOSi(CH 3 ) 2 CH 2 CH 2 CH 2 CN] is available commercially and may be prepared by known synthetic methods.
• the boron trifluoride may be in the form of a Lewis base complex, such as an etherate complex.
• the boron trifluoride may be added to a solution of the bis(cyanopropyl)tetramethyldisiloxane in an organic solvent (e.g., an aromatic hydrocarbon such as toluene, in particular a solvent capable of forming an azeotrope with water to assist in removing residual water from the reaction product).
• an organic solvent e.g., an aromatic hydrocarbon such as toluene, in particular a solvent capable of forming an azeotrope with water to assist in removing residual water from the reaction product.
• the stoichiometry of bis(3-cyanopropyl)tetramethyldisiloxane to BF 3 may be varied as may be desired in order to optimize the yield of the desired 3-cyanopropyldimethylfluorosilane, but typically the molar ratio of bis(3-cyanopropyl)tetramethyldisiloxane to boron trifluoride will be from about 0.3:1 to about 1:1.
• the mixture may be heated for a time and at a temperature effective to achieve fluorination and conversion of the bis(3-cyanopropyl)tetramethyldisiloxane to 3-cyanopropyldimethylfluorosilane. For example, reaction temperatures of from about 60° C. to about 100° C.
• the 3-cyanopropyldimethylfluorosilane may be recovered from the reaction product mixture by conventional purification methods such as washing the reaction product with aqueous acid and then fractionally distilling the organic layer. If a solvent such as toluene which is capable of forming an azeotrope with water is present, a fore-cut containing residual water (as an azeotrope with solvent) may be first collected before distilling the desired 3-cyanopropyldimethylfluorosilane, thereby reducing the water content of the recovered 3-cyanopropyldimethylfluorosilane.
• a solvent such as toluene which is capable of forming an azeotrope with water
• a method of making 3-cyanopropyldifluoromethylsilane in accordance with the present invention comprises a step of reacting allyl cyanide and difluoromethylsilane [HSi(CH 3 )F 2 ].
• the difluoromethylsilane may be obtained by carrying out an initial step of reacting a cyclic siloxane containing Si atoms bearing hydrogen and methyl substituents (e.g., 2,4,6-trimethylcyclotrisiloxane; 2,4,6,8-tetramethylcyclotetrasiloxane, 2,4,6,8,10-pentamethylcyclopentasiloxane; 2,4,6,8,10,12-hexamethylcyclohexasiloxane; and higher homologues) and boron trifluoride.
• the cyclic siloxane contains repeating units having the structure [—O—SiH(CH 3 )-]. Mixtures of such cyclic siloxanes may be employed as a starting material.
• the synthesis of difluoromethylsilane using such a reaction has not been previously reported and thus is considered to be an additional aspect of the present invention.
• the boron trifluoride may be in the form of a Lewis base complex, such as an etherate complex (e.g., boron trifluoride diethyl ether).
• the siloxane starting materials such as 2,4,6,8-tetramethylcyclotetrasiloxane are known compounds and may be readily obtained from commercial sources or prepared by conventional synthetic methods.
• One suitable procedure for reacting a cyclic siloxane such as 2,4,6,8-tetramethylcyclotetrasiloxane and BF 3 involves charging a mixture of 2,4,6,8-tetramethylcyclotetrasiloxane and an organic solvent such as an aromatic hydrocarbon (e.g., toluene) to a reaction vessel and then adding the BF 3 (e.g., in the form of boron trifluoride diethyl ether) incrementally to the contents of the reaction vessel, with agitation (stirring).
• the organic solvent may be selected to be one that is capable of forming an azeotrope with water.
• BF 3 per mole of Si in the cyclic siloxane
• from about 2 to about 4 moles of BF 3 per mole of 2,4,6,8-tetramethylcyclotetrasiloxane may be used.
• the resulting reaction mixture may be heated at a temperature effective to achieve the desired reaction to provide difluoromethylsilane (e.g., about 50° C. to about 100° C.).
• the difluoromethylsilane may then be isolated or separated from the reaction product using any suitable method such as distillation, then further reacted with allyl cyanide.
• the difluoromethylsilane and allyl cyanide are combined and heated for a time and at a temperature effective to achieve the desired reaction to provide 3-cyanopropyldifluoromethylsilane [NCCH 2 CH 2 CH 2 Si(CH 3 )F 2 ].
• a hydrosilylation catalyst such as, for example, Karstedt's catalyst, Wilkinson's catalyst (tris(triphenylphosphine)rhodium (I) chloride), the cobalt carbonyl complex Co 2 (CO) 8 , or H 2 PtCl 6 (Speier's catalyst) may additionally be present to accelerate the rate of reaction.
• allyl cyanide and a hydrosilylation catalyst such as Karstedt's catalyst may be introduced into a reaction vessel and heated to the desired reaction temperature (e.g., about 70° C. to about 110° C.).
• the difluoromethylsilane is then introduced into the reaction vessel, with such introduction being carried out incrementally or portion-wise. Additional amounts of hydrosilylation catalyst may be introduced during the course of the reaction.
• the molar ratio of allyl cyanide to difluoromethylsilane may suitably be from about 0.7:1 to about 1.3:1, for example.
• the desired 3-cyanopropyldifluoromethylsilane may be recovered from the reaction product by any suitable method, such as distillation. If a solvent such as toluene is present in the reaction product mixture that is capable of forming an azeotrope with water, a water/solvent azeotrope may first be removed by distillation, thereby reducing the water content of the 3-cyanopropyldifluoromethylsilane subsequently recovered by distillation.
• a solvent such as toluene
• the present invention further provides, in one aspect, a method of making a cyanoalkyldifluoromethylsilane, comprising a step of reacting a cyanoalkyldichloromethylsilane with ammonium bifluoride.
• Suitable cyanoalkyldichloromethylsilanes contain, as substituents on the silicon atom, a cyanoalkyl group (such as 2-cyanoethyl or 3-cyanopropyl), two chlorine atoms and a methyl group.
• the cyanoalkyldichloromethylsilane may, for example, be selected from the group consisting of 3-cyanopropyldichloromethylsilane [NCCH 2 CH 2 CH 2 Si(CH 3 )(Cl) 2 ] and 2-cyanoethyldichloromethylsilane [NCCH 2 CH 2 Si(CH 3 )(Cl) 2 ].
• Such compounds are known in the art and may be prepared by adaptation of synthetic methods such as reaction of dichloromethylsilane with acrylonitrile or 3-butene nitrile.
• Such reaction may be a hydrosilylation reaction catalyzed by a suitable catalyst, such as a copper-based hydrosilylation catalyst.
• 3-cyanopropyldichloromethylsilane [NCCH 2 CH 2 CH 2 Si(CH 3 )(Cl) 2 ] is converted to 3-cyanopropyldifluoromethylsilane [NCCH 2 CH 2 CH 2 Si(CH 3 )(F) 2 ] and 2-cyanoethyldichloromethylsilane [NCCH 2 CH 2 Si(CH 3 )(Cl) 2 ] is converted to 2-cyanoethyldifluoromethylsilane [NCCH 2 CH 2 Si(CH 3 )(F) 2 ].
• Ammonium bifluoride is sometimes also referred to as ABF, ammonium hydrogen difluoride, ammonium acid fluoride, H 4 NHF 2 or H 4 NF ⁇ HF.
• the fluorination reaction may be carried out by contacting the cyanoalkyldichloromethylsilane with ammonium bifluoride for a time and at a temperature effective to replace the chlorine atoms present in the cyanoalkyldichloromethylsilane with fluorine atoms.
• a mixture of the cyanoalkyldichloromethylsilane and ammonium bifluoride may be placed in a vessel and heated, with the desired product cyanoalkyldifluoromethylsilane, which has a lower boiling point than the corresponding cyanoalkyldichloromethylsilane, being removed by distillation as it is formed.
• the desired product cyanoalkyldifluoromethylsilane which has a lower boiling point than the corresponding cyanoalkyldichloromethylsilane, being removed by distillation as it is formed.
• about 0.5 to about 1.5 moles of ammonium bifluoride per mole of cyanoalkyldichloromethylsilane is utilized. Reaction temperatures of from about 30° C. to about 100° C. are generally suitable, for example.
• An inert organic solvent capable of forming an azeotrope with water such as toluene may be present in the reaction product mixture; azeotropic distillation of the reaction product mixture to remove water as an azeotrope with the organic solvent may be employed as a method of reducing the water content of the cyanoalkyldifluoromethylsilane that is recovered from the reaction product mixture.
• Tetramethyldisiloxane (TMDS), 35.31 g (262.9 mmol) and toluene 101.17 g (1.1 mol) were charged to the four neck flask.
• Boron trifluoride diethyl etherate (BF 3 ⁇ OEt 2 ), 25.31 g (178.3 mmol) was charged to the addition funnel using a cannula and nitrogen pressure. Dry ice was placed in the first dry ice condenser.
• the BF 3 ⁇ OEt 2 was added drop-wise to the reaction flask over a 25 minute period.
• the reaction mixture was then heated from 40 to 90° C. over the course of 4 hours during which the dry ice in the first condenser evaporated and the volatile material was allowed to collect in the second (two neck) flask cooled to dry ice temperature. After no more volatile material was coming over, the collected material was transferred to an evacuated stainless steel cylinder.
• the collected product was 83 wt. % FDMS and thus the isolated yield based on TMDS was 89%.
• This FDMS was used directly without purification for the synthesis of 3-cyanopropyldimethylfluorosilane, F1S 3 MN, according to Example 2 below.
• a 100 ml four-neck 14/20 flask was equipped with a magnetic stir bar, a 1 ⁇ 4 Teflon coated thermocouple connected to a J-Kem controller, and a dry ice condenser with outlet going to a nitrogen source. Rubber septa were secured on the remaining two necks. Allyl cyanide 9.57 g (142.6 mmol) and toluene 29.77 g (323.1 mmol) were charged to the reaction flask and heated to 60° C. A 1 ⁇ 8′′ Teflon line was connected from a cylinder containing fluorodimethylsilane (FDMS) through a rubber septum on the reaction flask.
• FDMS fluorodimethylsilane
• reaction mixture was combined with the material described in the previous paragraph and the combined mixture was purified by distillation. After first removing a fore-cut containing toluene, water and other impurities, the desired product F1S 3 MN was isolated under full vacuum (0.35 torr) at 80° C. Total product recovered was 28.90 g (199.0 mmol) which represents an isolated yield of 83% (based on allyl cyanide).
• a 250 ml three-neck 14/20 flask was equipped with a magnetic stir bar, a 1 ⁇ 4 Teflon coated thermocouple connected to a J-Kem controller, an addition funnel with septum secured on top and a dry ice condenser with outlet going to a nitrogen source.
• Bis(3-cyanopropyl)tetramethyldisiloxane 31.47 g (130.9 mmol) and toluene 63.10 g (693.5 mmol) were charged to the reaction flask.
• Boron trifluoride diethyl etherate (BF 3 ⁇ OEt 2 ) 11.09 g (78.1 mmol) was charged to the addition funnel using a cannula and nitrogen pressure.
• Example 4 An apparatus and procedure as described in Example 1 was used for Example 4. Thus, 2,4,6,8-tetramethylcyclotetrasiloxane 16.07 g (66.8 mmol) and toluene 100.06 g (1.09 mol) were charged to the four neck flask. Boron trifluoride diethyl etherate (BF 3 ⁇ OEt 2 ) 26.24 g (184.9 mmol) was charged to the addition funnel. A dry ice/isopropanol slush bath was placed in the second addition funnel and in the bath under the two neck flask. BF 3 ⁇ OEt 2 was added drop-wise to the reaction flask over 25 minutes. No reflux or significant exotherm was observed.
• BF 3 ⁇ OEt 2 Boron trifluoride diethyl etherate
• the reaction mixture was then heated initially to 60° C., whereupon refluxing commenced, and subsequently further heated to 90° C.
• the volatile product was collected in the second (two neck) flask and subsequently transferred to a storage cylinder.
• the collected product (22.10 g) was 76 wt. % FDMS and thus the isolated yield was 77%.
• Example 5 An apparatus and procedure as described in Example 1 was used for Example 5. Thus, a fresh sample of allyl cyanide, 14.00 g (208.7 mmol), prepared via the aqueous reaction between allyl bromide and potassium cyanide, was charged to the reaction flask and heated to 90° C. An 1 ⁇ 8′′ Teflon® line was connected from a cylinder containing DFMS (prepared according to the procedure provided in Example 4) through a rubber septum and into the reaction flask. Karstedt's catalyst (0.3 ml) was added to reaction flask and the addition of DFMS was initiated and continued at a rate to control the reflux in dry ice condenser.
• DFMS prepared according to the procedure provided in Example 4
• the reaction product mixture was distilled under a partial vacuum of 60 torr up to 100° C. to remove toluene, water and other impurities.
• the product was isolated under full vacuum (0.75 torr) up to 100° C.
• Total product recovered by distillation was 17.60 g.
• the product purity was estimated at 80% by NMR analysis. Thus, the isolated yield was about 45%.
• the product also contained 0.1351% water as determined by Karl Fisher titration.
• the product DCS 2 MN may be fluorinated, for example using ammonium bifluoride (ABF), to form the desired fluorinated product, DFS 2 MN.
• the fluorination reaction may be carried out by contacting the DCS 2 MN with ammonium bifluoride for a time and at a temperature effective to replace the chlorine atoms present in the DCS 2 MN with fluorine atoms.
• a mixture of DCS 2 MN and ammonium bifluoride may be together in a vessel and the desired product DFS 2 MN, which has a lower boiling point than DCS 2 MN, removed by distillation as it is formed.

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